EP1732546A2

EP1732546A2 - Novel pyrrolo (2,3-b)pyridine derivatives, the preparation and the pharmaceutical use thereof in the form of kinase inhibitors

Info

Publication number: EP1732546A2
Application number: EP05746934A
Authority: EP
Inventors: Sylvie Wentzler; Youssef El-Ahmad; Bruno Filoche-Romme; Conception Nemecek; Corinne Venot; Augustin Hittinger
Original assignee: Rhone Poulenc Rorer SA; Aventis Pharma SA
Current assignee: Aventis Pharma SA
Priority date: 2004-03-31
Filing date: 2005-03-30
Publication date: 2006-12-20
Also published as: MXPA06011161A; IL178310A0; CA2558923A1; JP4841543B2; FR2868422A1; JP2007530645A; US20090233956A1; US7968566B2; BRPI0509564A; AU2005229452A1; CN1950083A; UY28835A1; US20070093480A1; WO2005095399A2; WO2005095399A3; KR20070014151A; FR2868422B1; AR048344A1; US7528147B2; TW200602344A

Abstract

The invention relates to novel products of formula (I), wherein R is hydrogen or selected from R2 or R3, R1 is alkenyl or alkyl possibly substituted by CO-NR7R8, -NR7R8, carboxy, hydroxyl, alkoxy or halogen, identical or different R2 and R3 are alkyl or -O-alkyl or possibly substituted by -CO-NR7R8, -NR7R8, alkoxy, alkoxy-NR7R8, carboxy or phenyl, identical or different R4, R5 and R6 are hydrogen, halogen, cyano, amino, alkoxy or alkyl, R4 is also -CH=O, -CH=N-OH and -CH2NHOH, R7 and R8 are, in particular hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl or R7 and R8 form with an nitrogen atom a possibly substituted heterocycle, said products are embodied in the form of all types of isomers and salts used as drugs.

Description

NOVEL PYRROLO (2, 3-B) PYRIDINE DERIVATIVES, THEIR PREPARATION AND THEIR PHARMACEUTICAL USE AS KINASE INHIBITORS

The present invention relates to new pyrrolo (2,3-b) pyridine derivatives, their preparation process, their application as medicaments, the pharmaceutical compositions containing them and the pharmaceutical use of such derivatives for the prevention - and treatment of conditions capable of being modulated by inhibiting the activity of protein kinases. The present invention relates to new pyrrolo (2,3-b) pyridine derivatives having inhibitory effects for protein kinases. The products of the present invention can thus in particular be used for the prevention or treatment of conditions capable of being modulated by inhibiting the activity of protein kinases. The inhibition and regulation of protein kinases constitute in particular a new powerful mechanism of action for the treatment of a large number of solid tumors. Such conditions which can be treated by the products of the present application are therefore very particularly solid tumors. Such protein kinases belong in particular to the following group:

IGF1, Raf, EGF, PDGF, VEGF, Tie2, DR, Fltl-3, FAK, Src, Abl, cKit, cdkl-9, Auroral-2 cdc7, Akt, Pdk, S6K, Jnk, IR, FLK-1, FGFR1 , FGFR2, FGFR3, FGFR4, FGFR5, PLK, Pyk2 Such protein kinases belong more particularly to the following group: IGF1, cdc7, Auroral- 2, Src, Jnk, FAK, KDR, IR, Tie2 The protein kinase IGF1 is particularly indicated ( Insulin Growth Factor-1). The present invention thus relates to particularly new inhibitors of the IGF-1R receptor which can be used for oncology treatments. Cancer remains a disease for which existing treatments are clearly insufficient. Certain protein kinases play an important role in many cancers. Inhibition of these protein kinases is ^potentially important in cancer chemotherapy particular to suppress the growth been the survival of tumors. The present invention therefore relates to the identification of new products which inhibit such protein kinases. Protein kinases participate in signaling events that control the activation, growth and differentiation of cells in response, either to extracellular mediators or to changes in the environment. In general, these kinases belong to two groups: those which phosphorylate preferentially the serine and / or threonine residues and those which phosphorylate preferentially the tyrosine residues [SKHanks and T. Hunter, FASEB. J., 1995, 9, pages 576-

596]. The serine / threonine kinases are, for example, the isoforms of protein kinases C [A. C. Newton, J. Biol.

Che. , 1995, 270, pages 28495-28498] and a group of cyclin-dependent kinases, such as cdc2 [J. Pins, Trends in Bioche ical Sciences, 1995, 18, pages 195-197]. Tyrosine kinases include growth factor receptors such as the epidermal growth factor receptor (EGF) [S.Iwashita and M.Kobayashi, Cellular Signaling, 1992, 4, pages 123-132], and cytosolic kinases such as p56tck, p59fYn, ZAP-70 and csk kinases [C. Chan and. al., Ann. Rev. Immunol., 1994, 12, pages 555-592]. Abnormally high levels of protein kinase activity have been implicated in many diseases, resulting from abnormal cellular functions. This can result either directly or indirectly, from a dysfunction in the mechanisms controlling kinase activity, linked for example to a mutation, an over-expression or an inappropriate activation of the enzyme, or by an over- or under-production cytokines or growth factors, also involved in signal transduction upstream or downstream of kinases. In all ^" these cases, a selective inhibition of the action of kinases gives hope for a beneficial effect. The receptor, type 1 for insulin-like growth factor (IGF-IR) is a transmembrane receptor with tyrosine kinase activity which binds first to IGFI but also to IGFII and insulin with a lower affinity. The binding of IGFI to its receptor leads to oligomerization of the receptor, activation of tyrosine kinase, intermolecular autophosphorylation and phosphorylation of cellular substrates (main substrates: IRS1 and Shc). The receptor activated by its ligand induces mitogenic activity in normal cells. However IGF-IR plays an important role in so-called abnormal growth. Several clinical reports underline the important role of the IGF-I pathway in the development of human cancers: IGF-IR is often found overexpressed in many tumor types (breast, colon, lung, sarcoma ...) and its presence is often associated with a more aggressive phenotype. High concentrations of circulating IGF1 are strongly correlated with a risk of prostate, lung and breast cancer. In addition, it has been widely documented that IGF-IR is necessary for the establishment and maintenance of the transformed phenotype both in vitro and in vivo [Baserga R, Exp. Cell. Res., 1999, 253, pages 1-6]. IGF-IR kinase activity is essential for transformation activity several oncogenes: EGFR, PDGFR, the SV40 virus grand T antigen, activated Ras, Raf, and v-Src. Expression of IGF-IR in normal fibroblasts induces a neoplastic phenotype, which can then lead to tumor formation in vivo. The expression of IGF-IR plays an important role in the independent growth of the substrate. IGF-IR has also been shown to be a protector in chemotherapy-, radiation- induced apoptosis, and cytokine-induced apoptosis. In addition, the inhibition of endogenous IGF-IR by a dominant negative, the formation of triple helix or the expression of an antisense causes a suppression of the transforming activity in vitro and the decrease in the growth of tumors in animal models. The subject of the present invention is the products of formula (I):

in which :

R represents hydrogen or is chosen from the values of R2 and R3,

RI represents alkenyl or alkyl optionally substituted by --CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy or a halogen atom, R2 and R3 identical or different represent alkyl or -O-alkyl optionally substituted by -CO -NR7R8,

-NR.7R8, alkoxy, alkoxy-NR7R8, free or esterified carboxy where phenyl itself optionally substituted, R4, R5 and R6 identical or different are chosen from the hydrogen atom, halogen atoms and cyano radicals , amino, alkoxy or optionally substituted alkyl, R4 can also be chosen from following values: carboxaldehyde -CH = 0, formaldoxime - CH = N-OH and methylhydroxylamine -CH2NHOH;

R7 ^' and R8, identical or different, are chosen from hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, and heteroaryl, monocyclic or bicyclic, all these radicals being optionally substituted, or else R7 and R8 form with .1' atom d nitrogen to which they are linked a heterocyclic radical irisàtùrë or alternatively partially or totally saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted, all of the above radicals alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic, as well as the heterocyclic radical formed by R7 and R8 with the nitrogen atom to which they are attached, being optionally substituted by one or more identical or different chosen from the halogen atoms and the cyano, hydroxyl, alkyl, alkoxy, alkylthio, nit radicals ro, oxo, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, -C (= 0) -R9, -C (= O) -OR10, -N (R11) -C (= 0) - R9, -N (Rll) -C (= O) -OR10, -NR12R13, -C (= 0) - NR12R13, -N (R11) -C (= 0) -NR12R13, -S (0) n-R9 , -N (R11) -S (O) n- R9, -S (0) n-NR12R13 and -N (R11) -S (O) n-NR12R13, n represents an integer from 0 to 2, the latter radicals alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl being themselves optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy radicals, NR12R13, free or esterified carboxy, CF3, nitro, cyano, phenyl and phenylalkyl in which the radical • phenyl is itself optionally substituted by one or more identical or different radicals chosen from the halogen atoms and the hydroxyl, alkyl, alkoxy, free or esterified carboxy, CF3, nitro, cyano and pyridyl radicals; R9 represents alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl, all these radicals being optionally substituted, RIO represents, the values, _de _. R9 and hydrogen, R11 represents hydrogen or optionally substituted alkyl, R12 and R13, identical or different, represent hydrogen, acyl, alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, SO2-heteroaryl, -SO2-alkyl, -SO2-phenyl, -CO- NH-phenyle and phenyle, all these radicals being optionally substituted, or else R12 and R13 form, with the nitrogen atom to which they are linked, a heterocyclic radical which is unsaturated or partially or totally saturated, consisting of 3 to 10 members and containing one or several heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted, R14 represents the values of R9 and hydrogen, acyl and free and esterified carboxy, the radicals R9, RIO, R11, R12, R13 and R14 above as well as the cyclic radical which R12 and R13 can form with the nitrogen atom to which they are linked, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, alkyl-NH2, alkyl- NHC02alkyl, NH2, NHC02alkyl, hydroxyl, alkoxy, hydroxyalkoxy, free or esterified carboxy, CF3, SCF3, OCF3, OCHF2, S02CF3, nitro, cyano, heterocycloalkyl, heteroaryl radicals phenyl, the latter cyclic radicals being themselves optionally substituted by one or several identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkoxy, free or esterified carboxy, CF3, SCF3, OCF3, OCHF2, S02CF3, NH2, NHC02alkyl, nitro and cyano, all aryl, heteroaryl radicals and heterocycloalkyl above being further optionally substituted by an alkylenedioxy radical, all of the above alkyl, alkenyl, alkoxy or - O-alkyl and alkylthio radicals being linear or branched and containing at most 6 carbon atoms, all radicals ci above cycloalkyl containing at most 7 carbon atoms, all of the above aryl, heteroaryl and heterocycloalkyl radicals containing at most 10 carbon atoms, said products of formula (I) being in all the isomeric, racemic, enantiomeric and diastereo- forms isomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which: R represents hydrogen where is chosen from the values of R2 and R3,

RI represents alkenyl or alkyl optionally substituted by -CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy or a halogen atom, R2 and R3 identical or different represent alkyl or -O-alkyl optionally substituted by -CO- NR7R8,

-NR7R8, alkoxy, alkoxy-NR7R8, free or esterified carboxy or phenyl itself optionally substituted, R4, R5 and R6 identical or different are chosen from the hydrogen atom, halogen atoms and cyano, amino radicals , alkoxy or alkyl optionally substituted, R4 can also be chosen from the following values: carboxaldehyde -CH = 0, formaldoxime - CH = N-OH and methylhydroxyla ine -CH2NHOH;

R7 and R8, identical or different, are chosen from hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, and heteroaryl, monocyclic or bicyclic, ... all these radicals being optionally substituted, or else R7 and R8 form with the atom d nitrogen to which they are linked an unsaturated or partially or fully saturated heterocyclic radical consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted, all of the above radicals alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic, as well as the heterocyclic radical formed by R7 and R8 with the nitrogen atom to which they are attached, being optionally substituted by one or more identical or different chosen from halogen atoms and cyano, hydroxyl, alkyl, alkoxy, alkylthio, nitro, o xo, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroaryarylalkyl, -C (= 0) -R9, -C (= 0) -OR10, -N (R11) -C (= 0) -R9, -N (R11) -C (= 0) -OR10, -NR12R13, -C (= 0) - NR12R13, -N (R11) -C (= 0) -NR12R13, -S (0) n-R9, - N (R11) -S (0) n- R9, -S (0) n-NR12R13 and -N (R11) -S (0) n-NR12R13, n represents an integer from 0 to 2, the latter alkyl radicals, alkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl themselves being optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alk13, free or esterified carboxy, CF3, nitro, cyano, phenyle and phenylalkyle in which the phenyle radical is itself optionally substituted by one. or several identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, free or esterified carboxy, CF3, nitro, cyano and pyridyl radicals; R9 represents alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl, to all these radicals, being optionally substituted,

RIO represents the values of R9 and hydrogen,

R11 represents hydrogen or optionally substituted alkyl,

R12 and R13, identical or different, represent hydrogen, acyl, alkyl, cycloalkyl, piperidyl, piperrazinyl, pyrrolidinyl, azetidinyl, pyrazolyl, pyridyl, imidazolyl, pyrimidyl, thiazolyl, thiazolidinyl, -S02-thienyl, -S02-pyridyl alkyl, -SO2-phenyl, -CO-NH-phenyl and phenyl, all these radicals being optionally substituted, or else R12 and R13 form, with the nitrogen atom to which they are linked, a heterocyclic radical which is unsaturated or else partially or completely saturated consisting of 3 to 10 links and containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted,

R14 represents the values of R9 and hydrogen, acyl and carboxy free and esterified lès R9, RIO, Rll, R12, R13 and R14 above as well as the cyclic radical that can form R12 and R13 with the ^'atom nitrogen to which they are linked, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, -CH2-NH2, -CH2-NHC02alkyl, NH2, radicals. NHC02alkyl, hydroxyl, alkoxy, hydroxyalkoxy, free or esterified carboxy, CF3, SCF3, OCF3, OCHF2, S02CF3, nitro, cyano, piperidyle, morpholinyle, pipërazinyle, thienyle, pyridyle, imidazolyle, thiazolyle, thiazolidinyle et phenyle, the latter cyclic radicals being themselves optionally substituted by one or more identical or different radicals chosen from atoms of halogen and the alkyl, hydroxyl, alkoxy, free or esterified carboxy radicals, CF3, SCF3, OCF3, OCHF2, S02CF3, NH2, NHC02alkyl, nitro and cyano, all of the above aryl, heteroaryl and heterocycloalkyl radicals being optionally substituted by an alkylenedioxy radical, all of the above alkyl, alkenyl, alkoxy or - O-alkyl and alkylthio radicals being linear or branched and containing at most 6 carbon atoms, all of the above cycloalkyl radicals containing at most 7 atoms carbon, all of the above aryl, heteroaryl and heterocycloalkyl radicals containing at most 10 carbon atoms, said products of formula (I) being under all your possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

The subject of the present invention is the products of formula '(I

in which :

R represents hydrogen or is chosen from the values of R2 and R3, RI represents alkenyl or alkyl optionally substituted by -CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy or a halogen atom, R2 and R3 identical or different represent alkyl or -O-alkyl optionally substituted by -CO- NR7R8, -NR7R8, hydroxyl, alkoxy, alkoxy-NR7R8, free or esterified carboxy or phenyl itself optionally substituted, R4, R5 and R6 identical or different are chosen from 1 hydrogen atom, halogen atoms and _ _. _cyano, _ amino _L alkpxy pu alkyl_ optionally substituted, R7 and R8 identical or different are chosen from hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic, all these radicals being optionally substituted, or else R7 and R8 form, with the nitrogen atom to which they are linked, an unsaturated or partially or fully saturated heterocyclic radical consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted, all of the above alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic radicals, as well as the heterocyclic radical formed by R7 and R8 with the nitrogen atom to which they are attached, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and the cyano, hydroxyl, alkyl, alkoxy, alkylthio, ήitro, oxo, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, -C (= 0) -R9, -C (O) radicals , -N (R11) -C (= 0) -R9, -N (Rll) -C (= O) -OR10, -NR12R13, -C (= 0) - NR12R13, -N (R11) -C (= 0) -NR12R13, -S (0) n-R9, -N (R11) -S (O) n- R9, -S (0) n-NR12R13 and -N (R11) -S (O) n-NR12R13 , n represents an integer from 0 to 2, the latter alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl radicals themselves being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl radicals, alkyl radicals, alkoxy, -NR12R13, free or esterified carboxy, CF3, nitro, cyano, pyrrolidinyl, phenyl ^' and phenylalkyl in which the phenyl radical is itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, free or esterified carboxy radicals, CF3, nitro, cyano and pyridyl, R9 represents alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroaryl, RIO represents the values of R9 and hydrogen, Rll represents has hydrogen or optionally substituted alkyl,

R12 and R13, identical or different, represent hydrogen, acyl, alkyl, cycloalkyl and phenyl, these radicals being optionally substituted, or else R12 and R13 form, with the nitrogen atom to which they are attached, an unsaturated heterocyclic radical or else partially or fully saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from 0, S, N and NR14, this radical being optionally substituted, R14 represents the values of R9 and hydrogen, acyl and free and esterified carboxy, the radicals R9, RIO, R11, R12, R13 and R14 above being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkoxy, hydroxyalkoxy, free or esterified carboxy, CF3, nitro, cyano and phenyle itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkoxy, free or esterified carboxy radicals, CF3, nitro and cyano, all aryl radicals, heteroaryl and heterocycloalkyl above being additionally optionally substituted by an alkylenedioxy radical, all of the above alkyl, alkenyl, alkoxy or -O-alkyl and alkylthio radicals being linear or branched and containing at most 6 carbon atoms, all radicals above cycloalkyl containing at most 7 carbon atoms, all of the above aryl, heteroaryl and heterocycloalkyl radicals containing at most 10 carbon atoms, said products of formula (I) being in all the possible racemic, enantiomeric and diastereomeric forms -isomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of said pro duits of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R2 and R3 which are identical or different represent -O-alkyl containing at most 4 carbon atoms optionally substituted by -CO -NR7R8, -NR7R8, alkoxy, alkoxy-NR7R8 or free or esterified carboxy, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as addition salts with mineral and organic acids or with bases mineral and organic of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which ^• R2 and R3, which are identical or different, represent -O-alkyl containing at most 4 carbon atoms optionally substituted by - CO-NR7R8, -NR7R8, alkoxy, alkoxy-NR7R8, the other substituents of said products of formula (ï) having the values defined above and in the present invention, said products of formula (I) being in all the isomeric forms racemic, enantiomeric and diastereoisomeric, as well as the addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I). A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R2 and R3 which are identical or different represent -O-alkyl containing at most 4 carbon atoms optionally substituted by -CO -NR7R8 or -NR7R8, the other substituents of the said. products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with the mineral and organic acids or with the mineral and organic bases of the said products of formula (I).

A subject of the present invention is thus the products of formula ^: (I) as defined above and in the present invention in which RI represents alkyl optionally substituted by -CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy , or a halogen atom, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as the salts of 'addition with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which RI represents alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7R8, -NR7R8, free carboxy or esterified or hydroxyl, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic, enantiomeric and diastereomeric isomer forms, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which RI represents alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7R8, -NR7R8 or hydroxyl, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as the salts of addition with mineral and organic acids or with mineral and organic bases of the said products of formula (I). A subject of the present invention is thus the products of formula (I) as defined in any one of the other claims in which RI represents alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7R8 or -NR7R8, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which RI represents alkyl containing at most 4 carbon atoms optionally substituted by NR7R8, the other substituents of said products of formula ( I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the mineral and organic bases of the said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which: R4, R5 and R6 are such that one represents hydrogen and the others, identical or different, are chosen from the hydrogen atom, the halogen atoms and the optionally substituted cyano, amino or alkyl radicals, the other substituents of the said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

The present invention thus relates to the products of formula (I) as defined above and in. the present invention in which R4, R5 and R6 are such that R5 and R6, identical or different, are chosen from the hydrogen atom and the halogen atoms, and R4, identical or different from R5 and R6, is chosen among the halogen atoms, the amino radicals, carboxaldehyde -CH = 0, formaldoxime -CH = N-0H, methylhydroxylamine -CH2NHOH and alkyl optionally substituted by one or more identical or different radicals chosen from halogen atoms and radicals cyano, hydroxyl, alkoxy,, cycloalkyl, heterocycloalkyl, phenyl, heteroaryl and -NR12R13; R, RI, R2, R3, R12 and R13 having the values defined in any one of the other claims, said products of formula (I) being in all the isomeric, possible racemic, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R4, R5 and R6 represent hydrogen or are such that two of them represent hydrogen and the third represents a halogen atom or the cyano radical, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R4, R5 and R6 represent hydrogen, the other substituents of said products of formula (I) having the values defined ci above and in the present invention, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral and organic bases said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R4, R5 and R6 are such that two of them represent hydrogen and the third represents an atom of halogen or the cyano radical, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic, enantiomeric and diastereomeric isomeric forms , as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R4, R5 and R6- are such that two of them represent hydrogen and the third represents a halogen atom, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being under all possible racemic isomeric forms, enantiomers and diastereoisomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R4, R5 and R6 are such that two of them represent hydrogen and the third represents a chlorine atom or fluorine, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomeric forms, thus as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R4, R5 and R6 are such that two of them represent hydrogen and the third represents the cyano radical, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as the salts of addition with mineral and organic acids or with mineral and organic bases of the said products of formula (I). A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R6 represents hydrogen, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R5 and R6 represent hydrogen and R4 represents a halogen atom or the cyano radical, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with acids mineral and organic or with the mineral and organic bases of said products of formula (I).

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R4 and R6 represent hydrogen and R5 represents a fluorine atom, the other substituents of said products of formula (I) having the values defined above and in the present invention, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the basics mineral and organic of said products of formula (I).

In the products of formula (I) and in what follows, the terms indicated have the meanings which follow: - the term ^x Hal ', "Halo" or halogen designates the atoms of fluorine, chlorine, bromine or iodine . - the term alkyl or alk radical denotes a linear or branched radical containing at most 12 carbon atoms chosen from methyl, ethyl, - propyl, isopropyl, butyl, isobutyl, sec-butyl, tertbutyl, pentyl, isopentyl, sec-pentyl radicals , tert-pentyîe, neo-pentyle, hexyle, isohexyle, sec-hexyle, tert-hexyle and also heptyle, octyle, nonyle, décyle, undécyle et dodécyle, as well as their linear or branched position isomers, We quote more particularly the radicals alkyl having at most 6 carbon atoms and in particular the methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, terbutyl, linear or branched pentyl, linear or branched hexyl radicals. the term alkenyl radical denotes a linear or branched radical containing at most 12 carbon atoms and preferably 4 carbon atoms chosen for example from the following values: ethylene or vinyl, propenyl or allyl, 1-propenyl, n-butenyl, i-butenyl , 3-methylbut-2-ethyl, n-pentenyl, hexenyl, heptenyl, octenyl, cyclohexylbutenyl and decenyl as well as their linear or branched position isomers. Among the alkenyl values, the allyl or butenyl values are more particularly cited. - the term alkoxy or O-alkyl radical denotes a linear or branched radical containing at most 12 carbon atoms and preferably 6 carbon atoms chosen, for example, from methoxy, ethoxy, propoxy, isopropoxy, linear, secondary or tertiary butoxy, pentoxy radicals , hexoxy and heptoxy and their linear or branched position isomers, - the term alkoxycarbonyl or alkyl-O-CO- radical denotes a linear or branched radical containing at most 12 carbon atoms in which the alkyl radical has the meaning indicated above: mention may be made, for example methoxy- and ethoxycarbonyl radicals. - The term alkylenedioxy radical or -O-alkylene-O- denotes a linear or branched radical containing at most 12 carbon atoms in which the alkylene radical has the meaning indicated above: mention may be made, for example, of methylenedioxy and ethylenedioxy radicals. - The term alkylsulfinyl or alkyl-SO- denotes a linear or branched radical containing at most 12 carbon atoms in which the alkyl radical has the meaning indicated above and preferably contains 4 carbon atoms. - The term alkylsuifonyl or alkyl-SO2- denotes a linear or branched radical containing at most 12 carbon atoms in which the alkyl radical has the meaning indicated above and preferably contains 4 carbon atoms. - the term alkylsulfonylcarbamoyl or alkyl-SO2-NH-C (= 0) - designates a linear or branched radical containing at most 12 carbon atoms in which the alkyl radical has the meaning indicated above and preferably contains 4 carbon atoms . - The term alkylthio or alkyl-S- denotes a linear or branched radical containing at most 12 carbon atoms and represents in particular the methylthio, ethylthio, isopropylthio and heptylthio radicals. - the term cycloalkyl radical designates a monocyclic or bicyclic carbocyclic radical containing 3 to 10 members and designates in particular the cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl radicals, - the term -0-cycloalkyl radical designates a radical in which the cycloalkyl radical has the meaning indicated above - the term cycloalkenyl radical denotes a non-aromatic monocyclic or bicyclic carbocyclic radical containing at least one double bond and containing 3 to 10 members and designates in particular the cyclobutenyl, cyclopentenyl or cyclohexenyl radicals. the term cycloalkylalkyl radical denotes a radical in which cycloalkyl and alkyl ^" are chosen from the values indicated above: this radical thus denotes for example the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl and cycloheptylmethyl radicals. - the term acyl or r-CO radical - denotes a linear or branched radical containing at most 12 carbon atoms in which the radical r represents a hydrogen atom, an alkyl, cycloalkyl, cycloalkenyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl radical, these radicals having the optionally substituted values indicated above or below: thus the acyl radical represents in particular CO-alkyl, CO-aryl or CO-hereroaryl, for example the formyl, acetyl, propibnyl, butyryl or benzoyl radicals, or valeryryl, hexanoyl, acryloyl, crotonoyl, carbamoyl, pyrrolidinylcarboxy or furylcarboxy. - By acyloxy radical, we mean acyl- O- radicals in which acyl has the meaning indicated above: mention is made, for example, of the acetoxy or propionyloxy radicals. - By acylamino means acyl-NH- radicals in ^'which acyl has the meaning indicated above. the term aryl radical denotes unsaturated radicals, monocyclic or consisting of condensed, carbocyclic rings. As examples of such an aryl radical, mention may be made of phenyl or naphthyl radicals, Mention is made more particularly of the phenyl radical. - By arylalkyl is meant the radicals resulting from the combination of the alkyl radicals mentioned above optionally substituted and the aryl radicals also mentioned above, optionally substituted: mention is made, for example, of the benzyl, phenylethyl, 2-phenethyl, triphenylmethyl or naphthlenemethyl radicals. - The term heterocyclic radical denotes a saturated (heterocycloalkyl) or unsaturated (heteroaryl) carbocylic radical consisting of at most 6 links interrupted by one or more heteroatoms, identical or different, chosen from oxygen, nitrogen or sulfur atoms.

As radicals heterocycloalkyl, mention may be made of the dioxolane, dioxane, dithiolane, thiooxolane, thiooxane, oxiranyl, oxolanyl, dioxolanyl, piperazinyl, piperidinyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, morpholinyl or tetrahydrofuryl, tetrahydrothienyl, chromanyl, dihydrobenzofuranyl, indolinyl, piperidinyl , perhydropyranyl, pyrindolinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl or thioazolidinyl, piperidyl; tetrahydro-furan-2-yl, imidazolinyl, dihydropyrrolyl, tetrahydropyrrolyle, diazepine, perhydro-1,4-diazepine, tetrahydro-pyrrolo [3,4-c] pyrrole- 2-one, tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione and 1,4-dioxa-8-aza-spiro [4.5] decane, all these radicals being optionally substituted. Among the heterocycloalkyl radicals, mention may in particular be made of the piperazinyl, piperidinyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, morpholinyl, thioazolidinyl, piperidyl radicals; tetrahydro-furan-2-yl, imidazolinyl, dihydropyrrolyl, tetrahydropyrrolyle, diazepine, perhydro-1,4-diazepine, tetrahydro-pyrrplo [3,4-c] pyrrole-2-one, tetrahydro-pyrrolo [3,4- c] pyrrole-1,3-dione and 1,4-dioxa-8-aza-spiro [4.5] decane, all these radicals being optionally substituted - By heterocycloalkylalkyl radical is meant the radicals in which the heterocycloalkyl and alkyl radicals have the Previous meanings Among the 5-membered heteroaryl radicals, mention may be made of furyl radicals such as 2-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrblyl, diazolyl, thiazolyl, thiadiazolyl, thiatriazolyl, isothiazolyl, oxazolyl oxadolyl 4-isoxazolyle, imidazolyle, pyrazolyle, isoxazolyle. Mention may in particular be made, among the 6-membered heteroaryl radicals, of pyridyl radicals such as 2-pyridyl, 3-pyridyl and 4-pyridyl, pyrimidyl, pyrimidinyl, pyridazinyl, pyrazinyl and tetrazolyl. As condensed heteroaryl radicals containing at least one heteroatom chosen from sulfur, nitrogen and oxygen, mention may, for example, be made of benzothienyl, such as 3-benzothienyl, benzofuryl, benzopyrannyl, benzofurannyl, benzopyrrolyl, benzimidazolyl, benzoxazolyl, thionaphthyl. purinyl, quinolinyl, isoquinolinyl and naphthyridinyl. Among the condensed heteroaryl radicals, mention may be made more particularly of the benzothienyl, benzofurannyl, indolyl or quinolinyl, benzimidazolyl, benzothiazolyl, furyl, imidazolyl, indolizinyl, isoxazolyl, isoquinolinyl, isothiazolyl, pyridinyl pyridinol, pyrazinyl , quinazolinyl, 1,3,4-thiadiazolyl, thiazolyl, thienyl and triazolyl groups, these radicals being optionally substituted as indicated for the heteroaryl radicals. - The term cyclic amine designates a cycloalkyl radical containing 3 to 8 members in which a carbon atom is replaced by a nitrogen atom, the cycloalkyl radical having the meaning indicated above and which may also contain one or more other heteroatoms chosen from O, S, SO2, N or NR9 with R9 tel _. as defined above, as examples of such cyclic amines, mention may be made, for example, of the pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl, indolinyl, pyrindolinyl or tetrahydroquinoleinyl radicals, these radicals being optionally substituted The term patient designates human beings but also the others mammals. The term "Prodrug" denotes a product which can be transformed in vivo by metabolic mechanisms (such as hydrolysis) into a product of formula (I). For example, an ester of a product of formula (I) containing a hydroxyl group can be converted by hydrolysis in vivo to its parent molecule. Or an ester of a product of formula (I) containing a carboxy group can be converted by hydrolysis in vivo to its parent molecule. Mention may be made, as examples, of esters of products of formula (I) containing a hydroxyl group such as acetates, citrates, lactates, tartrates, malonates, oxalates, salicylates, propionates, succinates, fumarates, maleates, methylene-bis- b- hydroxynaphthoates, gentisates, isethionates, di-p-toluoyltartrates, methanesulfonates, ethanesulfonates, benzenesulfonates, p-toluenesulfonates, cyclohexylsulfamates and quinates. Esters of particularly useful products of formula (I) containing a hydroxyl group can be prepared from acidic residues such as those described by Bundgaard et. al., J. Med. Chem. , 1989,

32, page 2503-2507: these esters include in particular substituted (aminomethyl) benzoates, dialkylamino-methylbenzoates in which the two alkyl groups may be linked together or may be interrupted by an oxygen atom or by a nitrogen atom optionally substituted with either an alkyl nitrogen atom or still morpholino-methyl Dbenzoates, eg 3- or 4- (morpholinomethyl) -benzoates, and (4-alkylpiperazin-1-yl) benzoates, eg 3- or 4- (4-alkylpiperazin-1-yl) benzoates. The carboxy radical (s) of the products of formula (I) can be salified or esterified by various groups known to those skilled in the art, among which the following compounds may be mentioned, by way of nonlimiting examples. - among salification compounds, mineral bases such as, for example, an equivalent of sodium, potassium, lithium, calcium, magnesium or ammonium or organic bases such as, for example, methylamine, propylamine, trimethylamine, diethylamine, triethylamine, N, N-dimethylethanolamine, tris (hydroxymethyl) amino methane, ethanolamine, pyridine, picoline, dicyclohexylamine, morpholine, benzylamine, procaine, lysine , arginine, histidine, N-methylglucamine, - among the esterification compounds, alkyl radicals to form alkoxy carbonyl groups such as, for example, methoxycarbonyl, ethoxycarbonyl, tert-butoxy-carbonyl or benzyloxycarbonyl, these alkyl radicals which can be substituted by radicals chosen, for example, from halogen atoms, hydroxyl, alkoxy, acyl, acyloxy, alkylthio, amino or aryl radicals, such as, for example, in chloromé groups thyle, hydroxypropyl, methyloxy, propionyloxymethyl, methylthiomethyl, dimethylaminoethyl, benzyl or phenethyl. By esterified carboxy is meant for example radicals such as alkyloxycarbonyl radicals, for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butyl or tert-butyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl or cyclohexyloxycarbonyl. Mention may also be made of radicals formed with easily cleavable ester residues such as the methyloxymethyl and ethyloxymethyl radicals; acyloxyalkyl radicals such as pivaloyloxymethyl, pivaloyloxyethyl, acetoxymethyl or acetoxyethyl; the alkyloxycarbonyloxy alkyl radicals such as the methyl or ethyl methylcarbonyloxy radicals, the isopropyloxycarbonyloxy methyl or ethyl radicals. A list of such ester radicals can be found for example in European patent EP 0 034 536. By amidified carboxy is meant radicals of the type -CONR7R8 as defined above or below. By alkyl- or dialkyl-amino radical, we. means radicals in which the alkyl radical (s) preferably have 1 to 4 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl radicals: the radicals are thus for example methylamino, ethylamino, propylamino or butylamino, linear or branched, the dimethylamino, diethylamino, methylethylamino radicals. Amino radicals can also have one or two heterocycles which can optionally have an additional heteroome. Mention may be made, for example, of the pyrrolyl, imidazolyl, indolyl, piperidinyl, morpholinyl and piperazinyl radicals and in particular the piperidinyl, morpholinyl or piperazinyl radicals. By salified carboxy is meant the salts formed for example with an equivalent of sodium, potassium, lithium, calcium, magnesium or ammonium. Mention may also be made of the salts formed with organic bases such as methylamine, propylamine, trimethylamine, diethylamine, triethylamine. The sodium salt is preferred. When the products of formula (I) contain an amino radical salifiable by an acid, it is understood that these acid salts are also part of the invention. Mention may be made of the salts supplied with hydrochloric or methanesulphonic acids for example. The addition salts with mineral or organic acids of the products of formula (I) can be, for example, the salts formed with hydrochloric, hydrobromic, hydroiodic, nitric, sulfuric, phosphoric, propionic, acetic, trifluoroacetic, fόrmique, bérizoique maleïqë, fùmariqùe, sùccin qùê, tartaric, citric, oxalic, glyoxylic, aspartic, ascorbic, alkylmonosulfonic acids such as for example methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, alkoyldonic acids example methanedisulfonic acid, alpha, beta-ethanedisulfonic acid, arylmonosulfonic acids such as benzenesulfonic acid and aryldisulfonic acids. It may be recalled that stereoisomerism can be defined in its broad sense as the isomerism of compounds having the same developed formulas, but the different groups of which are arranged differently in space, such as in particular in monosubstituted cyclohexanes whose substituent can be in axial or equatorial position, and the different possible rotational conformations of ethane derivatives. However, there is another type of stereoisomerism, due to the different spatial arrangements of fixed substituents, either on double bonds or on rings, which is often called geometric isomerism or cis-trans isomerism. The term stereoisomer is used in the present application in its broadest sense and therefore relates to all of the compounds indicated above.

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which the substituents R, RI, R2, R3, R4, R5 and R6 of said products of formula (I) have the values defined above and in the present invention, in which the radical -NR12R13 is such that R12 and R13, identical or different, represent the atom hydrogen; and the acyl, alkyl, cycloalkyl, piperidyl, piperazinyl, pyrrolidinyl, azetidinyl, pyrazolyl, pyridyl, imidazolyl, pyrimidyl, thiazolyl, thiazolidinyl, -SO2-thienyl, - SO2-pyridyl, - SO2 -phenyl radicals, - CO-NH-phenyle and phenyle, all of these radicals being optionally substituted by one or more identical or different radicals, chosen from halogen atoms and alkyl radicals; CH2-NH2; CH2-NHC02alkyl; NH2; NHC02alkyl; hydroxyl; alkoxy; hydroxyalkoxy; free or esterified carboxy; CF3; SCF3; OCF3; OCHF2; SO2CF3; nitro; cyano; thienyl; piperidyl; morpholino itself optionally substituted by one or two alkyl radicals; and phenyl itself optionally substituted by one or more identical or different radicals, chosen from halogen atoms and alkyl, hydroxyl, alkoxy, free or esterified carboxy, CF3, SCF3, OCH3, OCHF2, S02CF3, NH2, NHC02alkyl radicals ,, nitro and cyano; where R12 and R13 form, with the nitrogen atom to which they are linked, a heterocyclic radical which is unsaturated or else partially or totally saturated, consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR11, this radical optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl radicals; -CH2-NH2; CH2-NHC02alkyl; NH2; NHC02alkyl; hydroxyl; alkoxy; hydroxyalkoxy; free or esterified carboxy; CF3; SCF3; OCF3; OCHF2; SO2CF3; nitro; cyano; and piperidyl radicals; morpholinyl; piperazinyl; thienyl; pyridyle, imidazolyle, thiazolyle, thiazolidinyle and phenyl, themselves optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkoxy, free or esterified carboxy, CF3, SCF3, NH2, NHC02alkyl, nitro and cyano radicals, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and. diastereoisomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

In particular R12 and R13, identical or different, may represent hydrogen; acyl such as, for example, alkyl- CO-, phenyl-CO-, pyrazolyl -CO-, pyridyl-CO-, imidazolyl-CO-, pyrimidyl-CO-, thiazolyl-CO-; alkyl optionally substituted with thienyl, alkoxy or phenyl itself optionally substituted with OCH3, SCF3, NHC02ALK or NH2; cycloalkyl; piperidyl optionally substituted with alkyl; piperazinyl, pyrrolidinyl, azetidinyl; pyrazolyl optionally substituted with alkyl; pyridyl, imidazolyl, pyrimidyl, thiazolyl, thiazolidinyl; -SO2-thienyl; -SO2-pyridyl; -SO2- alkyl; -SO2-phenyl optionally substituted with OCF3; -CO-NH-phenyle optionally substituted with OÇF3; and phenyl itself optionally substituted with OCH3, SCF3, piperidyl or morpholino the latter itself optionally substituted with one or two alkyl radicals.

A subject of the present invention is thus the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated above and in the present invention and R7 and R8, identical or different, are chosen from hydrogen, alkyl, cycloalkyl, phenyl, heterocycloalkyl and heteroaryl, monocyclic or bicyclic, all these radicals being optionally substituted, or else R7 and R8 form, with the nitrogen atom to which they are bonded, a heterocyclic radical which is unsaturated or else partially or totally saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR14 , this radical being optionally substituted, all of the above alkyl, cycloalkyl, phenyl, heterocycloalkyl and heteroaryl, mono-cyclic or bicyclic radicals, as well as the heterocyclic radical formed by R7 and R8 with the nitrogen atom to which they are linked, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, oxo, nitro, alkyl, alkoxy, alkylthio, cycloalkyl, phenyl, heterocycloalkyl, heteroaryl, -C (= 0) - R9, -C (= O) -OR10, -N (R11) -C (= 0) -R9, -N (R11) -C (= 0) -OR10, -NR12R13, -C (= 0) - NR12R13 and -N (R11) -C (= 0) -NR12R13, the latter alkyl, alkoxy, cycloalkyl, phenyl, heterocycloalkyl and h eteroaryl, themselves being optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, -NR12R13, free or esterified carboxy, pyrrolidinyl, phenyl and phenylalkyl radicals in which the phenyl radical is itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, free or esterified carboxy, CF3, nitro, cyano and pyridyl, R9 radicals. represents alkyl, cycloalkyl, phenyl, heterocycloalkyl and heteroaryl, all of these radicals being optionally substituted,

RIO represents the values of R9 and hydrogen, R11 represents hydrogen or optionally substituted alkyl,

R12 and R13, identical or different, represent hydrogen, acyl, alkyl, cycloalkyl and phenyl, these radicals being optionally substituted, or else R12 and R13 form with the nitrogen atom to which they are linked an heterocyclic radical which is unsaturated or else partially or completely saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR11, this radical being optionally substituted, R14 represents hydrogen, acyl, free and esterified carboxy, alkyl, cycloalkyl and phenyl, optionally substituted, the radicals R9, RIO, Rll, R12, R13 and R14 above being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkoxy, hydroxyalkoxy, free or esterified carboxy, CF3, nitro, cyano and phenyl radicals. -even optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkox radicals y, free or esterified carboxy, CF3, nitro and cyano, all of the above phenyl and heteroaryl radicals being optionally substituted by a dioxol radical, all of the above alkyl, alkenyl, alkoxy or -O-alkyl and alkylthio radicals being linear or branched and containing at most 4 carbon atoms, all of the above cycloalkyl radicals containing not more than 7 carbon atoms, all of the above heteroaryl and heterocycloalkyl radicals containing not more than 10 carbon atoms, said products of formula ( I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I). For example, R14 can represent a hydrogen atom; a cycloalkyl radical; an alkyl radical optionally, substituted for example by hydroxyl, alkoxy, hydroxyalkoxy or phenyl itself optionally substituted by one or more radicals chosen from halogen atoms and the radicals CF3, alkoxy and dioxol; a heterocyclic radical such as for example piperidyl or pyridyl; a phenyl radical itself optionally substituted by alkoxy, CF3 or halogen; a free or esterified carboxy radical; an acyl radical such as for example -CO-CH3 or -CO-furyl.

Examples of heterocyclic radicals which the above radicals can represent are given below: among these heterocyclic radicals below, those comprising at least one nitrogen atom constitute examples of radicals which R7 and R8 can form with l nitrogen atom to which they are linked and also R12 and R13 with the nitrogen atom to which they are linked. The following radicals are thus cited in a nonlimiting manner: pyrrolidinyl, piperidyl, pyrimidinyl, thienyl, thiazolyl, pyran, furyl, tetrahydrofuryl, tetrahydro-furan-2-yl, imidazolinyl, imidazolyl, piperazinyl, indolyl, pyrrole, pyropyl , purinyl and morpholinyl, thiomorpholinyl, azetidinyl, azepanyl, diazepine, spiro [4.5] decane, pyrrolyl, 2H-pyrrolyl, piperidinyl, indolinyl, pyrindolinyl, tetrahydroquinoline, thiazolidinyl, naphthyrridyl, or quinazolinyl, 1,4-dioxyrinyl aza-spiro [4.5] decane and tetrahydro-pyrrolo [3,4- c] pyrrolyl, all these radicals being optionally substituted.

More particularly, when R12 and R13 form a cyclic radical with the nitrogen atom to which they are linked, this cyclic radical can be chosen from the pyrrolidinyl, morpholinyl, piperazinyl radicals, piperidyl, or alternatively azetidinyl, all of these radicals being optionally substituted as indicated above.

In particular when R12 and R13 form a cyclic radical with the nitrogen atom to which they are linked, this cyclic radical can be chosen from piperidyl radicals itself optionally substituted by a piperidyl radical or a hydroxyl radical; azetidinyl. itself optionally substituted by NH-C02alk, CH2-NH2-C02alk, CH2-NH2 and NH2; and piperazinyl itself optionally substituted by an alkyl, phenylalkyl or phenolic radical in which the phenolic radical is itself optionally substituted by one or more radicals chosen from OCF3, OCHF2, SCF3 or SO2CF3.

The present invention particularly relates to the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated above and in the present invention, and R7. and R8, which are identical or different, are chosen from hydrogen, cycloalkyl, optionally substituted alkyl, optionally substituted pheny, heterocycloalkyl and optionally substituted monocyclic or bicyclic heteroaryl, or else R7 and R8 form, with the nitrogen atom to which they are attached, a heterocyclic radical containing one or more heteroatoms and optionally substituted, all of the above alkyl, phenyl and heterocyclic radicals, as well as the heterocyclic radical which can form R7 and R8 with the nitrogen atom to which they are linked, being optionally substituted by one or more radicals chosen from halogen atoms and hydroxyl radicals; oxo; nitro; cycloalkyl; alkoxy; OCF3; hydroxyalkoxy; alkylthio; acyl; free or esterified carboxy; optionally substituted pheny; optionally substituted amino; alkyl optionally substituted by one or more radicals chosen from halogen atoms and the hydroxyl, alkoxy, pyrrolidinyl, phenyl and amino radicals themselves, optionally substituted; and pyrrolidinyl, piperidyl, pyridyl and piperazinyl themselves optionally substituted by one or more radicals chosen from hydroxyl, alkyl, alkoxy, free or esterified carboxy, pheryl and phenylalkyl radicals themselves, optionally substituted, the amino radicals being optionally substituted with a or two identical or different radicals chosen from alkyl, hydroxyalkyl, alkoxyalkyl, acyl, phenyl and phenylalkyl themselves optionally substituted, the phenolic and phenylalkyl radicals being optionally substituted by one or more radicals chosen from halogen atoms and hydroxyl, alkyl radicals , alkoxy, CF3, free or esterified carboxy, pyridyl and dioxol, all the alkyl and alkoxy radicals being linear or branched and containing at most 4 carbon atoms said products of formula (I) being in all the possible isomeric forms racemic, enantiomers and diastereoisomers, as well as the salts addition with mineral and organic acids or with mineral and organic bases of said products of formula (I).

The identical or different radicals R7 and R8 can thus in particular represent hydrogen and the optionally substituted alkyl, cycloalkyl, phenyl and heterocyclic radicals: among the values of R7 and R8, there may be mentioned, for example, pyrimidinyl; thienyl; pyridyle; quinolyl; thiazolyl optionally substituted with one or two halogen atoms; pyran optionally substituted by one or more OCOAlk; phênyie optionally substituted by one or more radicals chosen from halogen atoms and alkyl, alkoxy, amino, alkylamino, dialkylamino and carboxy radicals free or esterified by an alkyl radical; alkyl substituted by pheny itself optionally substituted by one or more radicals chosen from halogen, alkyl, alkoxy, amino, alkylamino, dialkylamino, free carboxy or esterified by an alkyl radical; alkyl substituted by piperazinyl itself optionally ^" substituted by one of several radicals chosen by i Alk, Alk-OH and pyridyl; alkyl substituted by imidazolyl; substituted alkyl by one or more radicals chosen from NH2, NHAlk, N (Alk) 2 ,

N (alk) (phenylalkyl), N (Alk) (aminoalkyl) N (Alk) (alkylaminoalkyle) and N (Alk) (dialkylaminoalkyle); alkyl substituted by morpholinyl optionally substituted by one or two Alk; alkyl substituted with pyrrolidinyl; alkyl substituted by piperidyl itself optionally substituted by one or two Alk; alkyl substituted with thiomorpholinyl; alkyl substituted by azetidinyl; alkyl substituted by azepanyl optionally substituted by oxo.

Mention may also be made, as radical, that R7 and R8 can form, with the nitrogen atom to which they are linked, the dihydropyrrolyl, 1,4-dioxa-8-aza-spiro [4.5] decane or tetrahydro-pyrrolo radicals [3,4 -c] pyrrolyl, these radicals all being optionally substituted.

The radical which R7 and R8 can form with the nitrogen atom to which they are linked may in particular be optionally substituted by one or more identical or different radicals chosen from halogen atoms and the alkyl, hydroxyl, alkoxy and phenyl radicals. - even optionally substituted by one or more radicals chosen from halogen atoms and alkyl and alkoxy radicals, The pyrrolidinyl and quinazolinyl radicals can in particular be optionally substituted by oxo or thioxo. The piperazinyl radical can in particular be optionally substituted by one or more radicals chosen from Alk, Alk-OH and pyridyl. The acyl radical represents in particular the radicals -CO- alkyl with alkyl containing at most 4 carbon atoms, -CO-furyl or - CO-pyrrolidinyl.

A more particular subject of the present invention is the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated above and in the present invention, and R7 and R8, which are identical or different, are chosen from hydrogen and the alkyl, cycloalkyl, phenyl and heterocyclic radicals such as pyrrolidinyl, piperidyl, pyrimidinyl, thienyl, thiazolyl, pyran, furyl, tetrahydrofuryl, tetrahydro-furan-2-yl , imidazolinyl, piperazinyl, indolyl, pyrrole, benzopyran, quinolyl, pyridyl, purinyl and morpholinyl, these radicals being optionally substituted or else R7 and R8 form, with the nitrogen atom to which they are attached, a heterocyclic radical chosen from pyrrolidinyl radicals, imidazolyle, morpholinyle, pipérazinyle, pipêridyle, thiazolyle, diazepine, spiro [4.5] decane, pyrrolyle, dihydropyrrolyle, tétrahydropyrrolyle, têtrahydro-pyrrolo [ 3, 4-c] pyrrolyl, piperidinyl, indolinyl, pyrindolinyl, tetrahydroquinoline, thiazolidinyl, naphthyridyl, azetidine or quinazolinyl, these radicals being all optionally substituted, all of the above alkyl, phenyl and heterocyclic radicals being optionally substituted by one or several radicals chosen from halogen atoms and hydroxyl radicals; oxo; nitro; cycloalkyl; alkoxy; 0CF3; hydroxyalkoxy; alkylthio; acyl; free or esterified carboxy; phenyle eventually substituted; optionally substituted amino; alkyl optionally substituted with one or more radicals chosen from halogen atoms and the hydroxyl, alkoxy, pyrrolidinyl, phenyl and amino radicals themselves, optionally substituted; and pyrrolidinyl, piperidyl, pyridyl and piperazinyl themselves optionally substituted with one or more radicals chosen from the hydroxyl, alkyl, alkoxy, free or esterified carboxy, phenyl and phenylalkyl radicals themselves, optionally substituted, the amino radicals being optionally substituted with a or two identical or different radicals chosen from alkyl, hydroxyalkyl, alkoxyalkyl, acyl, phenyl and phenylalkyl themselves optionally substituted, the phenolic and phenylalkyl radicals being optionally substituted by one or more radicals chosen from halogen atoms and hydroxyl, alkyl radicals , alkoxy, CF3, free or esterified carboxy, pyridyl and dioxol, all the alkyl and alkoxy radicals being linear or branched and containing at most 4 carbon atoms said products of formula (I) being in all the possible isomeric forms racemic, enantiomers and diastereoisomers, as well as the salts of addition with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

The present invention particularly relates to the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated above and in the present invention, and

R7 and R8, which are identical or different, are chosen from hydrogen, cycloalkyl radicals and alkyl, phenyl and heterocyclic radicals such as pyrrolidinyl, piperidyl, furyl, tetrahydrofuryl, tetrahydro-furan-2-yl, imidazolinyl, piperazinyl, indolyl, pyrrolyl, benzopyrannyl, benzopyran-8-carboxylic, pyridyl, purinyl and morpholinyl, all these radicals being optionally substituted or else R7 and R8 form with the nitrogen atom to which they are linked a heterocyclic radical chosen from pyrrolidinyl, imidazolyl, morpholinyl, piperazinyl, piperidyl, thiazolyl, diazepine, spiro [4.5] decane, pyrrolyl, dihydropyrrolyl, tetrahydropyrrolyl, tetrahydro-pyrrolo [3, 4-pyrrolo radicals] radicals being all optionally substituted, all of the above alkyl, phenyl and heterocyclic radicals which represent R7 and R8 or which can form R7 and R8 with the nitrogen atom to which they are bonded, being optionally substituted by one or more selected radicals among the oxo radicals; cycloalkyl; CO-alkyl; -CO-furyl; hydroxyl; alkoxy; hydroxyalkoxy; alkylthio; free or esterified carboxy; optionally substituted pheny; alkyl optionally substituted with a radical chosen from hydroxyl, alkoxy, pyrrolidinyl, optionally substituted pheny and amino optionally substituted with one or two radicals chosen from optionally alkyl and pheny. substituted; amino optionally substituted with one or two identical or different radicals chosen from alkyl, hydroxyalkyl, alkoxyalkyl, CO-alkyl and phenyl itself optionally substituted; pyrrolidinyl, piperidyl, pyridyl and piperazinyl optionally substituted by one or more radicals chosen from free or esterified carboxy, alkyl, alkoxy, hydroxyl, phenylalkyl and phenyl optionally substituted, all the phenyl radicals being optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, CF3, free or esterified carboxy, pyridyl and dioxol radicals, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I). Thus R7 and R8 form in particular with the nitrogen atom to which they are linked a radical chosen from the following radicals: pyrrolidinyl; imidazolyl; dihydropyrrolyl; 1, 4-dioxa-8-aza-spiro [4.5] decane; morpholinyl; piperazinyl; piperidyl; thiazolyl; diazepine; perhydro-1,4-diazepine; 4-methyl-perhydro-1,4-diazepin-1-yl; tetrahydro-pyrrolo [3,4-c] pyrrole-2-one; tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione, these radicals being optionally substituted by one or more radicals as indicated above or also illustrated in the experimental part.

The present invention particularly relates to the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated above and in ia present invention, and

R7 and R8, identical or different, are chosen from the following radicals: - hydrogen; - benzopyran; - pyridyle itself optionally substituted by hydroxyl; - piperidyl optionally substituted by alkyl itself optionally substituted by phenyl; - purinyl; alkyl optionally substituted by one or more radicals chosen from hydroxyl; alkoxy; alkylthio; pyridyle; imidazolinyl; indolyl; pyrrolyl; furyl; tetrahydrofuryl; amino optionally substituted with one or two radicals identical or different chosen from alkyl, hydroxyalkyl, alkoxyalkyl and phenyl itself optionally substituted by alkyl; pyrrolidinyl itself optionally substituted by an alkyl radical; piperidyl itself optionally substituted by alkyl or phenylalkyl; piperazinyl itself optionally substituted with alkyl; phênyie optionally substituted by free or esterified dioxol or carboxy; - phenyl optionally substituted by one or more radicals chosen from alkoxy, piperidyl or piperazinyl itself optionally substituted by an alkyl radical; or else R7 and R8 form, with the nitrogen atom to which they are linked, a heterocyclic radical chosen from the following radicals: imidazolyl; - dihydropyrrolyle; 1,4-dioxa-8-aza-spiro [4.5] decane; - thiazolyl; tetrahydro-pyrrolo [3, 4-c] pyrrole-2-one; tetrahydro-pyrrolo [3, 4-c] pyrrole-1, 3-dione; - pyrrolidinyl optionally substituted by a radical chosen from pyridyl; amino itself optionally substituted by an alkyl radical and an acyl radical; and alkyl itself optionally substituted by a radical chosen from hydroxyl, alkoxy, pyrrolidinyl and amino itself optionally substituted by a phenyl radical; - morpholinyl optionally substituted by one or more alkyl radicals; - piperazinyl optionally substituted by one or more identical or different radicals chosen from oxo radicals; cycloalkyl; acyl; carboxy; pyridyle; alkyl containing not more than 4 carbon atoms itself optionally substituted by a hydroxyl, alkoxy or hydroxyalkoxy radical containing at most 4 carbon atoms and phenyl itself optionally substituted by a dioxol radical; phênyie itself optionally substituted by one or more radicals chosen from halogen atoms and hydroxyl, alkoxy and CF3 radicals; - piperidyl optionally substituted by one or more substituents chosen from hydroxyl, alkyl, hydroxyalkyl and piperidyl; - diazepine or perhydro-1,4-diazepine optionally substituted by an alkyl radical itself optionally substituted by pyrrolidinyl; said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

A more particular subject of the present invention is the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated above and in the present invention, and R7 and R8, which may be identical or different, are chosen from the hydrogen radicals, alkyl itself optionally substituted by a pyrrolidinyl or piperidyl radical and phenylene itself optionally substituted by one or more radicals chosen from the piperazinyl radical itself optionally substituted with one alkyl radical, or R7 and R8 together with the nitrogen atom to which they ^s' have linked a radical chosen from the following radicals: morpholinyl; thiazolyl; diazepine or perhydro-1,4-diazepine optionally substituted by an alkyl radical; l-tetrahydro-pyrrolo [3,4-c] pyrrole-2 one; piperazinyl optionally substituted by one or more identical or different radicals chosen from oxo and alkyl radicals itself optionally substituted by a hydroxyl, alkoxy or hydroxyalkoxy radical; piperidyl optionally substituted by hydroxyl, alkyl, hydroxyalkyl or piperidyl; the alkyl and alkoxy radicals containing at most 4 carbon atoms, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the mineral and organic bases of the said products of formula (I).

A more particular subject of the present invention is the products of formula (I) as defined above in which:

R and R6 represent a hydrogen atom, RI represents alkyl containing at most 2 carbon atoms optionally substituted by -CO-NR7R8 or -NR7R8, R2 and R3 identical or different represent -O-alkyl containing at most 3 carbon atoms optionally substituted by -CO-NR7R8 or -NR7R8,

R4 and R5 are such that one represents hydrogen and the other represents a halogen atom or a cyano radical,

R7 and R8 having the meanings indicated above, said products of formula (I) being in all forms. possible racemic isomers, enantiomers and diastereoisomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

A more particular subject of the present invention is the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5, R6, R7 and R8 have the meanings indicated above and in the present invention, it being understood that R7 and R8 do not both represent hydrogen, said products of formula (I) being in all the isomeric forms possible racemates, enantiomers and diastereoisomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I). The present invention relates more particularly to the products of formula (I) as defined above and in the present invention in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated in one any of the other claims, and R7 and R8 are such that either one of R7 and R8 represents hydrogen or alkyl and the other is selected from the values of R7 and R8 as defined in any of the other claims is R7 and R8 form, with the nitrogen atom to which they are linked, a heterocyclic radical as defined in any one of the other claims, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomeric forms , as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

Among the preferred products of the invention, there may be mentioned more particularly the products of formula (I) as defined above, the names of which follow: 2- {5,6-Dimethoxy-1- [2- (4-methyl -piperazin-1-yl) -ethyl] -1H-indol-3-yl} -1H-pyrrolo [2, 3-b] pyridine 2- (4- {2- [5,6-Dimethoxy-3- (1H -pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] -ethyl} -piperazin-1-yl) -ethanol 2- (l- {2- [5, 6-Dimethoxy-3 - (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] -ethyl} -piperidin-4-yl) -ethanol _l - {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} - [1,4 '] bipiperidinyl l- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - indol-1-yl] -ethyl} -piperidin-3-ol 2- { 5,6-Dimethoxy-1- [2- (4-methyl-perhydro-1,4-diazepin-1-yl) -ethyl] -1H-indol-3-yl} -1H-pyrrolo [2,3-b ] pyridine 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol- 1-yl] -1- (4-hydroxy-piperidin-1-yl ) -ethanone 2- [5,6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol- 1-yl] -l-thiazolidin-3-yl-ethanone 4- {[5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -acetyl} -l-methyl-pipêrazin-2-one 4-Chloro -2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridine 2- (5,6-dimethoxy-1-methyl-1H-indol -3-yl) -lH-pyrrolo [2,3- b] yridine-4-carbonitrile

4-chloro-2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H- indol-3-yl] -1H-pyrrolo [2,3-b] pyridine 2- ( l- {2- [3- (4-chloro-1H-pyrrolo [2,3-b] pyridin-2-yl) -5,6- dimethoxy-indol-1-yl] -êthyl} -piperidin-4- yl) -ethanol

4-chloro-2- {5,6-dimethoxy-l- [2- (4-methyl-pipêrazin-1-yl) - ethyl] -lH-indol-3-yl} -lH-pyrrolo [2,3- b] pyridine 2- {5, 6-dimethoxy-l- [2- (4-methyl-pipêrazin-1-yl) -ethyl] - 1H-indol-3-yl} -lH-pyrrolo [2, 3-b ] pyridine-4-carbonitrile 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -5-fluoro-1H- pyrrolo [2, 3-b] pyridine

2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H-indol-3- yl] -5-fluoro-1H-pyrrolo [2,3-b] pyridine 2- { 5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -5-fluoro-1H-pyrrolo [2,3-b] pyridine

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -l-morpholin-4-yl-ethanone 2 - [5-Methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1- (4-methyl- [1, 4 ] diazepan-1-yl) - ethanone

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -N- [4- (4-methyl-piperazin-1-yl) -phenyl] - acetamide 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1- (4-methyl-piperrazin-1-yl) -ethanone l- {4- [2- (2-Hydroxy-ethoxy) -ethyl] -piperazin-1-yl} -2- [5- Methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -1H- indol-6-yloxy] -ethanone (3aS, 6aS) -5- {2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -lH-indol-6- trifluoroacetate yloxy] - acetyl} -hexahydro-pyrrolo [3, 4-c] pyrrol-1-one 2- {5-Methoxy-1-methyl-6- [3- (4-methyl-perhydro-1,4-diazepin- 1-yl) -propoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3- b] pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4 -methyl-pipêrazin- 1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3-b] -pyridine

4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-pipêridyl- pipêridin-1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] - pyridine

4-Chloro-2- {5-Methoxy-1-methyl-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] - pyridine

4-Chloro-2- {1-methyl-5-methoxy-6- [2- (2-piperidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3-b] - pyridine,

said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

Among the preferred products of the invention, there may be mentioned more particularly the products of formula (I) as defined above, the names of which follow:

2- {5,6-Dimethoxy-1- [2- (-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine 2- (4- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} -piperazin-1-yl ) -ethanol 2- (1- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} -piperidin- 4-yl) -ethanol l - {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} - [ 1,4 '] bipiperidinyl 1- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} -piperidin- 3-ol 2- {5, 6-Dimethoxy-l- [2- (4-methyl-perhydro-1,4, diazepin-1-yl) -ethyl] -1H-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol- 1-yl] -1- (4-hydroxy -piperidin-1-yl) -ethanone 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol- 1-yl] -l-thiazolidin-3 -yl-ethanone 4- {[5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -acetyl} -l-methyl-piperazin- 2-one 4-Chloro-2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridine 2- (5,6-dimethoxy-1 methyl-lH-indol-3- yl) -IH-pyrrolo [2, 3- b] pyridine-4-carbonitrile

4-chloro-2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H- indol-3-yl] -IH-pyrrolo [2, 3-b] pyridine

2- (1- {2- [3- (4-chloro-1H-pyrrolo [2,3-b] pyridin-2-yl) -5,6- dimethoxy-indol-1-yl] -ethyl} -piperidin -4-yl) -ethanol 4-chloro-2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -lH-indol-3-yl} -lH -pyrrolo [2, 3-b] yridine 2- {5, 6-dimethoxy-l- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -lH- pyrrolo [2,3-b] pyridine-4-carbonitrile 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -5-fluoro-1H- pyrrolo [2, 3-b] pyridine

2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H-indol-3- yl] -5-fluoro-1H-pyrrolo [2,3-b] pyridine

2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -5-fluoro-1H-pyrrolo [2, 3- b] pyridine 2- [5-Methoxy-1-methyl-3- (IH-pyrrolo [2, 3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1-morpholin-4-yl ethanone 2- [ _5- Methoxy- ₁ -methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1- (4-methyl- [1, 4] diazepan-1-yl) - ethanone 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] - N- [4- (4-methyl-piperazin-1-yl) -phenyl] - acetamide 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl ) - 1H-indol-6-yloxy] -1- (4-methyl-pipera in-1-yl) -ethanone l- {4- [2- (2-Hydroxy-ethoxy) -ethyl] -piperazin-l- yl} -2- [5- Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -1H- indol-6-yloxy] -ethanone trifluoroacetate from (3aS, 6aS ) -5- {2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -lH-indol-6-yloxy] - acetyl} -hexahydro- pyrrolo [3, 4-c] pyrrol-1-one 2- {5-Methoxy-1-methyl-6- [3- (4-methyl-perhydro-1, 4-diazepin-1-yl) -propoxy] - lH-indol-3-yl} -lH-pyrrolo [2, 3- b] pyridine

4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-methyl-pipërazin-1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] -pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-pipêridyl- pipéridin-1-yl) -éthoxy] -lH-indol-3-yl} - 1H-pyrrolo [2,3-b] - pyridine

4-Chloro-2- {5-Methoxy-1-methyl-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3-b] - pyridine

4-Chloro-2- {1-methyl-5-methoxy-6- [2- (2-piperidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3-b] - pyridine, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula ( I).

The present invention also relates to a process for the preparation of products of formula (I) such as described above.

The products of formula (I) of the present invention as described above can be prepared as indicated in diagrams 1 to 6 described below: these diagrams thus describe stages of synthesis of the products of formula (I) of the present invention and are part of the present invention. . .. Scheme i thus describes a so-called access route A to x derivatives of formula (I): 2- (1H-Indol-3-yl) -lH-pyrrolo [2,3-b] pyridine. Scheme 2 thus describes a so-called route B for access to the derivatives of formula (I): 2- (Indol-3-yl) -1H-pyrrolo [2, 3-b] pyridine.

Schemes 3 and 4 respectively describe routes of introduction of the substituents in position RI and routes of introduction of the substituents in position R3 in the synthesis of the products of formula (I) of the present invention.

The 1H-pyrrolo [2,3-b] pyridine of general formula 1 according to the present invention:

in which RI, R2, R3, R4, R5, R6 and R are defined as above can be prepared according to diagrams 1 to 4 in the appendices: these diagrams are part of the present invention.

In scheme 1, more particularly, the treatment of 2-aminopyridines of general formula (A) with R ₅ ≠ H with N-iodosuccinimide or N-bromosuccinimide in a solvent such as acetic acid at a temperature between 20 ° C and 80 ° C as for example under the conditions described by Fuss A. and Koch V. (Synthesis, 1990, 8, 681-5) leads to the 3-halo-2-aminopyridines of general formula (B) . More particularly, the 3-trimethylsilanylethynylpyridin-2-ylamine of general formula (C) can be obtained by coupling of the Sonogashira type with the ethynyltrimethylsilane, for example under the conditions described by Knochel P. et al. (Tetrahedron, 2003, 59, 1571-1587) from the 3-halogeno-2-aminopyridines of general formula (B) in the presence of catalysts such as [1, l -bis (diphenylphosphino) ferrocene chloride] palladium ( II) or bis (triphenylphosphine) palladium (II) chloride, copper iodide, a base such as triethylamine and optionally lithium chloride in a solvent such as dimethylformamide at a temperature between 20 ° C. and 120 ° C.

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (D) can be obtained by cyclization of the derivatives of general formula (C) in the presence of a strong base such as potassium tert-butoxide or potassium hydride, in a solvent such as 1-methyl-2-pyrrolidinone at a temperature between 20 ° C and 120 ° C. More particularly, the 1H-pyrrolo [2, 3-b] pyridine 7-oxide of general formula (E) can be obtained by treatment of the derivatives of general formula (Dl) with 3-chloro-peroxybenzoic acid in a solvent ether such as 1,2-dimethoxyethane at a temperature in the region of 20 ° C under the conditions described in patent WO 03/000688 A1; 1H-pyrrolo [2, 3-b] pyridine of general formula (D) with R ₄ = C1 can be obtained from 1H-pyrrolo [2, 3-b] pyridine 7-oxide of general formula (E) by treatment with phosphorus oxychloride at a temperature between 20 ° C and 50 ° C. More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (F) can be obtained under the conditions described in patent WO 03/000688 A1 by protection of the nitrogen atom of the derivatives of general formula (D) by a group such as, for example, p-toluene sulfonyl or benzene sulfonyl by treatment with the corresponding sulfonyl chlorides in the presence of a strong base such as sodium hydroxide and a quaternary ammonium salt such as tetrabutylammonium hydrogen sulfate in a mixture of water and a solvent such as toluene at a temperature in the region of 20 ° C.

The 1H-pyrrolo [2,3-b] pyridine of general formula (G) can be obtained as in the conditions described in the patent cited above, by treatment of the derivatives of general formula (F) with a strong base such as n-butyllithium or tert-butyllithium in an ethereal solvent such as tetrahydrofuran followed by the addition of iodine in solution in a solvent such as tetrahydrofuran, at a temperature in the region of -78 ° C.

More particularly, the 1H-pyrrolo [2, 3-b] yridine of general formula (F), with R ₄ = I and GP≈acetyl can be obtained from the 1H-pyrrolo [2, 3-b] pyridine of formula general (D) with R ₄ = C1, as in the conditions described by M. Allegretti et al. (Synlett, 2001, 5, 609-612) by treatment with acetyl chloride in the presence of sodium iodide in a solvent such as acetonitrile at a temperature between 20 ° C and the reflux temperature of the solvent.

The IH-pyrrolo [2, 3-b] pyridine of general formula (F) with R ₄ = I and GP≈acetyl can lead to the derivatives of general formula (D) with R ₄ = I by treatment in a solvent such as methanol at a temperature between 20 ° C and the reflux temperature of the solvent in the conditions described in the reference cited above.

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (FI) can be obtained from the derivatives of general formula (F) with R ₄ = I by Stille coupling as under the conditions described by Javier Form et al. (Synth Commun,. 23 (21), 2965, 1993) by treatment with a stannic derivative, such as for example tetramethyltin, in the presence of a chloride such as bis (triphenylphosphine) palladium (II) chloride, chloride lithium, a phosphine such as triphenylphosphine in a solvent such as dimethylformamide at a temperature between 20 ° C and 120 ° C.

More particularly, the 1 H -indoles of general formula (I) can be obtained from the derivatives of general formula (H) as under the conditions described in patent WO 03/000688 A1 by treatment with iodine in the presence of a strong base such as for example potash and an organic base such as for example 4- (dimethylamino) pyridine followed by the addition of di-tert-butyl dicarbonate in a solvent such as dimethylformamide at a temperature between 20 ° C and 60 ° C.

More particularly, the 1 H -indoles of general formula (J) can be obtained from the derivatives of general formula (I) as under the conditions described in patent WO 03/000688 A1 by treatment with a strong base such as for example n -butyl lilthium and a boronic ester such as for example tributyl borate in an ethereal solvent such as tetrahydrofuran at a temperature between -100 ° C and 20 ° C. More particularly, lesH-pyrrolo [2, 3-b] pyridine of general formula (K) can be obtained by a Suzuki type coupling between the derivatives of general formula (J) and the derivatives of general formula (G) such as for example under the conditions described in patent WO 03/000688 A1 in the presence of a catalyst such as pallet tetrakis (triphenylphosphine), a base such as sodium hydrogencarbonate in aqueous solution, in a solvent such as dimethylformamide with a temperature between 20 ° C and the reflux temperature of the solvent.

In scheme 2, more particularly, the treatment of 1 H -indoles of general formula (H) with a strong base such as for example potassium hydroxide in a solvent such as dimethylformamide followed by the addition of iodine or bromine then by example of an alkyl halide (preferably methyl iodide) at a temperature in the region of 20 ° C. leads to the 3-halo-1H-indoles of general formula (N) as under the conditions described by Gordon W. Gribble (J. Nat. Prod, 2002, 65, 748-749).

The 3-trimethylsilanylethynyl-1H-indole of general formula (O) can be obtained from the derivatives of general formula (N) by a coupling of Sonogashira type as in the conditions described above for the derivatives of general formula (C).

The 3-ethynyl-1H-indoles of general formula (P) are obtained by treatment of the derivatives of general formula (O) by treatment with a fluorinated derivative such as for example potassium fluoride in a solvent such as methanol or fluoride tetrabutylammonium in a solvent such as tetrahydrofuran at a temperature between 20 ° C and the reflux temperature of the solvent. More particularly, the 3-ethynyl-pyridin-2-ylamine of general formula (L) can be obtained, as in the conditions described above for the derivatives of general formula (P), from the derivatives of general formula (C).

More particularly, the 3- (1H-indol-3-ethynyl) - pyridin-2-ylamine of general formula (M) can be obtained by coupling of the Sonogashira type under the conditions described above: - either between the 3-halogeno-2 -aminopyridines of general formula (B) and the 3-ethynyl-1H-indoles of general formula (P) - either between the 3-halo-1H-indoles of general formula (N) and the 3-ethynyl-pyridin-2- ylamine of general formula (L).

The 1H-pyrrolo [2,3-b] pyridine of general formula 1 can be obtained by treatment of the derivatives of general formula (M) with a strong base such as for example potassium tert-butoxide or potassium hydride in a solvent such as 1-methyl-2-pyrrolidinone at a temperature between 20 ° C and 120 ° C as under the conditions described by Knochel P. et al. (Tetrahedron, 2003, 59, 1571-1587).

In scheme 3, more particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (Q) can be obtained by alkylation of the derivatives of general formula (K) with an alkyl halide optionally substituted in the terminal position with: - an optionally substituted amine, cyclic or acyclic, a halogen to give the derivatives of general formula (Q2), an alkoxy group to give the derivatives of general formula (Q3),

- An alkoxycarbonyl group to give the derivatives of general formula (Q4), as for example under the conditions described by Oelgen D. et al. (Pharmazie, 57 (4), 238, 2002), in the presence of a base such as sodium hydride, in a solvent such as dimethylformamide at a temperature between 20 ° C. and the reflux temperature of the solvent. In the case of derivatives of general formula (Q2), the conditions described by D. Bogdal et al. (Synthetic Communication, 30 (18), 3341-3352, 2000) in dichloroethane in the presence of bases such as potassium hydroxide, potassium carbonate, of a quaternary ammonium such as tetrabutylammonium bromide at a temperature close to 20 ° C, can optionally be used.

Alternatively, the 1H-pyrrolo [2, 3-b] pyridine of general formula (Q4) with R'χ = 2- (CH ₂ ) ₂ C0 ₂ tBu, can be obtained by alkylation of the derivatives of general formula (K) with a t-butyl acrylate, as for example under the conditions described by Reddy MVR et al. (J.

Org Chem, 67 (15), 5382, 2002), in the presence of a base such as potassium carbonate, in a solvent such as dimethylformamide at a temperature between 20 ° C. and the reflux temperature of the solvent.

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (la), can be obtained by simultaneous deprotections of the p-toluene sulfonyl group and of the ester of the derivatives of general formula (Q4), as for example under the conditions described by Samét À. V. et al (Synth Commun, 31 (9), 1441, 2001), in the presence of a base such as potassium hydroxide, in a solvent such as methanol at a temperature between 20 ° C and the reflux temperature of the solvent.

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (1), where R _x = (CH ₂ ) nCONR ₇ R ₈ , can be obtained by amidification of the derivatives of general formula (la with amines HNR ₇ R ₈ , using peptide coupling agents, such as, for example, 6-benzotriazolyl-N, N, N ', N' -tetramethyluronium hexafluorophosphate (HBTU) or O- (7- azabenzotriazol-1-yl) - N, N, N ', N' -tetramethyluronium hexafluorophosphate (HIGH) under the conditions described by Dourtoglou V. and Gross B. (Synthesis, 572, 1984), in a solvent such as dimethylformamide a temperature between 20 ° C and the reflux temperature of the solvent.

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (R), can be obtained by reaction of the derivatives of general formula (Q2), with sodium or potassium iodide, as for example in the conditions described by Allen CFH et al. (J. Org Chem, 14, 754, 1949), in a solvent such as methylethyl ketone at a temperature between 20 ° C and the reflux temperature of the solvent.

More particularly, 1H-pyrrolo [2, 3-b] pyridine of general formula (S), can be obtained by reaction of the derivatives of general formula (R) with amines HNR ₇ R ₈ , as for example under the conditions described by Pujol MD et al., (Eur. J. Med. Chem., 31 (11), 889, 1996), in the presence of a base such as potassium carbonate, in a solvent such as methyl ethyl ketone at a temperature between 20 ° C and the reflux temperature of the solvent. More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (U) or (T) can be obtained from the 4-chloro 1H-pyrrolo [2, 3-b] pyridine of general formula (Ql ) or (SI) by the action of zinc cyanide, in the presence of zinc, of a catalyst such as, for example, 1,1 'bis (diphenylphosphino) ferrocene dichloride palladium (II) in a solvent such as by dimethylacetamide at a temperature between 20 and 150 ° C as for example under the conditions described by Fuqiang Jin et al. (Tetrahedron Letters 41, 2000, 3271-3273).

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (V) can be obtained from the derivatives of general formula (Ql) by a Buchschwald type coupling with the benzophenone imine in the presence of a base such as cesium carbonate, a catalyst such as palladium (II) acetate, a ligand such as, for example, 2,2 '-bis (diphenylphosphino) 1,1' -binaphthyl in a solvent such that toluene at a temperature between 20 and the reflux temperature of the solvent, for example under the conditions described by L. Bùchwald et al. (J. Org. Chem, 61, 1996, 7240-7241).

The 1H-pyrrolo [2, 3-b] pyridine of general formula (W) can be obtained from the derivatives of general formula (V) under conventional conditions described by Greene and Wuts in Protective Groups in Organic Synthesis, 3 ^rd edition , Wiley-Interscience, by hydrolysis of imine in an acid medium such as in aqueous hydrochloric acid in a solvent such as tetrahydrofuran at a temperature between 20 ° C and the reflux temperature of the solvent.

More particularly, the IH-pyrrolo [2, 3-b] pyridine of general formula. (X) with Φ = OH, can be obtained from the derivatives of general formula (Q3) with R ' _x = (CH ₂ ) _n OSiMe ₂ tBu [(CH ₂ ) _n 0TBDMS], as for example under the conditions described by Corey EJ and Venkateswarlu A. (J Am Chem Soc, 94, 6190, 1972), by reaction with a fluorinated derivative such as for example tetrabutylammonium fluoride in a solvent such as tetrahydrofuran at a temperature between 20 ° and the reflux temperature of the solvent. During this reaction, the derivatives of general formula (X) are also obtained with Φ = F. More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (1), can be obtained by deprotection of the derivatives of general formula (S), (T), (U), (W), (X) and (Q) under conventional conditions described by Greene and Wuts in Protective Groups in Organic Synthesis, 3 ^rd edition, Wiley-Interscience, 1999 .

In the case where the protective group is a p-toluene sulfonyl group, the N-deprotection of the derivatives of general formula (S), (T), (U), (W), (X) and (Q) takes place as for example under the conditions described above for the derivatives of general formula (la) or for example in the presence of tetrabutylammonium fluoride in a solvent such as tetrahydrofuran at a temperature between 20 ° C and the reflux temperature of the solvent.

In scheme 4, more particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (Q5) can be obtained from the derivatives of general formula (K1) as described above for the derivatives of general formula (Q ).

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (Y), can be obtained by debenzylation of the derivatives of general formula (Q5), as for example under the conditions described by Jung ME and Lyster MA (J Org Chem, 42, 3761, 1977), in the presence of trimethylsilane iodide in a solvent such as acetonitrile at a temperature between 20 ° C. and the reflux temperature of the solvent. More particularly, the 1H-pyrrolo [2,3-b] pyridine derivatives of general formula (Z) with Σ = CO-alkyl, can be obtained by reaction of the derivatives of general formula (Y) with a substituted alkyl halide such as that X (CH ₂ ) _n OCO-alkyl, as for example under the conditions described by Gonzalez-Gomez JC and Coll. in (Bioorg Med. Chem. Letters, 12 (2), 175, 2003), in the presence of a base such as sodium hydride in a solvent such as dimethyl formamide at a temperature between 20 ° C and the solvent reflux temperature.

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (1) with Σ = H, can be obtained by simultaneous deprotections of the p-toluene sulfonyl group and ester of (Y) with Σ = CO-alkyl , as for example under the conditions described above for the derivatives of general formula (la).

Alternatively, the 1H-pyrrolo [2, 3-b] pyridine of general formula (Z) with Σ = alkyl, can be obtained by reaction of the derivatives of general formula (Y) with an alkyl ether halide such as X (CH ₂ ) _n O-alkyl as for example under the conditions described by Leschot A. et al (Synth Commun, 32 (20), 3219, 2002), in the presence of a base such as cesium carbonate or potassium carbonate , in a solvent such as acetone, acetonitrile or dimethylformamide, at a temperature between 20 ° C and the reflux temperature of the solvent. Alternatively, the 1H-pyrrolo [2, 3-b] pyridine of general formula (Z) with Σ = (CH ₂ ) _n Cl, can be obtained by reaction of the derivatives of general formula (Y) with. a dialkyl ether dihalide such as X (CH ₂ ) _n O- (CH ₂ ) __ X as for example under the conditions above for the derivatives of general formula (Z) with Σ≈CO-alkyl.

Alternatively, leslH-pyrrolo [2, 3-b] pyridine of general formula (Z) with Σ = (CH ₂ ) nNR ₇ R8. can be obtained by reacting the derivatives of general formula (Z) with Σ = (CH ₂ ) _n Cl with amines HNR ₇ R ₈ , as for example under the conditions described above for the derivatives of general formula (S).

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (AA) with GP = p-toluene sulfonyl, can be obtained by alkylation of the derivatives of general formula (Y) with an acetate halide alkyl, as for example under the conditions described above for the derivatives of general formula (Z) with Σ = CO-alkyl.

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (lb) can be obtained by simultaneous deprotections of the p-toluene sulfonyl group and ester of (AA), as for example under the conditions described above for the derivatives of general formula (la).

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (1) with R ₃ = OCH ₂ CONR ₇ R ₈ can be obtained by amidification of the derivatives of general formula (lb), with amines HNR ₇ R ₈ , as for example under the conditions described in "Practical Guide to Combinatorial Chemistry", ISBN 0-8412-3485-x, p-51-97, in the presence of dicyclohexyl carbodiimide, hydroxy azabenzotriazole and a base in a solvent such as dimethylformamide at a temperature between 20 ° C and the reflux temperature of the solvent.

More particularly, the 6-hydroxy 1H-pyrrolo [2,3-b] pyridine of general formula (AB) can be obtained by debenzylation of the derivatives of general formula (K1), as for example under the conditions described above for the derivatives of general formula (Y).

More particularly, the IH-pyrrolo [2, 3-b] pyridine of general formula (AG) with GP = p-toluene sulfonyl can be obtained by bis-alkylation of the derivatives of general formula (AB) with an acetate halide d 'alkyl as for example under the conditions described above for the derivatives of general formula (AA).

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (AD), can be obtained by reaction of the derivatives of general formula (Y) with triflic anhydride, as for example under the conditions described by Parker KA and Ding QJ (Tetrahedron, 56 (52), 10249, 2000), in the presence of a base such as pyridine, in a solvent such as dichloromethane at a temperature between 0 ° C and the reflux temperature of the solvent .

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (AE) can be obtained by a Suzuki type coupling between the derivatives of general formula (AD) and the alkylboronic acids, as for example in the conditions described by Cockerill GS (J Chem Soc, Perkin Trans. 1, 2591, 2000), in the presence of a catalyst such as tetrakis palladium (triphenylphosphine), a base such as sodium hydrogen carbonate in aqueous solution, in a solvent such as dimethylformamide at a temperature between 20 ° C and the reflux temperature of the solvent.

More particularly, the IH-pyrrolo [2, 3-b] pyridine of general formula (AF) can be obtained by alkylation of the derivatives of general formula (Y) with an alkyl dihalogenide, as for example under the conditions described above for derivatives of. general formula (AA) •

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (AG), can be obtained by halogen exchange of the derivatives of general formula (AF), as for example under the conditions described above for the derivatives of general formula (R).

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (AH), can be obtained by reaction of the derivatives of general formula (AG), with amines HNR ₇ R ₈ , as for example under the conditions described above for the derivatives of general formula (S).

More particularly, the 1H-pyrrolo [2, 3-b] pyridine of general formula (1), can be obtained by deprotection of the derivatives of general formula (AC), (AE), (AH), and (Z), in classical conditions described by Greene and Wuts in Protective Groups in Organic Synthesis, 3 ^rd edition, Wiley-Interscience, 1999.

In the case where the protective group is a p-toluene sulfonyl group, deprotection of the derivatives of general formula (AC), (AE), (AH) and (Z) takes place as for example under the conditions described above for the derivatives of general formula (la).

Scheme 5 describes a synthetic route allowing access to derivatives 2- (1H-Indol-3-yl) -1H-pyrrolo [2,3-b] pyridine-4-carboxaldehyde. More particularly, the treatment of 4-cyano-IH-pyrrolo [2,3-b] pyridines of general formula (AI) with a reducing agent such as diisobutylaluminum hydride (DIBAH), in an aprotic solvent such as toluene at a temperature between -30 ° C and 20 ° C as for example under the conditions described by Anderson, BA et al. (J. Org. Chem., 1997, 62 (25), 8634-8639) leads to the -carboxaldehyde-1H-pyrrolo [2,3-b] pyridines of general formula (AJ). More particularly, the 4- (1,3-dioxolan) -IH- pyrrolo [2,3-b] pyridines of general formula (AK) can be obtained by reaction of the derivatives of general formula (AJ) with ethylene glycol in a solvent such as toluene, in the presence of an acid catalysis such as para-toluene sulfonic acid, at a temperature between 80 ° C and 120 ° C as for example under the conditions described by Pasto M. et al. (Tetrahedron: Asymmetry, 1995, 6 (9), 2329-2342).

The 4- (1,3-dioxolan) -2-iodo-1H-pyrrolo [2,3-b] pyridines of general formula (AL) can be obtained as under the conditions described in patent WO 03/000688 A1, by treatment of derivatives of general formula (AK) with a strong base such as n-butyllithium or tert-butyllithium in an ethereal solvent such as tetrahydrofuran followed by the addition of iodine in solution in a solvent such as tetrahydrofuran, to a temperature close to -78 ° C.

More particularly, lesH-pyrrolo [2, 3-b] pyridine of general formula (AM) can be obtained by a Suzuki type coupling between the derivatives of general formula (J) and the derivatives of general formula (AL) as described above for derivatives of general formula (K). More particularly, the 1H-pyrrolo [2, 3-b] pyridines of general formula (AN) can be obtained from the derivatives of general formula (AM) as described above for the derivatives of general formula (Q). ι More particularly, 1H-pyrrolo [2, 3-b] pyridine of general formula (AO) can be obtained by treatment of derivatives of general formula (AN) in the presence of an acid such as hydrochloric acid, in a solvent such as tetrahydrofuran at a temperature between 20 ° C and 60 ° C as for example under the conditions described by Ishimaru K. et al. (Heterocycles, 2001, 55 (8), 1591-1597).

Scheme 6 describes a synthetic route allowing the introduction of R4 substituents in the products of formula (I).

More particularly, the 1H-pyrrolo [2, 3-b] pyridines of general formula (AP) and (AP2) can be obtained by treatment of the derivatives of general formula (AO) with an amine, in the presence of a hydride such as sodium borohydride and a dehydrating agent such as magnesium sulfate, in a solvent such as methanol or ethanol at a temperature in the region of 20 ° C, as for example under the conditions described by Patra, PK and garlic. (Eur J Org Chem, 2001, 22, 4195-4206).

These 1H-pyrrolo [2, 3-b] pyridines of general formula (AP) can also be obtained either:

by treatment of the derivatives of general formula (AR) with a halide or a mesylate, in the presence of a base such as sodium carbonate, in a solvent such as acetonitrile at a temperature between 20 ° C. and the point d boiling of the solvent, as for example under the conditions described by Kaneko, T. et ail (Chem Pharm Bull, 2002, 50 (7), 922-929). Either by treatment of the derivatives of general formula (AU) with an amine, in the presence of a base such as sodium carbonate, in a solvent such as acetonitrile. at a temperature between 20 ° C and the boiling point of the solvent, as for example under the conditions described above. 1H-pyrrolo [2,3-b] pyridines of general formula (AQ) can be obtained from IH-pyrrolo [2,3- b] pyridines of general formula (AO) by treatment with hydroxylamine hydrochloride , in a solvent such as pyridine, at a temperature between 20 ° C and 50 ° C, as for example under the conditions described by Schroeder, MC et al. (J Heterocyclic Chem, 1992, 29 (6), 1481-1498). More particularly, the 4-aminomethyl-1H-pyrrolo [2,3-b] pyridines of general formula (AR) can be obtained by reduction of the oxime (AQ) with a metal such as zinc in the presence of an acid such as acetic acid or formic acid, in a solvent such as water and / or ethanol and at a temperature in the region of 20 ° C., for example under the conditions described by Prasitpan, N. et al. (Synth Commun, 1990, 20 (22), 3459-3466).

More particularly, the 1H-pyrrolo [2, 3-b] pyridines of general formula (AS) can be obtained by treatment of the derivatives of general formula (AR) with substituted sulphony chlorides, substituted isocyanates or acid chlorides sustitués, in the presence of a base such as triethylamine, in an aprotic solvent such as dichloromethane at a temperature between 0 ° and 20 ° C, as in the conditions described by Metz, P. et al. (Synlett, 1996, (8), 741-742), by Hergueta, AR. et ail (Chem Pharm Bull, 2002, 50 (10), 1379-1382) and by Coelho, PJ et al. (Synlett, 2001, (9), 1455-1457). The 1H-pyrrolo [2,3-b] pyridine-4-methanol of general formula (AT) can be obtained by reduction of the derivatives of general formula (AO) by a hydride such as sodium borohydride, in an ethereal solvent such that tetrahydrofuran, at a temperature in the region of 20 ° C, as for example under the conditions described by. Wang, EC et al. (Heterocycles, 2002, 57 (11), 2021-2033).

More particularly, the IH-pyrrolo [2, 3-b] pyridines of general formula (AU), with X≈Cl can be obtained from the 1H-pyrrolo [2,3-b] pyridine-4-methanol of general formula (AT), as under the conditions described by Fucase K. et al. (Tetrahedron Lett, 1991, 32 (32), 4019-4022) by treatment with thionyl chloride in the presence of DMF in a solvent such as dichloromethane at a temperature between 0 ° C and 20 ° C.

1H-pyrrolo [2, 3-b] pyridine of general formula (AU), with X = 0SO2Me can be obtained from 1H-pyrrolό [2,3-b] pyridine-4-methanol of general formula (AT) , as in the conditions described by Altamura M .. et al. (J Org Chem, 1993, 58 (1), 272-274) by treatment with methanesulfonic anhydride in the presence of a base such as pyridine in a solvent such as dichloromethane at a temperature between -10 ° C and 20 ° C.

More particularly, the 1H-pyrrolo [2, 3-b] pyridines of general formula (AV) can be obtained by treatment of the derivatives of general formula (AO) with Grignard reagents in a solvent such as tetrahydrofuran at a temperature comprised between 0 ° and 20 ° C, as in the conditions described by Labrosse, JR et al. (Synth Commun, 2002, 32 (23), 3667-3674) More particularly, the 1H-pyrrolo [2, 3-b] yridine of general formula (AW), with B = CORa, CONHRb, SO2Rc) can be obtained from the derivatives of general formula (AP2) as described above for the derivatives of general formula (AS).

More particularly, leslH-pyrrolo [2, 3-b] yridine of general formula (AX),. can be obtained by deprotection of the derivatives of general formula (AW) under conventional conditions described by Greene and Wuts in Protective Groups in Organic Synthesis, 3rd edition, Wiley-Interscience, 1999.

More particularly, the 1 H -indoles of general formula (1) can be obtained from the derivatives of general formula (AX) as under the conditions described by Madar, D. J., et al. (Tet Lett, 2001, 42, 3681-3684) by treatment with an acid such as trifluoroacetic acid or para-toluene sulfonic acid in a solvent such as dichloromethane or toluene at a temperature between 20 ° C and 100 ° C.

More particularly, lesH-pyrrolo [2, 3-b] pyridine of general formula (1), can be obtained by deprotection of the derivatives of general formula (AP), (AQ), (AR), (AS) or (AV) under classical conditions described by Greene and Wuts in Protective Groups in Organic Synthesis, 3rd edition, Wiley-Interscience, 1999.

The present invention also relates to the processes for preparing: products of general formula (D) and very particularly the reactions starting from 2-amino pyridines (A) according to scheme 1. - products of general formula (1) and very particularly the reactions according to scheme 2.

It may be noted that in the reactions for the preparation of the products of formula (I) according to the present invention and in particular in the reactions indicated in the diagrams, the intermediate products or the products of formula (I) can be if necessary in protected form, the any reactive functions being possibly protected by protective groups. The intermediate products or the products of formula (I), in protected form or not, can be subjected, if desired and if necessary, to obtain products of formula (I) or other products of formula (I) with the one or more of the following transformation reactions, in any order: a) an esterification reaction with an acid function, b) a saponification reaction with an ester function with an acid function, c) an oxidation reaction of an alkylthio group with sulfoxide or corresponding sulfone, d) a reaction of transformation from ketone function to oxime function, e) a reaction for reduction of the free or esterified carboxy function into alcohol function, f) a reaction of transformation from alkoxy function into hydroxyl function, or alternatively of hydroxyl function in alkoxy function, g) an oxidation reaction in alcohol function in aldehyde, acid or ketone function, h) a reaction for the transformation of nitrile radical into tetrazolyl, i) r reduction action of the nitro compounds into amino compounds, j) a reaction of elimination of the protective groups which the protected reactive functions can carry, k) a salification reaction with a mineral or organic acid or with a base to obtain the corresponding salt, 1) a resolution reaction of the racemic forms into split products, said products of formula (I) thus obtained being in all the isomeric forms possible racemates, enantiomers and dastomeroisomers. It can be noted that such. reactions for converting substituents into other substituents can also be carried out on the starting materials as well as on the intermediates as defined above before continuing the synthesis according to the reactions indicated in the process described above. The products of formula (I) according to the present invention could also be prepared by the application or the adaptation of known methods and in particular of the methods described in the literature such as for example those described by RCLarock in: Comprehensive Organic Transformations, VCH publishers, 1989. To prepare the products of formula (I), it may therefore be necessary to protect reactive functional groups such as for example hydroxy, amino, imino, thio or carboxy groups, when these are desired in the final product but when their participation is not desired in the synthesis reactions of the products of formula (I). It is in particular possible to use conventional protective groups in accordance with standard standard practices such as those described for example by TW Greene and PGMWuts in "Protective Groups in Organic Chemistry" John Wiley and Sons, 1991. The various reactive functions which certain compounds of the reactions defined above can, if necessary, be protected: these are, for example, hydroxyl, acyl, free carboxy or still amino and monoalkylamino which can be protected by the appropriate protective groups.

The following non-exhaustive list of examples of protection of reactive functions can be cited: the hydroxyl groups can be protected for example by alkyl radicals such as tert-butyl, trimethyl-silyl,. tert-butyldimethylsilyl, methoxymethyl, tetrahydro-pyrannyl, benzyl or acetyl, - the amino groups can be protected for example by the acetyl, trityl, benzyl, tert-butoxycarbonyl, benzyloxycarbonyl, phthalimido or other radicals known in peptide chemistry , - the acyl groups such as the formyl group can be protected for example in the form of cyclic or non-cyclic ketals or thiocetals such as dimethyl or diethyl ketal or ethylene dioxyketal, or diethylthiocetal or 1 ethylenedithioketal, - the acid functions products described above can be, if desired, amidified with a primary or secondary amine, for example in methylene chloride in the presence, for example, of 1-ethyl-3- (dimethylaminopropyl) carbodiimide hydrochloride at room temperature:

- The acid functions can be protected, for example, in the form of esters formed with easily cleavable esters such as benzylic or terbutylic esters or esters known in the chemistry of peptides. These reactions a) to k) indicated above can be carried out, for example, as indicated below. a) The products described above can, if desired, be the subject, on the possible carboxy functions, of esterification reactions which can be carried out according to the usual methods known to those skilled in the art. b) Any transformations of ester functions into acid function of the products described above can, if desired, be carried out under the usual conditions known to those skilled in the art, in particular by acid or alkaline hydrolysis, for example with soda or potash in an alcoholic medium such as, for example , in methanol or also with hydrochloric or sulfuric acid. c) The possible alkylthio groups of the products described above, in which the alkyl radical is optionally substituted by one or more halogen atoms, in particular of fluorine, can be, if desired, converted into the corresponding sulfoxide or sulfone functions in the usual conditions known to one skilled in the art such as, for example, peracids such as peracetic acid or metachloroperbenzoic acid or alternatively by ozone, oxone, sodium perriodate in a solvent such as for example methylene chloride or dioxane at room temperature. Obtaining the sulfoxide function can be promoted by an equimolar mixture of the product containing an alkylthio group and of the reagent such as in particular a peracid. Obtaining the sulfone function can be promoted by a mixture of the product containing an alkylthio group with an excess of the reagent such as in particular a peracid. d) The reaction for converting a ketone function into an oxime can be carried out under the usual conditions known to a person skilled in the art, such as in particular an action in the presence of an optionally O-substituted hydroxylamine in an alcohol such as for example 1 ethanol, at room temperature or by heating. e) The possible free or esterified carboxy functions of the products described above can be, if desired, reduced in alcohol function by methods known to a person skilled in the art: any esterified carboxy functions can be, if desired, reduced in alcohol function by methods known to one skilled in the art and in particular with lithium hydride and aluminum in a solvent such as for example tetrahydrofuran or dioxane or ethyl ether. The possible free carboxy functions of the products described above can be, if desired, reduced in alcohol function in particular by boron hydride. f) The possible alkoxy functions such as in particular the methoxy of the products described above can be, if desired, transformed into a hydroxyl function under the usual conditions known to a person skilled in the art, for example by boron tribromide in a solvent such as by for example methylene chloride, with pyridine hydrobromide or hydrochloride or alternatively with hydrobromic or hydrochloric acid in water or trifluoroacetic acid at reflux. g) The possible alcohol functions of the products described above can, if desired, be converted into an aldehyde or acid function by oxidation under the usual conditions known to those skilled in the art, such as for example by the action of manganese oxide to get the aldehydes or Jones reagent to access the acids. h) The optional nitrile functions of the products described above can, if desired, be converted into tetrazolyl under the usual conditions known to those skilled in the art, such as for example by cycloaddition of a metal azide such as for example the azide. sodium or a trialkyltin azide on the nitrile function as indicated in the method described in one article referenced as follows: J. Organometallic Chemistry. , 33, 337 (1971) KOZIMA S. & coll. It may be noted that the reaction for converting a carbamate into urea and in particular a sulfonylcarbamate into sulfonylurea, can be carried out for example at reflux of a solvent such as, for example, toluene in the presence of the appropriate amine. It is understood that the reactions described above can be carried out as indicated or alternatively, if necessary, according to other usual methods known to those skilled in the art. i) The removal of protective groups such as for example those indicated above can be carried out under the usual conditions known to those skilled in the art, in particular by acid or basic hydrolysis carried out with an acid such as hydrochloric acid, benzene sulfonic or para-toluene sulfonic, formic or trifluoroacetic or else by a catalytic hydrogenation or by a base such as potassium hydroxide, soda or tetrabutylammonium fluoride. The phthalimido group can be eliminated by hydrazine. Oh will find a list of different protective groups usable for example in patent BF 2 499 995. j) The products described above can, if desired, be subject to salification reactions for example with a mineral or organic acid or by an inorganic or organic base according to the usual methods known to those skilled in the art. k) Any optically active forms of the products described above can be prepared by splitting the racemates according to the usual methods known to those skilled in the art.

Possible reactive functions can be: hydroxy or amino functions: conventional protective groups are used to protect these functions. Mention may be made, for example, of the following protecting groups for the amino radical: tert-butyl, tert-amyl, trichloroacetyl, chloroacetyl, benzhydryl, trityl, formyl, benzyloxycarbonyl, paratoluenesulfonyl, acetyl, benzenesulfonyl or benzoyl. As protecting group for the hydroxy radical, mention may be made of radicals such as formyl, benzyl, acetyl, chloroacetyl, tetrahydropyrannyl, trimethylsilyl, tert-butyl dimethylsilyl. It is understood that the above list is not limiting and that other protective groups, for example known in peptide chemistry can be used. A list of such protective groups can be found, for example, in French patent BF 2,499,995, the content of which is incorporated here by reference. The possible reactions for removing protective groups are carried out as indicated in said patent BF 2,499,995. The preferred mode of elimination is acid hydrolysis using the acids chosen from hydrochloric, benzene sulfonic or para-toluene sulfonic, formic or trifluoroacetic acids. Hydrochloric acid is preferred. The optional hydrolysis reaction of the> C = NH group into a ketone group is also preferably carried out using an acid such as aqueous hydrochloric acid, for example at reflux. The terbutyldimethylsilyl protective group can be removed for example by means of hydrochloric acid. The optional esterification of a free OH radical is carried out under conventional conditions. One can use for example an acid or a functional derivative, for example, an anhydride such as acetic anhydride in the presence of a base such as pyridine. The esterification or the optional salification of a COOH group is carried out under the conventional conditions known to those skilled in the art. The optional amidation of a COOH radical is carried out under conventional conditions. A primary or secondary amine can be used on a functional derivative of the acid, for example a symmetrical or mixed anhydride. The products which are the subject of the present invention are endowed with interesting pharmacological properties: it has been found that they have in particular inhibitory properties of protein kinases. Among these protein kinases, mention is made in particular of IGF1R. Tests given in the experimental part below illustrate the inhibitory activity of products of the present invention against such protein kinases. These properties therefore make the products of general formula (I) of the present invention usable as medicaments for the treatment of malignant tumors. The products of formula (I) can also be used in the veterinary field. A subject of the invention is therefore the application, as medicaments, of products of general formula (I) which are pharmaceutically acceptable. The subject of the invention is particularly the application, as medicaments, of products of formula (I) whose names follow: 2- {5,6-Dimethoxy-l- [2- (4-methyl-pipêrazin-i- yl) -ethyl] -1H-indol-3-yl} -1h-pyrrolo [2,3-b] pyridine 2- (4- {2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2- yl) -indol-1-yl] -ethyl} -piperazin-1-yl) -ethanol 2- (l- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2- yl) -indol-1-yl] -ethyl} -piperidin-4-yl) -ethanol

1 '- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - indol-1-yl] -ethyl} - [1,4 '] bipipridridinyl l- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol -1-yl] -ethyl} -piperidin-3-ol 2- {5,6-Dimethoxy-l- [2- (4-methyl-perhydro-1,4, diazepin-1-yl) -ethyl] -lH -indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine 2- [5,6-Dimethoxy-3- (IH-pyrrolo [2, 3-b] pyridin-2-yl) -indol- 1-yl] -1- (4-hydroxy-piperidin-1-yl) -ethanone 2- [5, 6-Dimethoxy-3- (IH-pyrrôlo [2, 3-b] pyridin-2-yl) -indol - 1-yl] -l-thiazolidin-3-yl-ethanone 4- {[5,6-Dimethoxy-3- (IH-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl ] -acetyl} -1-methyl-piperazin-2-one 4-Chloro-2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridine 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3- b] pyridine-4-carbonitrile

4-chloro-2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H- indol-3-yl] -lH-pyrrolo [2, 3-b] pyridine

2- (1- {2- [3- (4-chloro-1H-pyrrolo [2,3-b] pyridin-2-yl) -5,6- dimethoxy-indol-1-yl] -ethyl} -piperidin -4-yl) -ethanol 4-chloro-2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -1H-indol-3-yl} -IH -pyrrolo [2,3-b] pyridine 2- {5, 6-dimethoxy-l- [2- (4-methyl-pipêrazin-1-yl) -ethyl] - 1H-indol-3-yl} -lH- pyrrolo [2,3-b] pyridine-4-carbonitrile 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -5-fluoro-1H- pyrrolo [2, 3-b] pyridine

2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H-indol-3- yl] -5-fluoro-1H-pyrrolo [2, 3-b] pyridine

2- {5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -5-fluoro-1H-pyrrolo [2,3- b] pyridine 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1-morpholin-4-yl -ethanone 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1- (4-methyl- [ 1,4] diazepan-1-yl) - ethanone 2- [5-Methoxy-1-methyl-3- (IH-pyrrolo [2, 3-b] pyridin-2-yl) - 1H-indol-6-yloxy ] -N- [4- (4-methyl-piperazin-1-yl) -phenyl] - acetamide 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1- (4-methyl-piperazin- 1-yl) -ethanone l- {4- [2- (2-Hydroxy-ethoxy) -ethyl] -piperazin-1-yl} -2- [5- Methoxy-1-methyl-3- (1H-pyrrolo [ 2,3-b] pyridin-2-yl) -1H- indol-6-yloxy] -ethanone Trifluoroacetate from (3aS, .6aS) -5- {2- [5-Methoxy-1-methyl-3- (1H -pyrrolo [2, 3-b] pyridin-2-yl) -1H-indol-6-yloxy] - acetyl} -hexahydro-pyrrolo [3, 4-c] pyrrol-1-one 2- {5-Methoxy- l-methyl-6- [3- (4-methyl-perhydro-1, 4-diazepin-1-yl) -propoxy] -1H-indol-3-yl} -IH-pyrrolo [2,3- b] pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-methyl-pipêrazin-1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] -pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-pipêridyl- pipëridin-1-yl) -ethoxy] -lH-indol-3-yl} - 1H-pyrrolo [2,3-b] - pyridine

as well as their prodrugs, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with the pharmaceutically acceptable mineral and organic bases of said products of formula (I).

The invention particularly relates to the use as medicines, _^ products of formula (I) whose names follow: - 2- {5,6-Dimethoxy-l- [2- (4-methyl-piperazin -1-yl) - ethyl] -1H-indol-3-yl} -1H-pyrrolo [2, 3-b] pyridine 2- (4- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b ] pyridin-2-yl) ^• indol-1-yl] -ethyl} -piperazin-1-yl) -ethanol 2- (l- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) ^• indol-1-yl] -ethyl} -piperidin-4-yl) -ethanol l - {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2 , 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} - [1, '] bipiperidinyl 1- {2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3 -b] pyridin-2-yl) - indol-1-yl] -ethyl} -piperidin-3-ol 2- {5, 6-Dimethoxy-1- [2- (4-methyl-perhydro-1, 4- diazepin-1-yl) -ethyl] -1H-indol-3-yl} -1H-pyrrolo [2, 3-b] pyridine 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3- b] pyridin-2-yl) -indol- 1-yl] -1- (4-hydroxy-piperidin-1-yl) -ethanone 2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3 -b] pyridin-2-yl) -indol- 1-yl] -1-thiazolidin-3-yl-ethanone

4- {[5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -acetyl} -l-methyl-pipërazin-2-one 4 -Chloro-2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH- pyrrolo [2,3-b] pyridine 2- (5,6-dimethoxy-1-methyl-1H -indol-3-yl) -lH-pyrrolo [2, 3- b] pyridine-4-carbonitrile

4-chloro-2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H- indol-3-yl] -lH-pyrrolo [2, 3-b] pyridine 2- ( l- {2- [3- (4-chloro-1H-pyrrolo [2,3-b] pyridin-2-yl) -5,6- dimethoxy-indol-1-yl] -êthyl} -piperidin-4- yl) -ethanol

4-chloro-2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -lH-indol-3-yl} -lH-pyrrolo [2, 3- b] pyridine 2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -lH-pyrrolo [2,3-b ] pyridine-4-carbonitrile 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -5-fluoro-1H- pyrrolo [2, 3-b] pyridine

2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H-indol-3- yl] -5-fluoro-1H-pyrrolo [2, 3-b] pyridine 2- { 5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -5-fluoro-1H-pyrrolo [2, 3-b] pyridine

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -l-morpholin-4-yl-ethanone 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - 1H -indol-6-yloxy] -1- (4-methyl- [1,4] diazepan-1-yl) - ethanone 2- [5-Methoxy-1-methyl-3- (IH-pyrrolo [2, 3- b] pyridin-2-yl) - 1H-indol-6-yloxy] -N- [4- (4-methyl-piperazin-1-yl) -phenyl] - acetamide 2- [5-Methoxy-1-methyl- 3- (1H-pyrrblo [2, 3-b] pyridin-2-yl) - 1H-indol-6-yloxy] -1- (-methyl-piperazin-1-yl) -ethanone 1- {.4- [ 2- (2-Hydroxy-ethoxy) -ethyl] -piperazin-1-yl} -2- [5- Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -1H- indol-6-yloxy] -ethanone (3aS, 6aS) -5- {2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-) trifluoroacetate yl) -1H-indol-6-yloxy] - acetyl} -hexahydro-pyrrolo [3, 4-c] pyrrol-1-one 2- {5-Methoxy-1-methyl-6- [3- (4-methyl -perhydro-1,4-diazepin-1-yl) -propoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3- b] pyridine

4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-methyl-pipêrazin-1-yl) -ethoxy] -! H-indol-3-yl} -lH-pyrrolo [2 , 3-bJ -pyridine

4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-piperidyl-piperidin-1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] - pyridine

4-Chloro-2- {5-Methoxy-1-methyl-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] -1H-indol-3-yl} -lH-pyrrolo [2,3-b] - pyridine

4-Chloro-2- {1-methyl-5-methoxy-6- [2- (2-piperidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3-b] - pyridine, as well as their prodrugs, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral bases and pharmaceutically acceptable organic products of said products of formula (I). The products can be administered parenterally, buccally, perlingually, rectally or topically. A subject of the invention is also pharmaceutical compositions, characterized in that they contain, as active principle, at least one of the drugs of general formula (I). These compositions can be presented in the form of solutions or injectable suspensions, tablets, coated tablets, capsules, syrups, suppositories, creams, ointments and lotions. These pharmaceutical forms are prepared according to the usual methods. The active principle can be incorporated into excipients usually used in these compositions, such as aqueous vehicles or not, talc, gum arabic, lactose, starch, magnesium stearate, cocoa butter, fatty substances of animal or vegetable origin, paraffinic derivatives, glycols, various wetting agents, dispersants or emulsifiers, preservatives. The usual dose, which varies depending on the subject treated and the condition in question, can be, for example, from 10 mg to 500 mg per day in humans, orally. The present invention thus relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of medicaments intended to inhibit the activity of protein kinases and in particular d protein kinase. The present invention thus relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is a protein tyrosine kinase. The present invention thus relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is chosen from the following group: IGF1, Raf, EGF, PDGF, VEGF, Tie2, KDR, Fltl-3, FAK, Src, Abl, cKit, cdkl-9, Auroral-2 , cdc7, Akt, Pdk, S6K, Jnk, IR, FLK-1, FGFR1, FGFR2, FGFR3, FGFR4, FGFR5, PLK, Pyk2 The present invention thus relates to the use of products of formula (I) as defined above above or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is more particularly chosen from the following group: IGF1, cdc7, Auroral-2, Src, Jnk, FAK, KDR, IR, Tie2 The present invention relates thus particularly the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is IGF1R. The present invention also relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is in a cell culture and also this use in a mammal . The present invention thus relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended for preventing or treating a disease characterized by dysregulation of the activity of a protein kinase and in particular such a disease in a mammal. The present invention relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended for preventing or treating a disease belonging to the following group : disorders of the proliferation of blood vessels, fibrotic disorders, disorders of the proliferation of mesangial cells, metabolic disorders, allergies, asthma, thromboses, nervous system diseases, retinopathies, psoriasis, rheumatoid arthritis, diabetes, muscle degeneration, oncology diseases, cancers. The present invention thus relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended to treat diseases in oncology. The present invention particularly relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended for treating cancers. Among these cancers, the present invention is particularly interested in the treatment of solid tumors and in the treatment of cancers resistant to cytotoxic agents. Among these cancers, the present invention relates very particularly to the treatment of breast, stomach, colon cancer. , lungs, ovaries, uterus, brain, kidney, larynx, lymphatic system, thyroid, urogenital tract, tract including vesicle and prostate, bone cancer, pancreas, melanomas. The present invention relates more particularly to the treatment of breast, colon and lung cancer. The present invention also relates to the use of products of formula (I) as defined above or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended for the chemotherapy of cancers. As medicaments according to the present invention intended for the chemotherapy of cancers, the products of formula (I) according to the present invention can be used alone or in combination with chemotherapy or radiotherapy or alternatively in combination with other therapeutic agents. The present invention thus relates in particular to the pharmaceutical compositions as defined above containing, for example, active principles of other chemotherapy drugs against cancer. From. such therapeutic agents can be commonly used anti-tumor agents. Examples of known protein kinase inhibitors that may be mentioned include butyrolactone, flavopiridol, 2- (2-hydroxyethylamino) -6-benzylamino-9-methylpurine, olomucine, Glivec and Iressa. The products of formula (I) according to the present invention can thus also be advantageously used in combination with anti-proliferative agents: as examples of such anti-proliferative agents but without however being limited to this list, mention may be made of aromatase inhibitors, antiestrogens, topoisomerase I inhibitors, topoisomerase II inhibitors, agents active on microtubules, alkylating agents, histone desacetylase inhibitors, farnesyl transferase inhibitors, COX inhibitors -2, MMP inhibitors, mTOR inhibitors, antineoplastic antimetabolites, platinum compounds, compounds which decrease the activity of protein kinases and also antiangiogenic compounds, gonadorelin agonists, antiandrogens , bengamides, biphophonates and trastuzumab. Mention may thus be made, by way of examples, of anti-microtubule agents such as taxoides, vinka-alkaloids, alkylating agents such as cyclophosphamide, DNA-intercalating agents such as cis-platinum, interactive agents on topoisomerase such as camptothecin and derivatives, anthracyclines such as adriamycin, antimetabolites such as 5-fluorouracil and derivatives and the like. The present invention therefore relates to products of formula (I) as protein kinase inhibitors, said products of formula (I) being all possible racemic, enantiomeric and diastereomeric isomer forms, as well as addition salts with acids. inorganic and organic or with the pharmaceutically acceptable inorganic and organic bases of the said products of formula (I) as well as their prodrugs. The present invention particularly relates to products of formula (I) as defined above as IGF1R inhibitors. The starting materials for the synthesis of the products of formula (I) according to the present invention can be known, described in the documents of a person skilled in the art, and available commercially or can be prepared according to usual methods known in the art. tradesman or according to the methods described in the attached diagrams. The experimental part below gives more particularly an illustration of the syntheses described on the diagrams of the present invention with the preparation of Examples 1 to 175 of the present application. The examples whose preparation follows, whether they are preparations of products or preparations of pharmaceutical compositions, illustrate the present invention without however limiting it.

In the following preparations, the methods of analysis and purification used to characterize the products are as follows: Mass spectrometry: The spectra were performed using electronic impact (IE) and / or chemical desorption-ionization (IC) (reactant gas: ammonia) on a Finnigan SSQ 7000 spectrometer. Analysis methods: Method A Unless explicitly stated on the contrary, the analyzes by reverse phase liquid chromatography coupled with mass spectrometry (LC / MS) were carried out on a Micromass model LCT device connected to an HP 1100 device. The abundance of the products was measured using an HP G1315A diode array detector on a wave range of 200-600 nm (DAD) and a Sedex 65 light scattering detector. The mass spectra were acquired over a range of 180 to 800. The data were analyzed using Micromass MassLynx software. The separation was carried out on a Hypersil BDS C18 column, 3 μm (50 x 4.6 mm), eluting with a linear gradient of 5 to 90% acetonitrile containing 0.05% (v / v) of acid trifluoroacetic acid (TFA) in water containing 0.05% (v / v) TFA in 3.5 min at a flow rate of 1 cm ³ / min. The total analysis time, including the period of rebalancing of the column, is 7 min.

Purification methods: Method B

In general, the compounds obtained were purified by reverse phase liquid chromatography coupled to mass spectrometry (LC / MS) using a Waters FractionsLynx system composed of a Waters model 600 gradient pump, a pump model 515 regeneration system, a Waters Reagent Manager dilution pump, a Waters model 2700 auto-injector, two Rheodyne LabPro valves, a Waters model 996 diode array detector, a spectrometer Mass Waters model ZMD and a Gilson fraction collector model 204, The system is controlled by Waters FractionLynx software. Separation is carried out alternately on two Waters Symmetry columns (Cι ₈ , 5μM, 19x50 mm, catalog reference 186000210), one column being regenerated by a water / acetonitrile 95/5 (v / v) mixture containing 0.07% (v / v) trifluoroacetic acid, while the other column is used for separation. The elution ^"columns is provided by a linear gradient of acetonitrile containing 0.07% (v / v) trifluoroacetic acid in water containing 0.07% (v / v) trifluoroacetic acid at a flow rate of 10 cm ³ / min. At the outlet of the separation column, one thousandth of the effluent is separated by an LC Packing Accurate, diluted with methyl alcohol at a flow rate of 0.5 cm ³ / min and sent to the detectors, 75% to the diode array detector, and the remaining 25% to the mass spectrometer. The rest of the effluent (999/1000) is sent to the fraction collector where the flow is eliminated until the mass of the expected product is not detected by the FractionLynx software The molecular formulas of the expected products are supplied to the FractionLynx software which triggers the collection of the product when the detected mass signal corresponds to the ion [M + H] ⁺ and / or to [M + Na] ⁺ . In some cases, depending on the results of LC / MS ana lytic, when an intense ion corresponding to [M + 2H] ⁺⁺ has been detected, the value corresponding to half of the calculated molecular mass (MW / 2) is also provided to the FractionLynx software, Under these conditions, the collection is also triggered when the mass signal of the ion [M + 2H] ⁺⁺ and / or [M + Na + H] ⁺⁺ are detected. The products were collected in tared glass tubes.

Solutions with a volume greater than 0.5 cm ³ are purified in two batches, the others in one batch. The fractions are collected in hemolysis tubes previously labeled and tared, only the tubes containing the expected molecular weight compound are exploited. Unless explicitly stated otherwise, the binary elution gradient used for these purifications is as follows:

In the text, the method referenced “Method D” uses the same equipment as that described above but with the elution gradient below.

In the text, the method referenced “Method E” uses the same equipment as that described above but with the elution gradient below.

In the text, the method referenced “Method F” uses the same equipment as that described above but with the elution gradient below.

In the text, the method referenced “Method G” uses the same equipment as that described above but with the elution gradient below

EXAMPLE 1 2- (5,6-dimethoxy-1-vinyl-1H-iήdol-3-yl) -lH-pyrrolo [2,3-b] pyridine trifluoroacetate 2- (5,6-dimethoxy-) trifluoroacetate l-vinyl-1H-indol- 3-yl) -lH-pyrrolo [2,3-b] pyridine can be prepared as follows: In a 10 cm ³ flask closed with a septum, a solution of 2 - (5, 6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine (0.5 g; 1.117 mmol) in dimethylformamide (5 cm ³ ), then l-bromo-2-chloro ethane (0.865 g; 0.5 cm 3 6.032 mmol) is added. The reaction mixture is stirred at room temperature and then sodium hydride (0.1 g; 3.35 mmol) is added in 33 successive portions. When the reaction mixture turns green, add 1-bromo-2-chloro ethane (0.865 g; 0.5 cm ³ ; 6.03 mmol). The reaction is followed by TLC (cyclohexane / ethyl acetate 50/50) until the starting product disappears. The reaction mixture is poured onto a mixture of 20 cm ³ of water and a saturated solution of ammonium chloride (20 cm ³ ). Ethyl acetate (50 cm ³ ) is added, then it is decanted and extracted with ethyl acetate (30 cm ³ ). The combined extracts are washed with a saturated solution of ammonium chloride (30 cm ³ ), dried over magnesium sulphate and evaporated under reduced pressure. The evaporation product is taken up in a mixture of cyclohexane / ethyl acetate 50/50 then left at room temperature for 24 hours. The solid formed is filtered, rinsed with a mixture of cyclohexane / ethyl acetate 72/25 (15 cm ³ ) and then dried under reduced pressure. The compound obtained is purified by LCMS (Method B). Is isolated 2- [1- (2-chloro-ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-] pyridine, (0.33 g), the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.30 (s: 3H); 3.73 (s: 3H); 3.90 (s: 3H); 4.09 (t, J = 6 Hz: 2H); 4.63 (t, J = 6 Hz: 2H); 6.76 (S: 1H); 6.95 (s: 1H); 7.26 (d, J ≈ 8.5 Hz: 2H); 7.27 (s: 1H); 7.32 (dd, J = 8 and 5 Hz: 1H); 7.55 (s: 1H); 7.58 (d, J = 8.5 Hz: 2H); 7.96 (dd, J ≈ 8 and 1.5 Hz: 1H); 8.38 (dd, J = 5 and 1.5 Hz: 1H). Mass spectrum: (IE): m / z = 509 [M] ⁺ ; m / z = 354 [M - C ₇ H ₇ NS0 ₂ ] ⁺ (base peak)

Also isolated is the 2- (5,6-dimethoxy-1-vinyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridine trifluoroacetate (0.042 g), the characteristics of which are as follows : NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.89 (s: 3H); 3.93 (s: 3H); 4.86 (broad d, J = 8.5 Hz: 1H); 5.32 (broad d, J = 15.5 Hz: 1H); 6.97 (d, J = 2 Hz: 1H); 7.11 (dd, J = 8 and 5 Hz: 1H); 7.46 (s: 1H); 7.47 (s: 1H); 7.63 (dd, J = 15.5 and 8.5 Hz: 1H); 7.99 (broad d, J = 8 Hz: 1H); 8.21 (dd, J = 5 and 1.5 Hz: 1H); 8.34 (s: 1H); 11.96 (mf: 1H). Mass spectrum (IE): m / z = 319 [M] ⁺ (base peak)

2- (5,6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine is obtained as described in patent WO030006881A1. EXAMPLES 2 to 79 a) Preparation: 2- [1- (2-iodo-ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine can be prepared as follows: In a 10 cm ³ flask, a solution of 2- [1- (2-chloro-ethyl) -5,6-dimethoxy-1H- is placed indol-3-yl] -1- (toluene-4-sulfonyl) -iH-pyrrolo [2, 3-] pyridine (0.331 g ^" ; 649 μmol), described in example 1, and sodium iodide (0.195 g; 1.298 .mmol) in methyl ethyl .. ketone (5 cm ³ ). The reaction mixture is brought to reflux for 16 hours. After evaporation, the residue is taken up in a mixture of water (15 cm ³ ) and ethyl acetate ( 15 cm ³ ).

After decantation and extraction with ethyl acetate (2x15 cm ³ ), the organic extracts are combined, dried over magnesium sulphate, then evaporated under reduced pressure. The evaporation residue is chromatographed on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (50/50). The fractions containing the expected compound are combined and evaporated, providing 2- [1- (2-iodo-ethyl) -5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene- -suifonyl) - 1H-pyrrolo [2,3-b] pyridine, (0.24 g; 69%), the characteristics of which are as follows: LC / MS analysis: tr = 3.9 min., m / z = 601.99 [M + H] ⁺

b) Alkylation of Examples 2 to 79 In tared and labeled glass tubes (1.2 x 10 cm), the amines are placed below in solution in dimethylformamide at a concentration of 90 μmoles per 0.5 cm ³ of dimethylformamide. The compound 2- [1- (2-iodo-ethyl) -5,6-dimethoxy-1H-indol-3- yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is dissolved in dimethylformamide at a concentration of 30 μmol per 0.5 cm ³ of solvent.

In reactors suitable for parallel synthesis, 0.5 cm ³ of each of the solutions prepared above is distributed as well as 0.5 cm ³ per well of the 2- [1- (2-iodo-ethyl) solution. 5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine in the dimethylformamide described above and then 0.01 is added 0.015 g of potassium carbonate. The reactors being closed using a septum, they are placed under orbital stirring at 80 ° C for 16 hours. After returning to ambient temperature, the contents of the reactors are filtered and then purified by reverse phase liquid chromatography coupled to mass spectrometry (Method B). After evaporation of the fractions, weighing and analysis of the results of liquid chromatography in reverse phase coupled with preparative mass spectrometry, the intermediate compounds which are used in the next step are isolated and identified.

c) Detosylation of Examples 2 to 79 Each compound previously isolated is dissolved in a methanolic potassium solution at 0.1 g / cm ³ (0.5 cm ³ ) then each tube is capped and stirred at room temperature for 60 hours. The contents of each tube are evaporated under reduced pressure, diluted with distilled water (1.5 cm ³ ) and extracted with dichoromethane (3 x 0.9 cm ³ ). The organic extracts are combined, dried over magnesium sulphate, filtered in glass tubes (1.2 x 10 cm), tared and labeled, then evaporated. The compounds isolated after evaporation are weighed and diluted with dimethyl sulfoxide (0.5 cm ³ ) then subjected to purification by reverse phase liquid chromatography. coupled with mass spectrometry in preparation mode (Method B). The fractions containing the compounds of expected molar mass are evaporated, weighed and diluted to the concentration of 10 mM in dimethyl sulfide. The expected compounds are identified and characterized by analysis in reverse phase liquid chromatography coupled with mass spectrometry (Method A). The results obtained are reported in the table below.

EXAMPLE 80 {{[5,6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] -ethyl} - (2-. Methoxy) trifluoroacetate -ethyl) -methyl-amino a) The trifluoroacetate of {2- [5, 6-dimethoxy-3- (1H-pyrrolo ^, 3-b] pyridin-2-yl) -indol-1-yl] -ethyl} - (2-methoxy-ethyl) -methyl-amino can be prepared in the following way: The trifluoroacetate of (2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -IH-pyrrolo [ 2, 3-b] pyridin-2-yl] - indol-1-yl} -ethyl) - (2-methoxy-ethyl) -methyl-amino, (0.0152 g; 22.46 μmol) is dissolved in a methanolic potash solution (0.5 cm ³ ; 0.1 g of potash / cm ³ methanol) then stirred at room temperature for 48 hours. After evaporation, the residue is taken up with stirring in 0.7 cm ³ of a mixture of dimethylsulfoxide and 12N aqueous hydrochloric acid (50/50 v / v). After returning to room temperature, it is added. of dimethyl sulfoxide (0.35 cm ³ ) then purified by reverse phase liquid chromatography coupled to mass spectrometry (Method B). The fractions containing the expected compound are combined and evaporated. Is isolated the trifluoroacetate of {2- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] -ethyl} - (2-methoxy- ethyl) -methylamine, (0.0094 g; 80%), the characteristics of which are as follows: LÇ / MS analysis: tr = 2.4 min., m / z = 409.24 [M + H]

b) (2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-2-yl] - indol-1-yl trifluoroacetate } -ethyl) - (2-methoxy-ethyl) -methyl-amine can be prepared as follows: In a 5 cm ³ conical bottom eathon reactor, a solution of 2- [1- (2-chloro- ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-] pyridine, (0.021 g; 50 μmol) in N- methyl pyrrolidone (0.5 cm ³ ) then the 2-methoxy-N-methyl amino (0.013 g;. 150 μmol), potassium carbonate (0.021 g; 150 μmol) are added. The reaction mixture is stirred and heated to 70 ° C overnight. After returning to ambient temperature, it is filtered and evaporated to dryness, then the residue is taken up in dimethylsulfoxide and purified by reverse phase liquid chromatography coupled to mass spectrometry (Method B). After treatment and evaporation of the fractions, the trifluoroacetate is isolated from (2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-2-yl ] -indol-1-yl} - ethyl) - (2-methoxy-ethyl) -methylamine, (0.015 g; 45%), the characteristics of which are as follows: LC / MS analysis. (Method B): tr = 5.6 min., M / z = 563.35 [M + H] ⁺ EXAMPLE 81 Trifluoroacetate of 2- [(3- {2- [5,6-dimethoxy- 3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] - ethylamino} -propyl) - (2-hydroxy-ethyl) -amino] -ethanol a) 2- [(3- {2- [5, 6-dimethoxy-3- (1H- pyrrolo [2, 3-b]]) trifluoroacetate pyridin-2-yl) -indol-1-yl] -ethylamino} - propyl) - (2-hydroxy-ethyl) -amino] -ethanol can be prepared as follows: The trifluoroacetate of 2- [[3- ( 2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-2-yl] - indol-1-yl} -ethylamino) -propyl ] - (2-hydroxy-ethyl) -amino] - ethanol, (0.013 g; 17.6 μmol) is dissolved in a methanolic potash solution (0.5 cm ³ ; 0.1 g of potash per cm ³ of methanol ) then stirred at room temperature for 48 hours. After evaporation, the residue is taken up with stirring in 0.7 cm ³ of a mixture of dimethylsulfoxide and 12N aqueous hydrochloric acid (50/50 v / v). After returning to ambient temperature, 0.35 cm ³ of dimethylsulfoxide is added and then purified by reverse phase liquid chromatography coupled to mass spectrometry (Method B). The fractions containing the expected compound are combined and evaporated, leading to 2- [(3- {2- [5,6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) trifluoroacetate) -indol-1-yl] - ethylamino} -propyl) - (2-hydroxyethyl) -amino] -ethanol, (0.005 g; 39%), the characteristics of which are as follows: LC / MS analysis: tr = 3, 1 min., M / z = 482.02 [M + H] ⁺

b) 2- [[3- (2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl)) -H-pyrrolo [2, 3-b] pyridin-2-yl] trifluoroacetate - indol-1-yl} -êthylamino) -propyl] - (2-hydroxy-ethyl) -amino] - ethanol can be prepared as follows: In a 5 cm ³ conical bottom eathon reactor, a solution of 2- [1- (2-chloro-ethyl) -5,6- dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-] pyridine, (0.02 g, 50 μmol) in N-methyl pyrrolidone (0.5 cm ³ ) then the N- (3-aminopropyl) di-ethanol amino (0.024 g, 150 μmol), potassium carbonate (0.021 g, 150 μmol). The reaction mixture is stirred and heated to 70 ° C overnight. After returning to ambient temperature, it is filtered and evaporated to dryness, then the residue is taken up in dimethylsulfoxide and purified by chromium togr phie ^""" liquidated in reverse phase coupled with mass spectrometry (Method B). After treatment and evaporation of. fractions, isolate the trifluoroacetate from 2- [[3- (2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-2- yl] - indol-1-yl} -êthylamino) -propyl] - (2-hydroxy-ethyl) -amino] - ethanol, (0.013 g, 35%) with the following characteristics: LC / MS analysis (Method B ): tr = 5 min., m / z = 636.43 [M + H] ⁺

EXAMPLE 82 Trifluoroacetate of 2- (4- {3- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] -propyl} - piperazin-1-yl) -ethanol

a) The trifluoroacetate of 2- (4- {3- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] -propyl} - piperazin-1-yl) -ethanol can be prepared as follows: In a hemolysis tube (1.3 x 10 cm), place a 2- [4- (3- {5, 6-) trifluoroacetate solution dimethoxy-3- [1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-2-yl] - indol-1-yl} -propyl) -piperazin-1-yl] -ethanol , (0.038 g; 52.2 μmol), in a methanolic potash solution (3 cm ³ , 0.1 g of potassium hydroxide per cm ³ of methanol) and then stirred at 20 ° C for 72 hours. The solid formed is filtered and then purified by reverse phase liquid chromatography coupled to mass spectrometry (Method E). The fractions containing the expected compound are combined then evaporated under reduced pressure, providing the trifluoroacetate of 2- (4- {3- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl ] -propyl} -piperazin-1-yl) - ethanol, (0.022 g; 90%), the characteristics of which are as follows: LC / MS analysis: tr ≈ 2.7 min., m / z = 464.29 [M + H] ⁺ b) 2- [4- (3- {5,6-dimethoxy-3- [1- (toluene-4-sulfonyl)) -1H-pyrrolo [2,3-b] pyridin-2 trifluoroacetate -yl] - indol-1-yl} -propyl) -piperazin-1-yl] -ethanol can be prepared as follows: In a hemolysis tube (1.3 x 10 cm) a solution of 2- [1- (3-iodo-propyl) -5, 6-dimethoxy-1H-indol- 3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] yridine, (0 , 04 g; 65 μmol) in dimethylformamide (0.5 cm ³ ) then potassium carbonate (0.027 g; 195 μmol) and N- (2-hydroxyethyl) piperazine (0.025 g; 195 μmol) are successively added. The reactor is stirred at 60 ° C for 16 hours. After returning to 21 ° C and filtration, the solution obtained is purified by reverse phase liquid chromatography coupled to mass spectrometry (Method B). The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing 2- [4- (3- {5,6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo] trifluoroacetate [ 2,3- b] pyridin-2-yl] -indol-1-yl} -propyl) -piperazin-1-yl] - ethanol, (0.038 g, 69%), used as it is in the next step.

c) 2- [1- (3-iodo-propyl) -5,6-dimethoxy-1H-indol-3-yl] - 1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b ] pyridine can be prepared as follows: In a 50 cm ³ monocol, place 2- [l- (3-chloro-propyl) -5, 6-dimethoxy-1H-indol-3-yl] -1 - (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine, (0.395 g; 753.8 μmoles) and sodium iodide (0.169 g; 1.13 mmol) in methyl ethyl ketone (10 cm ³ ) at reflux. After 16 hours, sodium iodide (0.169 g; 1.13 mmol) is added and the reflux is maintained for an additional 5 hours. The reaction mixture is evaporated under reduced pressure, then the residue is dissolved in 50 cm ³ of ethyl acetate, transferred to a separating funnel and washed with 2 times 30 cm ³ of distilled water. The organic extract is dried over magnesium sulfate, filtered and evaporated under reduced pressure to yield the compound

10 crude which is purified by chromatography on silica gel (10 g, silica 20-40 μm), eluting at 10 cm ³ / min. with a mixture of cyclohexane and ethyl acetate (70/30; v / v). The fractions containing the expected compound are combined and evaporated to give 2- [1- (3-iodo-

Propyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine, as an amorphous solid (0.287 g, 62%) the characteristics of which are as follows: Mass Spectrum (IE): m / z = 615 [M] ⁺ ; m / z = 460 [M -

20. C ₇ H ₇ NS0 ₂ ] ⁺ ; m / z = 333 [460 - I] ⁺ (base peak) d) 2- [1- (3-chloro-propyl) -5,6-dimethoxy-1H-indol-3- yl] -1- ( toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine can be prepared as follows:

25 In a 25 cm ³ three-necked flask kept under argon, a solution of 2- (5, 6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo is placed [2 , 3-b] (0.447 g; 998 μmol) dissolved in dimethylformamide (10 cm ³ ) then sodium hydride (0.0898 g; 2.99 0 mmol) is added. The mixture is stirred at 21 ° C. for 10 minutes and then 1-bromo-3-chloro propane (0.514 g; 2.99 mmol) is added. The reaction is carried out at this temperature for 1.5 hours. The reaction mixture is poured onto 100 cm ³ of water and then extracted 3 times with 50 cm ³ of ethyl acetate. The 5 organic extracts are combined, washed with 50 cm ³ of a saturated ammonium chloride solution, dried over magnesium sulfate and then evaporated. An oil is isolated and triturated in di-isopropyl ether. The solid formed is filtered. Is isolated 2- [1- (3-chloro-propyl) -5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b ] pyridine, in the form of a white solid (0.395 g; 75.5%), the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.30 (s : 3H); 2.31 (mt: 2H); 3.66 (t, J = 6.5 Hz: 2H); 3.74 (s: 3H); 3.90 (s: 3H); 4.41 (wide t, J = 6.5 Hz: 2H); 6.79 (s: 1H); 6.96 (S: 1H); 7.21 (s: 1H); 7.26 (broad d, J = 8.5 Hz: 2H); 7.32 (dd, J = 8 and 5 Hz: 1H); 7.51 (s: 1H); 7.58 (d, J = 8.5 Hz: 2H); 7.96 (dd, J = 8 and 1.5 Hz: 1H); 8.37 (dd, J = 5 and 1.5 Hz: 1H). Mass spectrum (IE): m / z = 523 [M] ⁺ ; m / z = 368 [M - C ₇ H ₇ NS0 ₂ ] ⁺ (base peak) Le 2- (5,6-dimethoxy-1H-indol-3-yl) -1- (toluene-4- s ^' ulfonyl ) -1H-pyrrolo [2,3-b] pyridine was prepared as described in patent O03000688A1.

EXAMPLE 83 2- (5, 6-dimethoxy-1- [3- (4-methyl-perhydro-1,4, diazepin-1-yl) -propyl] -lH-indol-3-yl} -lH trifluoroacetate -pyrrolo [2, 3-b] pyridine

a) 2- {5,6-dimethoxy-l- [3- (4-methyl-perhydro-1,4-diazepin-1-yl) -propyl] -lH-indol-3-yl} -IH trifluoroacetate -pyrrolo [2, 3-b] pyridine can be prepared in the same way as previously (Example 82a), but from 2- {5, 6-dimethoxy-1- [3- (4-methyl-perhydro) trifluoroacetate -1, 4-diazepin-1-yl) -propyl] -1H-indol-3-yl} -1- (toluene-4-suifonyl) -1H pyrrolo [2, 3-b] pyridine, (0.053 g, 63 , 9 μmol). This gives 2- {5, 6-dimethoxy-1- [3- (4-methyl-perhydro-1,4, diazepin-l-) trifluoroacetate yl) -propyl] -1H-indol-3-yl} -IH-pyrrolo [2, 3-b] pyridine, (0.023 g, 45%), the characteristics of which are as follows: LC / MS analysis: tr = 2, 8 mins. m / z = 448.30 [M + H] ⁺ b) 2- {5, 6-dimethoxy-1- [3- (4-methyl-perhydro-1, 4-diazepin-1-yl) trifluoroacetate - propyl] -lH-indol-3- yl} -l- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine can be prepared in the same way as above (Example 82b), but starting from 2- [1- (3-iodo-propyl) -5,6- dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridine , (0.04 g, 65 μmol), potassium carbonate (0.027 g; 195 μmol) and 1-methylhomopiperazine (0.022 g; 195 μmol), we obtain 2- {5, 6-dimethoxy-1 trifluoroacetate - [3- (4-methyl-perhydro-1,4-diazepin-l-yl) -propyl] -lH-indol-3-yl} -l- (toluene-4-suifonyl) -1H pyrrolo [2, 3 -b] pyridine, (0.053 g; 98%) used as such in the next step. c) 2- [1- (3-iodo-propyl) -5,6-dimethoxy-1H-indol-3-yl] - 1- (toluene- -suifonyl) -H-pyrrolo [2, 3-b] pyridine is prepared according to example 82c.

EXAMPLES 84 TO 87

Step 1: Alkylation The amines specified in the table below are weighed and placed in solution in dimethylformamide (concentration of 120 μmoles in 0.5 cm of dimethylformamide).

In reactors suitable for parallel synthesis, 0.5 cm ³ of each amine solution is distributed, then the potassium carbonate is added (0.017 g per well) and finally 40 μmol are distributed per 2- [ 1- (3- iodo-propyl) -5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine (example 82c) dissolved in dimethylformamide (0.5 cm ³ ). The calypso reactor is closed and then placed under orbital stirring at 50 ° C for 16 hours. After returning to 20 ° C., the solutions obtained above are purified by reverse phase liquid chromatography coupled to mass spectrometry (Method B). After evaporation, weighing, dilution and analysis by reverse phase liquid chromatography coupled to mass spectrometry (Method A), the expected compounds are isolated and used in the next step.

Step 2: deprotection

Each compound obtained previously is treated with 1 cm ³ of a methanolic potassium solution (0.1 g of potassium hydroxide per cm ³ of methanol) for 48 hours at 21 ° C. The solutions are evaporated under reduced pressure then the solids obtained dissolved in dimethyl sulfoxide (0.5 cm ³ ). 0.5 cm ³ of 5M aqueous hydrochloric acid are added to the solutions thus obtained, then the compounds obtained are purified by two reverse phase liquid chromatography coupled to successive mass spectrometry (Method E). After treatment of the fractions and analysis by reverse phase liquid chromatography coupled to mass spectrometry (Method A), the following compounds are identified and characterized:

EXAMPLE 88 2- [5,6-Dimethoxy-1- (2-methoxy-ethyl) -1H-indol-3-yl] -1H-pyrrolo [2,3-b] pyridine

a) 2- [5, 6-dimethoxy-1- (2-methoxy-ethyl) -lH-indol-3-yl] -lH-pyrrôlo [2, 3-b] pyridine is prepared as follows: A a solution of 3.1 cm ³ of methanolic potassium hydroxide (0.1 g / cm ³ ; 1.78 M) 0.080 g of 2- [5, 6-dimethoxy-1- (2-methoxy-ethyl) is added ) -1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine, at a temperature in the region of 20 ° C. The reaction medium is stirred at this same temperature for 5 hours. The reaction medium is then heated at 50 ° C for 4 hours. After cooling, the solid formed is filtered through sintered glass, washed twice with 3 cm ³ of methanol, then 5 times with 5 cm ³ of water. The solid is dried in an oven (35 ° C) under vacuum. 0.019 g of 2- [5, 6-dimethoxy-1- (2-methoxy-ethyl) -1H-indol-3-yl] -1H-pyrrolo [2, 3-b] pyridine are thus obtained, the characteristics of which are following: NMR spectrum ^ (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.29 (S: 3H); 3.73 (t, J = 5 Hz: 2H); 3.87 (S: 3H); 3.90 (s: 3H); 4.37 (broad t, J = 5 Hz: 2H); 6.79 (br s: 1H); 7.03 (dd, J = 8 and 5 Hz: 1H); 7.22 (s: 1H); 7.44 (s: 1H) 7.87 (broad d, J = 8 Hz: 1H); 7.87 (s: 1H) 8.03 (dd, J = 5 and 1.5 Hz: 1H); 11.79 (s broad 1H). Mass spectrum (IE): m / z = 351 [M + H] ⁺ (base peak)

b) 2- [5,6-dimethoxy-1- (2-methoxy-ethyl) -1H-indol-3- yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b ] pyridine is prepared as follows: To a solution of 0.1 g of 2- [5, 6-dimethoxy-1H- indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [ 2,3- b] pyridine in 2.5 cm ³ of anhydrous dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20 ° C., 0.01 g of sodium hydride (60%) is added. Stirring is maintained at this temperature for 30 minutes. 0.023 cm ³ of bromoethyl methyl ether is added. The reaction medium is stirred at the same temperature for 16 hours. 3 cm ³ of water and 3 cm ³ of ethyl acetate are added. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified on a flash-pack chromatography cartridge (silica, dichloromethane, as eluent). The fractions containing the product are concentrated under reduced pressure. 0.082 g of 2- [5, 6-dimethoxy-1- (2-methoxyethyl) -1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo is thus obtained. 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (El): m / z = 505 [M] ⁺ ; m / z = 350 (base peak) The compound 2- (5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is prepared according to the process described in the patent O03000688A1.

EXAMPLE 89: 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -indol-1-yl] -ethanol a) 2- [5, 6- dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - indol-1-yl] -ethanol is prepared as follows; To a solution of 0.18 g of 2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine-2-yl] - indol- 1-yl} -ethanol in 10 cm ³ of methanol, at a temperature close to 20 ° C, is added 1.65 cm ³ of an aqueous solution of potassium hydroxide 5N. The reaction medium is heated at reflux for 4 hours. After cooling, the solid formed is filtered through sintered glass, washed twice with 3 cm ³ of methanol, then 5 times with 5 cm ³ of water. The solid is purified by flash chromatography pack (silica, dichloromethane / methanol 95/05 by volume as eluent). 0.045 g of 2- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridine-2-yl) - indol-1-yl] -ethanol is obtained, the characteristics of which are as follows: Spectrum ^X NMR (300 MHz, (CD ₃₎ ₂ SO d6, δ in ppm): 3,80 (mf: 2H); 3.87 (s: 3H); 3.91 (s: 3H); 4.26 (wide t, J = 5.5 Hz: 2H); 5.00 (mf: 1H); 6.78 (d, J = 2 Hz: 1H); 7.03 (dd, J = 8 and 5 Hz: 1H); 7.19 (s: 1H); 7.45 (s: 1H); 7.87 (broad d, J = 8 Hz: 1H); 7.89 (s: 1H); 8.13 (dd, J = 5 and 1.5 Hz: 1H); 11.78 (broad s: 1H). Mass spectrum (IE): m / z = 337 [M] ⁺ (base peak)

b) 2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -IH- pyrrolo ^, 3-b] pyridine-2-yl] -indol-1-yl} -ethanol is prepared as follows: To a solution of 0.46 g of 2- [5,6-dimethoxy-1- (2- tert-butyldimethylsilyloxy-ethyl) -indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine in 9.5 cm ³ of anhydrous tetrahydrofuran, under an inert atmosphere argon at a temperature in the region of 20 ° C., 1.52 cm ³ of tetrabutylammonium fluoride (TBAF) is added dropwise. The reaction medium is stirred at the same temperature for 6 hours. The reaction medium is concentrated ^" under reduced pressure. The residue obtained is purified on flash chromatography (silica, dichloromethane / methanol 98/02 in volumes as eluent, argon). The fractions containing the product are concentrated under reduced pressure. 0.187 g of 2- {5,6-dimethoxy-3- [1- (toluene-4-sulfonyl) -1H- pyrrolo [2,3-b] pyridine-2-yl] -indol-1-yl} -ethanol whose characteristics are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.30 (s: 3H); 3.74 (s: 3H); 3.83 (mt: 2H); 3.88 (s: 3H); 4.30 (t, J = 6 Hz: 2H); 5.00 (mf: 1H); 6.75 (s: 1H); 6.95 (s: 1H); 7.20 (S: 1H); 7.25 (d wide, J = 8 Hz: 2H); 7.31 (dd, J = 8 and 5 Hz: 1H); 7.50 (s: 1H ); 7.58 (d, J = 8 Hz: 2H); 7.95 (dd, J = 8 and 1.5 Hz: 1H); 8.37 (dd, J = 5 and 1.5 HZ: 1H ).

c) 2- [5,6-dimethoxy-1- (2-tert-butyldimethylsilyloxy-ethyl) -indol-3-yl] -ri- (toluêήe-4-sulfonyl) -lH-pyrrolo [2,3- b ] pyridine) is prepared as follows: To a solution of 0.5 g of 2- (5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine in 12.5 cm ³ of anhydrous dimethylformamide, under an inert argon atmosphere at a temperature close to

20 ° C, 0.049 g of sodium hydride (60%) is added. Stirring is maintained at this temperature for 30 minutes. 0.264 cm ³ of 2-tert-butyldimethylsilyloxy-ethylbromide is added. The reaction medium is stirred at the same temperature for 16 hours. 25 cm ³ of water and 20 cm ³ of ethyl acetate are added. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography (silica, dichloromethane / methanol 98/02 by volume as eluent, argon). The fractions containing the product are concentrated under reduced pressure. 0.47 g of 2- [5, 6-dimethoxy-1- (2-te ^" rt-butyldimethylsilyl-oxy-ethyl) -indol-3-yl] -1- (toluene-4-sulfonyl) is thus obtained - 1H-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 605 [M] ⁺ ; m / z = 450 (base peak)

Compound 2- (5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is prepared according to the process described in the patent WO03000688A1.

EXAMPLE 90: 3- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridine-2-yl) -indol-1-yl] -propanol

a) 3- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridine-2-yl) -indol-1-yl] -propanol is prepared by following the procedure described in example 88a but from

0.24 g of 3- [5, 6-dimethoxy-3- (1- (toluene-4-sulfonyl) -1H- pyrrolo [2,3-b] pyridine-2-yl) -indol-1-yl] -propanol and a solution of 9.3 cm ³ of methanolic potassium hydroxide (0.1 g / cm ³ ; 1.78 M). After purification by flash-pack chromatography (silica, dichloromethane / methanol 98/02 by volume as eluent), one obtains

0.103 g of 3- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridine-

2-yl) -indol-1-yl] -propanol the characteristics of which are as follows: NMR spectrum ^ (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm),: 1.99 (mt: 2H) ; 3.48 (mt: 2H); 3.88 (s: 3H); 3.92 (s: 3H); 4.27 (broad t, J = 7 Hz: 2H); 4.66 (wide t, J = 5 Hz: 1H); 6.78 (d, J = 2 Hz: 1H); 7.03 (dd, J = 8 and 5 Hz: 1H); 7.17 (S: 1H); 7.45 (s: 1H); 7.87 (s: 1H); 7.87 (dd, J = 8 and 1.5 Hz: 1H); 8.13 (dd, J = 5 and 1.5 Hz: 1H); 11.73 (mf: 1H). Mass spectrum (El): m / z = 351 [M] ⁺ (base peak)

b) 3- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -IH- pyrrolo [2X-b] pyridine-2; -yl] -indol-1-yl} -propanol ^" and 2- [5,6-dimethoxy-1- (3-fluoropropyl) -indol-3-yl] -1- (toluene-4 sulfonyl) -IH-pyrrolo [2, 3-b] pyridine are prepared as follows the procedure described, in Example 89b but using 0.605 g of 2- [5,6-dimethoxy-1- (3-tert-butyldimethylsilyloxy-propyl) -indol- 3-yl] -1- (toluene- 4-suifonyl) -1H-pyrrolo [2,3-b] pyridine and 1.95 cm ³ of tetrabutylammonium fluoride (TBAF) After purification by flash chromatography (silica, dichloromethane / methanol 98/02 in volumes as effluents , argon), 0.243 g of 3- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine-2-yl] - indol- is obtained 1-yl} -propanol, the characteristics of which are as follows: Mass spectrum (EI): m / z = 505 [M] ⁺ (base peak) and 0.046 g of 2- [5, 6-dimethoxy-1- ( 3-fluoropropyl) -indol- 3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine d have the following characteristics: Mass spectrum (El): m / z = 507 [M] ⁺ (base peak)

c) 2- [5,6-dimethoxy-1- (3-tert-butyldimethylsilyloxypropyl) -indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b ] pyridine is prepared by following the procedure described in Example 89c but using 0.285 cm ³ of 2-tert-butyldimethylsilyloxy-propylbromide and 0.5 g of

2- [5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridine and 0.049 g of sodium hydride (to 60%). After purification by flash chromatography (silica, dichloromethane / methanol 98/02 by volume as eluent, argon), 0.605 g of 2- [5, 6-dimethoxy-1- (3-tert-butyldimethylsilyloxy-propyl) - indol-3-yl] -1- (toluene-4-sulfonyl) is obtained -lH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 619 [M] ⁺ (base peak)

The compound 2- (5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is prepared according to the process described in the patent O03000688A1.

EXAMPLE 91 2- [1- (3-Fluoro-propyl) -5,6-dimethoxy-1H- indol-3-yl] -1H-pyrrolo [2, 3-b] pyridine Le 2- [1- (3 -fluoro-propyl) -5,6-dimethoxy-1H-indol-3-yl] -1H-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 88a but starting from 0.042 g of 2- [5, 6-dimethoxy-1- (3-fluoropropyl) -indol- 3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine and 1 , 63 cm ³ of an aqueous solution of potassium hydroxide 5N. After purification by flash chromatography pack (silica, dichloromethane / methanol 98/02 by volume as eluent), 0.008 g of 2- [1- (3-fluoro-propyl) -5,6-dimethoxy-1H-indol- is obtained. 3-yl] -lH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, d in ppm): 2.22 (dt, J = 26 and 6.5 Hz: 2H); 3.88 (s: 3H); 3.91 (s: 3H); 4.33 (t, J = 6.5 Hz: 2H); 4.52 (dt, J ≈ 48 and 6.5 Hz: 2H); 6.80 (broad d, J = 2 Hz: 1H); 7.04 (dd, J = 8 and 5 Hz: 1H); 7.18 (s: 1H); 7.45 (s: 1H); 7.88 (broad dd, J = 8 and 1.5 Hz: 1H); 7.89 (s: 1H); 8.14 (dd, J = 5 and 1.5 Hz: 1H); 11.78 (broad s: 1H). Mass spectrum (El): m / z = 353 [M] ⁺ (base peak)

EXAMPLE 92 Acid 3- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridine-2-yl) -indol-1-yl] -propionic: a) The 3- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridine-2-yl) -indol-1-yl] -propionic acid is prepared by following the procedure described in Example 88a but from 1 g of 3- [5, 6-dimethoxy-3- (1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridine-2-yl) -indol-l-ylj -methylpropionate and a solution of 74 cm ³ of methanolic potassium hydroxide (0.1 g / cm ³ ; 1.78 M. We obtain 0 ^~ , ^" 601 g of acid 3- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridine-2-yl) -indol-1-yl] -propionic having the following characteristics: NMR spectrum ^ (300 MHz, (CD ₃ ) ₂ SO d6, d in ppm): 2.82 (t, J = 6.5 Hz: 2H); 3.88 (s: 3H); 3.90 (S: 3H); 4 , 44 (t, J = 6.5 Hz: 2H); 6.78 (wide d, J = 2 Hz: 1H); 7.03 (dd, J = 8 and 5 Hz: 1H); 7.22 ( s: 1H); 7.44 (s: 1H); 7.86 (wide d, J = 8 Hz: 1H); 7.87 (s: 1H); 8.13 (wide dd, J = 5 and 1 , 5 Hz: 1H); 11.78 (broad s: 1H). Mass Spectrum (IE): m / z = 365 [M] ⁺ (base peak)

b) 3- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridine-2-yl] -indol-1-yl} -propionate methyl is prepared as follows: To a solution of 1 g of 2- (5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine in 20 cm ³ of anhydrous dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20 ° C., 0.34 g of potassium carbonate and 0.243 cm ³ of acrylate is added dropwise The reaction medium is stirred at the same temperature for 16 hours, 20 cm ³ of water and 20 cm ³ of ethyl acetate are added.

After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography (silica, dichloromethane as eluent, argon), the fractions containing the product are concentrated under reduced pressure. 1 g of 3- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine-2-yl] -indol-1-yl is thus obtained } -methylpropionate, the characteristics of which are as follows: Mass Spectrum (IE): IE: m / z = 533 [M] ⁺ (base peak), m / z = 378

The compound 2- [5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine is prepared according to the process described in the patent O03000688A1.

EXAMPLE 93: 3- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3- b] pyridin-2-yl) -indol-1-yl] -l-morpholin-4-yl-propan-1 -one

3- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - indol-1-yl] -l-morpholin-4-yl-propan-l-one is prepared as follows: To a solution of 0.035 g of 3- [5, 6-dimethoxy- 3- (1H-pyrrolo [2,3-b] pyridine-2-yl) -indol-1-yl acid ] - propionic acid in 3 cm ³ of dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20 ° C, 0.036 g of O- (1H-benzotriazol-1-yl) - N, N, N ', N is added '-tetramethyluronium hexafluorophosphate. The reaction medium is stirred at this same temperature for 1 hour. 0.01 cm ³ of morpholine and then 0.017 cm ³ of diisopropylethylamine are added. After 3 hours of stirring at the same temperature, 10 cm ³ of water and 10 cm ³ of ethyl acetate are added. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, dichloromethane / methanol 98/02 by volume as eluent). The fractions containing the product are concentrated under reduced pressure. 0.025 g of 3- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin- 2-yl) -indol-1-yl] -l-morpholin-4-yl-propan-l-one whose characteristics are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, ppm in ppm ): 2.90 (t, J = 6.5 Hz: 2H); from 3.30 to 3.55 (mt: 8H); 3.88 (s: 3H); 3.90 (s: 3H); 4.47 (broad t, J = 6.5 Hz: 2H); 6.78 (d, J = 2 Hz: 1H); 7.03 (dd, J = 8 and 5 Hz: 1H); 7.19 (s: 1H); 7.44 (s: 1H); 7.86 (s: 1H); 7.87 (broad d, J = 8 Hz: 1H); 8.13 (dd, J = 5 and 1.5 Hz: 1H); 11.78 (broad s: 1H). Mass spectrum (IE): m / z = 434 [M] ⁺ (base peak)

EXAMPLE 94: 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -indol-1-yl] -1- (4-hydroxy-piperidin-1- yl) - ethanone

a) 2- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -1- (4-hydroxy-piperidin-1- yl) -ethanone is prepared by following the procedure described in Example 93 but using 0.2 g of 2- [5,6-dimethoxy-3- (1H-pyrrolo [2, 3-b] acid) pyridine-2-yl) -indol-1-yl] - acetic acid and 0.07 g of 4-hydroxypiperidine. After purification by flash chromatography pack (silica, dichloromethane / methanol 98/02 by volume as eluent), 0.096 g of 2- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3- b] pyridin) is obtained. -2-yl) -indol-1-yl] -1- (4-hydroxy-piperidin-l-yl) - ethanone with the following characteristics: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): from 1.20 to 1.55 (mt: 2H); from 1.70 to 1.95 (mt: 2H); 3.12 and from 3.20 to 3.45 (respectively t wide, J = 11 Hz and mt: 2H in total); from 3.75 to 4.00 (mt: 2H); 3.78 (mt: 1H); 3.84 (s: 3H); 3.91 (s: 3H); 4.81 (d, J = 3.5 Hz: 1H); 5.21 (limit AB, J ≈ 16.5 Hz: 2H); 6.79 (d, J = 2 Hz: 1H); 7.03 (dd, J = 8 and 5 Hz: 1H); 7.10 (s: 1H); 7.46 (s: 1H); 7.76 (s: 1H); 7.88 (dd, J = 8 and 1.5 Hz: 1H); 8.13 (dd, J = 5 and 1.5 Hz: 1H); 11.76 (broad s: 1H). Mass spectrum (IE): m / z = 434 [M] ⁺ (base peak) b) 2- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridine-) acid 2-yl) -indol-1-yl] -acetic is prepared by following the procedure described in Example 88a but from 1 g of 2- {5, 6-dimethoxy-3- [1- (toluene- 4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine-2-yl] -indol-1-yl}-tert-butyl acetate and a solution of 73 cm ³ of methanolic potassium hydroxide ( 0.1 g / cm ³ ; 1.78 M). 0.701 g of 2- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridine-2-yl) -indol-1 ^ yl] -acetic acid is obtained, the characteristics of which are following: Mass Spectrum (IE): m / z = 351 [M] ⁺ (base peak) c) 2- {5, 6-dimethoxy-3- [1- (toluene-4-sulfonyl) -IH- tert-butyl pyrrolo [2,3-b] pyridine-2-yl] -indol-1-yl} -acetate is prepared by following the procedure described in Example 89c but starting with 1.91 g of bromoacetate tert-butyl and 4 g of 2- (5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridine. obtains 4.5 g of 2- {5,6-dimethoxy-3- [1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine-2-yl] -indol-1-yl } -tert-butyl acetate, the characteristics of which are as follows: Mass Spectrum (CI): m / z = 562 [M + H] ⁺ (base peak)

EXAMPLE 95: 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -indol-1-yl] -l-thiazolidin-3-yl-ethanone

2- [5, 6-dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - indol-1-yl] -l-thiazolidin-3-yl-ethanone is prepared by following the procedure described in Example 93 but using 0.2 g of 2- [5, 6-dimethoxy-3- (1H-pyrrolo ^, 3-b] pyridine-2-yl) -indol acid -1-yl] -acetic and 0.061 g of thiazolidine. 0.133 g of 2- [5.6- dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol-1-yl] - 1-thiazolidin-3-yl-ethanone with the following characteristics: NMR spectrum (400 MHz , (CD ₃ ) ₂ SO d6, at a temperature of 373 K, δ in ppm): 3.16 (mf: 2H); from 3.85 to 3.95 (t: 2H); 3.86 (s: 3H); 3.90 (s: 3H); 4.66 (broad s: 2H); 5.16 (s: 2H); 6.72 (d, J = 1.5 Hz: 1H); 7.01 (dd, J = 8 and 4.5 Hz: 1H); 7.11 (s: 1H); 7.49 (s: 1H); 7.76 (s: 1H); 7.86 (dd, J = 8 and 1.5 Hz: 1H); 8.13 (dd, J = 4.5 and 1.5 Hz: 1H); 11.45 (mf: 1H). Mass spectrum (IE): m / z = 422 [M] ⁺ (base peak)

EXAMPLE 96: 4- {[5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -indol-1-yl] -acetyl} -l-methyl-piperazin-2 - one

4- {[5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -acetyl} -l-methyl-piperazin-2-one is prepared by following the procedure described in Example 93 but starting from 0.1 g of 2- [5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridine-2 acid -yl) -indol-1-yl] -acetic and 0.039 g of 1-methyl-piperazin-2-one. 0.088 g of 4- {[5, 6-dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -acetyl} -1-methyl-piperazin is obtained -2-one with the following characteristics: 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm). At room temperature, we observe a mixture of rotamers 50/50. _* 2.94 and 2.96 (2 s: 3H in total); 3.39 and 3.54 (2 mts: 2H in total); 3.75 and 3.91 (2 mts: 2H in total); 3.85 (s: 3H); 3.91 (s: Λ 3H); 4.07 and 4.34 (2 s wide: 2H in total); 5.25 and 5.30 (2 s wide: 2H in total); 6.79 (d, J = 1.5 Hz: 1H); 7.04 (dd, J = 8 and 5 Hz: 1H); 7.13 and 7.15 (2 s wide: 1 hour in total); 7.46 (s: 1H); 7.71 and 7.74 (2 s: 1H in total); 7.88 (broad d, J = 8 Hz: 1H); 8.14 (dd, J = 5 and 1.5 Hz: 1H); 11.79 (mf: 1H). Mass spectrum (IE): m / z = 447 [M] ⁺ (base peak)

EXAMPLE 97 4-Chloro-2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridine a) 4-chloro-2- ( 5, 6-dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 89a but starting from 2.8 g of 4-chloro-2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine and 25.5 cm ³ of an aqueous solution of potassium hydroxide 5N. 1.81 g of 4-chloro-2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridine are obtained, the characteristics of which are as follows : NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.86 (S: 3H); 3.89 (s: 3H); 3.92 (s 3H); 6.73 (s: 1H); 7.16 (d, J = 5 Hz: 1H) 7.17 (s: 1H); 7.46 (s: 1H); 7.86 (s: 1H) 8.09 (d, J = 5 HZ: 1H); 12.16 (mf: 1H). Mass spectrum (IE): m / z = 341 [M] ⁺ (base peak)

b) 4-chloro-2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) - 1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 89c but using 7.1 g of 4-chloro-2- (5,6-dimethoxy-1H-indol-3-yl) -1- (toluene-4 -suifonyl) -IH- pyrrolo ^, 3-b] pyridine and 1.10 cm ³ of methyl iodide. After purification by flash chromatography (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent, argon), 5.69 g of 4-chloro-2- (5,6-dimethoxy-1-methyl- 1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine whose characteristics- ticks are as follows: Mass Spectrum (IE): m / z = 495 [Mj ⁺ m / z = 340 (base peak) c) 4-chloro-2- (5, 6-dimethoxy-1H-indol- 3-yl) -1- (toluene-4-suifonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared as follows: To a solution of 10 g of 1- (toluene-4-suifonyl) - 1H- 2-iodo-4-chloro-pyrrolo [2, 3-b] pyridine, 245 cm ³ of anhydrous dimethylformamide and 7.42 g- of 1-tertbutyloxycarbonyl-5,6-dimethoxyindol-3-boronic acid , under an inert argon atmosphere at a temperature in the region of 20 ° C., 67 cm ³ of a saturated aqueous solution of sodium bicarbonate and 1.34 g of tetrakis (triphenylphosphine) palladium are added. The reaction medium is heated at 130 ° C for 45 minutes. After cooling, the reaction medium is concentrated under reduced pressure. The oil obtained is taken up in 300 cm ³ of water and 300 cm ³ of ethyl acetate. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent, argon). The fractions containing the product are concentrated under reduced pressure. 7.52 g of 4-chloro-2- (5,6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo are thus obtained [2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 481 [M] ⁺ ; m / z = 326 (base peak)

The compounds 1- (toluene-4-sulfonyl) -1H-2-iodo-4-chloropyrrolo [2,3-b] pyridine and 1-tert-butyloxycarbonyl-5,6-dimethoxyindol-3 acid -boronics are prepared according to the process described in patent O03000688A1. EXAMPLE 98 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH- pyrrolo [2, 3-b] pyridine-4-carbonitrile a) 2- (5, 6- dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridine-4-carbonitrile can be prepared as follows: A suspension of 0.14 g of 2- (5, 6-dimethoxy-1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2,3-b] pyridine-4-carbonitrile in 1.3cm ³ of a 5N aqueous potassium hydroxide solution and 5 cm ³ of methanol is brought to a temperature in the region of 60 ° C. for approximately 30 minutes. After returning to the vicinity of 20 ° C, the insoluble material is drained, washed with water until neutral pH. The insoluble material is purified by flash chromatography on a silica column [eluent: dichloromethane / methanol (98/2 by volume)]. 0.05 g of 2- (5.6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridine-4-carbonitrile is obtained in the form of a solid the characteristics of which are as follows: TLC silica [eluent: dichloromethane / methanol (98/2 by volume)] Rf = 0.17 NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3, 87 (s: 3H); 3.89 (s: 3H); 3.92 (s: 3H); 6.87 (broad s: 1H); 7.17 (s: 1H); 7.44 (broad d, J = 5 Hz: 1H); 7.49 (br s: 1H); 7.95 (s: 1H); 8.25 (d, J = 5 Hz: 1H); 12.44 (mf: 1H). Mass spectrum (El): m / z = 332 [M] ⁺ (base peak); m / z = 317 [M - CH ₃ ] ⁺ ; m / z = 289; [m / z = 317 - C0] ⁺

b) 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine-4-carbonitrile can be prepared as follows: To a suspension, degassed with argon for approximately 15 minutes, of 0.2 g of 4-chloro-2- (5, 6-dimethoxy-1- methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, 0.084 g zinc cyanide, 0.013 g zinc powder in 20 cm ³ of N, N-dimethylacetamide, 0.029 g of [1,1 '-bis (diphenylphosphino) ferrocene] palladium (II) is added. The reaction mixture is brought to a temperature in the region of 150 ° C. for approximately 2.5 hours. After cooling to about 20 ° C, the reaction mixture was filtered through ^"Celite and the insoluble matter is washed with 100 cm ³ of dichloromethane. The filtrate is washed with three times 100 cm ³ of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa) The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (50/50 by volume)]. 0.14 g of 2 is obtained. - (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine-4-carbonitrile in the form of a lacquer with the following characteristics: TLC silica [eluent: cyclohexane / ethyl acetate (50/50 by volume)] = Rf 0.40 Mass Spectrum (El): m / z = 486 [M] ⁺ ; m / z = 331 [M - C ₇ H ₇ 0 ₂ S] ⁺ (base peak); m / z = 316 [331 - CH ₃ ] ⁺ -; m / z = 155 [C ₇ H ₇ 0 ₂ S ⁺ ]; m / z = 91 [C ₇ H ₇ ⁺ ]

4-chloro-2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared as described in Example 97b.

EXAMPLE 99 4-chloro-2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] -1H-pyrrolo [2, 3-b] pyridine

a) 4-chloro-2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] -lH-pyrrolo [2, 3-b] pyridine can be prepared as follows: A solution of 0.54 g of 4-chloro-2- [5, 6-dimethoxy- 1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl ] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine and 1.8 g of potassium hydroxide in 18 cm ³ of methanol is brought to the vicinity of 60 ° C. for approximately 2 hours. After cooling to approximately 20 ° C., the precipitate is drained, washed twice with 3 cm ³ of methanol and three times 5 cm ³ of water, then dried in an oven under reduced pressure (13 kPa) at a temperature close to 40 ° C for about 8 hours. 0.241 g of 4-chloro- 2- [5,6-dimethoxy-1- (2-morpholin ~ 4-yl-ethyl) -lH-indol-3- yl] -lH-pyrrolo [2, 3-b is obtained ] pyridine in the form of a solid, the characteristics of which are as follows: Melting point: 240 ° C. (Banc-Kofler) NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.48 (t, J = 4.5 Hz: 4H); 2.74 (t, J = 6.5 Hz: 2H); 3.49 (t, J = 4.5 Hz: 4H); 3.87 (S: 3H); 3.89 (s: 3H); 4.32 (wide t, J = 6.5 Hz: 2H); 6.71 (s: 1H); 7.14 (d, J = 5 Hz: 1 H); 7.20 (s: 1H); 7.42 (s: 1H); 7.92 (s: 1H); 8.07 (d, J = 5 Hz: 1 H); 12.13 (mf: 1 H). Mass spectrum (El): m / z = 440 [M] ⁺ (base peak); m / z = 340 [M - C ₅ H ₁₀ NO] +; m / z = 100 [C ₅ H ₁₀ NO] +

b) 4-chloro-2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -IH -pyrrolo [2, 3-b] pyridine can be prepared as follows:. A suspension of 1 g of 4-chloro-2- (5,6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, 0.655 g of 4- (2-chloroethyl) -morpholine hydrochloride, and 1.11 g of potassium carbonate in 10 cm ³ of dimethylformamide is heated to around 95 ° C for about 3 hours. After cooling to a temperature in the region of 20 ° C., the reaction mixture is poured into 20 cm ³ of water, extracted with three times 100 cm ³ of ethyl acetate. The phases The combined organics are washed with 100 cm ³ of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (90/10 by volume)]. 0.54 g of 4-chloro-2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] -1- (toluèri.e-) is obtained 4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine in the form of a solid, the characteristics of which are as follows: TLC silica [eluent: dichloromethane / methanol (98/2 by volume)] Rf = 0.18 Mass spectrum (El): m / z = 594 [M] ⁺ ; m / z = 481 [M - C ₆ HnNO] ⁺ ; m / z = 439 [M- C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 326 [m / z = 481 - C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 100 [C ₅ H ₁₀ NO ⁺ ] (base peak)

4-chloro-2- (5, 6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine is prepared as described in 'example 97c.

EXAMPLE 100: 2- (1- {2- [3- (4-chloro-1H-pyrrolo [2, 3-b] pyridin-2-yl) -5, 6-dimethoxy-indol-1-yl] -ethyl } -piperidin- 4-yl) -ethanol

a) 2- (1- {2- [3- (4-chloro-1H-pyrrolo [2,3-b] pyridin-2- yl) -5,6-dimethoxy-indol-l-yl] -ethyl } -piperidin-4-yl) - ethanol can be prepared as in Example 99a: But from 0.160 g of 2- [1- (2- {3- [4-chloro-l- (toluene-4- suifonyl) -IH-pyrrolo [2, 3-b] pyridin-2-yl] -5,6- dimethoxy-indol-1-yl} -ethyl) -piperidin-4-yl] -ethanol,

0.58 g of potassium hydroxide in 10 cm ³ of methanol.

There is thus obtained, after flash chromatography on a silica column [eluent: dichloromethane / methanol (80/20 by volume)], 0.078 g of 2- (1- {2- [3- (4-chloro-1H-pyrrolo [2 , 3-b] pyridin-2-yl) -5, 6-dimethoxy-indol-1-yl] -ethyl} - piperidin-4-yl) -ethanol in the form of a solid, the characteristics of which are as follows: Melting point: 200 ° C. (Kofler) NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm) : from 1.00 to 1.25 (mt: 2H); 1.25 to 1.40 (mt: 3H); 1.63 (very large d, J = 13 Hz: 2H); 1.99 (wide t, J = 11.5 Hz-: .2H); 2.70 (t, J = 6.5 Hz: 2H) 2.93 (wide d, J = 11.5 Hz: 2H); 3.43 (mf: 2H) 3.88 (s: 3H); 3.90 (s: 33HH)) ;; 44,, 3322 ((mmtt :: 33HH)); 6.71 (br s: 1H); 7.15 (d, J ≈ 5 Hz: 1 H) 7.20 (s: 1 H); 7.42 (s: 1H); 7.92 (S: 1H) 8.07 (d, J = 5 Hz: 1H); 12, 16 (mf: 1 H). Mass spectrum (El): m / z = 482 [M] ⁺ ; m / z = 142 [C ₈ H ₁₆ NO] ⁺ (base peak)

b) 2- [1- (2- {3- [4-chloro-l- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridin-2-yl] -5, 6- dimethoxy-indol-1-yl} - ethyl) -piperidin-4-yl] -ethanol can be prepared as follows: A suspension of 0.280 g of 4-chloro-2- [1- (2-iodoethyl) -5, 6-dimethoxy-IH-indol-3-yl] -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine, 0.061 g potassium carbonate, 0.114 g 2-piperidin-4-yl- ethanol in 30 cm ³ of acetonitrile is brought to a temperature in the region of 60 ° C. After approximately 5 hours of heating at this temperature, 0.061 g of potassium carbonate and 0.114 g of 2-piperidin-4-yl-ethanol are added and the mixture acts at this same temperature for approximately 2 hours. After returning to a temperature in the region of 20 ° C., the mixture is concentrated to dryness under reduced pressure (13 kPa), then taken up in 50 cm ³ of water and extracted with three times 40 cm ³ of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under pressure reduced (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: dichloromethane / methanol (95/5 by volume)]. 0.16 g of 2- [1- (2- {3- [4-chloro-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-2-yl] is obtained - 5, 6-dimethoxy-indol-1-yl} - ethyl) -piperidin-4-yl] -ethanol in the form of an oil, the characteristics of which are the following: Mass spectrum (IE): m / z = 636 [ M] ⁺ ; m / z = 481 [M - C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 142 [C ₈ H ₁₆ NO] ⁺ (base peak)

c) 4-chloro-2- [1- (2-iodo-ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2 , 3-b] pyridine can be prepared as follows: A suspension of 0.760 g of 4-chloro-2- [1- (2-chloro-ethyl) -5,6-dimethoxy-1H-indol-3-yl ] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine and 0.315 g of sodium iodide in 70 cm ³ of 2-butanone is brought to reflux for about 24 hours. The reaction mixture is evaporated to dryness under reduced pressure (13 kPa), taken up in 50 cm ³ of water, and extracted with three times 50 cm ³ of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). 0.98 g of 4-chloro-2- [1- (2-iodo-ethyl) -5,6- dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -IH are obtained. - pyrrolo [2, 3-b] pyridine in the form of a yellow oil, the characteristics of which are as follows: TLC silica [eluent: dichloromethane / ethyl acetate (90/10 by volume)] Rf = 0.71 Spectrum of Mass (IE): m / z = 635 [M] ⁺ (base peak); m / z = 480 [M- C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 353 [480 - 1] ⁺ ; m / z = 338 [353 - CH ₃ ] ⁺ ; m / z = 91 [C ₇ H ₇ ] d) 4-chloro-2- [1- (2-chloro-ethyl) -5,6-dimethoxy-1H- indol-3-yl] -1- (toluene-4-sulfonyl) -IH-pyrrolo [2 , 3-b] pyridine can be prepared as follows: To a solution of 1 g of 4-chloro-2- (5, 6-dimethoxy- IH-indol-3-yl) -1- (toluene-4- suifonyl) -1H-pyrrolo [2,3-b] pyridine and 0.013 g of tetrabutylammonium bromide in 25 cm ³ of 1,2-dichloroethane, 0.79 g of potassium hydroxide and 0.61 are added g of potassium carbonate. The suspension obtained is brought to the vicinity of 50 ° C for approximately 5 hours. After returning to a temperature in the region of 20 ° C. and stirring at this temperature for approximately 16 hours, the reaction mixture is filtered through celite; the insoluble material is washed with three times 10 cm ³ of dichloromethane. The filtrate is washed with three times 50 cm ³ of water, dried over filtered magnesium sulfate and concentrated to dryness under reduced pressure. The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (75/25 by volume)]. 0.62 g of 4-chloro-2- [1- (2-chloro-ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH is obtained. -pyrrolo [2, 3-b] pyridine in the form of a solid, the characteristics of which are as follows: TLC silica [eluent: cyclohexane / ethyl acetate (50/50 by volume)] Rf = 0.41 Mass Spectrum (IE): m / z = 543 [M] ⁺ ; m / z = 388 [M - C ₇ H ₇ 0 ₂ S] ⁺ (base peak); m / z = 91 [C ₇ H ₇ ] ⁺

4-chloro-2- (5,6-dimethoxy- IH- indol -3 -yl) -1- (toluene-4-tallow onyl) -1H-pyrrolo [2, 3 -b] pyridine is prepared as described in example 97c. EXAMPLE 101: 4-chloro-2- {5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] -IH-indol-3-yl} -IH-pyrrolo [2 , 3-b] pyridine a) 4-chloro-2- {5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] -IH-indol-3-yl} -IH-pyrrolo [2, 3-b] pyridine can be prepared as in Example 100a: But from 0.2 g of 4-chloro-2- {5, 6-dimethoxy-1- [2- ( 4-methyl-piperazin-1-yl) -ethyl] -lH-indol- 3-yl} -l- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine and 0.65 g of potassium hydroxide in 7 cm ³ of methanol. There is thus obtained, after flash chromatography on a silica column [eluent: dichloromethane / methanol (80/20 by volume)], 0.05 g of 4-chloro-2- {5,6-dimethoxy- 1- [2- ( 4-methyl-piperazin-1-yl) -ethyl] -lH-indol-3-yl} -lH- pyrrolo [2, 3-b] pyridine in the form of a solid, the characteristics of which are as follows: Melting point : 192 ° C (Kofler) NMR spectrum ^X H (300 MHz, (CD ₃₎ ₂ SO d6, d in ppm): 2.16 (s: 3H); 2.33 (mf: 4H); from 2.40 to 2.55 (mt: 4H); 2.74 (broad t, J = 6.5 Hz: 2H); 3.88 (S: 3H); 3.91 (s: 3H); 4.30 (wide t, J = 6.5 Hz: 2H); 6.71 (br s: 1H); 7.15 (d, J = 5 Hz: 1 H); 7.20 (s: 1H); 7.43 (s: 1H); 7.93 (S: 1H); 8.08 (d, J = 5 Hz: 1 H); 12.14 (mf: 1 H). Mass spectrum (IE): m / z = 453 [M] ⁺ ; m / z = 113 [C ₆ Hι ₃ N ₂ ] ⁺ ; (base peak) m / z = 70 [C ₄ H ₈ N] ⁺

b) 4-chloro-2- {5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] -H-indol-3-yl} -l- (toluene- 4-suifonyl) -1H- pyrrolo [2, 3-b] pyridine can be prepared as in Example 100b: But from 0.98 g of 4-chloro-2- [1- (2-iodoethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine, 0.21 g of potassium carbonate and 0.31 g of 1-methylpiperazine in 100 cm ³ of acetonitrile. There is thus obtained, after flash chromatography on a silica column [eluent: dichloromethane / methanol (90/10 by volume)], 0.52 g of 4-chloro-2- {5, 6-dimethoxy-1- [2- ( 4-methyl-piperazin-1-yl) -ethyl] -lH-indol-3-yl} -l- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3 ^ b] pyridine in the form of an oil the characteristics of which are as follows: Mass Spectrum (IE): m / z = 607 [M] ⁺ ; m / z = 452 [M - C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 113 [C ₅ Hι ₃ N ₂ ] ⁺ (base peak); m / z = 70 [C ₄ H ₈ N] ⁺

EXAMPLE 102: 2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] -1H-indol-3-yl} -1H-pyrrolo [2, 3-b ] pyridine-4-carbonitrile

2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine Carbonitrile can be prepared in the following manner: In a suspension, degassed with argon for approximately 15 minutes, of 0.3 g of 4-chloro-2- (5, 6-dimethoxy-1-methyl-1H -indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, 0.104 g of zinc cyanide, 0.016 g of zinc powder in 20 cm ³ of N, N- dimethylacetamide, 0.036 g of [1,1 '-bis (diphenylphosphino) ferrocene] palladium (II) is added. The reaction mixture is brought to a temperature in the region of 150 ° C. for approximately 1 hour. After returning to the vicinity of 20 ° C. and stirring of the mixture for 18 hours, the reaction mixture is filtered through celite and the insoluble material is washed with 100 cm ³ of dichloromethane. The filtrate is washed twice with 100 cm ³ of water and then with 100 cm ³ of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: dichloromethane / methanol (90/10 by volume)]. 0.08 g of 2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] -1H-indol-3-yl} -1H-pyrrolo is obtained [2 , 3-b] pyridine-4-carbonitrile in the form of a solid, the characteristics of which are as follows: Melting point: 196 ° C. (Kofler) NMR spectrum (300 MHz-, (CD ₃ ) ₂ SO d6, δ in ppm): 2.17 '(s 3H); 2.34 (mf: 4H); from 2.40 to 2.55 (mt: 4H) 2.75 (t, J = 6.5 Hz: 2H); 3.89 (S: 3H); 3.92 (s: 3H); 4.33 (broad t, J = 6.5 Hz: 2H); 6.88 (d, J = 1.5 Hz: 1H); 7, 23 (S: IIHH)) ;; 77,, 4455 ((dd ,, J = 5 Hz: IH); 7.49 (S: IH)! 8.03 (S: IH); 8.26 (d, J = 5 HZ IH); 12, 43 (broad s: IH). Mass spectrum (El): m / z = 444 [M] ⁺ ; m / z = 113 [C ₅ H ₁₃ N ₂ ] ⁺ (base peak); m / z = 70 [C ₄ H ₈ N] ⁺

EXAMPLE 103 5-chloro-2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH-pyrrolo [2,3-b] pyridine

a) 5-chloro-2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridine can be prepared as follows: A suspension 0.44 g of 5-chloro-3- (5,6-dimethoxy-1-methyl-1H-indol-3-ylethynyl) -pyridin-2-ylamine and 0.58 g of potassium tert-butoxide in 25 cm ³ of 1-methyl-pyrrolidin-2-one is heated to a temperature in the region of 70 ° C for approximately 4.5 hours. The mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 40 cm ³ of water and the pH of the suspension obtained is brought to approximately 4-5 by addition of glacial acetic acid. After. stirring for approximately 10 minutes, the solid is drained, washed with three times 5 cm ³ of water and then air dried. After recrystallization from 160 cm ³ of propan-1-ol, 0.28 g of 5-chloro-2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo is obtained [ 2, 3-b] pyridine in the form of a beige solid, the characteristics of which are as follows: Melting point: 282 ° C. (Capillary Bùchi). NMR (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.84 (s: 3H); 3.88 (s: 3H); 3.89 (s: 3H); 6.76 (br s: 1H); 7.14 (s: 1H); 7.42 (S: 1H); 7.81 (s: 1H); 7.91 (d, J = 3 Hz: 1 H); 8.09 (d, J = 3 HZ: 1H); 11.99 (mf: 1H). Mass spectrum (El): m / z = 341 [M] ⁺ (base peak); m / z = 326 [M - CH ₃ ] ⁺

b) 5-chloro-3- (5,6-dimethoxy-1-methyl-1H-indol-3-ylethynyl) -pyridin-2-ylamine can be prepared as follows: A suspension of 0.43 g of 5-chloro-3-ethynyl-pyridin-2-ylamine, 0.6 g of 3-iodo-5, 6-dimethoxy-1-methyl-1H-indole (example 103-f), 0.072 g of iodide of copper, in a mixture of 60 cm ³ of triethylamine and 30 cm ³ of dimethylformamide is degassed with argon for 15 minutes. 0.066 g of bis (triphenylphosphine) palladium (II) chloride is added to the preceding suspension. The mixture is stirred near 20 ° C for about 6 hours; 0.075 g of 5-chloro-3-ethynyl-pyridin-2-ylamine is added and the mixture stirred at this same temperature for 2 days. The mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 100 cm ³ of water and extracted with three times 100 cm ³ of dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (50/50 in volume)]. 0.44 g of 5-chloro-3- (5,6-dimethoxy-1-methyl-1H-indol-3-ylethynyl) -pyridin-2-ylamine is thus obtained in the form of a solid, the characteristics of which are following: Melting point: 192 ° C (Banc-Kôfler) Mass spectrum (El): m / z = 341 [M] ⁺ (base peak); m / z = 326 [M - CH ₃ ] ⁺ c) 5-chloro-3-ethynyl-pyridin-2-ylamine can be prepared as follows: A suspension of 1 6 g of 5-chloro-3-trimethylsilanylethynyl -pyridin-2-ylamine and 1.24 g of potassium fluoride in 80 cm ³ of methanol is brought to reflux for approximately 3.5 hours. After returning to a temperature in the vicinity of 20 ° C., the mixture is filtered through celite, the insoluble material is washed three with 50 cm ³ of methanol. The filtrate is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 100 cm ³ of dichloromethane. The solution obtained is washed with three times 60 cm ³ of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). 0.97 g of 5-chloro-3-ethynyl-pyridin-2-ylamine is thus obtained in the form of a solid, the characteristics of which are as follows: TLC silica [eluent: cyclohexane / ethyl acetate (50/50 in volumes)] Rf = 0.72 Mass Spectrum (CI): m / z = 153 [M + H] ⁺ (base peak)

d) 5-chloro-3-trimethylsilanylethynyl-pyridin-2-ylamine can be prepared as follows: A suspension of 2.54 g of 5-chloro-3-iodo-pyridin-2-ylamine, of 2.12 cm ³ of ethynyl-trimethylsilane, 0.38 g of copper iodide, 0.47 g of lithium chloride, in 7 cm ³ of triethylamine and 75 cm ³ of dimethylformamide is degassed under argon for approximately 15 minutes. 0.408 g of [1,1 '-bis (diphenylphosphino) ferrocene] palladium (II) chloride is added to the preceding suspension. The mixture is heated to around 0 ° C for about 19 hours and then concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 50 cm ³ of water, extracted with three times 100 cm ³ of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (70/30 by volume)]. 1.63 g of 5-chloro-3-trimethylsilanylethynyl-pyridin-2-ylamine is obtained in the form of a solid, the characteristics of which are as follows: Melting point: 108 ° C. (Banc-Kofler) Mass spectrum (IC ): m / z = 225 [M + H] ⁺ (base peak)

e) 5-chloro-3-iodo-pyridin-2-ylamine can be prepared as follows: A mixture of 6.43 g of 5-chloro-pyridin-2-ylamine and 12.38 g of N- iodosuccinimide in 300 cm ³ of glacial acetic acid is heated to around 55 ° C for 6 hours. After returning to a temperature of approximately 20 ° C., the mixture is stirred for approximately 18 hours and then concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 400 cm ³ of water; the pH of the suspension obtained is brought to approximately 8 by addition of a saturated aqueous solution of sodium hydrogencarbonate. The precipitate is drained, washed with water, dried at 40 ° C under reduced pressure (13 kPa) for about 3 hours. 12.35 g of 5-chloro-3-iodo-pyridin-2-ylamine are obtained in the form of a solid, the characteristics of which are as follows: TLC silica [eluent: cyclohexane / ethyl acetate (50/50 by volume)] Rf = 0.68 Mass spectrum (El): m / z = 254 [M] ⁺ (base peak); m / z = 127 [M - I] ⁺ ; m / z = 100 [127 - HCN] ⁺ ; m / z = 92 [127 - Cl] ⁺

f) The. 3-iodo-5,6-dimethoxy-1-methyl-1H-indole can be prepared as follows: To a solution of 0.5 g of 5,6-dimethoxy-1H-indole in 15 cm ³ of dimethylformamide is added 0.465 g of potassium hydroxide powder. A solution of 0.725 g of bi-sublimed iodine in 15 cm ³ of dimethylformamide is added dropwise to the preceding mixture. After stirring the reaction medium for approximately 3 hours at a temperature in the region of 20 ° C., 0.21 cm ³ of iodomethane is added dropwise while maintaining at this same temperature while cooling with a water bath. After stirring in the vicinity of 20 ° C for 1.5 hours, the mixture is poured onto a solution of 1.5 g of sodium thiosulfate in 150 cm ³ of water cooled in the vicinity of 5 ° C and stirred for approximately 10 minutes . The precipitate is drained, washed with five times 5 cm ³ of water cooled to around 5 ° C, then dried under vacuum (13 kPa) on phosphorus pentoxide. 0.78 g of 3-iodo-5, 6-dimethoxy-1-methyl-1H-indole is obtained in the form of a solid, the characteristics of which are the following: Melting point: 80-90 ° C with decomposition (Banc - Kofler) Mass spectrum (El): m / z = 317 [M] ⁺ (base peak); m / z = 302 [M - CH ₃ ] ⁺ ; m / z = 190 [M - I] ⁺ EXAMPLE 104: 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -5- fluoro-1H-pyrrolo [2, 3-b] pyridine a) 2- (5, 6- dimethoxy-1-methyl-1H-indol-3-yl) -5-fluoro- 1H-pyrrolo [2, 3-b] pyridine can be prepared as in Example 103a: But from 0.19 g-- of 3- (5, 6- ^ dimethoxy-1- methyl-1H-indol-3-ylethynyl) -5-fluoro-pyridin-2-yiamine, 0.263 g of potassium tert-butoxide in 15 cm ³ of l- methyl-pyrrolidin-2-one. This gives, after flash chromatography on a silica column [eluent: dichloromethane / ethyl acetate (90/10 by volume)], 0.046 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3 -yl) -5- fluoro-1H-pyrrolo [2, 3-b] pyridine in the form of a solid, the characteristics of which are as follows: Melting point: 283 ° C. (Buchi capillary) NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.83 (S: 3H); 3.87 (s: 3H); 3.89 (s: 3H); 6.76 (br s: 1H); 7.13 (s: 1H); 7.41 (s: 1H); 7.70 (dd, J = 9.5 and 3 Hz: 1 H); 7.80 (S: 1H); 8.06 (dd, J = 3 and 2.5 Hz: 1H); 11.87 (mf: 1 H). Mass spectrum (El): m / z = 325 [M] ⁺ (base peak); m / z = 310 [M - CH ₃ ] ⁺ ; m / z = 282 [M - CO] ⁺

b) 3- (5,6-dimethoxy-1-methyl-1H-indol-3-ylethynyl) -5- fluoro-pyridin-2-ylamine can be prepared in the following manner: In a suspension, degassed with argon for about 15 minutes, 0.57 g of 3-ethynyl-5,6-dimethoxy-1-methyl-1H-indole, 0.316 g of 5-fluoro-3-iodo-pyridin-2-ylamine, 0 0.06 g of copper iodide in 39.5 cm ³ of triethylamine and 20 cm ³ of dimethylformamide, 0.049 g of bis (triphenylphosphine) chloride is added palladium (II) and the mixture is stirred at a temperature in the region of 20 ° C for 18 hours then concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 150 cm ³ of dichloromethane. The organic solution is washed with five times 50 cm ³ of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (50/50 by volume)]. 0.14 g of 3- (5, 6-dimethoxy-1-methyl-1H-indol-3-ylethynyl) -5-fluoro-pyridin-2-ylamine is obtained in the form of a solid, the characteristics of which are as follows : TLC silica [eluent: dichloromethane / methanol (98/2 by volume)] Rf = 0.28 Mass Spectrum (CI): m / z = 326 [M + H] ⁺ (base peak)

c) 5-fluoro-3-iodo-pyridin-2-ylamine can be prepared as in Example 103e: But starting with 5 g of 5-fluoro-pyridin-2-ylamine and 11.04 g of N -iodosuccinimide in 250 cm ³ of glacial acetic acid. 6.1 g of 5-fluoro-3-iodo-pyridin-2-ylamine are thus obtained in the form of a solid, the characteristics of which are as follows: Melting point: 70 ° C. (Banc-Kofler) Mass spectrum ( IC): m / z = 239 [M + H] ⁺ (base peak)

d) 3-Ethynyl-5,6-dimethoxy-1-methyl-1H-indole can be prepared as in Example 103c: But starting with 1.71 g of 5,6-dimethoxy-1-methyl-3 -trimethylsilanylethyl-1H-indole and 1.04 g of potassium fluoride in 70 cm ³ of methanol. 1 g of 3-ethynyl-5,6-dimethoxy-1-methyl-1H-indole is thus obtained in the form of a solid, the characteristics of which are as follows:. TLC silica (eluent: dichloromethane) Rf = 0.49 Mass spectrum (El): m / z = 215 [M] ⁺ (base peak); m / z = 200 [M - CH ₃ ] ⁺ m / z = 172 [M - CO] ⁺ e) 5,6-dimethoxy-1-methyl-3-trimethylsilanylethynyl-1H-indole can be prepared as follows : To a suspension of 3.81 g of 3-iodo-5,6-dimethoxy-1-methyl-1H-indole, of 2.36 g of ethynyl-trimethyl silane, of _. 0.457 g of copper iodide in 150 cm ³ of triethylamine, degassed under argon for 15 minutes, is added 0.421 g of bis (triphenylphosphine) palladium (II) chloride. The mixture is stirred at a temperature in the region of 20 ° C for approximately 18 hours and then heated in the vicinity of 50 ° C for approximately 24 hours. After returning to a temperature in the region of 20 ° C., the mixture is diluted with 100 cm ³ of ethyl acetate, washed with 150 cm ³ of water. The aqueous phase is re-extracted with twice 150 cm ³ of ethyl acetate; the combined organic phases are washed with 200 cm ³ of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated to -sec under reduced pressure (13 kPa). After filtration through silica and elution with dichloromethane, 1.71 g of 5, 6-dimethoxy-1-methyl-3-trimethylsilanylethynyl-1H-indole are obtained in the form of a solid, the characteristics of which are as follows: Melting point : 124 ° C (Banc-Kôfler) Mass spectrum (El): m / z = 287 [M] ⁺ (base peak); m / z = 272 [M - CH ₃ ] ⁺ m / z = 214 [M - SiMe ₃ ] ⁺

3-iodo-5,6-dimethoxy-1-methyl-1H-indole is described in Example 103f. EXAMPLE 105: 2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] -5-fluoro-1H-pyrrolo [2, 3-b] pyridine

a) 2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H-indol-3-yl] -5-fluoro-1H-pyrrolo [2, 3-b] pyridine can be prepared as follows: To a solution of 0.83 g of 2- [5,6-dimethoxy-l- (2- mόrpholin-4-yl-ethyl) -IH-indol-3-yl] -5 -fluorô-l- (toluene- 4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine in 100 cm ³ of methanol brought to reflux, a solution of 2.08 g of potassium hydroxide in 7 cm ³ water is added. The mixture is stirred 3.5 hours at reflux. After returning to around 20 ° C, the mixture is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 50 cm ³ of water and extracted with three times 80 cm ³ of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: ethyl acetate / methanol (90/10 by volume)]. 0.37 g of 2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] -5-fluoro-1H-pyrrolo is obtained [2, 3 -b] pyridine in the form of a solid, the characteristics of which are as follows: Melting point: 205-210 ° C (Banc-Kôfler) NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, d in ppm) : 2.49 (broad t, J = 4.5 Hz: 4H); 2.73 (t, J = 6.5 Hz: 2H); 3.61 (broad t, J = 4.5 Hz: 4H); 3.87 (s: 3H); 3.89 (s: 3H); 4.32 (wide t, J = 6.5 Hz: 2H); 6.78 (br s: 1H); 7.20 (s: 1H); 7.41 (s: 1H); 7.70 (dd, J = 9.5 and 3 Hz: 1 H); 7.89 (s: 1H); 8.07 (dd, J = 3 and 2.5 Hz: 1 H); 11.88 (mf: 1 H). Mass spectrum (El): m / z = 424 [M] ⁺ ; m / z = 100 [C ₅ H ₁₀ NO] ⁺ (base peak) b) 2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -1H- indol-3-yl] -5-fluoro-1- (toluene-4-sulfonyl) -lH -pyrrolo [2, 3-b] pyridine can be prepared as in example 100b: But from 1 g of 5-fluoro-2- [1- (2-iodoethyl) -5,6-dimethoxy- 1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] yridine, 0.223 g of potassium carbonate, 0.28 cm ³ of morpholine in 100 cm ³ acetonitrile. 0.83 g of 2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] - 5-fluoro-1- (toluene-4) is thus obtained -suifonyl) -lH-pyrrolo [2, 3-b] pyridine in the form of a solid the characteristics of which are as follows: Melting point: 182 ° C. = 620 [M '+ H) ⁺ ; m / z = 579 [M + H) ⁺ (base peak)

c) 5-fluoro-2- [1- (2-iodo-ethyl) -5,6-dimethoxy-1H- indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2 , 3-b] pyridine can be prepared as in Example 100c: But from 2 g of 5-fluoro-2- [1- (2-chloroethyl) -5,6-dimethoxy-IH-indol- 3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine, 0.85 g of sodium iodide in 100 cm ³ of 2-butanone. 2.2 g of 5-fluoro-2- [1- (2-iodo-ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) are thus obtained - 1H-pyrrolo [2,3-b] pyridine in the form of a solid, the characteristics of which are as follows: Melting point: 176 ° C. (Banc-Kofler) Mass spectrum (El): m / z = 619 [M ] ⁺ ; m / z = 492 [M - I] ⁺ ; m / z = 464 [M - C ₇ H ₇ 0 ₂ S] ⁺ (base peak); m / z = 337 [464 - I] ⁺ d) 5-fluoro-2- [1- (2-chloro-ethyl) -5,6-dimethoxy-1H- indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2 , 3-b] pyridine can be prepared as in Example 100d: But from 2 g of 2- (5, 6-dimethoxy-1H-indol-3-yl) -5-fluoro-1- (toluene- 4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine, 0.028 g of tetrabutylammonium bromide, 1.89 g of potassium hydroxide and 1.38 g of potassium carbonate in 50 cm ³ of 1,2-dichloro-ethane. There is thus obtained, after flash chromatography on a silica column [eluent: dichloromethane / methanol (98.5 / 1.5 by volume)], 2.05 g of 5-fluoro-2- [1- (2-chloro-ethyl ) -5,6- dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3 -b] pyridine in the form of a solid, the characteristics of which are as follows : Melting point: 150 ° C (Kδfler) Mass spectrum (El): m / z = 527 [M] ⁺ ; m / z = 372 [M - C ₇ H ₇ 0 ₂ S] ⁺ (base peak)

e) 2- (5,6-dimethoxy-1H-indol-3-yl) -5-fluoro-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine can be prepared from as follows: A mixture of 3.1 g of 5-fluoro-2-iodo-l- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine, 2.4 g of acid 1-tert -butyloxycarbonyl-5, 6-dimethoxy-IH-indole-3-boronic, 20.3 cm ³ of a saturated aqueous solution of sodium hydrogen carbonate in 100 cm ³ of dimethylformamide is degassed with argon for approximately 15 minutes then 0.43 g of tetrakis palladium (triphenylphosphine) is added. The mixture is heated to around 110 ° C for about 2 hours and then concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 500 cm ³ of water, extracted with three times 250 cm ³ of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The residue is taken up in 100 cm ³ of diisopropyl ether, drained, washed three times 20 cm ³ of diisopropyl ether, dried under reduced pressure (13 kPa) in the presence of potassium hydroxide in pellets at a temperature in the region of 20 ° C. 2.66 g of 2- (5, 6-dimethoxy-1H-indol-3-yl) -5-fluoro-1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine are obtained in the form of a solid, the characteristics of which are as follows: Melting point: 218 ° C. (Kofler) Mass spectrum (El): m / z = 465 [M] ⁺ ; m / z = 310 [M - C ₇ H ₇ 0 ₂ S] ⁺ (base peak)

The 1-tert-butyloxycarbonyl-5,6-dimethoxy-1H-indole-3-boronic acid is prepared as described in patent WO 03000688A1. f) 5-fluoro-2-iodo-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine can be prepared as follows: In a solution, cooled to about -78 ° C, 3.5 g of 5-fluoro-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine in 100 cm ³ of tetrahydrofuran, is added dropwise, maintaining the temperature from the medium in the vicinity of -75 ° C, 7.54 cm ³ of a 1.6N solution of n-butyllihium in hexane. After stirring for approximately one hour at this same temperature, a solution of 6.12 g of bi-sublimed iodine in 50 cm ³ of tetrahydrofuran is poured dropwise. After the temperature has returned to around 20 ° C., the reaction mixture is diluted with 600 cm ³ of ethyl acetate, washed three times with 100 cm ³ of a 5% aqueous solution of sodium thiosulfate, dried over magnesium sulphate, treated with vegetable black, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 30 cm ³ of diisopropyl dioxide, drained, washed with three times 5 cm ³ of diisopropyl oxide, dried under reduced pressure (13 kPa). 3.6 g of 5-fluoro- are obtained. 2 -iodo-l- (toluene- 4-tallow onyl) -lH-pyrrolo [2, 3 -b] pyridine in the form of a solid, the characteristics of which are as follows: Melting point: 158 ° C. (Kofler) Spectrum Mass (El): m / z = 416 [M] ⁺ ; m / z = 352 [M - S0 ₂ ] ⁺ ; m / z = 155 [C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 91 [C ₇ H ₇ ] ⁺ (base peak) g) 5-fluoro-1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine can be prepared from as follows: A mixture of 2.3 g of 5-fluoro-1H-pyrrolo [2,3-b] pyridine, of 3.54 g of 4-methyl-benzene-sulfonyl chloride, of 7.56 g of sodium hydroxide dissolved in 55 cm ³ of water, 0.115 g of tetrabutylammonium hydrogen sulphate in 125 cm ³ of toluene is stirred for about 24 hours near 20 ° C. The mixture is diluted with 500 cm ³ of ethyl acetate; the organic phase is washed with three times 200 cm ³ of water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: dichloromethane]. 3.85 g of 5-fluoro-1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine are obtained in the form of a solid, the characteristics of which are as follows: Melting point: 160 ° C (Banc-Kôfler) Mass Spectrum (El): m / z = 290 [M] ⁺ ; m / z = 226 [M - S0 ₂ ] ⁺ -; m / z = 155 [C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 91 [C ₇ H ₇ ] ⁺ (base peak)

h) 5-fluoro-1H-pyrrolo [2, 3-b] pyridine can be prepared as follows: A mixture of 3.8 g of 5-fluoro-3-trimethylsilanyl-ethynyl-pyridin-2-ylamine and 3.4 g of potassium tert-butoxide in 100 cm ³ of 1-methyl-pyrrolidin-2-one is brought to the vicinity of 130 ° C. for approximately 4 hours. After returning to a temperature in the region of 20 ° C., the mixture is poured onto 1000 cm ³ of a saturated aqueous solution of sodium chloride and extracted with 5 times 250 cm ³ of diethyl ether. The organic phases are combined, washed with 5 times 100 cm 3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). 2.35 g of 5-fluorb-1H-pyrrolo [2, 3-b] pyridine are obtained in the form of a solid, the characteristics of which are as follows: Melting point: 110 ° C. (Banc-Kofler) Mass spectrum (EI): m / z = 136 [M] ⁺ (base peak); m / z = 109 [M - HCN] ⁺

i) 5-fluoro-3-trimethylsilanylethynyl-pyridin-2-ylamine can be prepared as described in example 103d: But from 14 g of 5-fluoro-3-iodo-pyridin-2-ylamine, from 12 , 47 cm ³ of ethynyl-trimethyl silane, 2.24 g of copper iodide, 2.74 g of lithium chloride, 41.33 cm ³ of triethylamine and 2.15 g of chloride of [1, l -bis (diphenylphosphino) ferrocene] palladium (II) in 441 cm ³ of dimethylformamide. 7.91 g of 5-fluoro-3-trimethylsilanylethyl-pyridin-2-ylamine are thus obtained, after flash chromatography on a column of silica (eluent: dichloromethane), in the form of a solid, the characteristics of which are as follows: melting: 65 ° C (Kofler) Mass spectrum (El): m / z = 208 [M] ⁺ ; m / z = 193 [M - CH ₃ ] ⁺ (base peak)

5-fluoro-3-iodo-pyridin-2-ylamine is described in Example 104c. EXAMPLE 106 2- (5,6-dimethoxy-1- [2- (4-methyl-piperrazin-1-yl) -ethyl) -1H-indol-3-yl} -5-fluoro-1H-pyrrolo [2 , 3- b] pyridine a) 2- {5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -IH-indol-3-yl} -5-fluoro -lH-pyrrolo [2, 3-b] pyridine can be prepared as in Example 105a: But starting from 0.82 g of 2- [5,6-dimethoxy-1- [2- (4-methyl- piperazin-1-yl) -ethyl] -IH-indol-3-yl] -5-fluoro-l- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine dissolved in 100 cm ³ of methanol and 2 g of potassium hydroxide dissolved in 7 cm ³ of water. Thus, after flash chromatography on a silica column [eluent: dichloromethane / methanol (70/30 by volume)], 0.37 g of 2- {5,6-dimethoxy-1- [2- (4-methyl- piperazin-1-yl) -ethyl] -IH-indol-3-yl} -5-fluoro-1H-pyrrolo [2, 3-b] pyridine in the form of a solid with the following characteristics: Melting point : 210 ° C (Kofler) ³ -H NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.16 (s: 3H); 2.32 (mf: 4H); from 2.40 to 2.55 (t: 4H); 2.73 (broad t, J = 6.5 Hz: 2H); 3.87 (s: 3H); 3.89 (s: 3H); 4.30 (wide t, J = 6.5 Hz: 2H); 6.76 (br s: 1H); 7.18 (s: 1H); 7.42 (s: 1H); 7.71 (dd, J = 9.5 and 3 Hz: 1 H); 7.88 (S: 1H); 8.07 (mt: 1H); 11.87 (mf: 1 H). Mass spectrum (El): m / z = 437 [M] ⁺ ; m / z = 113 [C ₆ H ₁₃ N ₂ ] ⁺ (base peak); m / z = 70 [C ₄ H ₈ N] ⁺

b) 2- [5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -IH-indol-3-yl] -5-fluoro-1- (toluene- 4-sulfonyl) -IH- pyrrolo ^, 3-b] pyridine can be prepared as described in Example 100b: But starting from 1 g of 5-fluoro-2- [1- (2-iodoethyl) - 5, 6-dimethoxy-IH-indol-3-yl] -1- (toluene-4- suifonyl) -IH-pyrrolo [2, 3-b] pyridine, 0.223 g of potassium carbonate, 0.323 g of 1-methyl-piperazine in 100 cm ³ of acetonitrile. 0.83 g of 2- [5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - IH-indol-3-yl] -5-fluoro- is thus obtained l- (toluene-4-suifonyl) -lH-pyrrolo [2,3-b] pyridine in the form of a solid, the characteristics of which are as follows: Melting point: 188 ° C. (Banc-Kofler) Mass spectrum ( E1): m / z = 591 [M] ⁺ ; m / z = 491 [M - C ₄ H ₈ N] ⁺ ; m / z = 436 [M - C ₇ H ₇ 0 ₂ S] ⁺ ; m / z = 113 [C ₆ H _ι3 N ₂ ] ⁺ (base peak); m / z = 70 [C ₄ H ₈ N] ⁺

EXAMPLE 107 Acid [1-carboxymethyl-5-methoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -IH-indol-6-yloxy] -acetic

a) The [1-carboxymethyl-5-methoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -IH-indol-6-yloxy] -acetic acid is prepared in the following manner : In a hemolysis tube containing {5-methoxy-1-methoxycarbonylmethyl-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-2-yl] acetate - 1H-indol-6-yloxy} -acetic, (0.056 g; 97.1 μmol), 0.3 cm ³ of a methanolic potassium solution (0, lg / cm ³ ) is placed and then stirred at 20 ° C. for 16 hours. The reverse phase liquid chromatography analysis coupled with mass spectrometry shows that the expected is formed but is not the majority. The purification attempts carried out at this stage of the reaction are unsuccessful and the compounds obtained, all containing mixtures of starting and expected product, are evaporated and reacted with 2 cm ³ of methanolic potash (0.1 g / cm ³ ) for 20 hours. The reaction mixture takes on a milky color. Evaporated to dryness and taken up in a mixture of 1.cm ³ of dimethyl sulfoxide and 1 cm ³ of a solution aqueous hydrochloric acid 6M. The solution thus obtained is purified by reverse phase liquid chromatography coupled to mass spectrometry (Method C) after filtration of the white precipitate which has formed. After evaporation of the fractions, the tubes containing the expected compound are combined to obtain the acid [1- carboxymethyl-5-methoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -lH-iïidôl -6-yloxy] -acetic, (0.015 g; 31%), the characteristics of which are as follows: LC / MS analysis: tr = 2.9 min [M + H] ⁺ ; m / z = 396.17 [M + H] ⁺ b) The methyl ester of {5-methoxy-1-methoxycarbonylmethyl-3- [1- (toluene-4-sulfonyl) -IH-pyrrolo acid [2 , 3-b] pyridin-2-yl] -IH-indol-6-yloxy} -acetic is prepared in the following way: In a hemolysis tube 1.3 x 10 cm a solution of 5-methoxy-3 is placed - [1- (toluene-4-suifonyl) -1H- pyrrolo [2, 3-b] pyridin-2-yl] -lH-indol-6-ol, (0.043 g; 100 μmol), in solution in dimethylformamide (10 cm ³ ) then potassium carbonate (0.027 g;

200 μmol) and stirred for 5 minutes at room temperature. Add methyl bromoacetate (0.028 cm ³ ; 300 μmol) and then heat to 50 ° C for

4 hours, TLC control (eluent cyclohexane / ethyl acetate 50/50 v / v) showing that the reaction is finished. The reaction mixture is poured onto 5 cm ³ of distilled water and then the reaction mixture is extracted with ethyl acetate (15 cm ³ ). The combined extracts are washed with water (20 cm ³ ), dried over magnesium sulfate, filtered and evaporated to give a crude compound which is purified by chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (60/40 v / v). The fractions containing the expected compound are combined and evaporated to give the methyl ester of {5-methoxy-1-methoxycarbonylmethyl- acid. 3- [1- (toluene-4-suifonyl) -1H-pyrrolo [2,3-b] pyridih-2-yl] - IH-indol-6-yloxy} -acetic, (0.056 g; 97%) whose characteristics are as follows: LC / MS analysis: tr = 4.1, m / z = 578.1 [M + H] ⁺

c) 5-methoxy-3- [1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3- b] pyridin-2-yl] -1H-indol-6-ol is prepared as follows : In a three-necked flask of 100 cm ³ , a solution _d_e ..2- (.6-benzylQxy-5-methylQχy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo is treated [2, 3-b] pyridine, (0.52 g; 993 μmol), in acetonitrile (40 cm ³ ) with trimethyl silyl iodide (0.353 cm ³ ; 2.483 mmol; 2.5 eq.) at 50 ° C for 2 hours then for 16 hours at 20 ° C. After evaporation, the reaction mixture is taken up in a mixture of dichloromethane (50 cm ³ ) and water (50 cm ³ ) and then decanted. The aqueous phase is extracted with dichloromethane (250 cm ³ ); the extracts are combined, dried over magnesium sulfate and evaporated to give a compound which is purified by chromatography on silica gel (10 g, silica 35 μm), eluting with a mixture of cyclohexane and ethyl acetate ( 60/40 vol / vol). The fractions containing the expected compound are combined and evaporated, resulting in a solid which is triturated in diisopropyl ether to obtain 5-methoxy-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2 , 3-b] pyridin-2-yl] -1H-indol-6-ol (0.215 g; 50%) whose characteristics are as follows: NMR spectrum ^X H (300 MHz, (CD ₃₎ ₂ SO d6, δ in ppm): 2.30 (s: 3H); 3.75 (s: 3H); 6.75 (s: 1H); 6.90 (s: 1H); 6.93 (br s: 1H); 7.26 (broad d, J = 8.5 Hz: 2H); 7.304 (dd, J = 8 and 5 Hz: 1 H); 7.42 (d, J = 2.5 Hz: 1 H); 7.57 (broad d, J = 8.5 Hz: 2H); 7.94 (dd, J = 8 and 1.5 Hz: 1 H); 8.34 (dd, J = 5 and 1.5 Hz: 1 H); 8.71 (br s: 1H); 11.08 (br s: 1H). EXAMPLE 108 Acid {5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-2-yl] -lH-indol-6 - yloxy} -acetic a) {5-Methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-2-yl] -IH acid -indol-6-yloxy} -acetic is prepared as follows: In a 10 cm ³ flask, place a solution of {5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-2-yl] -lH-in.dol-6-yloxy} -acetate. methyl, (0.91 g; 1.751 mmol), in methanolic potash (74 cm ³ to 1 g / cm ³ ) with stirring at 20 ° C for 16 hours. After reaction, the precipitate formed is filtered, rinsed with methanol (20 cm ³ ). In a 250 cm ³ Erlenmeyer flask, a suspension of the above solid is placed in water (30 cm ³ ) and then the pH is adjusted to 4 with 2N aqueous hydrochloric acid. The yellow solid formed is triturated in the reaction mixture, then filtered, rinsed with water and dried under reduced pressure. Is isolated {5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-2-yl] -lH-indol-6- yloxy} -acetic, (0.666 g; 98%), the characteristics of which are as follows: Mass spectrum (CI): m / z = 352 [M + H] ⁺ (base peak)

b) The methyl ester of {5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-2-yl] - 1H acid -indol-6-yloxy} -acetic is prepared as follows: In a three-necked 25 cm ³ under argon, a solution of 5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) is placed ) - 1H-pyrrolo [2,3-b] pyridin-2-yl] -lH-indol-6-ol, (0.558 g; 1.247 mmol) in solution in dimethylformamide (10 cm ³ ) then the hydride is added sodium (0.045 g; 1.49 mmol) and stirred for 10 minutes at temperature 005/095399

152 ambient. As soon as the evolution of gas ceases, methyl bromoacetate (0.142 cm ³ ; 1.496 mmol) is added dropwise, then the mixture is left to stir at ambient temperature for 3 hours. The reaction mixture is poured into 100 cm ³ of distilled water and the solid formed is filtered and washed with water. (30 cm ³ ). The solid is dissolved in dichloromethane (150 cm ³ ) then the solution thus obtained is washed ^" with distilled water (50 cm ³ ), dried over magnesium sulphate then evaporated under reduced pressure, leading to {5-methoxy- methyl l-methyl-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-2-yl] -lH-indol-6-yloxy} -acetate '' a brown-colored oil (0.5 g; 77%), the characteristics of which are as follows: LC / MS analysis: tr = 4.1 min; m / z = 520.13 [M + H ⁺ )

c) 5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) -1H- pyrrolo [2,3-b] pyridin-2-yl] -lH-indol-6-ol is prepared in the following way: In a three-necked flask of 250 cm ³ and at 20 ° C, a solution of 2- (6-benzyloxy-5-methoxy-1-methyl-1H-indol-3-yl) -1- ( toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine (1.5 g; 2.79 mmol) in acetonitrile (120 cm ³ ) then trimethyl silyl iodide is added dropwise (0.956 cm ³ ; 6.97 mmol). The reaction mixture is heated at 50 ° C for 4 hours and then evaporated to dryness under reduced pressure. The evaporation residue is taken up in dichloromethane (200 cm ³ ) then washed with distilled water (1 x 200 cm ³ ). The extracts are combined, washed with distilled water, dried over magnesium sulfate and evaporated under reduced pressure, to yield the crude compound which is purified by chromatography on silica cartridge (AIT FlashSmart Pack, BP-0610300-093 , 50 g silica), eluting at 15 cm ³ / min with a dichloromethane / ethyl acetate mixture (95/5 v / v). The fractions containing the expected product are combined and evaporated to give 5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-2-yl] -1H- indol-6-ol ( 0.87 g; 70%) in the form of an ocher meringue used as is for the next step. d) 2- (6-Benzyloxy-5-methoxy-1-methyl-1H-indol-3-yl) - 1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared as follows: In a 25 cm ³ three-necked flask placed under argon, a solution of 2- (6-benzyloxy-5-methoxy-1H-indol-3-yl) - 1- (toluene-4-sulfonyl) is placed -H-pyrrolo [2, 3-b] pyridine (1 g, 1.9 mmol) in dimethylformamide (10 cm ³ ) then sodium hydride (0.063 g; 2.101 mmol) is added and the mixture is left to stir for 15 minutes. When the evolution of gas ceases, methyl iodide (0.131 cm ³ , 2.101 mmol) is added dropwise, then the mixture is left to react at 21 ° C. for 2 hours. The reaction medium is poured onto 100 cm ³ of distilled water, then extracted with 2 times 100 cm ³ of dichloromethane. The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The evaporation compound is triturated in diisopropyl ether. The powdery solid compound thus obtained is filtered and rinsed. We isolate 2- (6-benzyloxy-5-methoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine (0.888 g; 86%) in the form of a beige solid, the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.30 (s: 3H); 3.77 (s: 3H); 3.87 (s: 3H); 5.21 (S: 2H); 6.76 (s: 1H); 7.00 (s: 1H); 7.27 (broad d, J = 8.5 Hz: 2H); 7.29 (s: 1H); 7.31 (dd, J = 8 and 5 Hz: 1 H); 7.39 (broad t, J = 7.5 Hz: 1 H); 7.47 (wide t, J = 7.5 Hz: 2H); 7.51 (S: 1H); from 7.55 to 7.65 (mt: 4H); 7.95 (dd, J = 8 and 1.5 Hz IH) 8.36 (dd, J = 5.5 and 1.5 Hz IH).

2- (6-Benzyloxy-5-methoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine was prepared as described in WO03000688A1.

Examples 109 to 146

Preparation of the reagents: A ^" solution ^" of acid ^" [5-methxyxyl-methyl ^" -3 ^~ - (1H ^ pyrrolo [2,3-b] pyridin-2-yl) -IH-indol-6-yloxy ] - 10 acetic, (prepared as in Example 108), (0.228 g; 0.585 mmol), in dimethylformamide (3.25 cm ³ ; Solution A) as well as a solution of N, N'- dicyclohexylcarbodiimide (0.465 g, 2.25 mmol) in dimethylformamide (3.75 cm ³ ; Solution C) and that a mixture of 1-hydroxybenzotriazole (0.206 g; 1.52 mmol) and dimethylaminopyridine (0.015 g; 0.12 mmol ) in dimethylformamide (3.75 cm ³ ; Solution D) are prepared and placed in tanks. Each amine in the table below can be weighed and diluted in dimethylformamide. Table 1: reagent used

PREPARATION OF THE NON-COMMERCIAL AMINES USED Preparation of Perhydropyrrolo [3,4-c] pyrroledione-1,3-cis (Example 118): a) Perhydropyrrolo [3,4-c] pyrrole-1,3-dione-cis is prepared as follows: In a 1000 cm ³ autoclave, place a solution of 5-benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione, (11.5 g; 49.9 mmol ) in ethanol (200 cm ³ ) then the palladium on charcoal (5%; 2 g; 0.9 mmol) is added. After having purged the reactor using nitrogen, the autoclave is placed under 58 bars of hydrogen at 70 ° C for 16 hours. After returning to 20 ° C., filtration and washing of the catalyst, the mixture is evaporated under reduced pressure and then the solid obtained is recrystallized from methanol (100 cm ³ ) and dried under reduced pressure to constant weight. Is isolated perhydropyrroio [3,4-c] pyrrole-1,3-dione, (3.6 g) whose characteristics are as follows. :. Melting Point: 222 ° C (Kofler)

b) 5-Benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione is prepared as follows: In a 1000 cm ³ flask, a suspension of 2-acetyl-5 is placed benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione, (107.7 g; 395 mmol) in ethanol which is warmed while adding a 4N aqueous solution of sodium hydroxide (200 cm ³ ). The reaction mixture is stirred for 30 minutes and then evaporated under reduced pressure. The evaporation residue is taken up in a mixture of water (100 cm ³ ) and ethyl acetate (300 cm ³ ) which is acidified to pH 4 by addition of aqueous hydrochloric acid

4N (100 cm ³ ). After decantation and extraction with ethyl acetate (2 x 200 cm ³ ), the organic extracts are combined, washed with brine (100 cm ³ ), dried over magnesium sulfate, filtered and evaporated under reduced pressure. The evaporation residue is crystallized from ethanol (100 cm ³ ) and then 7.5 g of the solid obtained are recrystallized from acetonitrile (25 cm ³ ). The solid obtained is filtered, washed with acetonitrile (5 cm ³ ) and then dried under reduced pressure to constant weight. 5-Benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione (5.8 g) is isolated, the characteristics of which are as follows: Melting point: 158 ° C. (Kofler). c) 2-acetyl-5-benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione is prepared as follows: In a three-necked flask of 2000 cm ³ , a mixture of N- acetyl maleimide (64 g; 460 mmol) and n-butoxymethyl n-trimethylsilylmethyl benzylamine (128 g; 460 mmol) in dichloromethane (1000 cm ³ ) then the reaction mixture is cooled to 10 ° C. While maintaining effective agitation, the trifluoroacetic acid (0.5 cm ³ ) is poured. The temperature of the reaction mixture increases to ^"38 ° C over 15 minutes. It is added ^carbonate" potassium (100 g) and stirred the reaction mixture for 48 hours at 20 ° C. The solid is removed by filtration, then the filtrate is evaporated under reduced pressure. The oil obtained is purified by chromatography on silica gel (silica, 40-63 μm, eluent cyclohexane / ethyl acetate 65/35 v / v). The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing 2-acetyl-5-benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione, (107.7 g; 86% ), in the form of a brown oil which is used directly in the next step.

d) The N-acetyl maleimide is prepared as follows: In a three-necked flask of 1000 cm ³ , a solution of maleimide (68 g; 700 mmol) is placed in acetic anhydride (500 cm ³ ) then the mixture is brought reaction reflux for 3 hours. After returning to 20 ° C, the reaction mixture is evaporated under reduced pressure leading to an oil which is crystallized from ethyl acetate (100 cm ³ ). After filtration of the solid and washing with ethyl acetate (25 cm ³ ) and diisopropyl ether (100 cm ³ ), drying under reduced pressure at constant weight, the N-acetyl maleimide is isolated, (64.1 g; 65.8%), the characteristics of which are as follows: Melting point: 58 ° C. (Kofler) Preparation of perhydropyrrolo [3,4-c] pyrrole-1-one-cis (Example 128): a) Hexahydro-pyrrolo [3,4-c] pyrrole-1-one is prepared as follows: In a 250 cm ³ autoclave, place a solution of 5-benzyl-hexahydro-pyrrolo [3,4-c] pyrrole-1-one, (7.2 g; 33 mmol) in absolute ethanol (100 cm ³ ) then 5% palladium on charcoal (1.5 g) is added. After purging with nitrogen, the autoclave is placed under 56 bars. hydrogen at 70 ° C for 16 hours. After returning to 20 ° C., the catalyst is filtered and the filtrate is evaporated under reduced pressure. The compound obtained is taken up in acetonitrile (15 cm ³ ) at reflux, filtered hot on paper and then crystallized. After crystallization, the solid obtained is filtered, washed with acetonitrile (3 cm ³ ) then with diethyl ether (20 cm ³ ) and finally dried under reduced pressure at constant weight. The hexahydropyrrolo is isolated [3, 4-c] pyrrole-l-one, (1.3 g; 31%), the characteristics of which are as follows: Melting point: 145 ° C. (Kofler)

b) The 5-benzyl-hexahydro-pyrrolo [3,4-c] pyrrole-l-one is prepared in the following manner: In a three-necked flask of 1000 cm ³ , the 5-benzyl-3-hydroxy-hexahydro- is placed pyrrolo [3,4-c] pyrrole-1-one, (7 g; 30 mmol) suspended in dichloromethane (50 cm ³ ) then cooled in an ice bath. At 3 ° C., trimethylsilane (7.1 g; 60 mmol) is poured in slowly. The reaction mixture is homogeneous and is left to react at 25 ° C for 10 minutes and then cooled to 3 ° C to pour the trifluoroacetic acid (50 cm ³ ). The reaction mixture is stirred at 20 ° C for 16 hours and then evaporated under reduced pressure. The residue is taken up in a mixture of ethyl acetate (100 cm ³ ) and 4 N aqueous sodium hydroxide (50 cm ³ ), decanted and washed with water (100 cm ³ ). After drying over magnesium sulfate, evaporation under reduced pressure, a yellow oil is isolated which is purified by chromatography on silica gel (silica 40-63 μm, eluent ethyl acetate / methanol 90/10). The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing 5-benzyl-hexahydro-pyrrolo [3,4-c] pyrrole-1-one, (1, 1 g) which one. use directly in the next step. c) 5-Benzyl-3-hydroxy-hexahydro-pyrrolo [3,4-c] pyrrole-1-one is prepared as follows: In a three-necked flask of 500 cm ³ , a suspension of lithium aluminum tetrahydride (2 g; 55 mmol) in tetrahydrofuran, cooled to 3 ° C. in an ice bath, is added a solution of 5-benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione, ( 12.7 g; 55 mmol), {preparation described for the preparation of perhydropyrrolo [3,4-c] pyrrole-1,3-dione-cis (b)}. The reaction mixture is stirred at this temperature for 25 minutes then water (2 cm ³ ), 4N aqueous sodium hydroxide (2 cm ³ ) and water (6 cm ³ ) are successively added. The solid thus formed is removed by filtration; the filtrate is dried over magnesium sulphate then evaporated under reduced pressure leading to a white solid which is triturated in diisopropyl ether (50 cm ³ ). The solid formed is filtered, washed with diisopropyl ether (25 cm ³ ) and then dried under reduced pressure at constant weight. 5-Benzyl-3-hydroxy-hexahydro-pyrrolo [3,4-c] pyrrol-1-one is isolated (7 g; 55%), the characteristics of which are as follows: Melting point: 138 ° C. (Kofler ).

EXAMPLE 137 Preparation of (3aR, 6aS) -2-phenyl-tetrahydro-pyrrolό [3,4-c] pyrrole- ^ 1,3-dione hydrochloride

a) (3aR, 6aS) -2-phenyl-tetrahydro- hydrochloride pyrrolo [3,4-c] pyrrole-1,3-dione is prepared as follows: In a three-necked flask of 250 cm ³ , a suspension of 2-phenyl-tetrahydro-pyrrolo [3, 4-c] pyrrole is placed -1, 3-dione (8 g; 37 mmol), in ethanol (80 cm ³ ) then the reaction mixture is brought to 70 ° C. The solution thus obtained is treated hot with 4.9 N hydrochloric ethanol (37 mmol) and then allowed to return to 20 ° C. The solid formed is filtered, washed with ethanol (10 cm ³ ) and then with ^" diethyl ^" C2 ^" oxide 5 ^~ cm ³ ), dried ^~~ sb ^" ù £ f reduced pressure ^" to ^"" weight- 2-phenyl-tetrahydro-pyrrolo [3, 4-c] pyrrole-1,3-dione hydrochloride (6.85 g; 73.1%) is isolated, the characteristics of which are as follows: Melting point: 250 ° C (Kofler) b) 2-phenyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione is prepared as follows: In a 5000 cm ³ autoclave, a solution of 5-benzyl-2-phenyl-tetrahydro-pyrrolo [3,4- c] pyrrole-1,3-dione, previously freed from its hydrochloride by treatment with 4 N sodium hydroxide (93.2 g; 304 mmol) in l absolute ethanol (1200 cm ³ ), then add 5% palladium on charcoal (11 g) After having purged with nitrogen, the autoclave is placed under 64 bars of hydrogen at 70 ° C. for 12 hours. back to 20 ° C., the catalyst is filtered and the filtrate is evaporated under reduced pressure. u is triturated in diisopropyl ether (500 cm ³ ) and the solid obtained is filtered, washed with diisopropyl ether and finally dried under reduced pressure at constant weight. 2-phenyltetrahydro-pyrrolo [3, 4-c] pyrrole-1,3-dione (6,6 g; 92%) is isolated, the characteristics of which are as follows: Melting point: 128 ° C. (Kofler ) c) The 5-benzyl-2-phenyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione is prepared as follows: In a three-necked flask of 2000 cm ³ , a mixture of phenyl maleimide is placed (77.85 g; 450 mmol) and n- (buthoxy-methyl) -n- (trimethylsilylmethyl) benzylamine (180 g; 450 mmol) in dichloromethane (1000 cm ³ ) then, while maintaining effective stirring, poured trifluoroacetic acid (0.1 cm ³ ). The temperature of the reaction mixture increases to 36 ° C during the 2 hours of reaction, then "potassium carbonate- (100" g-) ^{~ is added} and the reaction mixture is stirred for 0.25 hours at 20 ° C. The solid is removed by filtration, then the filtrate is evaporated under reduced pressure The oil obtained is dissolved in acetone (2000 cm ³ ) then treated with 4.9 N hydrochloric ethanol (490 mmol) and stirred at 20 ° C. for 16 hours The solid formed is filtered, washed with acetone (150 cm ³ ) and with diethyl ether (250 cm ³ ), dried under reduced pressure to constant weight. 5-Benzyl-2-phenyl-tetrahydro-pyrrolo [3, 4-c] pyrrole-1,3-dione, (129 g), which is used directly in the next step.

Example 138 Preparation of (3aR, 6aS) -2-benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1, 3-dione hydrochloride

a) (3aR, 6aS) -2-benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione hydrochloride is prepared as follows: In a 5000 cm ³ autoclave, a solution of 2,5-dibenzyl-tetrahydro-pyrrolo [3, 4 c] pyrrole-1,3-dione (253 g; 790 mmol) in ethanol (2000 cm ³ ) then the palladium on activated carbon is added to 5% (2 g; 0.9 mmol). After having purged the reactor using nitrogen, the autoclave is placed under 59 bars of hydrogen at 70 ° C for 16 hours. After returning to 20 ° C., filtration and washing of the catalyst, concentrated under reduced pressure up to 2000 cm ³ of reaction mixture, then 9.6 N hydrochloric ethanol (90 cm ³ ) is added. The crystallized solid obtained is filtered, then washed with ethanol (100 cm ³ ) and with ethylene oxide (250 cm ³ ) and finally dried under reduced pressure at constant weight. The 2-benzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione hydrochloride (3.6 g) is isolated, the characteristics of which are as follows: Melting point: 240 ° C. (Kofler) b) 2,5-dibenzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione is prepared in the following manner: In a three-necked flask of 2000 cm ³ , a mixture of benzyl maleimide is placed, ( 70.4 g; 376 mmol) and of n- (buthoxy-methyl) -n- (trimethylsilylmethyl) benzylamine (105 g; 376 mmol) in dichloromethane (1000 cm ³ ) then, while maintaining effective stirring, 1 trifluoroacetic acid (1 cm ³ ) .. The temperature of the reaction mixture increases to 33 ° C for one hour of reaction then potassium carbonate (50 g) is added and the reaction mixture is stirred for 10 minutes at 20 ° vs. The solid is removed by filtration, then the filtrate is evaporated under reduced pressure. The oil obtained is taken up in diisopropyl ether (500 cm ³ ) and then triturated until crystallization. The solid formed is filtered, washed with diisopropyl ether (50 cm ³ ) dried under reduced pressure at constant weight. Is isolated 2, 5-dibenzyl-tetrahydro-pyrrolo [3,4-c] pyrrole-1,3-dione, (70 g; 58%), the characteristics of which are as follows: Melting point: 100 ° C. (Kofler )

In ^a reactor assembly adapted for the synthesis parallel printer is dispensed successively 0.25 cm ³ of solution A (50 micromol per reactor), 0.25 cm ³ of solution B, each amine solution from the above table, 0.25 cm ³ of solution C and 0.035 cm ³ of triethylamine. The reactors are closed then stirred and heated at 88 ° C for 4.5 hours. After returning to ambient temperature, the reactors are stirred for 48 hours. The content of each reactor is filtered and each filtrate is adsorbed on an extraction cartridge on solid phase (2 g of SCX phase per cartridge at 0.8 mm³ / g, prior wetting with methanol: 5 volumes; first elution of methanol 5 volumes ) then desorbed by second elution. methanol / 2M ammonia, 5 volumes. After evaporation of the ammoniacal methanol, the compounds are diluted in 1 cm ³ of dimethylsulfoxide and purified by reverse phase liquid chromatography coupled to mass spectrometry (Method C). The fractions containing the expected compounds are evaporated, weighed, diluted to 10 μm in dimethyl sulfoxide and analyzed by reverse phase liquid chromatography coupled to mass spectrometry. 1. The compounds thus purified are characterized by their retention time and their molecular peak. (Table below). 2. The compounds resulting from the coupling of [5-methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - IH-indol-6-yloxy] -acetic acid (prepared as in Example 88) and the precursors mentioned in lines 16, 17, 18 and 19 of the table above are subjected to an additional purification cycle by reverse phase liquid chromatography coupled to mass spectrometry (Method D ). The fractions containing the expected compounds are evaporated, weighed, diluted to 10 mM in dimethyl sulfoxide and then analyzed by reverse phase liquid chromatography coupled to mass spectrometry. Purified compounds are characterized by their time retention and their molecular peak (Table below). 3. The compounds resulting from the coupling of [5-methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - IH-indol-6-yloxy] -acetic acid and the precursors mentioned in lines 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31 and 35 are subjected to an additional purification cycle by liquid chromatography in reverse phase coupled with mass spectrometry ( Method D). The fractions containing the expected compounds are evaporated, weighed, diluted to 10 mM and analyzed by reverse phase liquid chromatography coupled to mass spectrometry. The purified compounds are characterized by their retention time and their molecular peak (Table below). 4. The compounds resulting from the coupling of [5-methoxy-1-methyl-3- (1h-pyrrolo [2, 3-b] pyridin-2-yl) - IH-indol-6-yloxy] -acetic acid and the precursors mentioned in lines 29 and 30 are subjected to an additional purification cycle by reverse phase liquid chromatography coupled to mass spectrometry (Method D). The fractions containing the expected compounds are evaporated, weighed, diluted to 10 mM and analyzed by reverse phase liquid chromatography coupled to mass spectrometry. The purified compounds are characterized by their retention time and their molecular peak (Table below)

EXAMPLE 139 Acid 4- {2- [5-methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -IH-indol-6-yloxy] - acetylamino} - 1-benzopyran-8-carboxylic acid The methyl ester of 4- {2- [5-methoxy-1-methyl-3- (lh-pyrrolo [2, 3-b] pyridin-2-yl) -lH acid -indol-6-yloxy] -acetylamino} -l-benzopyran-8-carboxylic acid resulting from the coupling of [5-methoxy-1-methyl-3- (lh- pyrrolo [2,3-b] pyridin-2-yl) -IH-indol-6-yloxy] -acetic (obtained as described in Example 88) with the precursor mentioned in line 31 of the table above is dissolved in 1 cm ³ of a methanolic potash solution (0.1 g of potash per cm ³ of methanol) then stirred at room temperature for 16 hours. After evaporation, the compound is diluted in a mixture of dimethyl sulfoxide (0.75 cm ³ ) and 12N aqueous hydrochloric acid (0.25 cm ³ ). The solution obtained is filtered and - purified by liquid chromatography in reverse phase - coupled to mass spectrometry (Method F). Is isolated 4- {2- [5-methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -IH-indol-6-yloxy] -acetylamino} acid -1- benzopyran-8-carboxylic acid (0.0016 g, 30%), the characteristics of which are as follows: LC / MS analysis: tr = 3.5 min, m / z = 526.88 [M + H ⁺ )

EXAMPLE 147 2- [1-Methyl-5-methoxy-6- (2-morpholin-4-yl-ethoxy) -IH-indol-3-yl] -lH-pyrrolo [2, 3-b] pyridine a) Le 2- [1-methyl-5-methoxy-6- (2-morpholin-4-yl-ethoxy) - IH-indol-3-yl] -lH-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 89a but using 0.24 g of 2- [1-methyl-5-methoxy-6- (2-morpholin-4-yl-ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine and 1.93 cm ³ of an aqueous solution of potassium hydroxide 5N. 0.116 g of 2- [1-methyl-5-methoxy-6- (2-morpholin-4-yl-ethoxy) -lH-indol-3-yl] -IH-pyrrblo [2, 3-b] pyridine is obtained whose characteristics are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): from 2.50 to 2.65 (mt: 4H); 2.76 (t, J = 6 Hz: 2H); 3.60 (wide t, J = 5 Hz: 4H); 3.79 (S: 3H); 3.87 (s: 3H); 4.16 (t, J = 6 Hz:. 2H); 6.73 (d, J = 1.5 Hz: ^• 1H); 6.99 (dd, J = 8 and 5 Hz: 1 H); 7.16 (s: 1H); 7.42 (s: 1H); 7.77 (S: 1H); 7.82 (broad d, J = 8 Hz: 1 H); 8.09 (dd, J = 5 and 1.5 Hz: 1 H); 11.71 (broad s: IH). Mass spectrum (IE): m / z = 407 [M] ⁺ (base peak) b) 2- [1-methyl-5-methoxy-6- (2-morpholin-4-yl-ethoxy) - IH -indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine is prepared as follows: To a solution of 0.24 g of 2- [1- methyl-5-methoxy- 6- (2riodo-ethoxy) -lH-i.ndol-3-yl] -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridine in 24 cm ³ of acetonitrile, under an inert argon atmosphere at a temperature in the region of 20 ° C., 0.11 g of potassium carbonate and 0.14 cm ³ of morpholine are added. The reaction medium is heated at 60 ° C for 24 hours. After cooling, the reaction medium is concentrated under reduced pressure. The oil obtained is taken up with 10 cm ³ of water and 10 cm ³ of ethyl acetate. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, ethyl acetate / cyclohexane 30/70 by volume as eluent). The fractions containing the product are concentrated under reduced pressure. This gives 0.24 g of 2- [1-methyl-5-methoxy-6- (2-morpholin-4-yl-ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl ) -lH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (CI): m / z = 561 [M + H] ⁺ (base peak)

c) 2- [1-methyl-5-methoxy-6- (2-iodo-ethoxy) -lH-indol-3- yl] -1- (toluene- -suifonyl) -IH-pyrrolo [2, 3- b] pyridine is prepared as follows: To a solution of 0.59 g of 2- [1-methyl-5-methoxy- 6- (2-chloro-ethoxy) -IH-indol-3-yl] -1 - (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine in 42 cm ³ of 2-butanone, under an inert argon atmosphere at a temperature in the region of 20 ° C, 0.260 g of sodium iodide is added. The reaction medium is heated at reflux for 24 hours. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, dichloromethane as eluent). The fractions containing the product are concentrated under reduced pressure. 0.565 g of 2- [1-methyl-5-methoxy-6- (2-iodo-ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo are thus obtained 2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 601 [M] ⁺ , m / z = 446 (base peak)

d) 2- [1-methyl-5-methoxy-6- (2-chloro-ethoxy) -lH-indol- 3-yl] -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3 -b] pyridine is prepared as follows: To a solution of 0.94 g of 2- [1-methyl-5-methoxy-6-hydroxy) -IH-indol-3-yl] -1- (toluene- 4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridine in 22 cm ³ of dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20 ° C, 0.101 g of sodium hydride is added (at 60 % in oil). The reaction medium is stirred at this same temperature for 15 minutes. Then 0.525 cm ³ of 1-chloro-2-bromoethane is added. After 2 hours of stirring at the same temperature, 0.1 g of sodium hydride (60% in oil) and 0.525 cm ³ l-chloro-2-bromoethane are again added. The reaction medium is kept stirring at this same temperature for 20 hours. 20 cm ³ of water and .20 cm ³ of ethyl acetate are added, after decantation, the organic phase is dried over magnesium sulphate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, ethyl acetate / cyclohexane 35/65 by volume as wastewater). The fractions containing the product are concentrated under reduced pressure. 0.596 g of 2- [1-methyl-5-methoxy-6- (2-chloro-ethoxy) -1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo are thus obtained 2,3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 509 [M] ⁺ , m / z = 354 (base peak) e) 2- [1-methyl -5-methoxy-6-hydroxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared as follows: To a solution 1.2 g of 2- [1-methyl-5-methoxy-6-benzyloxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b ] pyridine in 90 cm ³ of acetonitrile, under an inert argon atmosphere at a temperature in the region of 20 ° C., 0.798 cm ³ of iodotrimethylsilane is added. The reaction medium is heated at 50 ° C for 4 hours. After cooling, 60 cm ³ of water and 60 cm ³ of ethyl acetate are added, after decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent, argon). The fractions containing the product are concentrated under reduced pressure. 0.825 g of 2- [1-methyl-5-methoxy-6-hydroxy) -1H-indol-3- yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b are thus obtained ] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 447 [M] ⁺ , m / z = 292 (base peak)

The compound 2- [1-methyl-5-methoxy-6-benzyloxy) -1H-indol-3- yl] -1- (toluene- -sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is prepared according to the process described in patent O03000688A1.

EXAMPLE 148: 2- {1-Methyl-5-methoxy-6- [2- (4-methyl- piperazin-1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3- b] pyridine a) 2- {1-methyl-5-methoxy-6- [2- ( 4-methyl-piperazin-1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 89a but starting from 0.195 g of 2- [1-methyl-5-methoxy-6- (2- (4-methylpiperazin-4-yl-ethoxy) -lH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine and 1.53 cm ³ of a 5N aqueous potassium hydroxide solution After purification by flash-pack chromatography (silica, dichloromethane / methanol 90/10 by volume as effluents, argon), 0.086 g of 2- {l-methyl-5-methoxy-6- [2- (4-methyl-piperazin-1-yl) - ethoxy] -IH-indol-3-yl} is obtained - 1H-pyrrolo [2,3-b] pyridine, the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.18 (s: 3H); 2.37 (mf: 4H); 2.50 to 2.65 (mt: 4H); 2.78 (t, J = 6 Hz: 2H); 3.83 (s: 3H); 3.90 (s: 3H ); 4.17 (t, J = 6 Hz: 2H); 6.77 (d, J = 2 Hz: 1H); 7.03 (dd, J = 8 and 5 Hz: 1 H); 7.20 (s: 1H); 7.46 (s: 1H); 7.80 (s: 1H); 7.86 (broad dd, J = 8 and 1.5 Hz: 1 H); 8.13 (dd, J = 5 and 1.5 Hz: 1 H); 11.75 (broad s: 1 H). Mass spectrum (IE): m / z = 419 [M] ⁺ , m / z = 127 (base peak)

b) 2- [1-methyl-5-methoxy-6- (2- (4-methylpiperazin-4-yl-ethoxy) -lH-indol-3-yl] -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 147b but from 0.1 cm ³ of N-methylpiperazine and 0.27 g of 2- [1-methyl -5-methoxy- .6- (2-iodo-ethoxy) -IH-indol-3-yl] -1- (toluene- -sulfonyl) - 1H-pyrrolo [2,3-b] pyridine After purification by flash - chromatography pack (silica, dichloromethane / methanol 90/10 by volume as eluent, argon), we obtain 0.197 g of 2- [1-methyl-5-methoxy-6- (2- (4-methylpiperazin-4-yl-ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) - IH- pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 573 [M] ⁺ , m / z≈ 127 (base peak)

EXAMPLE 149: 1- {2- [1-Methyl-5-methoxy-3- (1H-pyrrolo [2, 3- b] pyridin-2-yl) -IH-indol-6-yloxy] -ethyl} -piperidin -4-ol

a) 1- {2- [1-methyl-5-methoxy-3- (IH-pyrrolo [2, 3-b] pyridin-2-yl) -IH-indol-6-yloxy] -ethyl} -piperidin -4-ol is prepared by following the procedure described in Example 89a but using 0.23 g of 1- {2- [1-methyl-5-methoxy-3- (1- (toluene- -sulfonyl) ) -lH-pyrrolo [2,3-b] pyridin-2-yl) -IH-indol-6-yloxy] -ethyl} -piperidin-4-ol and 1.8 cm ³ of an aqueous solution of 5N potassium hydroxide. After purification by flash chromatography pack (silica, dichloromethane / methanol 90/10 by volume as eluent, argon), 0.017 g of l- {2- [5-l-methyl-methoxy-3- (1H-pyrrolo [ 2,3-b] pyridin-2-yl) -IH-indol-6-yloxy] -ethyl} -piperidin-4-ol the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.41 (mt: 2H); 1.72 (very large d, J = 12 Hz: 2H); 2.16 (broad t, J = 11 Hz: 2H); 2.73 (t, J = 6 Hz: 2H); 2.84 (mt: 2H); 3.45 (mt: 1H); 3.81 (s: 3H); 3.88 (s: 3H); 4.13 (t, J = 6 Hz: 2H); 4.55 (d, J = 4 Hz: 1 H); 6.75 (broad d, J = 2 Hz: 1 H); 7.00 (dd, J = 8 and 5 Hz: 1 H); 7.16 (s: 1H); 7.42 (s: 1H); 7.77 (S: 1H); 7.84 (broad d, J = 8 Hz: 1 H); 8.12 (broad dd, J = 5 and 1.5 Hz: 1 H); 11.73 (broad s: 1 H). Mass spectrum (IE): m / z = 420 [M] ⁺ , m / z = 128 (base peak) b) 1- {2- [1-methyl-5-methoxy-3- (1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-2-yl) -IH-indol -6-yloxy] -ethyl} - piperidin-4 is prepared by following the procedure described in Example 147b but from 0.089 g of 4-hydroxypiperidine and 0.265 g of 2- [1-methyl-5-methoxy -6- (2-iodo-ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine. After purification by flash chromatography pack (silica, dichloromethane / methanol 90/10 by volume as eluent, argon), 0.234 g of l- {2- [1-methyl-5-methoxy-3- (1- (toluene) is obtained -4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-2-yl) -1H- indol-6-yloxy] -ethyl} -piperidin-4-ol the characteristics of which are as follows: Mass Spectrum (IC): m / z = 575 [M + H] ⁺ (base peak)

EXAMPLES 150 TO 159

a) 2- [6- (2-iodo-ethoxy) -5-methoxy-1-methyl-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3 -b] pyridine is prepared in the following way: In a 50 cm ³ monocol, a solution of 2- [6- (2-chloro-ethoxy) -5-methoxy-1-methyl-1H-indol- is placed 3-yl] - 1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine, (0.660 g, 1.294 μmol) in methyl ethyl ketone (10 cm ³ ) then iodide is added sodium (0.29 g; 1.941 mmol). The reaction mixture is heated at reflux for 16 hours. Analysis by thin layer chromatography (cyclohexane / ethyl acetate 50/50) shows that the reaction is complete. After returning to 20 ° C., the reaction mixture is evaporated under reduced pressure and the residue is taken up in a mixture of water (50 cm ³ ) and dichloromethane (50 cm ³ ) which is decanted; the organic extract is washed with water (30 cm ³ ) and dried over magnesium sulfate. After evaporation, the compound obtained is purified by chromatography on silica geï (FC-10-Si-BP-Sup cartridge, 10 g silica with a particle size of 15-35 μm, eluting with a mixture of cyclohexane / ethyl acetate 70/30). The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing 2- [6- (2-iodoethoxy) -5-methoxy-1- ethyl-1H-indol-3-yl] -1- (toluene -4- sulfonyl) -IH-pyrrolo [2, 3-b] pyridine, (0.695 g; 89%), the characteristics of which are as follows: LC / MS analysis: tr = 4.0, m / z = 601.96 [M + H] ⁺

b) 2- [6- (2-chloro-ethoxy) -5-methoxy-1-methyl-IH-indol- 3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3 -b] pyridine is prepared as follows: In a 50 cm ³ argon inert flask, a solution of 5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) is placed - 1H-pyrrolo [2,3-b] pyridin-2-yl] -lH-indol-6-ol, (0.8 g; 1.788 mmol) dissolved in dimethylformamide (5 cm ³ ) then the hydride is added sodium (0.064 g; 2.146 mmol). The reaction mixture takes on a brown color and l-bromo-2-chloroethane (0.308 g; 2.146 mmol) is added. The reaction mixture is stirred 1.30 minutes at 20 ° C. and then sodium hydride (0.064 g; 2.146 mmol) and l-brόmo-2-chloroethane (2 x 0.5 cm ³ ) are added again. Analysis by thin layer chromatography (cyclohexane / ethyl acetate 50/50) shows that the reaction is complete. The reaction mixture is diluted with water (150 cm ³ ) and ethyl acetate (50 cm ³ ), extracted with ethyl acetate (2 x 50 cm ³ ). The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure leading to the crude compound which is purified by chromatography on silica gel (Cartridge AIT, FC 25 Si-BP-Sup, eluent: cyclohexane / acetate ethyl 65/35 at 10 cm ³ / min.). The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing 2- [6- (2- chloro-ethoxy) -5-methoxy-1-methyl-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine expected, (0.66 g ; 72%) in the form of a powder, the characteristics of which are as follows: 5 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.30 (S: 3H); 3.75 (s: 3H); 3.87 (s: 3H); 4.04 (broad t, J = 5 Hz: 2H); 4.36 (wide t, J = 5 Hz: 2H); 6.75 (s: 1H); 6.99 (s: 1H); 7.20 (s: 1H); 7.26 (broad d, J = 9 Hz: 2H); 7.30

, ^ Q - (dd -, - J - = _ 8 — etS — Hz -: - - IH -) - ^ __, - 54 -. (- &, ___ I_.s_SL_Hz ____ 2H); 7.59 (br s: 1H); 7.94 (dd, J = 8 and 1.5 Hz: 1 H); 8.35 (dd, J = 5 and 1.5 Hz: 1 H). c) The alkylation of Examples 150 to 159 In 10 glass reactors (1.3 x 10 cm), each amine in the table below is weighed and dissolved in dimethylformamide (0.5 cm ³ ). To this solution is added 2- [6- (2-iodo-ethoxy) -5-methoxy-1-methyl-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine (0.05 g / reactor, 83 μmol / reactor) in dimethylformamide (0.5 cm ³ / reactor) then potassium carbonate (0.035 g / reactor, 249 μmol) / reactor). The reactors are closed and then placed in an oil bath at 60 ° C for 4 hours 30 minutes. The contents of each reactor are filtered and then transferred to a cartridge

25 extraction on solid phase (Varian Mega BondElut-SCX, ref: 12256011, lgr, 6 cm ³ , Lot 1728002, MFG code 3102) previously conditioned with methanol (12 cm ³ ). The solid phase extraction cartridges are eluted with methanol (2 x 6 cm ³ ) and then with 2M methanol / ammonia (2

30 x 6 cm ³ ). The ammonia elution fractions are combined and evaporated to give the crude compounds. The crude compounds are purified by chromatography on silica gel (24 cm ³ cartridge containing 10 g of 40-60 μm silica, dichloromethane gel), eluting with a

35 mixture of dichloromethane / methanol in proportions variable but adapted to each case (from 97/3 to 80/20). The fractions containing the expected compounds are combined and evaporated, leading to the corresponding intermediate compounds which are used in the detosylation step.

d) Deprotection of Examples 150 to 159 In 10 hemolysis tubes (1.3 × 10 cm) containing the compounds resulting from the reactions described above, a methanolic potassium solution (1.5 cm ³ per tube, 0, 1 g of potassium hydroxide / cm ³ methanol) and then stirred at 20 ° C for 16 hours. After evaporation under reduced pressure, the residues are taken up in dimethylformamide (0.6 cm ³ ) and then the solutions thus obtained are eluted on extraction cartridges on solid phase (Varian, Mega Bond Elut, SCX, 2g, 6 cm ³ , Ref 19102, previously conditioned with methanol (2 x 6 cm ³ ) After a first elution with methanol (6 cm ³ ), the cartridges are eluted with 2N ammoniacal methanol (5 cm ³ ) the ammonia eluate is evaporated at The compounds thus obtained are finally purified by chromatography on silica gel (2 g cartridges of silica gel, 40-60 μm, dichloromethane), eluting with a mixture of dichloromethane and methanolic ammonia 2M (95/5) at 5 cm ³ / min. The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing the expected compounds. Each of the compounds is dissolved in dimethylformamide (0.6 cm ³ ) and then eluted on extraction cartridges on solid phase (Varian, Mega Bond Elut, SCX, 0.5 g, 3 cm ³ ) previously conditioned with methanol ( 2 x 3 cm ³ ). After a first elution with methanol (4.8 cm ³ ), the cartridges are elected with 2N ammoniacal methanol

_i ₀ _ ~ (-4- _r 8 — cm ³ -) —- ^ _ .. l- ^ éiuat — ammonia — es — evaporated — to — c ~ providing the expected compounds which are characterized by liquid chromatography in reverse phase coupled with mass spectrometry (Method A). The retention times and molecular ions are given in the following table.

ΕXEMPEES-r6O-rTβ4r a) 2- [6- (3-iodo-propoxy) -5-methoxy-1-methyl-IH-indol- 3-yl] -1- (toluene-4-sulfonyl) -lH- pyrrolo [2, 3-b] pyridine is prepared as follows: In a 50 cm ³ monocol, a solution of 2- [6- (3-chloro-propoxy) -5-methoxy-1-methyl- is placed. IH-indol-3- yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, (0.415 g; 792 μmol) in methyl ethyl ketone (10 cm ³ ) and then add sodium iodide (0.178 g; 1.18 mmol). The reaction mixture is heated at reflux for 16 hours. Analysis by thin layer chromatography (cyclohexane / ethyl acetate 50/50) shows that starting material is still present. Additional sodium iodide (0.178 g;

1.18 mmol) and the reflux is maintained for 3 hours.

After returning to 20 ° C., the precipitate is dissolved in dichloromethane (200 cm ³ ) then washed with water (50 cm ³ ) and dried over magnesium sulfate. After evaporation, the residue is taken up in ethyl acetate (20 cm ³ ); the insoluble material is removed and the filtrate is evaporated under reduced pressure. 2- [6- (3-iodopropoxy) -5-methoxy-1-methyl-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3 are isolated -b] pyridine (0.367 g; 75%), the characteristics of which are as follows: LC / MS analysis: tr = 4.32 min. ; m / z = 615.96 [M + H] ⁺ b) 2- [6- (3-chloro-propoxy) -5-methoxy-1-methyl-IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3 - b] pyridine is prepared in the following manner: In a 50 cm ³ inert argon flask, a 5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) solution is placed -1H-pyrrolo [2,3-b] pyridin-2-yl] -1H-indol-6-ol, (0.45 g; 1.006 mmol) in solution in dimethylformamide (5 cm ³ ) and then the sodium hydride (0.06 g; 2.01 mmol). The reaction mixture takes ^"to a dark color and the added T ^ S ^ bromo-chloro propane (0.199 cm ^3, 2.01 mmol). The reaction mixture is stirred for 30 minutes at 20 ° C. The reaction mixture was diluted with dichloromethane (50 cm ³ ) and water (100 cm ³ ), decanted and extracted with dichloromethane (2 x 15 50 cm ³ ). The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated under pressure reduced resulting in an oil. The oil is taken up in diisopropyl ether (10 cm ³ ) then triturated, leaving crystals. After filtration, washing with diisopropyl ether and drying under reduced pressure, the 2 is isolated. - [6- (3-chloro-propoxy) -5-methoxy-1-methyl-IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine , in the form of ocher-colored crystals (0.415 g; 79%), the characteristics of which are as follows: 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.27 (mt : 2H); 2.30 (s : 3H); 3.75 (s: 3H); 3.87 (S: 3H); 3.89 (t, J = 6.5 Hz: 2H); 4.20 (t, J = 6.5 Hz: 2H); 6.74 (s: 1H); 6.97 (s: 30 1H); 7.19 (s: 1H); 7.26 (broad d, J = 8.5 Hz: 2H); 7.29 (dd, J = 8 and 5 Hz: 1 H); 7.50 (s: 1H); 7.57 (d, J = 8.5 Hz: 2H); 7.93 (dd, J = 8 and 1.5 Hz: 1 H); 8.34 (dd, J = 5 and 1.5 Hz: 1 H). c) The alkylation of Examples 160 to 164 In 5 hemolysis tubes 1.2 x 10 cm, the 5 amines described in the table below are weighed and placed in solution in dimethylformamide (0.5 cm ³ ). A solution of 2- [6- (3-iodo-propoxy) -5-methoxy-1-methyl-1H- indol-3-yl] -1 is placed in 5 hemolysis tubes (1.2 × 10 cm) - (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine, (81.2 μmol / tube), in dimethylformamide (0.5 cm ³ / tube) to which the solutions of amines described below. Using a spatula, we

JL-CL. add potassium carbonate (0.035 g / tube). The reactors are closed and then heated with stirring at 65 ° C for 3 hours. After returning to ambient temperature, the content of each reactor is filtered and the filtrates purified by reverse phase liquid chromatography

15 coupled with mass spectrometry (2 injections per sample, Method B). The fractions containing the expected compounds are combined and then evaporated under reduced pressure, providing the compounds which are used in the next step. 20

d) Detosylation of Examples 160 to 164 In 5 hemolysis tubes (1.2 × 10 cm) containing the compounds obtained above, a methanolic potassium solution (1.6 cm ³ per tube, 0.1 g solution) is added 25 of potassium hydroxide per 1 cm ³ of methanol) then stirred at 0 ° C for 16 hours before evaporating to dryness. The evaporation residues are taken up in a mixture of dimethylformamide (0.8 cm ³ ) and acetic acid (0.2 cm ³ ), then purified by liquid phase chromatography inverse coupled to mass spectrometry (method B, 2 injections per sample). The fractions containing the expected compounds are combined and then elected on solid phase extraction cartridges (Varian Mega BondElut-SCX cartridges, lgr, 6 cm ³ ) previously conditioned with methanol (2 x 6 cm ³ ). After elution with methanol (2 6 cm ³ ) then elution with 2M ammonia methanol (2 x 6 cm ³ ), the ammonia eluates are combined which are evaporated under reduced pressure. Dry extracts

-1-0- -are — rep-ris — in — a — mixture — of — dichloromethane — and- methanol (90/10), then filtered through silica cartridges (Thermoquest, Hypersep Silica, 0.1 g, # 60300-494). The eluates are evaporated under reduced pressure, leading to the expected compounds which are characterized by their retention time and molecular peak.

EXAMPLES 165 TO 167 a) 2- {6- [2- (2-chloro-ethoxy) -ethoxy] -5-methoxy-1-methyl-1H-indol-3-yl} -l- (toluene-4- suifonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared as follows: In a 50 cm ³ monocol, a 2- {6- [2- (2-chloro-ethoxy) -ethoxy solution is placed ] -5-methoxy-1-methyl-1H- indol-3-yl} -l- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine, (0.145 g, 261.7 μmol) in methyl ethyl eetone (-3— © m -) -— then — one -— add-iodide iodide- of so_dium_ (0.118 g; 785 μmol). The reaction mixture is heated at reflux for 16 hours. Analysis by thin layer chromatography (cyclohexane / ethyl acetate 50/50) shows that starting material is still present. Additional sodium iodide (0.178 g; 1.18 mmol) is introduced and reflux is maintained for 3 hours.

After returning to 20 ° C., the precipitate is dissolved in dichloromethane (30 cm ³ ) then washed with water (10 cm ³ ) and dried over magnesium sulfate. After evaporation, the residue is taken up in diisopropyl ether (10 cm ³ ); the solid formed is removed and the filtrate is evaporated under reduced pressure. Is isolated 2- {6- [2- (2-chlorp-ethoxy) -ethoxy] -5-methoxy-1-methyl-1H- indol-3-yl} -l- (toluene-4-sulfonyl) -lH -pyrrolo [2,3-b] pyridine, (0.137 g; 81%) which is used as it is.

b) 2- {6- [2- (2-chloro-ethoxy) -ethoxy] -5-methyloxy-1-methyl-1H-indol-3-yl} -l- (toluene-4-sulfonyl) -lH -pyrrolo [2, 3-b] pyridine is prepared as follows: In a 10 cm ³ flask, a solution of 5-methoxy-1-methyl-3- [1- (toluene-4-sulfonyl) is placed -1H- pyrrolo [2, 3-b] pyridin-2-yl] -lH-indol-6-ol, (2.998 g; 670 μmol) in dimethylformamide (3 cm ³ ) then add sodium hydride ( 0.603 g; 2.01 mmol) and stirred for 5 minutes. The reaction mixture takes on a green color, then the bis (2-chloroethyl) ether is added. (0.235 cm ³ ; 2.01 mmol). The dream mix is. then stirred for 1.5 hours at 20 ° C. Analysis by thin layer chromatography (cyclohexane / ethyl acetate 50/50) shows that the starting compound is consumed. The reaction mixture is poured onto water (30 cm ³ ) and then extracted with dichloromethane (20 cm ³ ). The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give the crude compound which is purified by

-1-0— & hroma-feog-raphie— & ur-gel - de - s-ilice ^ - (- Cartridge — AIT -, - Column- Flash Silica 20-40 μm, 25g, ref: FC-25SI-BP -SUP, 10 cm ³ / min, cyclohexane / ethyl acetate 70/30 to 50/50). The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing 2- {6- [2- 15 (2-chloro-ethoxy) -ethoxy] -5-methoxy-1-methyl-IH-indol-3- yl} -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine, (0.145 g; 39%) which is used as it is for the next step. c) The alkylation of Examples 165 to 167

In 3 hemolysis tubes (1.2 x 10 cm) the amines described in the table below are placed which are dissolved in dimethylformamide (1 cm ³ per tube). A solution of 2- {6- [2- (2-chloro-ethoxy) -ethoxy] -5-methoxy- is placed in 4 hemolysis tubes (1.2 x 10 cm)

25 1-methyl-1H-indol-3-yl} -l- (toluen -4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, (0.032 g per tube, 50 μmol per reactor) and then added each amine solution previously described as well as potassium carbonate (0.021 g; 150 μmol per tube). The reactors are closed then

30 heated to 65 ° C with stirring for 6 hours. After returning to 20 ⁶ C, the content of each tube is filtered and then diluted with acetic acid (0.2 cm ³ ). The solutions thus obtained are eluted on solid phase extraction cartridges (Varian, Mega Bond Eiut,

35 SCX, 2g, 6 cm ³ , # 19102) previously conditioned methanol (2 x 6 cm ³ ). After a first elution with methanol (6 cm ³ ), the cartridges are eluted with 2N ammoniacal methanol (5 cm ³ ); the ammonia residue is evaporated to dryness to yield the expected compounds which are used in the next step.

d) Detosylation of Examples 165 to 167 In 3 hemolysis tubes (1.2 x 10 cm) containing the compounds obtained above, a methanolic potassium solution (1.5 cm ³ , 0.1 g solution of potassium hydroxide) is added with 1 cm of methanol) then each reaction mixture is stirred at 20 ° C for 16 hours. The content of. each tube is diluted with acetic acid (0.2 cm ³ ) then placed on an extraction cartridge (Varian, Mega Bond Elut, SCX, 2g, 6 cm ³ , Ref. 19102, Lot 1706002) previously conditioned methanol (2 x 6 cm ³ ). After a first elution with methanol (6 cm ³ ), the cartridges are eluted with 2N ammoniacal methanol (2 x 5 cm ³ ); the ammonia residue is evaporated to dryness then each sample is diluted in dimethylsulfoxide (0.5 cm ³ ) and purified by reverse phase liquid chromatography coupled to mass spectrometry (Method G).

The fractions containing the expected compound are combined and then evaporated under reduced pressure, providing the expected compounds. The fractions are deposited on SCX cartridges (Varian Mega BondElut-SCX cartridges, ref: 12256011, 1 g, 6 cm ³ , Lot 1728002, MFG code 3102) previously conditioned with methanol (2 x 6 cm ³ ). After elution with methane (2 x 6 cm ³ ), the cartridges are eluted with 2N ammoniacal methanol (2 x 6 cm ³ ) and the ammonia eluates are evaporated under reduced pressure to give the expected compounds characterized by their retention time and peak (Table below)

EXAMPLE 168 2- [5-Methoxy-6- (2-methoxy-ethoxy) -1-methyl-IH-indol-3-yl] -1H-pyrrolo [2, 3-b] pyridine

a) 2- [5-Methoxy-6- (2-methoxy-ethoxy) -1-methyl-1H- indol-3-yl] -lH-pyrrolo [2,3-b] pyridine is prepared by following the mode procedure described in Example 89a but using 0.102 g of 2- [5-methoxy-6- (2-methoxy-ethoxy) - 1-methyl-1H-indol-3-yl] -1- (toluene-4 -sulfonyl) -1H-pyrrolo [2, 3-b] pyridine and 0.80 cm ³ of 5N potassium hydroxide. After purification by flash chromatography pack (silica, dichloromethane / methanol 92.5 / 7.5 by volume as eluent, argon), 0.033 g of 2- [5- methoxy-6- (2-methoxy-ethoxy) is obtained. 1-methyl-IH-indol-3-yl] -IH- pyrrolo [2, 3-b] pyridine the characteristics of which are as follows: NMR spectrum! H (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm ): 3.39 (S: 3H); 3.76 (mt: 2H); 3.83 (s: 3H); 3.91 (s: 3H); 4.21 (mt: 2H); 6.78 (d, J = 2 Hz: 1 H); 7.04 (dd, J = 8 and 5 Hz: 1 H) 7.17 (S: 1 H); 7.46 (s: 1H); 7.80 (s: 1H) 7.88 (dd, J = 8 and 1.5 Hz: 1H); 8.13 (dd, J = 5 and 1.5 Hz: 1 H); 11.75 (broad s: 1 H). Mass spectrum (IE): m / z = 351 [M] ⁺ (base peak) b) 2- [5-Methoxy-6- (2-methoxy-ethoxy) -1-methyl-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3 -b] pyridine is prepared by following the procedure described in Example 147d but starting with 0.195 g l-bromo-2-5 methoxyethane instead of l-chloro-2-bromoethane used in Example 147d and 0.224 g of 2- [1-methyl-5-methoxy-6-hydroxy] -IH-indol-3-yl] -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridine. After purification by flash chromatography pack (silica, ethyl acetate /

-1-0 cyclohexane ao 20 —. In_ olumes as — eluant -, —_ aπg.on) _, ___ we get 0.121 g of 2- [5-methoxy-6- (2-methoxy-ethoxy) -1- methyl IH-indol-3-yl] -IH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: Mass spectrum (IE): m / z = 505 [M] ⁺ (base peak)

EXAMPLE 169: 2- [5-Methoxy-6- (2-hydroxy-ethoxy) -1-methyl-1H-indol-3-yl] -1H-pyrrolo [2,3-b] pyridine a) 2- [5-Methoxy-6- (2-hydroxy-ethoxy) -1-methyl-1H-indol-3-yl] -lH-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in example 89a but

20 from 0.5 g of 2- [5-methoxy-6- (2-acetyloxy-ethoxy) - 1-methyl-IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH -pyrrolo [2, 3-b] pyridine and 8.43 cm ³ of an aqueous solution of potassium hydroxide 5N. After purification by flash-pack chromatography (silica, dichloromethane /

25 methanol 95/05 by volume as eluent, argon), 0.103 g of 2- [5-methoxy-6- (2-hydroxy-ethoxy) -1-methyl-1H-indol-3-yl] -lH- is obtained pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ at 30 ppm): from 3.75 to 3.85 (mt: 2H) ; 3.82 (s: 3H); 3.90 (s: 3H); 4.09 (t, J = 5.5 Hz: 2H); 4.88 (wide t, J = 5 Hz: 1 H); 6.76 (d, J = 2 Hz: 1 H); 7.02 (dd, J = 8 and 5 Hz: 1 H); 7.15 (s: 1H); 7.44 (s: 1H); 7.79 (s: 1H); 7.86 (dd large, J = 8 and 1.5 Hz: 1H); 8.12 (dd, J ≈ 5 and 1.5 Hz: 1 H); 12.24 (f: 1H). Mass spectrum (IE): m / z = 337 [M] ⁺ (base peak)

b) 2- [5-methoxy-6- (2-acetyloxy-ethoxy) -1-methyl-1H-indol-3-yl] -1- (toluene- -sulfonyl) -lH-pyrrolo [2, 3- b] pyridine is prepared by following the procedure described in Example 147d but starting with 0.246 cm ³ 2-bromo-ethylacetate and 0.5 g of 2- [1-methyl-5-methoxy-6-hydroxy ] -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine. After purification by flash chromatography pack (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent), 0.506 g of 2- [5-methoxy-6- (2-acetyloxy-ethoxy) -1-methyl is obtained. -lH-indol-3- yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine the characteristics of which are as follows: Mass spectrum (IE): m / z = 533 [M] ⁺ , m / z = 292 (base peak)

EXAMPLE 170 2- (5-Methoxy-1,6-dimethyl-1H-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridine

a) 2- (5-methoxy-1,6-dimethyl-1H-ihdol-3-yl) -1H-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 89a but from 0.028 g of 2- (5-methoxy-1,6-dimethyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine and 0.283 cm ³ of a 5N aqueous potassium hydroxide solution. 0.01 g of 2- (5-methoxy-1,6-dimethyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridine is obtained, the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.33 (s: 3H); 3.83 (s: 3H); 3.94 (s: 3H); 6.78 (d, J = 2 Hz: 1 H); 7.03 (dd, J = 8 and 5 Hz: 1 H); 7.35 (br s: 1H); 7.40 (br s: 1H); 7.84 (s: 1H); 7.87 (broad dd, J = 8 and 1.5 Hz: 1 H); 8.12 (dd, J = 5 and 1.5 Hz: 1 H); 11.78 (broad s: 1 H). Mass spectrum (ES ⁺ ): m / z = 292 [M + H] ⁺ (base peak) b) 2- (5-methoxy-1,6-dimethyl-IH-indol-3-yl) -1 - (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is prepared in the following manner: To a solution of 0.1 g of 2- [1-methyl-5-methoxy-6- ( trifluorosulfonyloxy) -lH-indol-3-yl] -1- (toluene- - -suifony-1 -) —- 1H --- py: ι ^ r © l © - [- 2- _r 3 - b ^ anhydrous , under an inert argon atmosphere at a temperature in the region of 20 ° C., 0.012 g of methylboronic acid, 0.0715 g of potassium carbonate and 0.020 g of tetrakis (triphenylphosphine) palladium are added. The reaction medium is heated at 120 ° C for 24 hours. After cooling, 5 cm ³ of water and 5 cm ³ of ethyl acetate are added. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (silica, ethyl acetate / cyclohexane 30/70 by volume as eluent). The fractions containing the product are concentrated under reduced pressure. 0.03 g of 2- (5-methoxy-1,6-dimethyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo is thus obtained [2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (IE): m / z = 445 [M] ⁺ , m / z = 290 (base peak)

c) 2- [1-methyl-5-methoxy-6- (trifluorosulfonyloxy) -1H- indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine is prepared as follows: To a solution of 1 g of 2- [1-methyl-5-methoxy-6-hydroxy-IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH- pyrrolo [2, 3-b] pyridine in 30 cm ³ of dichloromethane, under an inert argon atmosphere at a temperature close to 0 ° C are added 0.451 cm ³ of triflic anhydride and 1.35 cm ³ of pyridine. The reaction medium is stirred at this same temperature for 3 hours. The ice bath is removed. After returning to a temperature in the region of 5 ° C., 15 cm ³ of water are added. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The resulting residue was purified ^'by flash-pack chromatography (silica, dichloromethane eluant). The fractions containing the

_L0 _._ product _._ are., Concentrated .... under .... pressio .__._ red_iii_.te. 1.12 g of 2- [1-methyl-5-methoxy-6- (trifluorosulfonyloxy) -1-H-indol-3-yl] -1- (toluene-4-sulfonyl) -lH- are thus obtained. pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows:

15 Mass Spectrum (CI): m / z = 580 [M + H] ⁺ (base peak)

The compound 2- [1-methyl-5-methoxy-6-hydroxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine. is prepared according to the method described in Example 147e. 0 EXAMPLE 171: 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-methyl-piperazin-1-yl) -ethoxy] -IH-indol-3-yl} -lH- pyrrolo [2, 3-b] -pyridine a) 4-chloro-2- {1-methyl-5-methoxy-6- [2- (4-methyl-piperazin-1-yl) -ethoxy] -IH- indol-3-yl} -1H-pyrrolo [2,3-b] - 5 pyridine is prepared by following the procedure described in Example 89a but using 0.300 g of 4-chloro 2- [1-methyl -5-methyloxy-6- (2- (4-methylpiperazin-4-yl- ethoxy) -lH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b ] pyridine and 2.22 cm ³ of a 5N aqueous solution of potassium hydroxide 0. 0.169 g of 4-chloro-2- {1-methyl-5-methoxy-6- [2- (4- methyl-piperazin- 1-yl) -ethoxy] -IH-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine the characteristics of which are as follows: NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.17 (S: 3H); 2.36 (mf: 4H); from 2.45 to 2.60 (mt: 4H); 2.77 (t, J = 6.5 Hz: 2H); 3.84 (S: 3H); 3.90 (s: 3H); 4.16 (t, J = 6.5 Hz: 2H); 6.71 (br s: 1H); 7.14 (d, J = 5 Hz: 1 H); 7.21 (S: 1H); 7.44 (s: 1H); 7.85 (s: 1H); 8.08 (d, J = 5 Hz: 1 H); 12.16 (mf: 1 H). Mass spectrum (IE): m / z = 453 [M] ⁺ , m / z = 127 (base peak) b) 4-chloro-2- [1-methyl-5-methoxy-6- (2- methoxy-ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 147b but at from 0.087 cm ³ of N-methylpiperazine and 0.25 g of 4-chloro-2- [1-methyl-5-methoxy-6- (2-iodo-ethoxy) -IH-indol-3-yl] - 1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine. We obtain 0.303 g of 4-chloro-2- [1-methyl-5-methoxy-6- (2- (4-methyl-piperazin-4-yl-ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine the characteristics of which are as follows: Mass spectrum (IE): m / z = 607 [M] ⁺ , m / z = 127 (peak basic)

c) 4-chloro-2- [1-methyl-5-methoxy-6- (2-iodo-ethoxy) - IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine is prepared by following the procedure described in Example 147c but using 1.15 g of 4, -chloro- 2- [1-methyl-5-methoxy-6- (2 -chloro-ethoxy) -IH-indol-3-yl] - 1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine and 0.950 g of sodium iodide. After purification by flash chromatography (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent, argon), 1.21 g of 4-chloro-2- [1-methyl-5-methoxy-6- (1.25 g) is obtained ( 2-iodo-ethoxy) -r-1H- indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine, the characteristics of which are as follows: Mass spectrum ( IE): m / z = 635 [M] ⁺ , m / z = 480 (base peak) d) 4-chloro-2- [1-methyl-5-methoxy-6- (2-chloro-ethoxy) - IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 147d but from 1.3 g of 4-chloro-2- [1-methyl-5-methoxy-6-hydroxy) - 1H-indol-3-yl] -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine and 0.675 cm ³ l-bromo-2-chloroethane. After purification by flash chromatography (silica, ethyl acetate / cyclόhexaria 40/60 by volume as eluent, argon), 1.16 g of 4-chloro-2- [1-methyl-5-meth xy-6 AJ_2_ are obtained. -chloro-ethoxy) -1H- indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (CI): m / z = 544 [M + H] ⁺ (base peak)

e) 4-chloro-2- [1-methyl-5-methoxy-6-hydroxy) -IH-indol- 3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3- b] pyridine is prepared by following the procedure described in Example 147e but using 1.8 g of 4-chloro-2- [1- methyl-5-methoxy-6-benzyloxy) -1H-indol-3 -yl] -1- (toluene-4-silfonyl) -1H-pyrrolo [2,3-b] pyridine and 1,124 cm ³ of iodotrimethylsilane. After purification by flash chromatography (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent, argon), 1.3 g of 4-chloro-2- [1-methyl-5-methoxy-6-hydroxy are obtained. ) -lH-indol-3- yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine the characteristics of which are the following: Mass spectrum (CI): m / z = 482 [M + H] ⁺ (base peak)

f) 4.-chloro-2- [1-methyl-5-methoxy-6-benzyloxy) -1H- indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3 -b] pyridine is prepared by following the procedure described in Example 89c but from 2.5 g of 4-chloro-2-

(5-methoxy-6-benzyloxy-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridine and 0.335 cm ³ of methyl iodide. After purification by flash- chromatography (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent, argon), 2.1 g of 4-chloro-2- (1-methyl-5-methoxy-6-benzyloxy-1H-indol) are obtained -3- yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: Mass spectrum (CI): m / z = 571 [M] ⁺ , m / z = 480 (base peak) g) 4-chloro-2- (5-methoxy-6-benzyloxy-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 97c but from 2.75 g of 1-t-butyloxycarbonyl-5-methoxy-6-benzyloxy-indol- acid 3-boronic and 3 g of 1- (toluene-4-sulfonyl) -1H-2-iodo-4-chloropyrrolo [2,3-b] pyridine. After purification by flash chromatography (silica, ethyl acetate / cyclohexane 40/60 by volume as eluent, argon), 2.53 g of 4-chloro-2- (5-methoxy-6-benzyloxy-1H) are obtained. indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: Mass spectrum (IE): m / z = 557 [M] ⁺ , m / z = 466 (base peak)

The compounds 1- (toluene-4-sulfonyl) -1H-2-iodo-4-chloropyrrolo [2,3-b] pyridine and 1-tert-butyloxycarbonyl-5-methoxy-6-benzyloxy- acid indol-3-boronic are prepared according to the process described in patent O03000688A1.

EXAMPLE 172: 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-piperidyl-piperidin-1-yl) -ethoxy] -lH-indol-3-yl} -lH- pyrrolo [2, 3-b] -pyridine

a) 4-chloro-2- {1-methyl-5-methoxy-6- [2- (-piperidyl-piperidin-1-yl) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [ 2,3-b] - pyridine is prepared by following the procedure described in Example 89a but using 0.41 g of 4-chloro-2- [1-methyl-5-methoxy-6- (2- (4-piperidyl-piperidin-1-yl) - ethoxy) -lH-indol-3-yl] -1- (toluene- -sulfonyl) -lH-pyrrolo [2, 3-b] pyridine and 2.73 cm ³ of an aqueous solution of potassium hydroxide 5N. 0.272 g of 5-chloro-2- {5-methoxy-1-methyl-6- [2- (4-piperidyl-piperidin-1-yl) -ethoxy] -IH-indol-3-yl} is obtained - H -pyrrolo [2,3-b] - pyridine whose characteristics are the following: NMR spectrum ^Ï H (300 MHz, (CD ₃₎ ₂ SO d6, δ in ppm): from 1.30 to 1.60 ( mt: 8H); 1.70 (d large, -0- j „__ =: -_ ι_2-Hz — s —- 2H-X; —2-y-αS - (- -large -, - ___ = __ il — Hz -; - 2H -) -; _ 2.18 (large t, J = 12 and 3.5 Hz: 1H); 2.46 (t: 4H); 2.75 (t, J = 6 Hz: 2H); 3.04 (d wide, J = 11 Hz: 2H); 3.83 (s: 3H); 3.90 (s: 3H); 4.15 (t, J = 6 Hz: 2H); 6.71 (s : IH); 7.155 (dd, J = 5.5 Hz: IH); 7.20 (s: IH); 7.44 (s: IH); 7.85 (s: IH); 8.19 (d , J = 5.5 Hz: IH); 12.14 (broad s: IH). Mass Spectrum (IE): m / z = 521 [M] ⁺ , m / z≈ 195 (base peak) 0 b ) Lé 4-chloro-2- [1-methyl-5-methoxy-6- (2- (4-pipéridy- pipéridin-1-yl) -éthoxy) -IH-indol-3-yl] -1- (toluene -4- sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is prepared by following the procedure described in Example 147b but from 0.212 g of 4-piperidinopiperidine and from 0.400 g of 4-chloro-2 - [1-methyl-5-methoxy-6- (2-iodoethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine . 0.415 g of 4-chloro-2- [1- methyl-5-methoxy-6- (2- (4-piperidyl-piperidin-1-yl) -ethoxy) -IH-indol-3-yl] -1 is obtained - (toluene-4-sulfonyl) -1H-pyrrolo 0 [2, 3-b] pyridine, the characteristics of which are as follows: Mass Spectrum (CI): m / z = 676 [M + H] ⁺

EXAMPLE 173: 4-Chloro-2- {5-Methoxy-1-methyl-6- [2- (2-pyrrolidin-5 ethylamino) -ethoxy] .- IH-indol-3-yl} -lH-pyrrolo [2 , 3-b] - pyridine a) -Chloro-2- {5-Methoxy-1-methyl-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] -IH-indol-3-yl} -lH-pyrrolo [2,3 -b] - pyridine is prepared by following the procedure described in Example 89a but using 0.22 g of 4-chloro-2- {1-methyl-5-methoxy-6- [2- (2- pyrrolidin-ethylamino) - ethoxy] -IH-indol-3-yl} -l- (toluene.-4-sulfonyl) -IH- pyrrolo [2,3-b] -pyridine and 1.6 cm ³ of a 5N aqueous potassium hydroxide solution. After purification by flash-pack chromatography (silica, chloroform / methanol / aqueous ammonia (28%) 12/3 / 0.5 by volume as eluent), 0.095 g of 4 ~ chloro-2- {5- methoxy-1 is obtained -methyl-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] - IH-indol-3-yl} -lH-pyrrolo [2, 3-b] -pyridine the characteristics of which are as follows: NMR spectrum ^ -H (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.70 (mt: 4H); from 1.70 to 2.10 (very spread mf: 1 H); 2.45 (mt: 4H); from 2.45 to 2.55 (mt: 2H); 2.73 (t, J = 6.5 Hz: 2H); 2.97 (t, J = 6 HZ: 2H); 3.84 (s: 3H); 3.91 (s: 3H); 4.13 (t, J = 6 Hz: 2H); 6.72 (br s: 1H); 7.15 (d, J ≈ 5.5 Hz: 1 H); 7.18 (s: 1H); 7.45 (s: 1H); 7.85 (S: 1H); 8.08 (d, J = 5.5 Hz: 1 H); 12.14 (broad s: 1 H). Mass spectrum (CI): m / z = 468 [M + H] +

b) 4-chloro-2- {1-methyl-5-methoxy-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] -lH-indol-3-yl} -l- (toluene-4- sulfonyl) -IH-pyrrolo [2,3-b] -pyridine is prepared by following the procedure described in Example 147b but using 0.100 cm ³ of N- (2-aminoethyl) pyrrolidine and 0.3 g 4-chloro-2- [1-methyl-5-methoxy-6- (2-iodoethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -1H- pyrrolo [2 , 3-b] pyridine. 0.229 g of 4-chloro-2- {5-methoxy-1-methyl-6- [2- (2-pyrrolidin-ethylamino) - ethoxy] -lH-indol-3-yl} -l- (toluene-) is obtained 4-sulfonyl) -IH- pyrrolo [2, 3-b] -pyridine, the characteristics of which are as follows: Mass Spectrum (CI): m / z = 622 [M + H] ⁺ (base peak) EXAMPLE 174; 4-Chloro-2- {1-methyl-5-methyloxy-6- [2- (2- piperidin-ethylamino) -ethoxy] -IH-indol-3-yl} -lH-pyrrolo [2, 3-b] -pyridine a) -Chloro-2- {1-methyl-5-methoxy-6- [2- (2-piperidin- pyridine is prepared by following the procedure described in Example 89a but using 0.240 g of 4-chloro 2- (1-methyl-5-methoxy-6- [2- (2-piperidin-ethylamino) - ethoxy ] -lH-indol-3-yl} -l- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] -pyridine and 1.7 cm ³ of an aqueous solution of potassium hydroxide 5N. After purification by flash-chromatography pack (silica, dichloromethane / methanol / aqueous ammonia (28%) 40/5 / 0.5 by volume as eluent), 0.092 g of 4-chloro-2- {l-methyl- is obtained 5-Methoxy-6- [2- (2-pyrrolidin-ethylamino) - ethoxy] -IH-indol-3-yl} -lH-pyrrolo [2, 3-b] -pyridine the characteristics of which are as follows: 1 H-NMR (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.40 (mt: 2H); 1.51 (mt: 4H); 1.88 (mf spread: 1H); 2.35 (mt: 4H); 2.39 (t, J ≈ 6.5 Hz: 2H); 2.71 (t, J = 6.5 Hz: 2H); 2.96 (t, J = 5.5 Hz: 2H); 3.83 (s: 3H); 3.91 (s: 3H); 4.13 (t, J = 5.5 Hz: 2H); 6.71 (br s: 1H); 7.15 (dd, J = 5.5 Hz 1H); 7.17 (s: 1H); 7.45 (s: 1H). ; 7.85 (s: 1H); 8.08 (d, J = 5.5 Hz: 1 H); 12.14 (broad s: 1 H). Mass spectrum (CI): m / z = 482 [M + H] ⁺ (base peak) b) 4-chloro-2- {1-methyl-5-methoxy-6- [2- (2- piperidin- ethylamino) -ethoxy] -lH-indol-3-yl} -l- (toluene-4- sulfonyl) -IH-pyrrolo [2, 3-b] -pyridine is prepared by following the procedure described in Example 147b but using 0.135 cm3 of N- (2-aminoethyl) piperidine and 0.3 g of 4-chloro-2- [1-methyl-5-methoxy-6- (2-iodo-5 ethoxy) -IH-indol-3-yl] -1- (toluene-4-sulfonyl) -IH- pyrrolo [2 , 3-b] pyridine. 0.246 g of 4-chloro-2- {1-methyl-5-methoxy-6- [2- (2-piperidin-ethylamino) - ethoxy] -lH-indol-3-yl} -l- is obtained (toluene- 4-sulfonyl) -1H-pyrrolo [2,3-b] -pyridine, the characteristics of which are

, 10 .... following.-; - - - - _ Mass Spectrum (CI): m / z = 636 [M + H] ⁺ (base peak)

EXAMPLE 175 2- (5,7-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridine a) 2- (5,7-dimethoxy-1- methyl-1H-indol-3-yl) -1H-15 pyrrolo [2,3-b] pyridine can be prepared as follows: To a solution of 0.31 g of 2- (5,7-dimethoxy-1 - methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine in 20 cm ³ of methanol are added

20 3.3 cm ³ of a 5N aqueous solution of potassium hydroxide. The mixture is heated to around 80 ° C for about 1 environ hours. The reaction medium is poured onto a mixture of 100 cm ³ of ice plus water, extracted with three times 75 cm ³ of ethyl acetate. The phases

25 combined organics are washed with 100 cm ³ of water and then with 100 cm ³ of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash column chromatography

30 of silica [eluent: dichloromethane]. 0.073 g of 2- (5,7-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridine are obtained in the form of a solid, the characteristics of which are as follows : Melting point: 220 ° C (Banc-Kôfler) 1H NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.86 (S: 3H); 3.90 (s: 3H); 4.01 (s: 3H); 6.43 (d, J = 2 Hz: 1 H); 6.71 (d, J = 2 Hz: 1 H); 6.99 (d, J = 1.5 Hz: 1 H); 7.01 (dd, J = 8 and 5 Hz: 1 H); 7.76 (s: 1H); 7.85 (broad d, J = 8 Hz: 1 H); 8.11 (dd, J = 5 and 1.5 Hz: 1 H); 11.74 (mf: 1 H). Spectrum ^"Mass (El): m / z = 307 [M] ⁺ (base peak); m / z = 292 [M - CH _3] ⁺

b) 2- (5,7-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine can be prepared from as follows: To a solution of 0.26 g of 2- (5, 7-dimethoxy-IH- indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b ] pyridine in 11.5 cm ³ of dimethylformamide, 0.028 g of 60% sodium hydride in oil is added in small portions. The suspension is stirred for approximately 1 hour in the vicinity of 20 ° C. then 0.04 cm ³ of iodomethane is added. After stirring for about 1 hour in the vicinity of 20 ° C., the mixture is poured onto 100 cm ³ of an ice-water mixture, extracted with three times 75 cm ³ of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. 0.3 g of 2- (5,7-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine is obtained in the form of a meringue the characteristics of which are as follows: Mass spectrum (El): m / z = 461 [M] ⁺ (base peak); • m / z = 306 [M - C ₇ H ₇ 0 ₂ S] ⁺

vs). 2 -. (5,7-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine can be prepared as described in the example 105th: But from 2.9 g of 2-iodo-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine, from 2.34 g of 1-tert-butyloxycarbonyl-5 acid , 7-dimethoxy-1H-indole-3-boronic, 19 cm ³ of a saturated aqueous solution of sodium hydrogenocarbonate in 63 cm ³ of dimethylformamide and 0.42 g of tetrakis palladium (triphenylphosphine) is added. 0.26 g -de- _2 is thus obtained, after flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (70/30 by volume)]. _^ (-S, _7 — dimethoxy-1H-indol-3 ^ sulfonyl) -lH-pyrrolo [2, 3-b] pyridine in the form of a solid, the characteristics of which are as follows: TLC silica [eluent: cyclohexane / acetate ethyl (70/30 by volume)] Rf = 0.51 Mass Spectrum (El): m / z = 447 [M] ⁺ (base peak); m / z = 292 [M - C ₇ H ₇ 0 ₂ S] ⁺

The preparation of 2-iodo-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine is described in patent WO 2003000688 A1.

d) The 1-tert-butyloxycarbonyl-5,7-dimethoxy-1H-indole-3-boronic acid can be prepared in the following manner: To a solution of 2.2 g of tert-butyl ester of the acid 3-iodo-5, 7-dimethoxy-indole-1-carboxylic, 1.8 cm ³ of tributyl borate in 33 cm ³ of tetrahydrofuran cooled to -100 ° C, are added dropwise 9.82 cm ³ of a 2.5N solution of n-butyllithium in hexane while maintaining the temperature in the vicinity of -100 ° C. The cooling bath is removed and when the temperature of the reaction medium reaches approximately -5 ° C., 2 g of ice are added. After one hour of stirring at a temperature in the region of 20 ° C, the mixture is concentrated dry under reduced pressure (13 kPa). The residue is extracted with 200 cm ³ of ethyl acetate, washed with 100 cm ³ of a saturated aqueous solution of sodium chloride. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). 2.34 g of 1-tert-butyloxycarbonyl-5,7-dimethoxy-1H-indole-3-boronic acid are thus obtained in the form of a solid which is used as it is for the following step.

e) The tert-butyl ester of 3-iodo-5,7-dimethoxy-indole-1-carboxylic acid can be prepared as follows: To a solution of 1.18 g of 5,7-dimethoxy- 1 H -indole in 34 cm ³ of dimethylformamide is added 0.94 g of potassium hydroxide powder. A solution of 1.71 g of bi-sublimed iodine in 34 cm ³ of dimethylformamide is added dropwise to the preceding mixture. After stirring the mixture for 3 hours at a temperature in the region of 20 ° C., 0.062 g of 4-dimethylaminopyridine is added, then a solution of 1.82 g of di-tert-butyl dicarbonate in 10 cm ³ of dimethylformamide. After stirring for approximately 18 hours in the vicinity of 20 ° C., the mixture is poured over 89 cm ³ of an aqueous solution containing 0.2% of sodium thiosulfate. The mixture is extracted with three times 200 cm ³ of ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (90/10 by volume)]. 2.2 g of tert-butylic acid are obtained from 3-iodo-5,7-dimethoxy-indole-1-carboxylic acid in the form of a solid, the characteristics of which are as follows: TLC silica [eluent: cyclohexane / ethyl acetate (70/30 by volume)] Rf≈ 0.67 Mass Spectrum (El): m / z = 403 [M] ⁺ ; m / z = 303 [M - C0 ₂ tBu] ⁺ - (base peak)

5, 7-dimethoxy-IH-indole was prepared according to the method described by P.J. Milligan and S La Berge, Journal of Médicinal Chemistry, 1970, Vol.13, N ° 6, 1248-1

Example 176: 4-chloro-5-fluoro-2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH-indol-3-yl] -lH-pyrrolo [2, 3 - a) 4-chloro-5-fluoro-2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -lH-indol-3-yl] -IH-pyrrolo [2, 3 -b] pyridine can be prepared by following the procedure described in Example 100a but using 0.260 g of 4-chloro-5-fluoro-2- [1- (2-morpholin-4-yl-ethyl) - 5, 6-dimethoxy-1H- indol-3-yl] -1- (toluene- -sulfonyl) -lH-pyrrolo [2,3- b] pyridine and 0.62 g of 85% potassium hydroxide. After purification by crystallization from 11 cm ³ of ketonitrile, 0.115 g of 4-chloro-5-fluoro- 2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -lH- is obtained. indol-3- yl] -lH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.47 ( m partially masked, 4H); 2.71 (broad t, J = 6.5 Hz, 2H); 3.57 (m, 4H); 3.86 (s, 3H); _. 3.89 (s, 3H); 4.31 (wide t, J = 6.5 Hz, 2H); 6.74 (d, J = 2.0 Hz, 1H); 7.19 (S, 1H); 7.42 (s, 1H); 7.93 (s, 1H); 8.19 (d, J = 2.0 Hz, 1H); 12.2 (broad s, 1 H). - Mass spectrum (El): m / z = 458 (M) ⁺ (base peak)

b) 4-chloro-5-fluoro-2- [1- (2-morpholin-4-yl-ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4- sulfonyl) -IH-pyrrolo [2, 3-b] pyridine can be prepared by following the procedure described in Example 100b but starting from 0.280 g of 4-chloro-5-fluoro-2- [1- (2 - iodo-ethyl) -5,6-dimethoxy-IH-indol-3-yl] -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine, 0.065 g of potassium carbonate , 0.075 g of morpholine. 0.270 g of 4-chloro-5-fluoro-2- [1- (2- morpholin-4-yl-ethyl) -5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene is thus obtained -4-sulfonyl) -1H-pyrrolo [2,3-b] -pyridine sous.fo_rme__ dJjune__r.êsin.e ___ orangLé_e_. _lon_t. the characteristics are as follows: - Rf CCM silica [eluent: cyclohexane / methanol (95/5 by volume)] = 0.52 - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2 , 27 (s, 3H); from 2.45 to 2.55 (m masked, 4H); 2.77 (t, J = 6.5 Hz, 2H); 3.58 (m, 4H); 3.70 (S, 3H); 3.87 (s, 3H); 4.35 (t, J = 6.5 Hz, 2H); 6.77 (s, 1H); 6.84 (s, 1H); 7.17 (s, 1H); 7.20 (broad d, J = 8.5 Hz, 2H); 7.49 (broad d, J = 8.5 Hz, 2H); 7.60 (s, 1H); 8.48 (d, J = 2.0 Hz, 1H) c) 4-chloro-5-fluoro-2- [1- (2-iodo-ethyl) -5,6- dimethoxy-IH-indol-3 -yl] -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridine can be prepared by following the procedure described in example 100c but starting from 0.260 g of 4-chloro- 5-fluoro-2- [1- (2-chloro-ethyl) -5, 6-dimethoxy-1H-indol-3-yl] -i- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3- b] pyridine and 0.104 g of sodium iodide. 0.283 g of 4-chloro-5-fluoro-2- [1- (2- iodo-ethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) is thus obtained. ) -lH-pyrrolo [2, 3-b] pyridine in the form of an orange resin, the characteristics of which are as follows: - Rf CCM silica [eluent: dichloromethane / ethyl acetate (95/5 by volume)] = 0 72 - Mass spectrum (El): m / z = 653 (M) ⁺ base peak d) 4-chloro-5-fluoro-2- [1- (2-chloro-ethyl) -5,6- dimethoxy- IH-indol-3-yl] -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridine can be prepared by following the procedure described in Example 100d but from 0.390 g of 4-chloro-5-fluoro-2- (5, 6-dimethoxy-1H- indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine and 0.005 g of tetrabutylammonium bromide in 30 cm ³ of 1,2-dichloroethane, 0.343 g of potassium hydroxide and 0.251 g of potassium carbonate. 0.260 g of 4-chloro-5-fluoro-2- [1- (2-chloroethyl) -5,6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) is obtained -lH-pyrrolo [2, 3-b] pyridine in the form of an orange resin, the characteristics of which are as follows: - TLC silica [eluent: dichloromethane / ethyl acetate (95/5 by volume)] Rf = 0, 56 - Mass Spectrum (El): m / z = 562 (M) ⁺ e) 4-chloro-5-fluoro-2- (5, 6-dimethoxy-IH-indol- 3-yl) -1- ( toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridine can be prepared by following the procedure described in Example 97c but starting from 0.750 g of 1- (toluene-4-sulfonyl) -lH -2-iodo-4-chloro-5-fluoropyrrolo [2, 3-b] pyridine, 0.534 g of 1-tert-butyloxycarbonyl-5, 6-dimethoxy-indol-3-boronic acid and 0.096 g g of tetrakis (triphenylphosphine) palladium. 0.390 g of 4-chloro-2- (5, 6-dimethoxy-1H- indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine is thus obtained the characteristics are the following: - 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.29 (s, 3H); 3.70 (s, 3H); 3.82 (s, 3H); 6.79 (S, 1H); 6.92 (s, 1H); 7.00 (s, 1H); 7.26 (broad d, J = 8.5 Hz, 2H); 7.52 (d wide, J = 8.5 Hz, 2H); 7.53 (s, 1H); 8.47 (d, J = 2.0 Hz, 1H); 11.3 (broad s, 1 H). - Mass spectrum (El): m / z = 499 (M) ⁺

The 1-tert-butyloxy-carbonyl-5,6-dimethoxy-indol-3-boronic acid is prepared according to the process described in patent WO03000688A1. f) 1- (toluene-4-sulfonyl) -LH-2-iodo-4-chloro-5- fluoro-pyrrolo [2, 3-b] pyridine can be prepared as follows- marière-: ^~ - To a solution of 0.650 g of 1- (toluene-4-sulfonyl) -1H-4-chloro-5-fluoro-pyrrolo [2,3-b] pyridine in 15cm ³ of tetrahydrofuran at about -78 ° C, is added 1.18 cm ³ of tert-BuLi drop by drop. After having stirred the reaction medium for 30 min at approximately - 78 ° C, a solution of 1.01 g of iodine in 6 cm ³ of tetrahydrofuran is added dropwise, and the temperature is maintained at -78 ° C for 2 h. The temperature is allowed to rise to approximately 0 ° C. After adding 5 cm ³ of a saturated aqueous ammonium chloride solution, the reaction mixture is extracted with 80 cm ³ of ethyl acetate, the organic phase is then washed with 3 times 20 cm ³ of water, then dried over magnesium sulfate and concentrated under reduced pressure (13KPa). 0.750 g of 1- (toluene-4-sulfonyl) -1H-2-iodo-4-chloro-5-fluoro-pyrrolo [2, 3-b] pyridine are thus obtained in the form of a cream-colored solid, the characteristics are as follows: - TLC silica [eluent: dichloromethane] Rf = 0.59 - Mass spectrum (El): m / z = 451 (M) + g) 1- (toluene-4-sulfonyl) -lH- 4-chloro-5-fluoropyrrolo [2, 3-b] pyridine can be prepared as follows: A mixture of 1.30 g of 4-chloro-5-fluoro-IH- pyrrolo [2, 3-b] pyridine, 1.6 g of 4-methyl chloride benzenesulfonyl, 3.40 g of sodium hydroxide dissolved in 16 cm ³ of water, 0.052 g of tetrabutylammonium hydrogen sulphate in 200 cm ³ of toluene is stirred for about 24 hours near 20 ° C. The mixture is diluted with 500 cm ³ of ethyl acetate; the organic phase is washed with three times 200 cm ³ of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: dichloromethane! . 1.90 g of 4-chloro-5-fluoro-1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine are thus obtained in the form of a powder, the characteristics of which are as follows: - Melting point: melting at 125 ° C. (Kofler Bank) - 1 H NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.36 (s, 3H); 6.93 (d, J = 3.0 Hz, 1H); 7.44 (broad d, J = 8.0 Hz, 2H); 7.99 (broad d, J = 8.0 Hz, 2H); 8.12 (d, J = 3.0 Hz, 1H); 8.52 (d, J = 2.5 Hz, IH) - Mass spectrum (El): m / z = 324 (M) ⁺ h) 4-chloro-5-fluoro-1H-pyrrolo [2, 3 -b] pyridine can be prepared as follows: A solution of 1.7 g of 5-fluoro-1H-pyrrolo [2,3- b] pyridine-7-oxide in 10 cm ³ of phosphorus oxychloride is brought to the reflux of P0C1 ₃ for 8 h. After vacuum distillation of P0Cl _{3 /} the residue is treated with 50g of ice, the pH of the solution obtained is brought to the vicinity of 8-9 by addition of sodium hydrogen carbonate. The aqueous phase is extracted with 5 times 80 cm ³ of ethyl acetate. The combined organic phases are then dried over magnesium sulphate filtered and concentrated to dryness under reduced pressure (13kPa). 1.3 g of 4-chloro-5-fluoro-1H-pyrrolo [2,3-b] pyridine are thus obtained in the form of a solid, the characteristics of which are as follows: Rf CCM silica [eluent: dichlorom ethane / methanol (98/2 by volume)] = 0.19 - 1 H NMR spectrum (400 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 6.56 (m, 1H ); 7.70 (m, 1H); 8.35 (d, J = 2.5 Hz, 1H); 12.15 (m wide, IH) - Mass Spectrum (El): m / z = 170 (M) ⁺ i) 5-fluoro-1H-pyrrolo [2, 3-b] pyridine 7-oxide can be prepared as follows: To a solution of 2.7 g of 5-fluoro-1H-pyrrolo [2,3-b] pyridine in 70 cm ³ of dimethoxyethane, 6.22 g of 3-chloro-perbenzoic acid is added. The reaction medium is left to stir in the vicinity of 20 ° C. for 1 h 30 min. After adding a solution of 2 g of potassium hydroxide in 20 cm ³ of methanol, extraction is carried out with 5 times 100 cm ³ of ethyl acetate. The organic phases are then washed with 2 times 15 cm ³ of a saturated ammonium chloride solution and then dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13kPa). The residue is purified by flash chromatography on a silica column [eluent: dichloromethane / methanol (95/5 by volume)], 3.6 g of a solid are obtained which is washed with 25 cm ³ of diethyl ether and then drained and dried. The residue is purified by flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (50/50 by volume)], 1.70 g of 5-fluoro-1H-pyrrolo [2, 3-b] pyridine are obtained 7-oxide in the form of a powder, the characteristics of which are as follows: - Melting point: melting at 178 ° C. (Kofler bench) - IR spectrum: KBr 3128; 3085; 2919; 2863; 2734; 2629; 2406; 1588; 1507; 1349; 1256; 1206; 1129; 1077; 990; 804; 723; 670 and 466 cm ^"1 j) 5-fluoro-1H-pyrrolo [2, 3-b] pyridine can be prepared as follows: A mixture of 3.80 g of 5-fluoro-3-trimethylsilanylethynyl-pyridin-2-ylamine and 3.40 g of potassium tert-butoxide in 100 cm ³ of 1-methyl-pyrrolidin-2-one is brought to around 130 ° C for about 4 hours. After returning to a temperature in the region of 20 ° C., the mixture is poured onto 1000 cm ³ of a saturated aqueous solution of sodium chloride and extracted with 5 times 250 cm ³ of ethylene oxide. The organic phases are combined, washed with 5 times 100 cm ³ of a saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13kPa. 2.35 g of 5-fluoro- are obtained. IH- pyrrolo [2, 3-b] pyridine in the form of a solid, the characteristics of which are as follows: - Melting point: melting at 110 ° C. (Banc-Kôfler) - mass spectrum (El): m / z = 136 (M) ⁺ base peak m / z = 109 (M - HCN) ⁺ k) 5-fluoro-3-trimethylsilanylethynyl-pyridin-2-ylamine can be prepared as follows: To a solution of 14 g of 5-fluoro-3-iodo-pyridin-2-ylamine in 440 cm ³ of dimethylformamide, degassed with argon, are added 12.47 cm ³ of ethynyl-trimethyl-silane, 2.24 g of copper iodide, 2, 74 g of lithium chloride, 41.33 cm ³ of triethylamine and 2.15 g of [1,1′-bis (diphenylphosphino) ferrocene] palladiu (II) chloride. The solution obtained is brought to a temperature in the region of 55 ° C for approximately 5 hours. After returning to a temperature in the region of 20 ° C, the mixture is concentrated under reduced pressure (13kPa); the residue is taken up in 300cm ³ of water, extracted with three times 100cm ³ of ethyl acetate. The combined organic phases are washed with three times 100 cm ³ of water. dried over magnesium sulfate, filtered and concentrated under reduced pressure

(13kPa). 7.91 g are thus obtained, after flash chromatography on a silica column (eluent: dichloromethane) of 5-fluoro-3-trimethylsilanylethynyl-pyridin-2-ylamine in the form of a solid, the characteristics of which are as follows: - Melting point: melting at 65 ° C. (Kofler bench) - Mass spectrum (El): m / z = 208 (M) ⁺ m / z = 193 (M - CH ₃ ) ⁺ base peak

1) 5-fluoro-3-iodo-pyridin-2-ylamine can be prepared as follows: A mixture of 9.9 g of 5-fluoro-pyridin-3-ylamine and 21.85 g of N-iodosuccinimide in 400 cm ³ of acetic acid is stirred for approximately 6 hours at a temperature in the region of 70 ° C. After concentration to dryness under reduced pressure (13 kPa), the residue is taken up in 250 cm ³ of water; the pH is brought to approximately 8 by addition of sodium hydrogen carbonate. The aqueous phase is extracted with five times 150 cm ³ of dichloromethane. The combined organic phases are washed with three times 100 cm ³ of water, then with five times 50 cm ³ of a 10% aqueous solution of sodium thiosulfate, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa ). 11 g of 5-fluoro-3-iodo-pyridin-2-ylamine are thus obtained, after flash chromatography on a column of silica (eluent: dichloromethane), in the form of a solid, the characteristics of which are as follows: - Melting point: melting at 76 ° C. (Kofler bench) - 1 H NMR spectrum (300 MHz, (CD ₃ ) ₂ S0 d6, δ in ppm): 5.98 (broad s, 2H); from 7.93 to 7.98 (m, 2H). - Mass spectrum (El): m / z = 238 (M) ⁺

Example 177: 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin-4-ylamine ((A003346712 (P-32441-067- 1)) a) 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2,3-b] pyridin-4-ylamine can be prepared from as follows: To a solution of 0.1 g of 2- (1-methyl) -5,6- dimethoxy-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] -pyridin-4-ylamine in 10 cm ³ of tetrahydrofuran, degassed with argon, are added 1.05 cm ³ of tetrabutyl ammonium fluoride. The solution obtained is brought to reflux for approximately 24 hours. After returning to a temperature in the region of 20 ° C, the mixture is concentrated under reduced pressure (13kPa); the residue is taken up in 50 cm ³ of a saturated solution of sodium hydrogen carbonate, extracted with three times 50 cm ³ of ethyl acetate then three times 100 cm ³ of dichloromethane. The combined organic phases are washed with three times 100 cm ³ of water, dried over magnesium sulfate, filtered and concentrated under reduced pressure (13kPa). There is thus obtained, after flash chromatography on a silica column [eluent: dichloromethane / methanol 90/10 by volume)], 0.015 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3- b] pyridin-ylamine in the form of a white solid, the characteristics of which are as follows: - 1 H NMR spectrum (400 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3 , 79 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 6.07 (br s, 2H); 6.13 (d, J = 5.0 Hz, 1H); 6.82 (br s, 1H); 7.09 (s, 1H); 7.43 (s, 1H); 7.63 (s, 1H); 7.67 (d, J = 5.0 Hz, 1H); 11.2 (broad s, 1 H) - Mass spectrum (El): m / z = 322 (M) + b) Le 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] -pyridin-4-ylamine can be prepared as follows: To a solution of 0.7 g of benzhydrylide- [2- ( 1- methyl) -5,6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] -pyridin- -yl] amino in 20cm ³ of tetrahydrofuran, 5.5 cm ³ of an aqueous solution of 2N hydrochloric acid are added. The solution obtained is kept stirring in the vicinity of 20 ° C for about 3 hours. The mixture is concentrated under reduced pressure (13kPa); the residue is taken up in 50 cm ³ of a saturated solution of sodium hydrogen carbonate, extracted 5 with three times 50 cm ³ of ethyl acetate then three times 25 cm ³ of dichloromethane. The combined organic phases are washed with three times 50 cm ³ of water, dried over magnesium sulfate, filtered and concentrated under reduced pressure (13kPa). We thus obtain, after flash dichloromethane / methanol 98/2 by volume)], 0.31 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] -pyridin-4-ylamine in the form of a pale pink solid the characteristics of which are the following: - TLC silica [eluent: dichloromethane / methanol (98/2 by volume)] Rf = 0.125 - Mass spectrum (EI): m / z = 476 (M) ⁺ c) Benzhydrylidene- [2- (1-methyl) -5,6-dimethoxy- IH-indol-3-yl) -1- (toluene -4-sulfonyl) -1H-pyrrolo [2, 3-b] - pyridin-4-yl] amine can be prepared as follows: To a solution of 0.8 g of 4-chloro-2- (5, 6-dimethoxy-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- 25 pyrrolo [2, 3-b] pyridine in 80cm ³ of toluene, degassed with argon, are added 1 , 7g of cesium carbonate, 0.4g of (R) - (+) -2, 2-bis (diphenylphosphino) -1,1 '-binaphthyl and 0,377g of benzophenone imine. The solution obtained is kept under stirring in the vicinity of 20 ° C for about 15 min and then 0.144 g of palladium acetate is added. The mixture is brought to reflux for 4 hours then, after returning to the vicinity of 20 ° C., filtered through sintered glass clogged with celite. The cake is washed with three times 20 cm ³ of dichloromethane, the filtrate is then concentrated under reduced pressure (13 kPa). We thus obtains, after flash chromatography on a silica column [eluent: cyclohexane / ethyl acetate (50/50 by volume)], 1.3 g of benzhydrylidene- [2- (1-methyl) -5,6- dimethoxy-1H -indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] -pyridin-4-yl] amine in the form of a yellow solid with the following characteristics: - 1 H NMR spectrum (400 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.31 (s, 3H); 3.72 (s, 3 ^' H); 3.82 (s, 3H); 3.86 (S, 3H); 6.49 (s, 1H); 6.61 (d, J = 5.0 Hz, 1H); .6._â8__ts., _ LHX _; _ 7 _ ,. 0.8 (.s _, __ IH); „_- 7 _ ,. 2J3„ _Cd__large., __ 8., _ 5_ Hz, 2H); 7.39 (broad d, J = 8.5 Hz, 2H); 7.41 (s, 1H); from 7.05 to 7.75 (very spread m, 10H); 8.02 (d, J = 5.0 Hz, 1 H). - Mass spectrum (CI): m / z = 641 (M + H) ⁺ 4-chloro-2- (5,6-dimethoxy-1H-indol-3-yl) -1- (toluene-4-sulfonyl ) -1H-pyrrolo [2, 3-b] pyridine is obtained as described in Example 97b.

Example 178: Cyclohexyl- [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amine ((A003341949 ( P-31916-162-1))): a) Cyclohexyl- [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin -4-ylmethyl] -aminate can be prepared as follows: To a solution of 0.14 g of cyclohexyl- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1 - (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -aminated in 10 cm ³ of tetrahydrofuran, 1 cm ³ of a 1M solution of tetrabutylammonium fluoride (TBAF) is added in solution in tetrahydrofuran, at a temperature close to 20 ° C. The reaction medium is stirred at this same temperature for 15 hours, then heated at reflux for 24 hours. After cooling, the reaction medium is evaporated to dryness under reduced pressure. 4 cm ³ of water are added. The solid formed is filtered on sintered glass, washed with water and then with ethyl ether. The solid obtained is taken up in water and the medium is made alkaline at PH = 10 with 0.1 N sodium hydroxide. The product is extracted 5 times with dichloromethane. The organic phases are combined, dried over magnesium sulphate, filtered, then concentrated under reduced pressure. 0.029 g of cyclohexyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrόlo [2,3-b] pyridin-4-ylmethyl] -amine are thus obtained. the characteristics are as follows: - NMR spectrum (300 MHz, (CDs ^ SO d6, δ in. ppm): 1.05 to 1.28 (m, 5H); from 1.48 to 1.76 (m, 3H); from 1.85 to 2.03 (m, 2H); from 3.17 to 3.42 (masked m, 1H); 3.80 (s, 3H); 3.85 (s, 3H); 3.88 (s, 3H); 4.05 (broad s, 2H); 6.82 (d, J = 2.0 Hz, IH); 7.02 (d, J = 5.0 Hz, IH) ; 7.11 (s, 1H); 7.45 (s, 1H); 7.75 (S, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.65 (wide , IH). - Mass spectrum (El): m / z = 418 (M) ⁺ ; -m / z = 321 (M - C _s HιιN) ⁺ base peak b) Cyclohexyl- [2- (5, 6-dimethoxy-1-methyl-IH- indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2,3- b] pyridin-4-ylmethyl] -aminate can be prepared from as follows: To a solution of 0.24 g of cyclohexylamine in 5 cm ³ of dichloromethane, under an inert atmosphere of argon at a temperature in the region of 20 ° C, 0.16 g of 2 is added - (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridin-4-carboxaldehyde and 0.4 g of sodium sulfate. Stirring is continued for 48 hours at room temperature. 5 cm ³ of methanol and 0.023 g of sodium borohydride are added. The reaction medium is stirred at the same temperature for 6 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up with 10 cm ³ of dichloromethane. The precipitate formed is filtered and the the filtrate is concentrated under reduced pressure and then purified by flash chromatography on a column (Si02, dichloromethane / methanol, 98/02 by volume as eluent). The fractions containing the product are combined and concentrated to dryness under reduced pressure to give 0.143 g of the. cyclohexyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene- -sulfonyl) -pyrrolo [2,3-b] pyridin-4-ylmethyl] -amin . - Mass spectrum (El): m / z = 572 (M) ⁺ ; m / z = 417 (M - C ₇ H ₇ S0a) ⁺ base peak; m / z = 320 (m / z = 417 - C ₆ HuN) ⁺ c) Le 2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl ) -lH-pyrrolo [2, 3-b] pyridin-4-carboxaldehyde can be prepared as follows: To a solution of 4.4 g of 2- (5, 6-dimethoxy-1-methyl-1H-indol) -3-yl) -4- (1,3-dioxolan) -2-yl-l- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridine in 100 cm ³ of tetrahydrofuran, at one temperature close to 20 ° C., 16.5 cm ³ of 5N hydrochloric acid are added. The reaction medium is stirred at this same temperature for 24 hours. 30 cm ³ of water and 30 cm ³ of dichloromethane are added. After decantation, the organic phase is dried over magnesium sulfate, filtered, concentrated under reduced pressure, then purified on a silica column, eluting with a mixture of cyclohexane and ethyl acetate 50/50 by volume. The fractions containing the product are combined and concentrated to dryness under reduced pressure to give 2.6 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4- sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde, the characteristics of which are as follows: - Mass spectrum (El): m / z = 489 (M) ⁺ ; m / z = 334 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak d) 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -4- (1,3 -dioxolan) -2-yl-1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridine can be prepared as follows: To a solution of 5 g of 2- (5, 6-dimethoxy-1H-indol-3-yl) -4- (1,3-dioxolan ) -2-yl-l- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridine in 185 cm ³ of anhydrous dimethylformamide (DMF), under an inert argon atmosphere at a temperature close to 20 ° C, 0.462 g of 60% sodium hydride suspended in oil is added. The reaction medium is stirred at the same temperature for 45 minutes. 0.719 cm ³ of methyl iodide is added to taste. The reaction medium is stirred at this same temperature for 20 hours. 200 cm ³ of water and 100 cm ³ of ethyl acetate are added. After decantation, the organic phase is dried over magnesium sulfate, filtered, concentrated under reduced pressure, then purified on a silica column, eluting with a mixture of dichloromethane and methanol 98/02 by volume. The fractions containing the product are combined and concentrated to dryness under reduced pressure to give 4.42 g of 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -4- (1,3- dioxolan) -2-yl-l- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: - Mass spectrum (El): m / z = 533 (M ) ⁺ ; m / z = 378 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak e) Le 2- (5, 6-Dimethoxy-IH-indol-3-yl) -4- (1,3- dioxolan) - 2-yl-l- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine can be prepared as follows: To a solution of 6.2 g of 4- (1,3-dioxolan ) -2-yl-2- iodo-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine, 135 cm ³ of anhydrous DMF and 7.42 g of acid 1 -t- butyloxycarbonyl-5, 6-dimethoxyindol-3-boronic, under an inert atmosphere of argon at a temperature close to 20 ° C, are added 41 cm ³ of a saturated solution of sodium bicarbonate and 0.611 g of tetrakis (triphenylphosphine) alladium. The reaction medium is heated at 130 ° C for 3 hours. After cooling, the reaction medium is concentrated under reduced pressure. The oil obtained is taken up in 80 cm ³ of water and 100 cm ³ of ethyl acetate. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography (SiO2, ethyl acetate / cyclohexane 50/50 by volume as

_10__êluantS -, _ arg_αnX .. .._ fractions containing the product are concentrated under reduced pressure. 5 g of 2- (5,6-dimethoxy-1H-indol-3-yl) -4- (1,3-dioxolan) -2-yl- 1- (toluene-4-sulfonyl) -lH- are thus obtained pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: 15 - Mass spectrum (El): m / z = 519 (M) ⁺ ; m / z = 364 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak

1-t-Butyloxycarbonyl-5,6-dimethoxyindol-3-boronic acid is prepared according to the method described in patent WO03000688A1.

F) 4- (1,3-dioxolan) -2-yl-2-iodo-1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine can be prepared as follows : To a solution of 5 g of 4- (1,3-dioxolan) -2-yl-l- (toluene- -sulfonyl) -IH-pyrrolo [2, 3-b] pyridine, in 100 25 cm ³ of tetrahydrofuran anhydrous, under an inert argon atmosphere at a temperature close to -78 ° C., 5.81 cm ³ of n-BuLi (2.5 M in hexane) are added dropwise. The reaction medium is stirred at this same temperature for 25 minutes, then a solution of 7.37 g of iodine in 50 cm ³ of tetrahydrofuran is added dropwise. The reaction medium is stirred at -78 ° C for 15 minutes. The cooling bath is removed. The temperature rises to ambient after 2 hours of stirring. The dream environment is agitated at the

35 room temperature for 20 hours. 15 cm ^{3 are added} of water and 15 cm ³ of ethyl acetate. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography (SiO2, 5 dichloromethane as eluent, argon). The fractions containing the product are concentrated under reduced pressure. 6.28 g of 4- (1.3-dioxolan) -2-yl-2-iodo-l- (to ύèhe-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine are thus obtained. characteristics are as follows: _.1_CL__ - Mass spectrum (ES): m / z = 471 (M + H) * base peak g) 4- (1,3 -dioxolan) -2-yl-l- ( toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridine can be prepared as follows: To a solution of 5.8 g of 1- (toluene-4-sulfonyl) - 15 lH-pyrrolo [ 2,3-b] pyridine-4-carboxaldehyde, in 250 cm ³ of toluene, under an inert argon atmosphere, 2.15 cm ³ of ethylene glycol and 0.735 g of para-toluene sulfonic acid are added. The reaction medium is heated at 120 ° C for three hours. After cooling, 50 cm ³ of water and 50 cm ³ of ethyl acetate are added. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is triturated with ethyl ether. The solid obtained is filtered and then washed with 20 cm ³ of ethyl ether. 5.3 g of 4- (1,3-dioxolan) -2-yl-1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine are thus obtained, the characteristics of which are as follows: - Mass spectrum (El): m / z = 344 (M) ⁺ ; m / z = 237 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak; m / z = 91 (C ₇ H ₇ ) ⁺

30 h) 1- (toluene-4-sulfonyl) -lH-pyrrolo ^ S- bJpyridine ^ -carboxaldehyde can be prepared as follows: To a solution of 10 g of 1- (toiuene-4-sulfonyl) - 1H -pyrrolo [2,3-b] pyridine-4-carbonitrile in 400 cm ³ of

35 toluene, under an inert argon atmosphere at a temperature close to -30 ° C., 50.5 cm ³ of diisobutylaluminum hydride (DIBAH) in solution 20% by weight in toluene (1M) is added dropwise. After 40 minutes of stirring at this same temperature, the cooling bath 5 is removed. The temperature is allowed to rise to 20 ° C. The reaction medium is kept stirring at a temperature in the region of 20 ° C for 1 hour. The reaction medium is cooled to 4 ° C. Oh add IN _10__ hydrochloric acid drop by drop until. PH = 6. The precipitate formed is filtered, then washed with 50 cm ³ of water and 280 cm ³ of ethyl acetate. After decanting the filtrate, the organic phase is dried over sodium sulfate, filtered, concentrated under reduced pressure and then purified by flash column chromatography (SiO2, dichloromethane as eluent, Ar). The fractions containing the product are concentrated under reduced pressure. 4.3 g of 1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine-4-carboxaldehyde are thus obtained, the characteristics of which are as follows:

20 - Mass spectrum (El): m / z = 300 (M) ⁺ ; m / z = 236 (M - S0 ₂ ) ⁺ ; m / z = 91; (C ₇ H ₇ ⁺ ) base peak i) 1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine-4-carbonitrile can be prepared as follows:

25 To a solution of 10 g of 4-chloro-1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine in 200 cm ³ of N, N-dimethylacetamide, under an inert atmosphere of argon is added 6.9 g of zinc cyanide and 1.07 g of zinc powder. After 45 minutes of stirring at a temperature

30 near 20 ° C, 2.4 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) (PdCl2, dppf) are added. The reaction medium is heated to a temperature in the region of 140 ° C. for 1 hour and a half. After cooling, the medium

35 is filtered on celite and then rinsed with dichloromethane. 150 cm ³ of water are added to the filtrate. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography on a column (SiO2, cyclohexane / ethyl acetate 75/25 by volume as eluent, Ar), 8.57 g of 1- (toluene-4-sulfonyl) -lH-pyrrolo are obtained. , 3- b] pyridihé-4-carbonitrile, the characteristics of which are the following: _ _. - Mass spectrum (El): m / z = 297 (M) X m / z = 233 (M - S0 ₂ ) X m / z = 91 (C ₇ H ₇ ) ⁺ base peak

The compound 4-chloro-1- (toluene-4-sulfonyl) -H-pyrrolo ^, 3-b] pyridine is prepared according to the process described in patent WO3000688A1. Example 179; [2- (5, 6-Dimethyl-1-methyl-1H-indol-3-yl) -IH- pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -aminate ( (A003364149 (P- 32520-098-1)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2,3-b] pyridin -4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amin can be prepared as follows: To a solution of 0.04 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol) 3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-

- trifluoromethylsulfanyl-benzyl) -aminated in 2 cm ³ of methanol, at a temperature in the region of 20 ° C., 0.265 cm ³ of 5N potassium hydroxide is added. The reaction medium is heated at reflux for 6 hours. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is taken up with 4 cm ³ of water, the solid formed is filtered through sintered glass, washed twice with 3 cm ³ of water, then dried under vacuum to give 0.030 g of [2- (5, 6- dimethoxy-1-methyl-IH-indol-3- yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -aminate with the following characteristics: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): Dice 2.85 to 3.00 (m spread, 1H); 3.80 (s, 3H); 3.85 (s, 3H); 3.87 (s, 3H); from 3.78 to 3.90 (masked m, 2H); 4.06 (br s, 2H); 6.79 (br s, 1H); 7.07 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H) 7.45 (s, 1H); 7.58 (wide d, J ≈ 8.5 Hz, 2H) ._ 7.68 (wide d, _ J _ = _ 81 _, _ 5_ _. Hz, 2H); 7.76 (s, 1H) 8.07 (d, J = 5.0 Hz, 1H); 11.7 (broad s, 1 H). -Mass spectrum (El): m / z = 526 (M) ⁺ ; m / z = 321 (M - C ₈ H ₆ SNF ₃ ) ⁺ base peak b) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene- 4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amin can be prepared as described in Example 178b from 0.065 g of 2- ( 5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-4-carboxaldehyde and 0.08 cm ³ of 4-trifluoromethylsulfanyl-benzylamine instead of the cyclohexylamine used in Example 178b. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.044 g of [2- (5, 6-dimethoxy-1- methyl-IH-indol-3-yl) - is obtained - 1- (toluene-4-sulfonyl) -IH- pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine with the following characteristics: - Spectrum of _. mass (El): m / z = 680 (M) ⁺ ; m / z = 525 (M - C ₇ H ₇ S0 ₂ ) ⁺ ; m / z = 320 (m / z = 525 - C ₈ H ₆ SNF ₃ ) ⁺ base peak

Example 180: ^' Phenyl- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -aminate ((A003390480 (P-32520-140-4)): a) Phenyl- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amine is prepared as described in Example 179a from 0.120 g of phenyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [ 2, 3-b] pyridin-4-ylmethyl] -amine instead of [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) - amine used in Example 179a and 0.95 cm ³ of 5N potassium hydroxide. 0.010 g of phenyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3- b] pyridin-4-ylmethyl] -aminate is obtained, the characteristics are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.81 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 4.61 (d, J = 6.0 Hz, 2H); 6.43 (t, J = 6.0 Hz, 1 H); 6.49 (broad t, J = 7.5 Hz, 1 H); 6.61 (broad d, J = 7.5 Hz, 2H); 6.91 (d, J = 2.0 Hz, 1H); from 6.96 to 7.05 (m, 3H); 7.11 (s, 1H); 7.47 (s, 1H); 7.76 (s, 1H); 8.02 (d, J = 5.0 Hz, 1H); 11.7 (broad s, 1 H). - Mass spectrum: (ES); m / z = 413; (M + H) ⁺ base peak b) Phenyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amine is prepared as described in Example 178b from 0.1 g of 2- (5,6-dimethoxy-1-methyl-1H-indol- 3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0.037, cm ³ of aniline instead of the cyclohexylamine used in Example 178b. After purification. by chromatography flash-pack (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.122 g of phenyl- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) is obtained - 1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -amino the characteristics of which are as follows: - Mass spectrum (ES): m / z = 567 (M + H) ⁺

Example 181; Benzyl- [2- (5, 6-dimethoxy-1-methyl-IH-indol- 3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -aminate ((A003389983 (P-32520 -141-1)): a) Benzyl- [2- (5, 6-dimethόxy-1-methyl-1H-indôl-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl ] -aminate is prepared as described in 1 / example 179a from 0.070 g of benzyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene- 4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -aminated instead of [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -1 - (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) - amine used in Example 179a and 0.54 cm ³ of 5N potassium hydroxide. 0.038 g of benzyl- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -aminate is obtained, characteristics are as follows: - Spectrum of. NMR (300 MHz, (CD ₃ ) ₂ S0 d6, δ in ppm): From 2.60 to 2.80 (spread m, 1 H); 3.78 (br s, 2H); 3, 81. (S, 3H); 3.85 (s, 3H); 3.87 (s, 3H); 4.03 (br s, 2H); 6.79 (d, J = 2.0 Hz, 1H); 7.06 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.23 (broad t, J = 7.5 Hz, 1H); 7.31 (wide t, J = 7.5 Hz, 2H); 7.41 (broad d, J = 7.5 Hz, 2H); 7.43 (s, 1H); 7.75 (s, 1H); 8.06 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum. (EI): m / z = 426 (M) ⁺ ; m / z = 321 (M - .C ₈ H ₆ SNF ₃ ) ⁺ base peak b) Benzyl- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3- yl) -1- (toluene-4-sulfonyl) -1 H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amin is prepared as described in Example 178b from 0.1 g of 2- (5,6- dimethoxy-l-methyl-lH-indol 3-yl) -1- (toluene- -sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0.045 cm ³ of benzylamine instead of the cyclohexylamine used in Example 178b. After purification by flash-pack chromatography (Si02, 5 dichloromethane / methanol 98/02 by volume as eluent), 0.071 g of benzyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-) is obtained yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -amino whose characteristics are the following: ¹⁰ _.. - Mass spectrum (ES): m / z = 581 (M + H) ⁺ ; m / z = 474 (M + H - C ₇ H ₉ N) ⁺ base peak

Example 182: [2- (5,6-Dimethyl-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -phenylethyl-amino ((A003391552 ( P-32520-158-1)):

A) The 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -phenylethyl-a is prepared as described in Example 179a from 0.16 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH- pyrrolo [2, 3-b] pyridin-4-ylmethyl] - 0 phenylethyl-amino instead of [2- (5, 6-dimethoxy-1-methyl- IH-indol-3-yl) -1- (toluene- 4-sulfonyl) -1H-pyrrolo [2,3- b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) - was used in Example 179a and 1.2 cm ³ of potassium hydroxide 5N. 0.038 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -phenylethyl-amine is obtained the characteristics are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): From 2.10 to 2.25 (spread m, 1H); 2.75 to 2.86 (m, 0 4H); 3.81 (s, 3H); 3.87 (s, 6H); 4.07 (br s, 2H); 6.80 (broad d, J = 2.0 Hz, 1H); 699 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.12 to 7.30 (m, 5H); 7.46 (s, 1H); 7.74 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). 5 - Mass spectrum (El): m / z = 440 (M) ⁺ ; m / z = 320 (M - C ₈ Hι ₀ N) ⁺ base peak b) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -lH -pyrrolo [2,3-b] pyridin-4-ylmethyl] -phenylethyl-amine is prepared as described in Example 178b from 0.15 g of 2- (5,6-dimethoxy-1-methyl-1H -indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2,3-b] .pyridin-4-carboxaldehyde and 0.192 cm ³ of phenylethylamine instead of the cyclohexylamine used in the example 178b. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 99/01 then dichloromethane / methanol 98.5 / 1.5 by volume as eluent), 0.17 g of [2- (5,6-dimethoxy- 1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -phenylethyl-amine, the characteristics of which are as follows: Mass spectrum (ES): m / z = 595 (M + H) ⁺ base peak; m / z = 474 (M + H - C ₈ HnN) ⁺

Example 183: [2- (5,6-Dimethoxy-1-methyl-IH-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin- -ylmethyl] -phenylpropyl-amine ((A003390226 (P -32520-144-1)): a) [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl ] -phenylpropyl-amine is prepared as described in Example 179a from 0.115 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4- sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - phenylpropyl-amino instead of [2- (5, 6-dimethoxy-1-methyl- IH-indol-3-yl) -1 - (toluene- -sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) - amine used in Example 179a and 0.85 cm ³ of hydroxide 5N potassium. 0.072 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -phenylpropyl-amine are obtained, characteristics are the following ^' : - NMR spectrum U (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.78 (m, 2H); 2.15 to 2.40 (spread m, 1H); 2.58 (broad t, J = 6.5 Hz, 2H); 2.64 (broad t, J = 7.5 Hz, 2H); 3.78 (s, 3H); 3.81 (s, 3H); 3.86 (s, 3H); 4.02 (br s, 2H); 6.82 (br s, 1H); 7.00 (d, J = 5.0 Hz, 1H); 7.09 (s, 1H); from 7.06 to 7.28 (m, 5H); 7.45 (s, 1H); 7.75 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (ES): m / z = 455 (M + H) ⁺ ; m / z = 320 (M + H - C ₉ H ₁₃ N) ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene -4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin- - ylmethyl] -phenylpropyl-amine is prepared as described in Example 178b from 0.15 g of 2- (5,6-dimethoxy -1- methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0.218 cm ³ of phenylpropylamine instead of cyclohexylamine used in Example 178b. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.120 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) - is obtained - 1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -phenylpropyl-a ine with the following characteristics: - Mass spectrum (El): m / z = 608 (M) ⁺ ; m / z = 453 (M - C ₇ H ₇ S0 ₂ ) ⁺ ; m / z = 320 (m / z = 453 - C ₉ H _U N) ⁺ base peak

Example 184: [2- (5,6-Dimethyl-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -thiophen-2-ylmethylamine ((A003391639 (P-32520-162-1)): a) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -thiophen-2-ylmethyl- amine is prepared as described in Example 179a from 0.11 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3) -yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -thiophen-2-ylmethyl-mine instead of [2- (5,6-dimethoxy -1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.85 cm ³ of 5N potassium hydroxide. 0.056 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -thiophen-2-ylmethyl are obtained -amine whose characteristics are the following: - NMR spectrum ^X H (300 MHz, (CD ₃₎ ₂ SO d6, δ in ppm): 2.87 (m spread out, IH); 3.81 (s, 3H); 3.87 (s, - _... -ggl- -_ir_g _. 5 (m, __ 2H ⁾ ; 4.04 ⁽ m, 2H ⁾ ; 6.81 ⁽ d, J = .. 2.0 Hz, 1H) ; from 6.95 to 7.01 (m, 2H); 7.03 (d, J = 5.0 Hz, IH); 7.11 (s, IH); 7.39 (dd, J = 2, 0 and 5.0 Hz, IH); 7.47 (s, IH); 7.77 (s, IH); 8.07 (d, J = 5.0 Hz, IH); 11.7 (s , IH) - Mass spectrum (ES): m / z = 433 (M + H) ⁺ ; m / z = 337 (M + H - C ₅ H ₄ S) ⁺ base peak; m / z = 320 (M + H - C ₅ H ₇ NS) ⁺ b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH- pyrrolo [2, 3-b] pyridin- - ylmethyl] -thiophen-2-ylmethyl-amine is prepared as described in Example 178b from 0.15 g of 2- (5,6-dimethoxy-1-methyl -IH-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and -0.158 cm ³ of thiophen-2-methylamine instead of cyclohexylamine used in Example 178b. After purification by flash chromatography pack (Si02, dichloromethane / methanol 99/01 then dichloromethane / methanol 98.5 / 1.5 by volume as eluent), 0.11 g of [2- (5,6-dimethoxy- 1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2,3-b] pyridin-4-ylmethyl] -thiophen-2-ylmethyl- amino whose characteristics are as follows: - Mass spectrum (ES): m / z = 587 (M + H) ⁺ base peak; m / z = 474 (M + H - C ₅ H ₇ NS) ⁺ Example 185: [2- (5, 6-Dimethoxy-1-methyl-IH-indol-3-yl) - IH-pyrrolo [2, 3 -b] pyridin-4-ylmethyl] -thiophen-2-yl-ethyl-amino ((A003391615 (P-32520-160-1)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH- pyrrolo [2, 3-b] pyridin- -ylmethyl] -thiophen-2-yl-ethyl- amine is prepared as described in Example 179a from 0.15 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -thiophen-2-yl-ethyl-amino instead of [2- (5,6-dimethoxy-1-methyl-1H-indol-3- yl) -1- (toluene-4-sulfonyl) - 1H-py rôlo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amino used in Example 179a and 1, 12 ... cm ³ of potassium hydroxide 5N. 0.082 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -thiophen-2-yl are obtained - ethylamine, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): From 2.25 to 2.38 (m spread, 1H); 2.86 (broad t, J = 6.5 Hz, 2H); 3.00 (t, J = 6.5 Hz, 2H); 3.80 (s, 3H); 3.86 (s, 6H); 4.07 (br s, 2H); 6.80 (broad d, J = 2.0 Hz, 1H); 6.87 (broad d, J = 3.5 Hz, 1 H); 6.91 (dd, J = 3.5 and 5.0 Hz, 1H); 7.01 (d, J = 5.0 Hz, 1H); 7.10 (s, 1H); 7.27 (broad d, J = 5.0 Hz, 1H); 7.47 (s, 1H); 7.76 (s, 1H); 8.04 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (ES): m / z = 447 (M + H) ⁺ ; m / z = 320 (M + H - C ₆ H ₉ NS) ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene -4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -thiophen-2-yl-ethyl-amine is prepared as described in Example 178b from 0.15 g of 2 - (5,6- dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0.179 cm ³ thiophen-2-ethylamine instead of the cyclohexylamine used in Example 178b. After purification by flash chromatography pack (Si02, dichloromethane / methanol 99/01 then dichloromethane / methanol 98.5 / 1.5 by volume as eluent), 0.15 g of [2- (5,6-dimethoxy-1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo is obtained. 3-b] pyridin-4-ylmethyl] -thiophen-2-yl-ethyl-amine, the characteristics of which are as follows: - Mass spectrum (ES): m / z = 601 (M + H) ⁺ ; m / z = 474 (MH - C ₆ H ₉ NS) ⁺ base peak

Example 186: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (2-methoxy-ethyl) - amino ((A003391652 (P-32520-163-1)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH- pyrrolo ^, 3-b ] pyridin-4-ylmethyl] - (2-methoxy-ethyl) -amine is prepared as described in Example 179a from 0.12 g of [2- (5,6-dimethoxy-1-methyl-1H-) indol-3-yl) -1- (toluene- -sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (2-methoxy-ethyl) -aminated instead of [2- (5 , 6-dimethoxiy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl- benzyl) -aminate used in Example 179a and 0.99 cm ³ of 5N potassium hydroxide. 0.081 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (2-methoxy- is obtained) ethyl) -amine whose characteristics are the following: - NMR spectrum ^X H (300 MHz, (CD ₃₎ ₂ SO d6, δ in ppm): 2.13 to 2.29 (m spread out, IH); 2.73 (broad t, J = 6.5 Hz, 2H); 3.25 (s, 3H); 3.45 (t, J = 6.5 Hz, 2H); 3.81 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 4.04 (br s, 2H); 6.81 (broad d, J = 2.0 Hz, 1H); 7.01 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.47 (s, 1H); 7.74 (S, 1H); 8.04 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H) ^' . - Mass spectrum (ES): m / z = 395 (M + H) ⁺ ; m / z = 320 (M + H - C ₃ H ₉ NO) ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4- ylmethyl] - (2-methoxy-ethyl) -amine is prepared as described in Example 178b from 0.15 g of 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0.134 cm ³ of 2-methoxyetylamine instead of the cyclohexylamine used in Example 178b. After purification by flash-chromatography (Si02, dichloromethane / methanol 99/01 then dichloromethane / methanol 98.5 / 1.5 in _vplumes as eluent), 0.11 g of [2- (5,6-dimethoxy- 1- methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (2-methoxy-ethyl) -amino of which the characteristics are as follows: - Mass spectrum (ES): m / z = 549 (M + H) ⁺ base peak; m / z = 474 (M + H - C ₃ H ₉ NO) ⁺

Example 187: 4- ({[2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amino} - methyl) - phenylamine ((A003393788 (P-33047-027-1)): 4- ({[2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) - 1H-pyrrolo [ 2, 3-b] pyridin-4-ylmethyl] -amino} -methyl) - phenylamine can be prepared as follows: To a solution of 0.07 g of 4- [({[2- (5, 6- dimethoxy-1-methyl-IH-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amino} -methyl) -phenyl] -carbamic acid ter-butyl ester in 1, 1.6 cm ³ of hydrochloric acid (4N in dioxane) are added 5 cm ³ of dioxane and 0.5 cm ³ of DMF at a temperature in the region of 20 ° C. The reaction medium is stirred at ambient temperature. for 24 hours The reaction medium is concentrated under reduced pressure, the residue obtained is taken up in 4 cm ³ of water, then it is neutralized with triethylamine, 4 cm ³ of dichloromethane are added, after decantation, the organic phase that is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is taken up with 5 cm ³ of water. The solid formed is filtered on sintered glass, washed twice with 3 cm ³ of water, then dried under vacuum to give 0.036 g of 4- ({[2- (5,6-dimethoxy-1-methyl-1H-indol) -3-yl) -lH-pyrrolo [2,3- b] pyridin-4-ylmethyl] -amino} -methyl) -phenylamine the characteristics of which are the following: - NMR spectrum E (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): From 3.60 to 3.78 (m spread, 2H); 3.81 (s, 3H); 3.87 (s, 6H); from 4.02 to 4.13 (spread m, 2H); 4.85 to 5.02 (spread m, 2H); 6.53 _. (d _. broad, J = 8.5 Hz, 2H); 6.80 (br s, 1H); from 7.01 to 7.10 (m, 3H); 7.12 (s, 1H); 7.45 (s, 1H); 7.77 (s, 1H); 8.09 (d, J = 5.0 Hz, 1H); 11.7 (m spread, 1H). - Mass spectrum (El): m / z = 441 (M) ⁺ ; m / z = 321 (M - C ₇ H ₈ N ₂ ) ⁺ "base peak

Example 188: 4 - [({[2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin- -ylmethyl] -amino} - methyl) - phenyl] -carbamic acid ter-butyl ester ((A003393158 (P- 33047-016-1)): a) 4- [({[2- (5, 6-dimethoxy-1-methyl-1H-) indol-3-yl) -1H-pyrrolo [2,3-b] pyridin 4-ylmethyl] -amino} -methyl) - phenyl] -carbamic acid ter-butyl ester is prepared as described in Example 179a from 0.16 g of 4 - [({[2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3 -b] pyridin-4-ylmethyl] -amino} - methyl) -phenyl] -carbamic acid ter-butyl ester instead of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsuifanyl-benzyl) -aminate used in Example 179a and 1.04 cm ³ 5N potassium hydroxide. 0.093 g of 4- [({[2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] is obtained amino} - methyl) -phenyl] -carbamic acid ter-butyl ester whose characteristics are the following: - NMR spectrum ⁽³⁰⁰ MHz, (CD ₃₎ ₂ SO d6, δ in ppm): 1.48 (S, 9H); 2.60 (m spread, 1H); 3.69 (m, 2H); 3.81 (s, 3H); 3.86 (s, 3H); 3.87 (s, 3H); 4.00 (m, 2H); 6.78 (broad d, J = 2.0 Hz, 5 1 H); 7.05 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.25 (broad d, J = 8.5 Hz, 2H); 7.40 (broad d, J = 8.5 Hz, 2H); 7.42 (s, 1H); 7.74 (s, 1H); 8.06 (d, J = 5.0 Hz, 1H); 9.22 (br s, 1H); 11.65 (br s, 1H). 10. .. .- Mass spectrum .... (ES) _: m / z = 542 (M + H) ⁺ base peak; m / z = 337 (M + H - Cι ₂ H ₁₅ N0 ₂ ) ⁺ b) 4- [({[2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1 - (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amino} -methyl) -phenyl] -carbamic acid ter-butyl

The ester is prepared as described in Example 178b from 0.15 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-carboxaldehyde and 0.340 cm ³ of (4- (aminomethyl) - phenyl) -carbamic acid ter-butyl ester instead of the 0 cyclohexylamine used in Example 178b. After purification by flash-chromatography pack (Si02, dichloromethane / methanol 99/01 then dichloromethane / methanol 98.5 / 1.5 by volume as eluent), 0.16 g of 4- [({[2- (5 , 6-dimethoxy-1-5 methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -amino} -methyl ) -phenyl] - carbamic acid ter-butyl ester, the characteristics of which are as follows: - Mass specter (ES): m / z = 696 (M + H) ⁺ ; m / z = 337 0 (M + H - C ₁₂ Hι ₅ N0 ₂ ) ⁺ base peak

Example 189; [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-phenyl) -aminate ( (A003403451. (P- 33047-052-1)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH- pyrrolo ^, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-phenyl) - amine is prepared as described in Example 179a from 0.08 g of [2- (5,6- 5 dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl ) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-phenyl) -aminated instead of [2- (5,6-dimethoxy-1-methyl-IH-indol-3 -yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4- 10 ... trifluoromethylsulfanyl-benzyl) -amine used. Example 179a and 0.53 cm ³ of 5N potassium hydroxide. 0.068 g of phenyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4- trifluoromethylsulfanyl-phenyl) -aminate, the characteristics of which are as follows: - NMR spectrum -U (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.80 (s, 3H); 3.86 (s, 3H); 3.88 (s, 3H); 4.67 (d, J = 6.0 Hz, 2H); 6.70 (broad d, J = 8.5 Hz, 2H); 6.90 (br s, 1H); 6.97 (d, J = 5.0 Hz, 20 1 H); 7.10 (s, 1H); 7.23 (broad t, J = 6.0 Hz, 1 H); 7.32 (broad d, J = 8 Hz, 2H); 7.47 (s, 1H); 7.77 (s, 1H); 8.04 (d, J = 5.0 Hz, 1H); 11.75 (m spread, 1H). - Mass spectrum (El): m / z = 512 (M) ⁺ ; m / z = 320 25 (M - C ₇ H ₅ SNF ₃ ) ⁺ - base peak b) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- ( toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-phenyl) -amine is prepared as described in Example 178b starting from 0.15 g 0 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0.219 cm ³ of 4- (trifluoromethylsulfanyl) aniline instead of the cyclohexylamine used in Example 178b. After purification by flash-pack chromatography (Si02, 5 dichloromethane / methanol 98/02 in volumes as effluents), 0.084 g of [2- (5, 6-dimethoxy-1- methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo is obtained [2, 3-b ] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-phenyl) -amine with the following characteristics: - Mass spectrum (ES): m / z = 667 (M + H) ⁺ base peak

Example 190: Cyclopropyl- [2- (5,6-dimethoxy-1-methyl-1H- indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -aminate ((AÔ03403453 ( P-33047-058-ï)): a) Cyclopropyl- [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin- 4-ylmethyl] -aminate is prepared as described in Example 179a from 0.06 g of cyclopropyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -aminated instead of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl ) -1- (toluene- -sulfonyl) -IH- pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -aminate used in Example 179a and 0.5 cm ³ 5N potassium hydroxide. 0.034 g of cyclopropyl- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -amine is obtained, characteristics are as follows: - 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): From 0.30 to 0.42 (m, 4H); 2.13 (m, 1H); 2.72 to 2.86 (spread m, 1H); 3.80 (s, 3H); 3.86 (s, 3H); 3.88 (s, 3H); 4.06 (br s, 2H); 6.81 (d, J = 2.0 Hz, 1H); 7.00 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.47 (s, 1H); 7.75 (s, 1H); 8.04 (d, J = 5.0 Hz, 1H); 11.65 (m spread, 1H). - Mass spectrum (El): m / z = 376 (M) ⁺ ; m / z = 320 (M - C ₃ H ₆ N) ⁺ base peak b) Cyclopropyl- [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -1- (toluene -4-sulfonyl) -1H-pyrrolo [2, 3- b] pyridin-4-ylmethyl] -amine is prepared as described in Example 178b from 0.15 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1 - (toluene- -sulfonyl) -1H- pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0.107 cm ³ of cyclopropylamine instead of the cyclohexylamine used in Example 178b. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.075 g of cyclopropyl- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) is obtained ) -1-

10 ... (toluene ^ -sulfonyl) -lH_-pyrrolo [2, .3-b] .pyridinr4- ylmethyl] -amino whose characteristics are the following: - Mass spectrum (El): m / z = 530 ( M) ⁺ ; m / z = 375 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak; m / z = 320 (m / z = 375 -

15 C ₃ H ₅ N) ⁺

Example 191: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-morpholin-4- yl- phenyl) -aminate ((A003403814 (P-33047-056-2)): a) Le [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1H- 0 pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-morpholin-4-yl-phenyl) -amine is prepared as described in Example 179a from 0.16 g of [2- (5, 6-dimethoxy-1-methyl-IH-indol- 3-yl) -1- (toluene- -sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-morpholin-4- yl-phenyl) -aminated instead of [2- 5 (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3 -b] pyridin- -ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 1.08 cm ³ of 5N potassium hydroxide. 0.068 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-0 yl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-morpholin is obtained -4-yl-phenyl) -amine whose characteristics are the following: - NMR spectrum ^X H (300 MHz, (CD ₃₎ ₂ SO d6, δ in ppm): 2.83 (m, 4H); 3.67 (m, 4H); 3.80 (s, 3H); 5 3.85 (s, 3H); 3.89 (s, 3H); 4.58 (d, J = 6.0 Hz, 2H); 6.02 (t, J = 6.0 Hz, 1 H); 6.56 (broad d, J = 8.5 Hz, 2H); 6.70 (broad d, J = 8.5 Hz, 2H); 6.91 (d, J = 2.0 Hz, 1H); 6.98 (d, J = 5.0 Hz, 1H); 7.10 (s, 1H); 7.48 (s, 1H); 7.75 (s, 1H); 8.01 5 (d, J = 5.0 Hz, 1H); 11.7 (m spread, 1H). - Mass spectrum (El): m / z = 497 (M) ⁺ ; m / z = 320 (M -. C ₁₀ Hι ₃ N ₂ O) ⁺ base peak b) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- ( toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridin-4- 10. ylmethyl] - (4-morpholin-4-yl-phenyl) -amine is prepared as described in Example 178b from 0.15 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin- 4-carboxaldehyde and 0.273 g of 4-morpholin-4-yl-phenylamine instead of the cyclohexylamine used in Example 178b. After purification by flash-chromatography pack (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.164 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) - is obtained - 1- (toluene-4-sulfonyl) -1H- 0 pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-morpholin-4-yl- phenyl) -aminate with the following characteristics: - Spectrum mass (El): m / z = 651 (M) ⁺ ; m / z = 496 (M - C ₇ H ₇ S0 ₂ ) ⁺ ; m / z = 177 (Cι ₀ H ₁₃ N ₂ O) ⁺ base peak 5 Example 192: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2 , 3-b] pyridin-4-ylmethyl] - (2-methyl-2H- pyrazol-3-yl) -aminate ((A003405576 (P-33047-062-1)): a) The [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (2-methyl-2H-pyrazol-3-0 yl) -amino is prepared as described in Example 179a from 0.08 g of trifluoroacetate of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl ) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (2-methyl-2H- pyrazol-3-yl) -aminated instead of [2- (5, 6-dimethoxy-1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amino used at l Example 179a and 0.62 cm ³ of 5N potassium hydroxide. After purification by flash-chromatography pack (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.024 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) is obtained - IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (2-methyl-2H-pyrazol-3-yl) -aminate with the following characteristics: - NMR spectrum H (300 MHz, (CD ₃ ) ₂ S0 d6, δ in ppm): 3.60 (s, 3H); 3.81 (s, 3H); 3.86 (s, 3H); 3.88 (s, 3H); 4.53 (d, J = 6.0 Hz, 2H); 5.28 (d, J = 2.0 Hz, 1H); 6.24 (broad t, J = 6.0 Hz, 1 H); 6.90 (d, J = 2.0 Hz, 1H); 7.00 (d, J = 2.0 Hz, 1H); 7.02 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.47 (S, 1H); 7.77 (s, 1H); 8.04 (d, J = 5.0 Hz, 1H); 11.7 (broad s, 1 H). - Mass spectrum (El): m / z = 416 (M) ⁺ ; m / z = 320 (M - C ₄ H ₆ N ₃ ) ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene- 4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (2-methyl-2H-pyrazol-3-yl) -amine is prepared as described in Example 178b starting from 0 , 15 g of 2- (5,6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2,3-b] pyridin-4- carboxaldehyde and 0.149 g of 1-methyl-1H-pyrazol-5-yl-amino instead of the cyclohexylamine used in Example 178b. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 98/02 by volume as eluent), then by chromatography on a Kromasil C8 column 10 μm, eluent: water / acetonitrile / TFA 70/30 / 0.1 by volume, 0.08 g of the trifluoroacetate of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - IH-pyrrolo [2, 3-b ] pyridin-4-ylmethyl] - (2-methyl-2H- pyrazol-3-yl) -amin, the characteristics of which are as follows: - Mass spectrum (El): m / z = 570 (M) ⁺ ; m / z = 415 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak; m / z = 320 (m / z = 415 - C ₄ H ₅ N ₃ ) ⁺

Example 193: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (1-methyl-piperidin- 4-yl) -aminate ((A003440113 (P-33047-137-1)):. ... a) .. The ..1.2- (-5.,. 6-dimethoxyrlrmethyl -IH-indoi-J-yl ) .- IH-_ pyrrolo [2,3-b] pyridin-4-ylmethyl] - (1-methyl-piperidin-4-yl) -amine is prepared as described in Example 179a from 0.07 g [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (1-methyl-piperidin-4-yl) -aminated instead of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.48 cm ³ of 5N potassium hydroxide. 0.042 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (1-methyl- is obtained. piperidin-4-yl) -amino whose characteristics are. the following: - 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.34 (m, 2H); 1.85 (m, 4H); 2.11 (s, 3H); 2.42 (m, 1H); 2.69 (m, 2H); 3.81 (s, 3H); 3.87 (s, 3H); 3.88 (s, 3H); 4.05 (s, 2H); 6.81 (d, J = 2.0 Hz, 1H); 7.02 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.44 (s, 1H); 7.75 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (ES: m / z = 434 (M + H) ⁺ ; m / z = 218 (M + 2H) ²⁺ / 2; base peak. B) The [2- (5, 6-Dimethoxy) -1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (1-methyl-piperidin-4- yl) -aminate is prepared as described in Example 178b from 0.15 g of 2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridin-4-carboxaldehyde and 0.175 g of 1-methyl-4-aminopiperidine instead of the cyclohexylamine used in Example 178b. After purification by flash-chromatography pack (Si02, dichloromethane / methanol 90/10 by volume as eluent), 0.070 g is obtained due [2- (5, 6-dimethoxy-1- methyl-IH-indol-3-yl) - 1- (toluene-4-sulfonyl) -1H- pyrrolo [2,3.-b _] _ pyridinτ4.-ylm_ethylL - .. (l-th yl) -aminate with the following characteristics: - Mass spectrum (CI) : m / z = 588 (M + H) ⁺ base peak

Example 194: (2,4-Dimethoxy-benzyl) - [2- (5,6-dimethoxy-1- methyl-IH-indol-3-yl) -1H-pyrrolo [2,3-b] pyridin-4- ylmethyl] -aminate ((A003408775 (P-32989-041-1)): a) Le (2,4-dimethoxy-benzyl) - [2- (5, 6-dimethoxy-1- methyl-1Hτindol-3-yl ) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amine is prepared as described in Example 179a from 0.05 g of (2,4-dimethoxy-benzyl) - [2- (5,6- dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amined instead [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.36 cm ³ of 5N potassium hydroxide. 0.03 g of (2,4-dimethoxy-benzyl) - [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] is obtained pyridin-4-ylmethyl] -amin, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.67 (broad s, 2H); 3.72 (s, 3H); 3.73 (s, 3H); 3.81 (s, 3H); 3.85 (s, 3H); 3.87 (s, 3H); 4.04 (br s, 2H); 6.49 (dd, J = 2.5 and 8.5 Hz, 1H); 6.52 (d, J = 2.5 Hz, 1H); 6.76 (d, J = 2.0 Hz, 1H); 7.06 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.28 (d,. J = 8.5 Hz, 1H); 7.42 (s, 1H); 7.75 (s, 1H); 8.06 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (ES): m / z = 487 (M + H) ⁺ base peak b) (2,4-dimethoxy-benzyl) - [2- (5, 6-dimethoxy-1-methyl-1H -indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -aminate is prepared as described in Example 178b from 2 g -2- (5,6- dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 3.39 g of 2,4-dimethoxybenzylamine instead of the cyclohexylamine used in Example 178b. After purification by flash chromatography pack (Si02, dichloromethane / methanol 98/02 by volume as eluent), 1.2 g of (2,4-dimethoxy-benzyl) - [2- (5, 6-dimethoxy-1) are obtained. -methyl-1H-indol-3- yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -aminate the characteristics of which are as follows: - Spectrum of mass (ES): m / z = 641 (M + H) ⁺ ; m / z = 486 (M + H - C ₇ H ₇ S0 ₂ ) ⁺

Example 195: [2- (5,6-Dimethoxy-1-methyl-IH-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-pipêridin-1- yl- phenyl) -aminate ((A003425429 (P-333047-107-1)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [ 2, 3-b] pyridin-4-ylmethyl] - (4-piperidin-1-yl-phenyl) -amine is prepared as described in Example 179a from 0.09 g of [2- (5,6 -dimethoxy-1-methyl-1H-indol- 3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-piperidin-1- yl-phenyl) -aminated instead of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3- b] pyridin- -ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.55 cm ³ of 5N potassium hydroxide. We obtains 0.016 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-piperidin-1 - yl-phenyl) -amin, the characteristics of which are as follows: 5 - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.45 (m, 2H); 1.59 (m, 4H); 2.83 (m, 4H); 3.82 (s, 3H); 3.88 (s, 3H); 3.90 (s, 3H); 4.57 (broad m, 2H); 6.00 (broad m, 1H); 6.55 (broad d, J = 8.5 Hz, 2H); 6.70 (broad d, J = 8.5 Hz, 2H); , .1.0 6.92 (broad, - IH). ;. 7.00 (broad d, J = 5.0 Hz, 1H). ; 7.11 (broad S, 1H); 7.49 (br s, 1H); 7.78 (br s, 1H); 8.02 (broad d, J = 5.0 Hz, 1H); 11.7 (broad s, 1 H). - Mass spectrum (El): m / z = 495 (M) ⁺ ; m / z = 320 15 (M - CιιHι ₅ N ₂ ) ⁺ ; m / z = 175 (CnHι ₅ N ₂ ⁺ ) base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-piperidin-1-yl-phenyl) -amino is prepared as described in Example 178b from 0.15 g of 2- 20 (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde and 0, 27 g of (4-piperidin-1-yl-phenyl) -amine instead of the cyclohexylamine used in Example 178b. After purification by flash-chromatography pack (Si02, 25 dichloromethane / methanol 99/01 by volume as eluent), 0.12 g of [2- (5, 6-dimethoxy-1- methyl-IH-indol-3-) is obtained yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-piperidin-1-yl-phenyl) -amino mixture (60/40) with [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridin-4-ylmethyl ] - (4-pipêridin-1-yl-phenyl) -imine. This mixture is dissolved in in 7 cm ³ of ethanol, at a temperature in the region of 20 ° C. 0.016 g is added

35 sodium borohydride. The dream environment is agitated at room temperature for 24 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up with 3 cm ³ of water and 4 cm ³ of dichloromethane. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography pack (Si02, dichloromethane / methanol 99.5 / 0.5 by volume as eluent), 0.095 g of [2- (5, 6-dimethoxy-1 --- methyl-IH-indol) is obtained .-3-yl) -1- (toluene.-4 -sulfonyl) -IH- pyrrolo ^, 3-b] pyridin-4-ylmethyl] - (4-pipêridin-1-yl-phenyl) -aminate with the characteristics are as follows: Mass spectrum (El): m / z = 649 (M) ⁺ ; m / z = 175 (C ₁ ιHι ₅ N ₂ ⁺ ) base peak

Example 196: [2- (5, 6-Dimethoxy-1-methyl-IH-indol-3-yl) - IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - [4- (2, 6 -dimethyl- morpholin-4-yl-phenyl) -amin ((A003425496 (P-333047-113- D): a) Le [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl ) -IH- pyrrolo ^, 3-b] pyridin-4-ylmethyl] - [4- (2, 6-dimethyl-morpholin-4-yl-phenyl) -amine is prepared as described in Example 179a from 0.08 g of [2- (5,6-dimethoxy-1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin- 4-ylmethyl] - [4- (2,6-dimethyl-morpholin-4-yl-phenyl) -amiήe instead of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene- -sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 1 cm ³ of hydroxide of potassium 5N. 0.017 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - [ 4- (2,6-dimethyl- morpholin-4-yl-phenyl) -amiήe whose characteristics teristics are the following: - NMR spectrum ^X H (300 MHz, (CD ₃₎ ₂ SO d6, δ in ppm): 1.09 (d, J = 7.0 Hz, 6H); 2.08 (m, 2H); 3.21 (m, 2H); 3.63 (m, 2H); 3.80 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 4.56 (broad d, J = 6.0 Hz, 2H); 6.00 (wide t, J ,0 6.0 Hz, 1 H); 6.55 (broad d, J = 8.5 Hz, 2H); 6.69 (broad d, J = 8.5 Hz, 2H); 6.91 (br s, 1H); 6.98 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.47 (s, 1H); 7.75 (s, 1H); 8.01 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (El): m / z = 525 (M) ⁺ ; m / z = 320 (M .- Cι ₂ Ha ₇ N_ ₂ 0). ⁺ .pic base. ; m / z = 2.06 ( _Cι ₂ H _ιa N ₂ 0) ⁺ b) [2- (5,6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - [4- (2, 6-dimethyl-morpholin-4-yl-phenyl) -amine is prepared as described in Example 178b starting from 0.15 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4 - Carboxaldehyde and 0.316 g of 4- (2,6-dimethylmorpholin-4-yl-phenyl) amino instead of the cyclohexylamine used in Example 178b. After purification by flash chromatography pack (Si02, dichloromethane / methanol 99/01 by volume as eluent), 0.1 g of [2- (Sjδ-dimethoxy-1-methyl-1H-indol ^ -S-yl) is obtained. -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - [4- (2,6- dimethyl-morpholin-4-yl-phenyl) -amixed (50/50) with [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin -4- ylmethyl] - [4- (2,6-dimethyl-morpholin-4-yl-phenyl) -imine. This mixture is dissolved in in 7 cm ³ of ethanol, at a temperature in the region of 20 ° C. 0.016 g sodium borohydride is added. The reaction medium is stirred at room temperature for 24 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up with 3 cm ³ of water and 4 cm ³ of dichloromethane. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography pack (Si02, dichloromethane / dethanol 99/01 by volume as eluent), 0.08 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) is obtained ) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - [4- (2,6-dimethyl-morpholin-4-yl-phenyl) -amino of which the characteristics are as follows: - Mass spectrum (El): m / z = 679 (M) ⁺ ; m / z = 206 (C ₁₂ H ₁₈ N ₂ 0 ⁺ ); m / z = 120 (C ₇ H ₈ N ₂ ⁺ ) base peak

Example 197: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-yl] -methanol ((A003377259 (P- 32520-113-1)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH- pyrrolo ^, 3-b] pyridin-4-yl] - methanol is prepared as described in Example 179a from 0.08 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-yl] -methanol instead of [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene- 4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.55 cm ³ of potassium hydroxide 5N . 0.036 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-yl] -methanol is obtained, the characteristics of which are the following: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): Dice 3.72 to 3.97 (m wide, 9H); 4.85 (br s, 2H); 5.32 (br s, 1H); 6.75 (br s, 1H); 7.03 (br s, 1H); 7.11 (br s, 1H); 7.45 (br s, 1H); 7.75 (br s, 1H); 8.08 (br s, 1H); 11.65 (br s, 1H). - Mass spectrum (El): m / z = 337 (M) ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4- yl] - methanol can be prepared as follows: To a solution of 0.47 g of 2- (5, 6-dimethoxy-1- methyl-1H-indol-3-yl) -1- (toluene-4- sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-carboxaldehyde in 10 cm ³ of methanol, at a temperature in the region of 20 ° C, 0.054 mg sodium borohydride is added. The reaction medium is stirred at room temperature for 4 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up with 10 cm ³ of water and 20 cm ³ of ethyl acetate. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography pack (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.45 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) is obtained ) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-4-yl] -methanol the characteristics of which are as follows

- Mass spectrum (ES): m / z = 492 (M + H) ⁺ base peak

Example 198: 1'- [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - [1,4 '] bipiperidinyl: ((A003408597 (P-33047-074-1)) a) Le l' - [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [ 2, 3-b] pyridin-4-ylmethyl] - [1,4 '] bipiperidinyl is prepared as described in Example 179a from 0.025 g of l'- [2- (5, 6-dimethoxy-1- methyl-1H-indol-3-yl) - 1- (toluene- -sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - [1,4 '] bipiperidinyl instead of [2- (5,6- dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4- trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.17 cm ³ of 5N potassium hydroxide. 0.01 g of l - [2- (5,6-dimethoxy-1-methyl-1H-indol- 3-yl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - [1,4 '] bipiperidinyl, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): From 1.30 to 1.56 (m, 8H); 1.71 (m, 2H); 2.01 (m, 2H); 2.17 (m, 1H); 2.42 (m, 4H); 2.94 (m, 2H); 3.78 (s, 2H); 3.80 (s, 3H); 3.86 (s, 3H); 3.88 (s, 3H); 6.87 (d, J = 2.0 Hz, 1H); 6.93 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.41 (s, 1H); 7, -76- (S -, - IH) - ;. 8- ,. 4._ (.d ,. -J. = .5, .0..Hz _^ -1H -; .ll, 2α (.S. Large, IH). - Mass spectrum (El): m / z = 487 (M) ⁺ ; m / z = 320 (M - Cι ₀ Hι ₉ N ₂ ) ⁺ base peak b) L '- [2- (5,6-dimethoxy-1-methyl-1H-indol-3 -yl) - 1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - [1,4 '] bipiperidinyl can be prepared as follows: To a solution of 0.003 g of 4-piperidino-piperidine in 0.5 cm ³ of THF, at a temperature in the region of 20 ° C., is added 0.003 g of sodium hydride. The reaction medium is stirred at room temperature for 20 minutes. 0.04 g of methanesulfonic acid 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2,3-b are added ] pyridin-4-ylmethyl ester. The reaction medium is heated at 60 ° C for 3 hours. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is taken up with 2 cm ³ of water and 3 cm ³ of ethyl acetate. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography pack (Si02, dichloromethane / methanol 90/10 by volume as eluent), 0.026 g of l - [2- (5,6-dimethoxy-1-methyl-1H-indol-3-) is obtained. yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridin-4-ylmethyl] - [1,4 '] bipiperidinyl, the characteristics of which are as follows: - Mass spectrum (ES): m / z = 642 (M + H) ⁺ ; m / z = 244 ((M + H - C ₇ H ₇ S0 ₂ + H) ²⁺ / 2 base peak c) Methanesulfonic acid 2- (5, 6-dimethoxy-1- methyl-IH-indol-3 -yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl ester can be prepared as follows: To a solution of 0.13 g of [2- (5, 6-dimethoxy-1- methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo ^, 3-b] pyridin-4-yl] -methanol in 5 cm ³ dichloromethane, at a temperature in the region of -10 ° C., 0.064 g of pyridine and 0.092 g of methanesulfonic anhydride are added. The reaction medium is stirred at this same temperature for one hour, then at room temperature for 24 hours. Ice and 15 cm ³ of dichloromethane are added. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-chromatography pack (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.044 g of methanesulfonic acid 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) is obtained. -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl ester with the following characteristics: - Mass spectrum (ES): m / z = 570 (M + H) ⁺ base peak

Example 199: [2- (5,6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -diethylamine ((A003416358 ( P-33047-091-1)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridin- -ylmethyl ] -diethylamine is prepared as described in Example 179a from 0.060 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene- 4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -diethylamine rather than [2- (5,6-dimethoxy-1-methyl-1H-indol-3- yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amin 5 used in Example 179a and 0.44 cm ³ potassium hydroxide 5N. 0.034 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -diethyl-amine is obtained. features are:

-10— - - Specter..de- R..M..N ..- -3-H .. (.30.0 MHz, -. (CD- ₃ -) - ₂ SÛ. D6 .., .. δ ..eπ_ ppm): 1.06 (t, J = 7.0 Hz, 6H); 2.53 (partially masked m, 4H); 3.81 (s, 3H); 3.83 (s, 2H); 3.87 (s, 6H); 6.86 (d, J = 2.0 Hz, 1H); 6.99 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.41 (s, 15 1H); 7.74 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (El): m / z = 392 M ⁺ ; m / z = 321 (M - C ₄ H ₉ N) ⁺ base peak b) Le [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1-20 (toluene- 4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -diethylamine can be prepared as follows: To a solution of 0.15 g of [2- (5, 6- dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3 -b] pyridin-4-yl] -methanol in 3 cm ³ of dichloromethane , at a temperature in the region of 20 ° C., 0.022 cm ³ of thionyl chloride is added, then two drops of DMF. The reaction medium is stirred at this same temperature for 4 hours.

Next, 8 cm ³ of acetonitrile, 0.160 cm ³ of diethylamine, 0.211 g of potassium carbonate and 0.1 g of sodium iodide are added. The reaction medium is heated at 50 ° C for 24 hours. After cooling, the reaction medium is filtered through sintered glass and the filtrate is

35 concentrated under reduced pressure. The residue obtained is taken up with 3 cm ³ of water and 4 cm of ethyl acetate. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-pack chromatography (Si02, dichloromethane / ethyl acetate 80/20 by volume as eluent), 0.036 g of [2- (5, 6-dimethoxy-1- methyl-IH-indol-3-) is obtained yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -diethyl-amine, the characteristics of which are as follows: - Mass spectrum (ES); m ^ z = 547 (M + HJ ⁺ base peak; m / z = 474 ((M + H) - C ₄ HnN) ⁺

Example 200: [2- (5,6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -piperidin-4-ol (( A003435835 (P-33047-129-1)): a) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridin- 4-ylmethyl] -piperidin-4-ol is prepared as described in Example 179a from 0.045 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (tpluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] - piperidin-4-ol instead of [2- (5, 6-Dimethoxy-1-methyl-1H- indol -3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3- b] pyridin- -ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) - amine used in Example 179a and 0 , 44 cm ³ of 5N potassium hydroxide. 0.03.1 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -piperidin-4 is obtained -ol the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.46 (m, 2H); 1.74 (m, 2H); 2.13 (m, 2H); 2.78 (m, 2H); 3.48 (m, 1H); 3.78 (s, 2H); 3.81 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 4.56 (m spread, 1H); 6.89 (br s, 1H); 6.93 (d, J = 5.0 Hz, 1H); 7.12 (s, 1H); 7.42 (s, 1H); 7.76 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.7 (broad s, 1 H) Mass spectrum (EI): m / z = 420 M ⁺ ; m / z = 321 (M - C ₅ H ₉ NO) ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH -pyrrolo [2,3-b] pyridin-4-ylmethyl] -piperidin-4-ol can be prepared as follows: To a solution of 0.055 g of 4-chloromethyl-2- (5, 6-dimethoxy-1 -methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridine in 3 cm ³ of acetonitrile, at a temperature in the region of 20 ° C, 0.027 g of piperidin-4-ol, 0.075 g of potassium carbonate and 0.016 g of sodium iodide are added. The reaction medium is heated at 80 ° C for one hour. After cooling, the reaction medium is filtered through sintered glass and the filtrate is concentrated under reduced pressure. The residue obtained is taken up with 3 cm ³ of water and 4 cm ³ of ethyl acetate. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.049 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin- is obtained. 4-ylmethyl] -piperidin-4-ol the characteristics of which are as follows: - Mass spectrum (ES): m / z = 575 (M + H) ⁺ base peak c) 4-chloromethyl-2- (5 , 6-dimethoxy-1-methyl-1H- indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3- b] pyridine can be prepared as follows: To a solution 0.4 g of [2- (5, 6-dimethoxy-1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2, 3-b] pyridin -4-yl] -methanol in 4 cm ³ of dichloromethane, at a temperature in the region of 20 ° C., 0.089 cm ³ of thionyl chloride and five drops of DMF are added. The reaction medium is stirred at this same temperature for 4 hours. Ice is added, then the reaction medium is neutralized with a saturated solution of sodium hydrogen carbonate. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-pack chromatography (Si02, dichloromêthaήe / ethyl acetate 97.5 / 2.5 by volume as eluent), 0.234 g of 4-chloromethyl-2- (5, 6-dimethoxy-1-methyl) is obtained -1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridine, the characteristics of which are. following: - Mass spectrum (El): m / z = 509 M ⁺ ; m / z = 354.-. .. M. -. C. ₇ H- ₇ S0 ₂ -) ⁺ peak ..de. base.

Example 201: 1- [2- (5,6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -azetidin-3-ylamine ((A003453957 (P-33047-148-1)): 1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -azetidin-3-ylamine can be prepared as follows: To a solution of 0.051 g of {1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3- yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -azetidin-3-yl} -carbamic acid ter-butyl ester in 3 cm ³ of methanol and 0.5 cm ³ of dichloromethane, at a 0.27 cm ³ of hydrochloric acid (4N in dioxane) is added at a temperature in the region of 20 ° C. The reaction medium is stirred at room temperature for 24 hours. The reaction medium is concentrated under reduced pressure. is taken up with 4 cm ³ of water, then it is neutralized with IN sodium hydroxide until pH = 10. 12 cm ³ of dichloromethane are added. After decantation, the organic phase is dried over sul magnesium fate, filtered and then concentrated under reduced pressure. 0.008 g of 1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3- b] pyridin-4-ylmethyl] -azetidin-3 are obtained. -ylamine, the characteristics of which are as follows: - 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.73 (m, 2H); 3.44 (m, 1H); 3.59 (m, 2H); 3.81 (s, 3H); 3.87 (s, 5H); 3.89 (s, 3H); 6.73 (d, J = 2.0 Hz, 1H); 6.92 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.44 (s, 1H); 7.73 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (ES): m / z = 392 (M + H) ⁺

Example 202: {1- [2- (5,6-Dimethoxy-1-methyl-1H-indol-3-yl) ^~ -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -azetidin-3 -yl} - carbamic acid ter-butyl ester ((A003452988 (P-33047-143- 1) ..).:... __ _{. „} __ _. a) The {l- [2- (5,6- dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -azetidin-3-yl} - carbamic acid ter-butyl ester is prepared as described in Example 179a from 0.13 g of {1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -azetidin-3-yl} - carbamic acid ter-butyl ester instead of [2- (5,6-dimethoxy-1-methyl-IH-indol-3 -yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amino used in Example 179a and 0.805 cm ³ potassium hydroxide 5N. 0.07 g of {1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] is obtained. azetidin-3- yl} -carbamic acid ter-butyl ester, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.37 (s, 9H); 2.97 (t, J = 7.0 Hz, 2H); 3.58 (t, J = 7.0 Hz, 2H); 3.81 (s, 3H); 3.88 (s, 3H); 3.90 (s, 5H); 4.10 (m, 1H); 6.73 (d, J = 2.0 Hz, 1H); 6.91 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.31 (broad d, J = 7.0 Hz, 1 H); 7.44 (s, 1H); 7.74 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.7 (broad s, 1 H) .- Mass spectrum (ES): m / z = 492 (M + H) ⁺ base peak; m / z = 436 (MH - C ₄ H ₈ ) ⁺ b) Le {l- [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) - 1- (toluene-4- sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4- ylmethyl] -azetidin-3-yl} -carbamic acid ter-butyl ester is prepared as described in Example 200b from 0.14 g of 4-chloromethyl-2- (5,6-dimethoxy-1-methyl- 1H- indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3- b] pyridine and 0.118 g of azetidin-3-yl-carbamic acid ter-butyl ester instead piperidin-4-ol used in Example 200b. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 95/5 by volume as eluent), 0.135 g of {l- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-) is obtained yl) -IH-pyrrolo [2,3- b] pyridin-4-ylmethyl] -azêtidin-3-yl} -carbamic acid ter-butyl ester the characteristics of which are as follows: Mass spectrum (ES): m / z = 646 (M + H) ⁺ base peak; m / z = 590 (MH - C ₄ H ₈ ) ⁺

Example 203: {1- [2- (5,6-dimethoxy-1- methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -azetidin dihydrochloride 3-yl} -methylamine ((A003453945A (P- 33047-150-1)): a) {1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) dihydrochloride -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -azetidin-3-yl} -methylamine is prepared as described in Example 201 from 0.027 g of {1 - [2- (5, 6- dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -azetidin-3-ylmethyl} -carbamic acid ter-butyl ester instead of {l- [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -lH-pyrrolo [2,3- b] pyridin-4- ylmethyl] -azetidin-3-yl} -carbamic acid terbutyl ester used in Example 201 and 1.35 cm ³ of hydrochloric acid (4N in dioxane). 5N potassium hydroxide. 0.005 g of {l- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] hydrochloride are obtained. azetidin-3-yl} - methylamine, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.83 (s, 3H); 3.88 (s, 3H); 3.92 (br s, 3H); from 2.90 to 4.35 (very spread out partially masked, 7 hours in total); 4.75 (m, 2H); from 7.05 to 5 7.10 (m, 3H); 7.60 (s, 1H); 7.81 (s, 1H); 7.85 to 8.03 (spread m, 3H); 8.17 (broad d, J = 5.0 Hz, 1H); from 140.7 to 11.2 (very spread m, 1H); 12.0 (wide m, 1 H) - Mass spectrum (ES): m / z = 406 (M + H) ⁺ peak of -1-0- -— -. base- - .- - - _

Example 204: {1- [2- (5,6-Dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -azetidin-3- ylmethyl} -carbamic acid ter-butyl ester ((A003453144 (P- 33047-145-1)): 15 a) {1- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3- yl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -azetidin-3-ylmethyl} -carbamic acid ter-butyl ester is prepared as described in Example 179a from 0.15 g of the {l- [2- (5,6- dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene- -sulfonyl) - 20 1H-pyrrolo [2, 3-b] pyridin-4- ylmethyl] -azetidin-3- ylmethyl} -carbamic acid ter-butyl ester instead of [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl ) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 25 179a and 0.909 cm ³ of potassium hydroxide 5N. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 95/5 by volume as eluent), 0.037 g of {l- [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-) is obtained yl) -1- (toluene- -sulfonyl) -lH-pyrrolo [2,3-30 b] pyridin-4-ylmethyl] -azetidin-3-ylmethyl} -carbamic acid ter-butyl ester. the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 1.36 (s, 9H); 2.97 (t, J = 7.0 Hz, 2H); 3.14 (m, 3H); from 3.19 to 3.35 (m mask, 2H); 3.81 (s, 3H); 3.87 (s, 5H); 3.89 (s, 3H); 6.75 (d, J = 2.0 Hz, 1H); 6.90 (spread m, 1H); 6.92 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.44 (s, 1H); 7.74 (s, 1H); 8.02 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (El): m / z = 505 M ⁺ ; m / z = 321 (M - C ₉ H ₁₆ N ₂ 0 ₂ ) ^{+ -} base peak b) The {l- [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) - 1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -azetidin-3-ylmethyl} -carbamic acid ter-butyl ester is prepared as described in Example 200b from 0.14 g of -chloromethyl-2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3 b] pyridine and 0.123 g of azetidin-3-ylmethyl-carbamic acid ter-butyl ester instead of piperidin-4-ol used in Example 200b. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 95/5 by volume as eluent), 0.154 g of {l- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-) is obtained yl) -lH-pyrrolo [2,3- b] pyridin-4-ylmethyl] -azêtidin-3-ylméthyl} -carbamic acid ter-butyl ester the characteristics of which are the following: - Mass spectrum (El): m / z = 659 M ⁺ ; m / z = 505 (M - C ₇ H ₆ S0 ₂ ) ⁺ ; m / z = 320 (m / z = 505 - C ₉ Hι ₇ N ₂ 0 ₂ ) ⁺ base peak

Example 205: [2- (5,6-Dimethoxy-1-methyl-1H-indol-3-yl) -4- (4-methylpiperazin-1-ylmethyl) -1H-pyrrolo [2,3-b] pyridine ( (A003438870 (P-33047-131-2)): a) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -4- (4-methylpiperazin-1-ylmethyl) 1H-pyrrolo [2,3-b] pyridine is prepared as described in Example 179a from

0.040 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -4- (4-methylpiperazin-1-ylmethyl) -1H- pyrrolo [2, 3-b] pyridine instead of [2- (5, 6-dimethoxy-1- methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylethylsulfanyl-benzyl) -amino used at l Example 179a and 0.28 cm ³ of 5N potassium hydroxide. 0.014 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -4- (4-methylpiperazin-1-ylmethyl) -lH-pyrrolo [2,3-b is obtained. ] pyridine, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.15 (s, 3H); 2.30 to 2.54 (m -1-0- - partially masked, 8H); 3, -7-9 - (- s, 2H-) _f - 3 _r 81 (s, - 3H) -; 3.87 (s, 3H); 3.89 (s, 3H); 6.89 (d, J = 2.0 Hz, 1H); 6.93 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.42 (s, 1H); 7.75 (s, 1H); 8.03 (d, J = 5.0 Hz, 1H); 11.7 (broad s, 1 H). 15 - Mass spectrum (EI): m / z = 419 M ⁺ ; m / z = 320 (M - C ₅ HιιN ₂ ) ⁺ base peak b) The [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4- sulfonyl) -4- (4-methylpiperazin-1-ylmethyl) -IH- pyrrolo ^, 3-b] pyridine is prepared as described in Example 200b from 0.055 g of 4-chloromethyl-2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridine and 0.03 cm ³ of 1-methylpiperazine to instead of piperidin-4-ol used in Example 200b. 0.043 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -4 - is obtained. (4-methylpiperazin-1-ylmethyl ) -lH-pyrrolo [2, 3-b] pyridine, the characteristics of which are as follows: - Mass spectrum (ES): m / z = 574 (M + H) ⁺ ; m / z = 308 (M + acetonitrile + 2H) ²⁺ / 2; m / z = 231 30 (MH + acetonitrile - C ₇ H ₇ S0 ₂ + H) ²⁺ / 2 base peak

Example 206: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin- -yl] - phenylmethanόl ((A003403794 (P-32989 -031-1)): a) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -IH- pyrrolo [2, 3-b] pyridin- -yl] -phenylmethanol is prepared as described in Example 179a from 0.105 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3- yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-4-yl] -phenylmethanol instead of [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amino used in Example 179a and of 0.85 cm ³ of 5N potassium hydroxide. 0.070 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) is obtained . phenylmethanol, the characteristics of which are as follows: - 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.80 (s, 3H); 3.86 (s, 3H); 3.89 (s, 3H) 6.11 (s, 1H); 6.69 (br s, 1H); 7.10 (s, 1H) from 7.15 to 7.24 (m, 2H); from 7.26 to 7.33 (m, 3H) 7.53 (wide d, J = 7.5 Hz, 2H); 7.70 (s, 1H) 8.09 (d, J = 5.0 Hz, 1H); 11.65 (m spread, 1H). - Mass spectrum (EI) (CI): m / z = 413 M ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -l- ( toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-yl] - phenylmethanol can be prepared as follows: To a solution of 0.1 of [2- (5, 6-dimethoxy) -1- methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -4-carboxaldehyde in 5 cm ³ of THF , at a temperature in the region of 6 ° C., 0.45 cm ³ of phenethylmagnesium bromide, 1M in THF, is added. The reaction medium is stirred at this same temperature for 30 minutes and then 24 hours at room temperature. 5 cm ³ of a saturated ammonium chloride solution and 10 cm ³ of dichlorometane are added. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.105 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo is obtained. b] pyridin-4-yl] -phenylmethanol, the characteristics of which are as follows: - Mass spectrum (El): m / z = 567 M ⁺ ; m / z = 412 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak Example 207: [2- (5, 6-Dimethoxy-1-methyl-IH-indol-3-yl) - 1H-pyrrolo [2 , 3-b] pyridin-4-yl] -propan-1-ol ((A003408773 (P-32989-039-1)): a) [2- (5, 6-dimethoxy-1-methyl-1H-) indol-3-yl) -1H- py-rrθ-lo - [- 2 -, - 3-b] -pyri-d-in-4 — yl-1— -ropan≈-l-≈o-1- est -prepared- as- described in Example 179a from 0.090 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3-b] pyridin-4-yl] -propan-1-ol instead of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.80 cm ³ of hydroxide 5N potassium. 0.060 g of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-yl] -propan-1-ol is obtained the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 0.90 (t, J = 7.0 Hz, 3H); 1.80 (m, 2H); 3.81 (s, 3H); 3.87 (s, 3H); 3.88 (s, 3H); 4.96 (m, 1H); 5.25 (d, J = 5.0 Hz, 1H); 6.75 (d, J = 2.0 Hz, 1H); 7.01 (d, J = 5.0 Hz, 1H); 7.11 (s, 1H); 7.44 (s, 1H); 7.74 (s, 1H); 8.07 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (ES): m / z = 366 (M + H) ⁺ base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -l- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-yl] - propan-1-ol can be prepared as follows: To a solution of 0.1 of [2- ( 5, 6-dimethoxy-1- methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -4-carboxaldehyde in 5 cm ³ of THF, at a temperature in the region of 6 ° C., 0.45 cm ³ of ethylmagnesium bromide, 1M in THF, is added. The reaction medium is stirred at this same temperature for 30 minutes and then 24 hours at room temperature. 5 cm ³ of a saturated ammonium chloride solution and 10 cm ³ of dichlorometane are added. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-pack chromatography (Si02, diçhlprpmêthane / ethyl acetate 80 / 20.- in_volumes, as eluent), 0.154 g is obtained. 0.90 g of [2- (5, 6-dimethoxy- 1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin- -yl] -propan-1-ol the characteristics of which are as follows : - Mass spectrum (EI): m / z = 519 M ⁺ ; m / z = 364 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak

Example 208: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-yl] -methylamine ((A003435888 (P- 32989-101-2)): a) [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -IH- pyrrolo ^, 3-b] pyridin-4-yl] - methylamine is prepared as described in Example 179a from 0.080 g of [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H -pyrrolo [2, 3-b] pyridin- -yl] -methylamine instead of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl ) -IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.80 cm ³ of potassium hydroxide 5N. After purification by flash-pack chromatography (Si02, dichloromethane / methanol 95/05 by volume as eluent), 0.015 g of [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) is obtained - IH-pyrrolo [2,3-b] pyridin-4-yl] -methylamine, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.80 ( s, 3H); 3.86 (s, 3H); 3.88 (s, 3H); 4.04 (s, 2H); 6.79 (d, J = 2.0 Hz, 1H); 7.07 (d, J = 5.0 HZ, 1H); 7.11 (s, 1H); 7.48 (s, 1H); 7.75 (S, 1H); 8.06 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (El): m / z = 336 M ⁺ "base peak b) [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene- 4-suifonyl) -IH-pyrrolo [2, 3-b] pyridin-4-yl] - methylamine can be prepared as follows: To a solution of 0.1 of [2- (5, 6-dimethoxy-1 - methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin-4-carbaldehyde oxime in 6 cm ³ of ethanol and 5 cm ³ d water, at a temperature in the region of 20 ° C., is added 0.040 g of zinc and 2 cm ³ of concentrated formic acid. The reaction medium is stirred at this same temperature for 24 hours at room temperature. The reaction medium is filtered on celite and the filtrate is concentrated under reduced pressure, 5 cm ³ of water and 10 cm ³ of dichlorometane are added. The reaction medium is alkalized to pH = 10 with IN solder. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure to obtain 0 , 06 g of [2- (5,6- dimethyl-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4 -yl] -methylamine, the characteristics of which are as follows: - Mass spectrum (El): m / z = 490 M ⁺ ; m / z = 335 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak c) The [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene- 4-sulfonyl) -IH-pyrrolo [2, 3-b] pyridin-4-carbaldehyde oxime can be prepared as follows: To a solution of 0.5 of [2- (5, 6-dimethoxy-1-methyl) -IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [2,3-b] pyridin-4-carboxaldehyde in 25 cm ³ of pyridine, at a temperature in the region of 20 ° C , is added 0.207 g of hydroxylamine hydrochloride. The reaction medium is heated at 50 ° C for 24 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is taken up with 10 cm ³ of water and 10 cm ³ of dichlorometane. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.510 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1 H-pyrrolo [2,3-b] pyridin-4 is obtained -carbaldehyde oxime, the characteristics of which are as follows: - Mass spectrum (El): m / z = 350 M ⁺ base peak; m / z = 332 (M - H ₂ 0) ⁺ ; m / z = 306 (M - CH ₂ NO) ⁺

Example 209: [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b] pyridin-4-carbaldehyde oxime ((A003425653 (P-32989- 091-2)): The [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH- pyrrolo [2,3-b] pyridin-4-carbaldehyde oxime is prepared as described in Example 179a from 0.060 g of 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3 -b] pyridin-4-carbaldehyde oxime instead of [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2 , 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.60 cm ³ of 5N potassium hydroxide After purification by flash-pack chromatography (Si02 , dichloromethane / methanol 98/02 by volume as eluent), 0.010 g of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3- b is obtained ] pyridin-4-carbaldehyde oxime, the characteristics of which are as follows: - 1 H-NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.82 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 7.07 (d, J = 2.0 Hz, 1H); 7.12 (s, 1H); 7.09 (d, J = 5.0 Hz, 1H); 7.45 (s, 1H); 7.80 (s, 1H); 8.11 (d, J = 5.0 Hz, 1H); 8.54 (s, 1H); 11.58 (s, 1H); 11.9 (broad s, 1 H). - Mass spectrum (El): m / z = 350 M ⁺ base peak; m / z = 332 (M - H ₂ 0) ⁺ ; m / z = 306 (M - CH ₂ NO) ⁺ Example 210: N- [2- (5, 6-Dimethoxy-1-methyl-1H-indol-3-yl) - 1H-pyrrolo [2, 3-b ] pyridin-4-ylmethyl] -4-trifluoromethoxybenzenesulfonamide ((A003453139 (P-32989-120-2)): N- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3- yl) -IH- pyrrolo [2,3-b] pyridin-4-ylmethyl] -4-trifluoromethoxy- _. benzenesulfonamide can be prepared as follows: To a solution of 0.050 g of N- (2,4-dimethoxy- benzyl) -N- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -4-trifluoromet oxy- benzenesulfonamide in 2 cm ³ of dichloromethane and 5 cm ³ of toluene, at a temperature in the region of 20 ° C., 0.053 g of para-toluenesulfonic acid is added. The reaction medium is stirred at this same temperature for 24 hours at room temperature then heated to a temperature in the region of 60 ° C. for 24 hours. After cooling, the reaction medium is concentrated under reduced pressure. 5 cm ³ of water and 10 cm ³ of dichlorometane. The reaction medium is basified to PH = 9 with IN sodium hydroxide. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is. purified on preparative LC / MS (water / acetonitrile / TFÀ). The solid obtained is taken up in 5 cm ³ of dichloromethane and 2 cm ³ of water, then basified with IN sodium hydroxide until pH = 9. 0.008 g of N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -4-trifluoromethoxy are obtained. - benzenesulfonamide, the characteristics of which are as follows - NMR spectrum ^ (300 MHz, (CD ₃ ) ₂ SO d6, δ en ppm): 3.82 (s, 3H); 3.88 (s, 3H); 3.90 (s, 3H); 4.38 (br s, 2H); 6.87 (d, J = 5.0 Hz, 1H); 6.95 (d, J = 2.0 Hz, 1H); 7.13 (s, 1H); 7.50 (s, 1H); 7.55 (broad d, J = 8.5 Hz, 2H); 7.78 (s, 1H); 7.96 (broad d, J = 8.5 Hz, 2H); 8.00 (d, J = 5.0 Hz, 1H); 8.50 (m, 1H); 11.75 (br s, 1H). - Mass spectrum (El): m / z = 560 M ⁺ base peak; m / z = 335 (M - C ₇ H ₄ S0 ₃ F ₃ ) ⁺

Example 211: N- (2,4-Dimethoxy-benzyl) -N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3- b] pyridin-4-ylmethyl] -4-trifluoromethoxy-benzenesulfonamide (((A003423534 (P-32989-083-2)) a) N- (2,4-dimethoxy-benzyl) -N- [2- (5, 6 -dimethoxy- 1-methyl-1H-indol-3-yl) -1h-pyrrolo [2,3-b] pyridin-4-ylmethyl] -4-trifluoromethoxy-benzenesulfonamide is prepared as described in Example 179a starting from 0.070 g of N- (2,4-dimethoxy-benzyl) -N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2,3- b] pyridin-4-ylmethyl] -4-trifluoromethoxy-benzenesulfonamide instead of [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3- b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) - amine used in Example 179a and 0.40 cm ³ of hydroxide of potassium 5N. 0.030 g of N- (2,4-dimethoxybenzyl) -N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo is obtained. 2, 3-b] p yridin-4-ylmethyl] -4-trifluoromethoxy-benzenesulfonamide, the characteristics of which are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.46 (s, 3H); 3.63 (s, 3H); 3.83 (s, 3H); 3.87 (s, .6H); 4.28 (br s, 2H); 4.79 (broad s _> 2H); 6.20 to 6.26 (m, 2H); 6.78 (d, J = 5.0 Hz, 1H); 6.88 (d, J = 8.5 Hz, 1 H); 6.99 (br s, 1H); 7.12 (s, 1H); 7.48 (s, 1H); 7.50 (broad d, J = 8.5 Hz, 2H); 7.78 (s, 1H); 7.88 (d wide, J = 8.5 Hz, 2H); 7.98 (d, J ≈ 5.0 Hz, 1H); 11.75 (br s, 1H). - Mass spectrum (ES): m / z = 711 (M + H) ⁺ base peak b) N- (2,4-dimethoxy-benzyl) -N- [2- (5,6-dimethoxy- 1 -methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo. [2, 3-b] pyridin-4-ylmethyl] -4-trifluoromethoxy-benzenesulfonamide can be prepared as follows: To a solution of 0.200 g of (2,4-dimethoxy-benzyl) - [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -aminated in 6 cm ³ of dichloromethane, under an argon atmosphere, at a temperature in the region of 20 ° C., 0.052 cm ³ of triethylamycium and 0.265 cm ³ of 4- (trifluoromethoxy) benzenesulfonyl chloride are added. The reaction medium is stirred at this same temperature for 24 hours. 2 cm ³ of water are added. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash chromatography pack (Si02, dichloromethane / methanol 98/02 by volume as eluent), 0.210 g of N- (2,4-dimethoxy-benzyl) -N- [2- (5,6-dimethoxy) is obtained -1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) - IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -4-trifluoromethoxy- benzenesulfonamide the characteristics of which are the following - Mass spectrum (ES): m / z = 865 (M + H) ⁺ base peak

Example 212: Thiophene-2-sulfonic acid [2- (5, 6-Dimethyloxy-1-methyl-IH-indol-3-yl) -IH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -amide ((A003453971 (P-32989-122-3)): a) Thiophene-2-suifonic acid [2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -lH-pyrrolo [ 2,3-b] pyridin-4-ylmethyl] -amide is prepared as described in Example 210 from 0.1 g of thiophene-2-sulfonic acid (2,4-dimethoxy-benzyl) - [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amide instead of N- (2,4-dimethoxy-benzyl) -N- [2- (5, 6-dimethoxy-1-methyl-1H-5 indol -3-yl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -4- trifluoromethoxy-benzenesulfonamide used in Example 210 and 0.110 g of para-toluenesulfonic acid. 0.025 g of thiophene-2-sulfonic acid [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-i is obtained _. P b] pyridin-4-ylmethyl] -amide _.. whose characteristics are as follows: - NMR (300 MHz, (CD ₃₎ ₂ S0 d6, δ in ppm): 3.81 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 4.40 (br s, 2H); 6.89 (d, J = 5.0 Hz, 1H); 6.91 (d, J = 2.0 Hz, 1H); 7.11 (s, 1H); 7.19 (dd, J = 3.5 and 5.0 Hz, 1H); 7.48 (s, 1H); 7.66 (dd, J = 1.0 and 3.5 Hz, 1H); 7.77 (s, 1H); 7.92 (dd, J = 1.0 and 5.0 Hz, 1H); 8.02 (d, J = 5.0 Hz, 1H); 8.51 (m spread, 1H); 11.75 (br s, 1H). 0 - Mass spectrum (EI): m / z = 482 M ⁺ ; m / z = 320 (M - C ₄ H ₄ N0 ₂ S ₂ ) ⁺ base peak b) Thiophene-2-sulfonic acid (2,4-dimethoxybenzyl) - [2- (5, 6-dimethoxy- 1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amide is prepared as described in Example 179a from 0.150 g of thiophene-2 -sulfonic acid (2,4-dimethoxy-benzyl) - [2- (5,6-dimethoxy- 1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -IH- pyrrolo [ 2,3-b] pyridin-4-ylmethyl] -amide instead of [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-0 sulfonyl) -1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 1 cm ³ of potassium hydroxide 5N. 0.100 g of thiophene-2-sulfonic acid (2,4-dimethoxybenzyl) - [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH is obtained. pyrrolo [2,3-b] pyridin-4-ylmethyl] -amide, the characteristics of which are as follows: - Mass spectrum (ES): m / z = 633 (M + H) ⁺ base peak c) Thiophene- 2-sulfonic acid (2,4-dimethoxybenzyl) - [2- (5,6-dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -amide is prepared as described in Example 211b from 0.80 g of the (2, -dimethoxy-benzyl) - [2- (5, 6-dimethoxy -1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -amino and 0.114 g of 2-thiophenesulfonyl chloride instead of 4- (trifluoromethoxy) benzene sulfonyl chloride used in Example 211b. 0.150 g of thiophene-2-sulfonic acid (2,4-dimethoxy-benzyl) - [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4) are obtained. -sulfonyl) -IH- pyrrolo ^, 3-b] pyridin-4-ylmethyl] -amide whose characteristics are the following: - Mass spectrum (EI): m / z = 786 M ⁺ ; m / z = 631 (M - C ₇ H ₇ S0 ₂ ) ⁺ base peak; m / z = 320 (m / z = 631 - C ₁₃ H ₁₃ N0 ₄ S ₂ ) ⁺

Example 213: N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -benzene sulfonamide trifluoroacetate (( A003454170A (P-32989-126- 3)): a) N- [2- (5, 6-dimethoxy-1- methyl-IH-indol-3-yl) -IH-pyrrolo trifluoroacetate [2, 3- b] pyridin-4-ylmethyl] -benzenulphonamide is prepared as described in Example 210 from 0.04 g of N- (2,4-dimethoxybenzyl) -N- [2- (5,6-dimethoxy -1-methyl-IH-indol-3-yl) -IH- pyrrolo [2, 3-b] pyridin-4-ylmethyl] -benzenesulfonamide instead of N- (2,4-dimethoxy-benzyl) -N- [ 2- (5, 6-dimethoxy-1- methyl-IH-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -4-trifluoromethoxy-benzenesulfonamide used in Example 210 and 0.045 g of para-toluenesulfonic acid. 0.011 g of N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -benzene sulfonamide trifluoroacetate is obtained. whose characteristics are as follows: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 3.81 (s, 3H); 3.87 (s, 3H); 3.89 (s, 3H); 4.3 ^~ 3 (d, J = 6.5 Hz, 2 ^' H); 6.91 (d, J = 5.0 Hz, 1H); 6.93 (d, J = 2.0 Hz, 1H); 7.11 (s, 1H); 7.49. (s, 1H); _ from 7.52 to 7.68. (m, _ 3H) ..;. 7.78. (S, .. 1H). ; 7.87 (broad d, J = 7.5 Hz, 2H); 8.01 (d, J = 5.0 Hz, 1H); 8.31 (broad t, J = 6.5 Hz, 1 H); 11.8 (br s, 1H). - Mass spectrum (ES): m / z = 477; (M + H) ⁺ b) N- (2,4-dimethoxy-benzyl) -N- [2- (5, e-dimethoxy- 1-methyl-1H-indol-S-yl) -lH-pyrrolo [ 2,3-b] pyridin-4-ylmethyl] -benzenesulfonamide is prepared as described in Example 179a from 0.090 g of N- (2,4-dimethoxybenzyl) -N- [2- (5,6 -dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -benzenesulfonamide instead of [2- (5,6- dimethoxy-1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) - IH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4- trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 0.6 cm ³ of 5N potassium hydroxide. 0.100 g of N- (2,4-dimethoxy-benzyl) -N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3- is obtained. b] pyridin-4-ylmethyl] -benzenesulfonamide, the characteristics of which are as follows: - Mass spectrum (ES): m / z = 627 (M + H) ⁺ base peak c) N- (2,4-dimethoxy -benzyl) -N- [2- (5, 6-dimethoxy- 1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H- pyrrolo [2, 3-b] pyridin -4-ylmethyl] -benzenesulfonamide is prepared as described in Example 211b from 0.80 g (2,4-dimethoxy-benzyl) - [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2, 3- b] pyridin-4-ylmethyl] -aminate and 0.110 g of benzenesulfonyl chloride instead of 4- (trifluoromethoxy) benzenesulfonyl chloride used in Example 211b. 0.060 g of N- (2,4-dimethoxybenzyl) -N- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (tbluêhe- -suifonyl) is obtained -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -benzenesulfonamide, the characteristics of which are as follows: _ _. .. - Mass spectrum (ES): m / z = 781 (M + H) ⁺ base peak

Example 214: 1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -3- trifluoroacetate 4-trifluoromethoxy-phenyl) -urea ((A003454230A (P-32989-128-2)) a) 1- [2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) trifluoroacetate -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] -3- (4-trifluoromethoxy-phenyl) -urea is prepared as described in Example 210 from 0.04 g of 1- (2 , 4-dimethoxy-benzyl) -1- [2- (5, 6-dimethoxy-1-methyl-1H- indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] - 3- (4- trifluoromethoxy-phenyl) -urea instead of N- (2,4-dimethoxy-benzyl) -N- [2- (5, 6-dimethoxy-1-methyl-IH-indol- 3-yl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] -4- trifluoromethoxy-benzenesulfonamide used in Example 210 and 0.045 g of para-toluenesulfonic acid. 0.0015 g of 1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl] trifluoroacetate is obtained -3- (4-trifluoromethoxy-phenyl) -urea whose characteristics are as follows: - NMR spectrum (300 MHz, (CD ₃ ) SO d6, δ in ppm): 3.78 (s, 3H); 3.80 (s, 3H); 3.86 (s, 3H); 4.63 (broad d, J = 6.5 Hz, 2H); 6.78 (broad t, J = 6.5 Hz, 1 H); 6.83 (br s, 1H); 6.93 (d, J = 5.0 Hz, 1H); 7.10 (s, 1H); 7.22 (broad d, J = 8.5 Hz, 2H); 7.43 (s, 1H); 7.52 (broad d, J = 8.5 Hz, 2H); 7.77 (S, 1H); 8.06 (d, J = 5.0 Hz, 1H); 8.82 (s, 1H); 11.75 (br s, 1H). - Mass spectrum (ES): m / z = 540 (M + H) ⁺ base peak b) 1- (2,4-dimethoxy-benzyl) -1- [2- (5, 6-dimethoxy- 1 -methyl-1H-indol-3-yl) -lH-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -3- (4-trifluoromethoxy-phenyl) -urea is prepared as described in Example 179a to from 0.150 g of 1- (2,4-dimethoxy-benzyl) -1- [2- (5,6-dimethoxy-1-methyl-1H- indol-3-yl) -1- (toluene-4-sulfonyl ) -lH-pyrrolo [2,3- b] pyridin-4-ylmethyl] -3- (4-trifluoromethoxy-phenyl) -urea instead of [2- (5, 6-dimethoxy-1-methyl-IH-indol) -3-yl) -1- (toluene-4-sulfonyl) -lH-pyrrolo [2,3-b] pyridin-4-ylmethyl] - (4-trifluoromethylsulfanyl-benzyl) -amine used in Example 179a and 1 cm ³ of 5N potassium hydroxide. 0.040 g of 1- (2,4-dimethoxybenzyl) -1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1H-pyrrolo [2, 3- b] pyridin-4-ylmethyl] -3- (4-trifluoromethoxyphenyl) -urea whose characteristics are as follows: - Mass spectrum (ES): m / z = 690 (M + H) ⁺ base peak c ) 1- (2,4-dimethoxy-benzyl) -1- [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H - pyrrolo [2,3-b] pyridin-4-ylmethyl] -3- (4-trifluoromethoxyphenyl) -urea can be prepared as follows: To a solution of 0.080 g of (2,4-dimethoxybenzyl ) - [2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -1- (toluene-4-sulfonyl) -1H-pyrrolo [2,3-b] pyridin-4-ylmethyl ] -aminated in 6 cm ³ of dichloromethane, under an argon atmosphere, at a temperature in the region of 20 ° C., 0.094 cm ³ of 4- (trifluoromethoxy) phenylisocyanate is added. The dream environment is stirred at this same temperature for 24 hours. 2 cm ³ of water are added. After decantation, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-pack chromatography (Si02 dichloromethane / methanol 98/02 by volume as eluent), 0.150 g of 1- (2,4-dimethoxy-benzyl) -1- [2- (5, 6-dlmêthόxy-) is obtained. 1-methyl-IH-indol-3-yl) -1- (toluene-4-sulfonyl) - 1H-pyrrolo [2, 3-b] pyridin-4-ylmethyl] -3- (4-trifluoromethoxy-phenyl) - urea of which. the. characteristics are as follows: - Mass spectrum (El): m / z = 843 (M) ⁺ ; m / z = 640 (M - C ₈ H ₄ N0 ₂ F ₃ ) ⁺ ; m / z = 485 (m / z = 640 - C ₇ H ₇ S0 ₂ ) ⁺ ; m / z = 203 (C ₈ H ₄ N0 ₂ F ₃ ⁺ ) base peak Example 215: 2- [5, 6-Dimethoxy-1-methyl-IH-indol-3-yl] -4- methyl-1H- pyrrolo [2, 3-b] pyridine ((A003338710 (P-31376-043-1)) a) 2- [5,6-dimethoxy-1-methyl-1H-indol-3-yl] -4- methyl -1H-pyrrolo [2, 3-b] pyridine is prepared as follows: To a solution of 0.13 g of 2- [5, 6-dimethoxy-1-methyl-1H-indol-3-yl] - 1- (toluene-4-sulfonyl) -4-methyl-1H-pyrrolo [2, 3-b] pyridine in 15 cm ³ of methanol is added 1.3 cm ³ of an aqueous solution of potassium hydroxide 5N to a temperature close to 20 ° C. The reaction medium is stirred at reflux for about 18 hours. The reaction mixture is evaporated under reduced pressure, the residue thus obtained is dissolved in 100 cm ³ of ethyl acetate, transferred to a separating funnel and washed with 50 cm ³ of distilled water. The aqueous phase is again extracted with 2 times 50 cm ³ of ethyl acetate, the combined organic phases are washed successively with 50 cm ³ of a saturated aqueous solution of sodium chloride and 50 cm ³ of water, distilled . The organic extract is dried over magnesium sulfate, filtered and evaporated under reduced pressure to yield the crude compound which is purified by chromatography on a Flash Chromabond RS 6 SiOH cartridge (3 g of silica). The elution was carried out at a flow rate of 10 cm ³ / min. with a heptane / isopropanol mixture (70/30 by volume). The fractions containing the expected compound are combined and evaporated to give 2- [5, 6-dimethoxy-1-methyl-1H-indol-3-yl] - 4-methyl-1H-pyrrblo [2, 3-b] pyridine sόus formed of a, pasty yellow solid (0.008 g, 8%) whose characteristics are the following: - NMR spectrum (300 MHz, (CD ₃ ) ₂ SO d6, δ in ppm): 2.55 (s, 3H); 3.81 (s, 3H); 3.86 (s, 3H); 3.89 (S, 3H); 6.73 (d, J = 2.0 Hz, 1H); 6.82 (d, J = 5.0 Hz, 1H); 7.10 (s, 1H); 7.47 (s, 1H); 7.75 (s, 1H); 7.98 (d, J = 5.0 Hz, 1H); 11.65 (br s, 1H). - Mass spectrum (ES): m / z = 322 (M + H) ⁺ b) 2- [5, 6-dimethoxy-1-methyl-IH-indol-3-yl] -1- (toluene-4 -sulfonyl) -4-methyl-1H-pyrrolo [2, 3-b] pyridine is prepared as follows: To a solution of 0.17 g of 2- [5,6-dimethoxy-1H-indol-3- yl] -1- (toluene-4-sulfonyl) -4-methyl-1H-pyrrolo [2, 3-b] pyridine in 7 cm ³ of anhydrous dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20 ° C 0.017 g of sodium hydride (60%) is added. 0.025 cm ³ of methyl iodide are added after 1 hour of stirring at the same temperature. Stirring is continued at this temperature for 4 hours. The reaction mixture is taken up in 50 cm ³ of water and then extracted with 100 cm ³ of ethyl acetate, the aqueous phase is again extracted with 2x50 cm ³ of ethyl acetate. The combined organic phases are washed successively with 50 cm ³ of a saturated aqueous solution of sodium chloride, then with 50 cm ³ of distilled water. After decantation, the organic phase is dried over sulphate magnesium, filtered and then concentrated under reduced pressure. The residue obtained is purified on a Flash Chromabond RS 6 SiOH cartridge (3 g of silica). The elution was carried out at a flow rate of 10 cm ³ / min. with a dichloromethane / methanol mixture (95/05 by volume). The fractions containing the expected compound are combined and evaporated to give 2- [5, 6-dimethoxy-1-methyl-1H-i dbl-3-yl] -1- (toluene-4-sulfoiiyl) -4-methyl- IH-pyrrolo [2, 3-b] pyridine in the form of a beige solid (0.130 g, 72%), the characteristics of which are as follows: - Mass spectrum (ES): m / z = 476 (M + H) ⁺ c) 2- [5, 6-dimethoxy-1H-indol-3-yl] -1- (toluene-4-sulfonyl) -4-methyl-1H-pyrrolo [2, 3-b] pyridine is prepared from as follows: To a solution of 0.61 g of 1- (toluene-4-sulfonyl) - 1H-2-iodo-4-methyl-pyrrolo [2, 3-b] pyridine in 14 cm ³ of anhydrous dimethylformamide on successively add 0.475 g of 1-tert-butyloxycarbonyl-5, 6-dimethoxyindol-3-boronic acid and 4.5 cm3 of a saturated aqueous solution of sodium bicarbonate. The reaction mixture is purged with argon using a bubbler tube for 30 minutes, 0.085 g of tetrakis (triphenylphosphine) palladium is loaded. The reaction medium is heated at 120 ° C. for 4 hours. After cooling, the reaction medium is filtered through celite, the filtrate is concentrated under reduced pressure. The oil obtained is taken up with 100 cm ³ of water and extracted with 2X100 cm ³ of ethyl acetate, the organic phase is washed successively with 2X 50 cm ³ of distilled water, 50 cm ³ of a saturated aqueous solution in sodium chloride, 50 cm ³ of distilled water. The organic phase is dried over magnesium sulphate in the presence of animal charcoal, filtered through celite and then concentrated under reduced pressure. The residue obtained is purified on a Flash Chromabond RS 70 SiOH cartridge (35 g of silica). The elution was carried out at a flow rate of 10 cm ³ / min. with a heptane / isopropanol mixture (90/10 by volume. The fractions containing the expected compound are combined and evaporated under reduced pressure. This gives 2- [5,6-dimethoxy-IH-indol-3-yl] -1 - (toluene-4-sulfonyl) -4-methyl- IH-pyrrolo [2, 3-b] pyridine in the form of a beige powder (0.17 g, 25%), the characteristics of which are as follows: - Mass spectrum ( ES): m / z = 462 (M + H) ⁺ 1-tert-butyloxy-carbonyl-5,6-dimethoxyindol-3-boronic acid is prepared according to the process described in patent O03000688A1. D) 1- (toluene -4-sulfonyl) -1H-2-iodo-4-methyl-pyrrolo [2, 3-b] pyridine is prepared as follows: To a solution of 0.5 g of 1- (toluene-4-sulfonyl) - 1H-4-methyl-pyrrolo [2, 3-b] pyridine, in 8 cm ³ of anhydrous tetrahydrofuran, under an inert atmosphere of argon at a temperature in the region of -70 ° C, are added dropwise 1.1 cm ³ of n-BuLi (2.5 M in hexane). The reaction medium is stirred at this same temperature for 1 hour, then a solution of 0.8 g of iodine in 4 cm ³ of tetrahydrofuran is added dropwise. The reaction medium is stirred at -78 ° C for 15 minutes. The reaction medium is stirred for 20 hours. 50 cm ³ of water are added and the reaction medium is extracted with ³ × 100 cm ³ of ethyl acetate. The organic phase is washed successively with 100 cm ³ of distilled water _. 100 cm ³ of a saturated aqueous solution of sodium chloride, 100 cm ³ of distilled water. The organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified on a Mâcherey-nagel cartridge (15 g of silica). The elution was carried out at a flow rate of 10 cm ³ / min. with a mixture (cyclohexane / ethyl acetate), (75/25), (V / V) The fractions containing the expected compound are combined and evaporated under reduced pressure. 1- (toluene-4-sulfonyl) -1H-2-iodo-4-methyl-pyrrolo [2,3-b] pyridine is thus obtained in the form of a brown oil (0.61 g, 43%) of which the characteristics are as follows: - Mass spectrum (El): m / z = 412 (M) ⁺ ; m / z = 348 (M - S0 ₂ ) ⁺ ; m / z = 221 (m / z = 348 - I) ⁺ ; m / z = 91; (C ₇ H ₇ ) ⁺ base peak. e) 1- (toluene-4-sulfonyl) -1H-4-methyl-pyrrolo [2, 3-b] pyridine is prepared as follows: To a solution of 10 g of 1- (toluene-4-sulfonyl ) -1H- 4-iodo-pyrrolo [2, 3-b] pyridine, in 120 cm ³ of dimethylformamide, under an inert argon atmosphere at a temperature in the region of 20 ° C, are added 4.020 g of triphenylphosphine, 5.4 g of lithium chloride, 2.115 g of bis (triphenylphosphine) palladium (II) chloride and 18.19 g of tettramethyltin. The reaction medium is heated to a temperature in the region of 120 ° C for 20 hours. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 200 cm ³ of ethyl acetate and extracted with 2 × 50 cm ³ of water. The organic phase The organic phase is dried over magnesium sulfate in the presence of animal charcoal, filtered through celite and then concentrated under reduced pressure. The residue obtained is taken up in 50 ml of methanol. The solid obtained is filtered through sintered glass. 5.1 g of 1- (toluene-4-sulfonyl) -1H-4-methyl-pyrrolo [2,3-b] pyridine are thus obtained in the form of a yellow solid, the characteristics of which are as follows: - Mass spectrum ( E1): m / z = 286 (M) ⁺ ; m / z = 222 (M - S0 ₂ ) ⁺ base peak; m / z = 91; (C ₇ H ₇ ) ⁺ f) 1- (toluene-4-sulfonyl) -1H-4-iodo-pyrrolo [2, 3- b] pyridine is prepared as follows: To a solution of 12 g of 1H-4-iodo-pyrrolo [ 2,3- b] pyridine, in 425 cm ³ of toluene, under an inert argon atmosphere at a temperature in the region of 20 ° C., are added 10.6 g of para-toluenesulfonyl chloride, 0.331 g of tetrabutylammonium hydrogen sulfate , and drop by drop, a 3.1N sodium hydroxide solution. The reaction medium is stirred at a temperature close to

_10_ 20 ° C for 16 hours. After decantation, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. 19.3 g of 1- (toluene-4-sulfonyl) -1H-4-iodo-pyrrolo [2,3-b] pyridine are thus obtained, the characteristics of which are as follows: 15 - Mass spectrum (EI): m / z = 398; (M) ⁺ ; m / z = 334 (M - S0 ₂ ) ⁺ base peak; m / z = 91 (C ₇ H ₇ ) ⁺

The compound 1H-4-iodo-pyrrolo [2, 3-b] pyridine is prepared according to the method described in Synlett, 2001, 5, 609-612.

EXAMPLE 216 PHARMACEUTICAL COMPOSITION Tablets corresponding to the following formula were prepared: Product of Example 94 0.2 g Excipient for a tablet finished at 1 g (detail of excipient: lactose, talc, starch, stearate magnesium).

EXAMPLE 217: PHARMACEUTICAL COMPOSITION Tablets corresponding to the following formula were prepared: Product of Example 101 0.2 g

30 Excipient for one tablet finished at 1 g (detail of excipient: lactose, talc, starch, magnesium stearate).

EXAMPLE 218: PHARMACEUTICAL COMPOSITION Tablets corresponding to the following formula were prepared: Product of the example 193 0.2 g Excipient for a tablet finished at 1 g (detail of the excipient: lactose, talc, starch, magnesium stearate).

Claims

1) Products of formula (I)

in which: R represents hydrogen or is chosen from the values of R2 and R3, RI represents alkenyl or alkyl optionally substituted by -CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy or a halogen atom, R2 and R3 identical or different represent alkyl or -O-alkyl optionally substituted by -CO-NR7R8, -NR7R8, alkoxy, alkoxy-NR7R8, free or esterified carboxy or phenyl itself optionally substituted, R4, R5 and R6 identical or different are chosen among the hydrogen atom, the halogen atoms and the cyano, amino, alkoxy or optionally substituted alkyl radicals, R4 can also be chosen from the following values: carboxaldehyde -CH = 0, formaldoxime - CH = N-OH and methylhydroxylamine -CH2NH0H;

R7 and R8, identical or different, are chosen from alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, and heteroaryl, monocyclic or bicyclic, all these radicals being optionally substituted, or else R7 and R8 form with the nitrogen atom to which they are linked a heterocyclic radical which is unsaturated or partially or completely saturated, consisting of 3 to 10 members. and containing one or more heteroatoms

- chosen from O, S, N and NR14, this radical being optionally substituted, all of the above alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic radicals, as well as the heterocyclic radical formed by R7 and R8 with the nitrogen atom to which they are attached, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and cyano, hydroxyl, alkyl, alkoxy, alkylthio, nitro, oxo, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl radicals -C (= 0) -R9, -C (= O) -OR10, -N (R11) -C (= 0) -R9, -N (Rll) -C (= O) -OR10, -NR12R13, - C (= 0) - NR12R13, -N (R11) -C (= 0) -NR12R13, -S (0) n-R9, -N (R11) -S (O) n- R9, -S (0) n-NR12R13 and -N (R11) -S (O) n-NR12R13, n represents an integer from 0 to 2, the latter alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl radicals their mê mes optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, -NR12R13, free or esterified carboxy, CF3, nitro, cyano, phenyl and phenylalkyl radicals in which the phenyl radical is itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, free or esterified carboxy, CF3, nitro, cyano and pyridyl radicals; R9 represents alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl, all these radicals; being optionally substituted, RIO represents the values of R9 and hydrogen, R11 represents hydrogen or optionally substituted alkyl,

R12 and R13, identical or different, represent hydrogen, acyl, alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, SO2-heteroaryl, -SO2-alkyl, -SO2-phenyl, -CO-NH-phenyl and phenyl, all these radicals being optionally substituted, or else R12 and R13 form with l 'nitrogen atom to which they are linked a heterocyclic radical which is unsaturated or else partially or totally saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted,. ___.._____ R14 represents the values of R9 and hydrogen, acyl and free and esterified carboxy, the radicals R9, RIO, R11, R12, R13 and R14 above as well as the cyclic radical which R12 and R13 can form with nitrogen atom to which they are linked, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, alkyl-NH2, alkyl-NHC02alkyl, NH2, NHC02alkyl, hydroxyl, alkoxy, hydroxyalkoxy radicals, free or esterified carboxy, CF3, SCF3, OCF3, 0CHF2, S02CF3, nitro, cyano, heterocycloalkyl, heteroaryl and phenyl, the latter cyclic radicals themselves being optionally substituted by one or more identical or different radicals chosen from halogen atoms and the alkyl, hydroxyl, alkoxy, free or esterified carboxy radicals, CF3, SCF3, 0CF3, 0CHF2, S02CF3, NH2, NHC02alkyl, nitro and cyano, all the aryl, heteroaryl and heterocycloalkyl radicals etan t further optionally substituted by an alkylenedioxy radical, all of the above alkyl, alkenyl, alkoxy or - O-alkyl and alkylthio radicals being linear or branched and containing at most 6 carbon atoms, all of the above cycloalkyl radicals containing plus 7 carbon atoms, all of the above aryl, heteroaryl and heterocycloalkyl containing at most 10 carbon atoms, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral bases and organic of said products of formula (I).

2) Products of formula (I) as defined in claim 1 in which: R represents hydrogen or is chosen from the values of R2 and R3,

RI represents alkenyl or alkyl optionally substituted by -CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy or a halogen atom, R2 and R3 identical or different represent alkyl or -O-alkyl optionally substituted by -CO- NR7R8, -NR7R8, alkoxy, alkoxy-NR7R8, free or esterified carboxy or phenyl itself optionally substituted, R4, R5 and R6 identical or different are chosen from the hydrogen atom, halogen atoms and cyano radicals , amino, alkoxy or optionally substituted alkyl, R4 can also be chosen from the following values: carboxaldehyde -CH = 0, formaldoxime - CH = N-OH and methylhydrόxylamine -CH2NHOH;

R7 and R8, identical or different, are chosen from hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl, and heteroaryl, monocyclic or bicyclic, all these radicals being optionally substituted, or else R7 and R8 form with the nitrogen atom to which they are linked a heterocyclic radical which is unsaturated or else partially or totally saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from 0, S, N and NR14, this radical being optionally substituted, all of the above alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic radicals, as well as the heterocyclic radical formed by R7 and R8 with the nitrogen atom to which they are attached, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and cyarib, hydroxyl, alkyl, alkoxy, alkylthio, nitro, oxo, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl radicals = 0) -R9, -C (= O) -OR10, -N (R11) -C (= 0) -R9, -N (R11) -C (= 0) -OR10, -NR12R13, -C (= 0) - NR12R13, -N (R11) -C (= 0) -NR12R13, -S (0) n-R9, -N (Rll) -S (O) n- R9, -S (0) n-NR12R13 and -N (R11) -S (O) -NR12R13, n represents an integer from 0 to 2, the latter alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl radicals being them-m mes optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, -NR12R13, free or esterified carboxy, CF3, nitro, cyano, phenyl and phenylalkyl radicals in which the phenyl radical is itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, free or esterified carboxy, CF3, nitro, cyano and pyridyl radicals; R9 represents alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl, all these radicals being optionally substituted, RIO represents the values of R9 and hydrogen, Rll represents hydrogen or optionally substituted alkyl,

R12 and R13, identical or different, represent hydrogen, acyl, alkyl, cycloalkyl, piperidyl, piperazinyl, pyrrolidinyl, azetidinyl, pyrazolyl, pyridyl, imidazolyl, pyrimidyl, thiazolyl, thiazolidinyl, -S02-thienyl,.-S02-pyridyl, -S02-alkyl, -02-alkyl, -0-phenyl CO-NH-phênyie and phênyie, all these radicals being optionally substituted, or else R12 and R13 form with the nitrogen atom to which they are linked ^" a heterocyclic radical which is partially or fully saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted, R14 represents the values of R9 and hydrogen, acyl and free and esterified carboxy, the radicals R9, RIO, Rll, R12, R13 and R14 above as well as the cyclic radical which R12 and R13 can form with the nitrogen atom to which they are linked, being optionally substituted by one or more identical or different radicals chosen from halogen atoms e t alkyl, -CH2-NH2, -CH2-NHC02alkyl, NH2, NHC02alkyl, hydroxyl, alkoxy, hydroxyalkoxy, free or esterified carboxy, CF3, SCF3, OCF3, OCHF2, S02CF3, nitro, cyano, piperidyl, morpholinyl, piperazine thienyl, pyridyl, imidazolyl, thiazolyl, thiazolidinyl and phenyl, the latter cyclic radicals themselves being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkoxy, free or esterified carboxy radicals , CF3, SCF3, OCF3, OCHF2, S02CF3, NH2, NHC02alkyl, nitro and cyano, all the aryl, heteroaryl and heterocycloalkyl radicals above being more optionally substituted by an alkylenedioxy radical, all the above radicals alkyl, alkenyl, alkoxy or - O-alkyl and alkylthio being linear or branched and containing at most 6 carbon atoms, all of the above cycloalkyl radicals containing not more than 7 carbon atoms, all of the above aryl, heteroaryl and heterocycloalkyl radicals containing not more than 10 carbon atoms, said products of formula (I) being in all the possible racemic isomers, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

3) Products of formula (I):

as defined in claim 1 or 2 in which: R represents hydrogen or is chosen from the values of R2 and R3,

RI represents alkenyl or alkyl optionally substituted by -CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy or a halogen atom, R2 and R3 identical or different represent alkyl or -O-alkyl optionally substituted by -CO- NR7R8, -NR7R8, alkoxy, alkoxy-NR7R8, free or esterified carboxy or phenyl itself optionally substituted, R4, R5 and R6 identical or different are chosen from the hydrogen atom, halogen atoms and cyano radicals , amino, alkoxy or optionally substituted alkyl,

R7 and R8, which may be identical or different, are chosen from hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic, all these radicals being optionally substituted, or else R7 and R8 form, with the nitrogen atom to which they are linked, an unsaturated or partially or fully saturated heterocyclic radical consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted, all of the above alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, aryl and heteroaryl, monocyclic or bicyclic radicals, as well as the heterocyclic radical formed by R7 and R8 with l nitrogen atom to which they are linked, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and cyano, hydroxyl, alkyl, alkoxy, alkylthio, nitro, oxo, cycloalkyl, heterocycloalkyl, aryl radicals , heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl, -C (= 0) -R9, -C (= O) -OR10, -N (R11) -C (= 0) -R9, - N (Rll) -C (= O) -OR10, -NR12R13, -C (= 0) - NR12R13, -N (Rll) -C (= 0) -NR12R13, -S (0) n-R9, -N (R11) -S (O) n- R9, -S (0) n-NR12R13 and -N (R11) -S (O) n-NR12R13, n represents an integer from 0 to 2, the latter alkyl, alkoxy radicals , cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, heteroarylalkyl being themselves optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, -NR12R13, carboxy radicals, carboxy free or esterified, CF3, nitro, cyano, pyrrolidinyl, pheny and phenylalkyl in which the pheny radical is itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy radicals, free or esterified carboxy, CF3, nitro, cyano and pyridyl,

R9 represents alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl, and heteroarylalkyl, all these radicals being optionally substituted, RIO represents the values of R9 and hydrogen, Rll represents hydrogen or optionally substituted alkyl, R12 and R13, identical or different, represent hydrogen, alkyl, alkyl, cycloalkyl and phenyl, these radicals being optionally substituted, or else RI2 and R13 form, with the nitrogen atom to which they are linked, an unsaturated or partially or fully saturated heterocyclic radical consisting of 3 to 10 members and containing a or several heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted,

R14 represents the values of R9 and hydrogen, acyl and free and esterified carboxy, the radicals R9, RIO, R11, R12, R13 and R14 above being optionally substituted by one or more identical or different radicals chosen from atoms ^' d' halogen and the alkyl, hydroxyl, alkoxy, hydroxyalkoxy, free or esterified carboxy, CF3, nitro, cyano and phenyl radicals itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl radicals , alkoxy, free or esterified carboxy, CF3, nitro and cyano, all the aryl, heteroaryl and heterocycloalkyl radicals above being additionally optionally substituted by an alkylenedioxy radical, all the above radicals alkyl, alkenyl, alkoxy or - O- alkyl and alkylthio being linear or branched and containing at most 6 carbon atoms, all of the above cycloalkyl radicals containing at most 7 carbon atoms, all radicals above aryl, heteroaryl and heterocycloalkyl containing at most 10 carbon atoms, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral bases and organic of said products of formula (I).

4) Products of formula (I) as defined in any one of the other claims in which R2 and R3 ', identical or different, represent -O-alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7R8, -NR7R8 , alkoxy, alkoxy-NR7R8 or free or esterified carboxy, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the isomeric forms possible racemic , enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

5) Products of formula (I) as defined in any one of the other claims in which R2 and R3 which are identical or different represent -O-alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7R8, -NR7R8, alkoxy, alkoxy-NR7R8, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic, enantiomeric and diastereomeric isomeric forms isomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

6) Products of formula (I) as defined in any one of the other claims in which R2 and R3 which are identical or different represent -O-alkyl containing at most 4 carbon atoms optionally

5 substituted with -CO-NR7R8 or -NR7R8, the other substituents of the said products of formula (I) having the values defined in any one of the other claims, the said products of formula (I) being in all of the. ÉQrme_s._ .isnm-e_r.e_.s_ .pos.sibles_. racemic, enantiomeric and diastereoisomeric, as well as the addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

7) Products of formula (I) as defined in any one of the other claims in which RI represents alkyl optionally substituted by -CO-NR7R8, -NR7R8, free or esterified carboxy, hydroxyl, alkoxy or a halogen atom, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic, enantiomeric and diastereomeric isomeric forms, as well as the salts of addition with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

8) Products of formula (I) as defined in any one of the other claims in which RI represents alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7R8, -NR7R8, free or esterified or hydroxylated carboxy, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

9) Products of formula (I) as defined in one of the further claims ^"wherein RI represents alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7_R8 ....-NR7R8 or. Hydroxyl , the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as the salts addition with mineral and organic acids or with mineral and organic bases of said products of formula (I).

10) Products of formula (I) as defined in any one of the other claims in which RI represents alkyl containing at most 4 carbon atoms optionally substituted by -CO-NR7R8 or -NR7R8, the other substituents of said products of formula ( I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the mineral and organic bases of the said products of formula (I).

11) Products of formula (I) as defined in any one of the other claims in which RI represents alkyl containing at most 4 carbon atoms optionally substituted with NR7R8, the other substituents of said products of formula (I) having the values defined in any one of _. other claims, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids ^" or with the mineral and organic bases of said products of formula (I).

12) Products of formula (I) as defined in any one of the other claims in which R4, R5 and R6 are such that one represents hydrogen and the others, identical or different, are chosen from the atom of hydrogen, halogen atoms and optionally substituted cyano, amino or alkyl radicals, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being under all possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

13) Products of formula (I) as defined in any one of the other claims in which

R4, R5 and R6 are such that R5 and R6, identical or different, are chosen from the hydrogen atom and the halogen atoms, and R4, identical or different from R5 and R6, is chosen from the atoms of halogen, amino radicals, carboxaldehyde -CH = 0, formaldoxime -CH = N-OH, methylhydroxylamine -CH2NHOH and alkyl optionally substituted by one or more identical or different radicals chosen from halogen atoms and cyano, hydroxyl, alkoxy,, cycloalkyl, heterocycloalkyl, phenyl, heteroaryl and -NR12R13 radicals; R, RI, R2, R3, R12 and R13 having the values defined in any one of the other claims, said products of formula (I) being in all the possible isomeric forms racemic, enantiomers and diastereoisomers, as well as the salts addition with mineral and organic acids or with mineral and organic bases, of said products of formula (I).

14) Products of formula (I) as defined in any one of the other claims in which R4, R5 and R6 represent hydrogen or are such that two of them represent hydrogen and the third represents a halogen atom or the cyano radical, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

15) Products of formula (I) as defined in any one of the other claims in which R4, R5 and R6 represent hydrogen, the other substituents of said products of formula (I) having the values defined in any of the others claims, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I ).

16) Products of formula (I) as defined in any one of the other claims in which R4, R5 and R6 are such that two of them represent hydrogen and the third represents a halogen atom or the cyano radical, the other substituents of the said products of formula (I) having the values defined in any one of the other claims, the said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as the salts of addition with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

17) Products of formula (I) as defined in any one of the other claims in which R4, R5 and R6 are such that two of them represent hydrogen and the third represents a halogen atom, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with the mineral and organic acids or with the mineral and organic bases of the said products of formula (I).

18) Products of formula (I) as defined in any one of the other claims in which R4, R5 and R6 are such that two of them represent hydrogen and the third represents a chlorine or fluorine atom, the others substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all of the possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

19) Products of formula (I) as defined in any one of the other claims in which R4, R5 and R6 are such that two of them represent hydrogen and the third represents the cyano radical, the other substituents of said products formula ... CQ .. having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the mineral and organic bases of said products of formula (I).

20) Products Products of formula (I) as defined in any one of the other claims in which R6 represents hydrogen, the other substituents of said products of formula (I) having the values defined in any of the other claims, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

21) Products of formula (I) as defined in any one of the other claims in which R5 and R6 represent hydrogen and R4 represents a halogen atom or the cyano radical, the other substituents of said products of formula (I) having the values set to any of the others claims, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I ).

22) A compound of formula (I) ^as' defined in any one of the further claims wherein R4 and R6 are hydrogen. And _R5_ represents. A ..of atom. Fluorine, the other substituents of said products of formula (I) having the values defined in any one of the other claims, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the mineral and organic bases of said products of formula (I).

23) Products of formula (I) as defined in any one of the other claims in which the substituents R, RI, R2, R3, R4, R5 and R6 of said products of formula (I) have the values defined in any one of the other claims, in which the radical -NR12R13 is such that R12 and R13, identical or different, represent the hydrogen atom; and the acyl, alkyl, cycloalkyl, piperidyl, piperazinyl, pyrrolidinyl, azetidinyl, pyrazolyl, pyridyl, imidazolyl, pyrimidyl, thiazolyl, thiazolidinyl, -S02-thienyl, - SO2-pyridyl, -S02-alkyl, -2-alkyl group, CO-NH-phenyl and phenyl, all these radicals being optionally substituted by one or more identical or different radicals, chosen from halogen atoms and alkyl radicals; CH2 NH2; CH2-NHC02alkyl; NH2; NHC02alkyl; hydroxyl; alkoxy; hydroxyalkoxy; free or esterified carboxy; CF3; SCF3; OCF3; OCHF2; SO2CF3; nitro; cyano; thienyl; piperidyl; morpholino itself optionally substituted by one or two radicals - alkyl; and pheny itself optionally substituted by one or more identical or different radicals, chosen from halogen atoms and alkyl, hydroxyl, alkoxy, free or esterified carboxy, CF3, SCF3, OCH3, OÇHF2, SO2CF3, NH2, NHC02alkyle , nitrp and çyano ...; .. or else R12 and R13 form with the nitrogen atom to which they are linked an heterocyclic radical which is unsaturated or else partially or completely saturated consisting of 3 to 10 members and containing one or more heteroatoms chosen from O, S, N and NR11 , this radical being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl radicals; -CH2-NH2; CH2-NHC02alkyl; NH2; NHC02alkyl; hydroxyl; alkoxy; hydroxyalkoxy; free or esterified carboxy; CF3; SCF3; OCF3; OCHF2; SO2CF3; nitro; cyano; and piperidyl radicals; morpholinyl; piperazinyl; thienyl; pyridyle, imidazolyle, thiazolyle, thiazolidinyle et phênyie, themselves optionally substituted by one or more identical or different radicals chosen among halogen atoms and the radicals alkyl, hydroxyl, alkoxy, free or esterified carboxy, CF3, SCF3, NH2, NHC02alkyle, nitro et cyano, the said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

24) Products of formula (I) as defined in one any of the other claims wherein R, RI ,. R2, R3, R4, R5 and R6 have the meanings indicated in any one of the other claims and R7 and R8, identical or different, are chosen from hydrogen, alkyl, cycloalkyl, phenyl, heterocycloalkyl and heteroaryl, monocyclic or bicyclic, all these radicals being optionally substituted, or else R7 and R8 form, with the nitrogen atom to which they are bonded, a heterocyclic radical which is unsaturated or else partially pu. fully saturated consisting of .3 to ..10 links and. containing one or more heteroatoms chosen from O, S, N and NR14, this radical being optionally substituted, all of the above alkyl, cycloalkyl, phenyl, heterocycloalkyl and heteroaryl, monocyclic or bicyclic radicals, as well as the heterocyclic radical formed by R7 and R8 with the nitrogen atom to which they are linked, being optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, oxo, nitro, alkyl, alkoxy, alkylthio, cycloalkyl, phenyl, heterocycloalkyl, heteroaryl, -C (= 0) -R9, -C (= O) -OR10, -N (R11) -C (= 0) -R9, -N (R11) -C (= O) -OR10, -NR12R13, -C (= 0) - NR12R13 and -N (R11) -C (= 0) -NR12R13, the latter alkyl, alkoxy, cycloalkyl, phenyl, heterocycloalkyl and heteroaryl radicals, themselves being optionally substituted by one or several identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, -NR12 radicals R13, free or esterified carboxy, pyrrolidinyl, phenyl and phenylalkyl in which the phenyl radical is itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and hydroxyl, alkyl, alkoxy, free carboxy or esterified, CF3, nitro, cyano and pyridyle,

R9 represents alkyl, cycloalkyl, phenyle, heterocyclo- alkyl and heteroaryl, all these radicals being optionally substituted, RIO represents the values of R9 and hydrogen, R11 represents hydrogen or optionally substituted alkyl, R12 and R13, identical or different, represent hydrogen, acyl, alkyl, cycloalkyl and phenyl, these radicals ment detector may be being substituted, ^"or R12 and R13 together with the nitrogen atom to which _1. 0 they are linked a heterocyclic radical unsaturated or partially or fully saturated consisting of 3 to 10 ring members and containing one or more heteroatoms selected among O, S, N and NR11, this radical being optionally substituted, 15 R14 represents hydrogen, acyl, free and esterified carboxy, alkyl, cycloalkyl and phenyl, optionally substituted, the radicals R9, RIO, R11, R12, R13 and R14 ci- above being optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl radicals, hydroxyl, alkoxy, hydroxyalkoxy, free or esterified carboxy, CF3, nitro, cyano and phenyl itself optionally substituted by one or more identical or different radicals chosen from halogen atoms and alkyl, hydroxyl, alkoxy, free carboxy radicals or esterified, CF3, nitro and cyano, all of the above phenyl and heteroaryl radicals also being optionally substituted by a dioxol radical, 0 all of the above alkyl, alkenyl, alkoxy or -O-alkyl and alkylthio radicals being linear or branched and containing at most 4 carbon atoms, all of the above cycloalkyl radicals containing not more than 7 carbon atoms, 5 all of the above heteroaryl and heterocycloalkyl radicals containing not more than 10 atoms carbon, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I ).

25) Products of formula (I) as defined in any ^'one of the further claims wherein R, RI, R2, R3, R4, R5 and R6 have the meanings indicated, in. Any one of the further claims, and R7 and R8, which may be identical or different, are chosen from hydrogen, cycloalkyl, optionally substituted alkyl, optionally substituted phenyl, heterocycloalkyl and optionally substituted monocyclic or bicyclic heteroaryl, or else R7 and R8 form a radical with the nitrogen atom to which they are attached heterocyclic group containing one or more heteroatoms and optionally substituted, all of the above alkyl, phenyl and heterocyclic radicals, as well as the heterocyclic radical which can form R7 and R8 with the nitrogen atom to which they are linked, being optionally substituted by a or several radicals chosen from halogen atoms and hydroxyl; oxo; nitro; cycloalkyl; alkoxy; OCF3; hydroxyalkoxy; alkylthio; acyl; free or esterified carboxy; optionally substituted phenyle; optionally substituted amino; alkyl optionally substituted by one or more radicals chosen from halogen atoms and the hydroxyl, alkoxy, pyrrolidinyl, phenyl and amino radicals themselves, optionally substituted; and pyrrolidinyl, piperidyl, pyridyl and piperazinyl themselves optionally substituted by one or more radicals chosen from hydroxyl, alkyl, alkoxy, free or esterified carboxy, pheny and phenylalkyl radicals themselves same optionally substituted, the amino radicals being optionally substituted by one or two identical or different radicals chosen from alkyl, hydroxyalkyl, alkoxyalkyl, acyl, phenyl and phenylalkyl themselves optionally substituted, the phenolic and phenylalkyl radicals being optionally substituted by one or more chosen radicals among the halogen atoms and the hydroxyl, alkyl, alkoxy, CF3, free or esterified carboxy, pyridyl and dioxol radicals, all the alkyl and alkoxy radicals being linear or branched and containing at most 4 carbon atoms said products of formula ( I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

26) Products of formula (I) as defined in any one of the other claims in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated in any of the other claims, and R7 and R8, identical or different, are chosen from hydrogen and alkyl, cycloalkyl, phenyl and heterocyclic radicals such as pyrrolidinyl, piprididyl, pyrimidinyl, thienyl, thiazolyl, pyran, furyl, tetrahydrofuryl, tetrahydro-furan-2-yl, imidazinyl, pipidylinyl pyrrole, benzopyran, quinolyl, pyridyle, purinyle and morpholinyle, these radicals being optionally substituted or else R7 and R8 form with the nitrogen atom to which they are linked a heterocyclic radical chosen from the pyrrolidinyl, imidazolyl, morpholinyl, piperazinyl, piperidyl radicals , thiazolyle, diazepine, spiro [4.5] decane, pyrrolyle, dihydropyrrolyle, tëtrahydro-pyrrolyle, tétrahydro-pyrrolo [3, 4-c] pyrrolyle, piperidinyl, indolinyl, pyrindolinyl, tetrahydroquinoline, thiazolidinyl, naphthyridyl, azetidine or quinazolinyl, these radicals being all optionally substituted, all the above radicals alkyl, phenyl and heterocyclic being optionally substituted by one or more radicals chosen from atoms of halogen and hydroxyl radicals; ôxb; nitro; cycloalkyl; alkoxy; OCF3; hydroxyalkoxy; alkylthio; acyl; free carboxy _. _ u esterified; optionally substituted pheny; optionally substituted amino; alkyl optionally substituted by one or more radicals chosen from halogen atoms and the hydroxyl, alkoxy, pyrrolidinyl, phenyl and amino radicals themselves, optionally substituted; and pyrrolidinyl, piperidyl, pyridyl and piperazinyl themselves optionally substituted with one or more radicals chosen from hydroxyl, alkyl, alkoxy, free or esterified carboxy, phenyl and phenylalkyl radicals themselves, optionally substituted, the amino radicals being optionally substituted with a or two identical or different radicals chosen from alkyl, hydroxyalkyl, alkoxyalkyl, acyl, phenyl and phenylalkyl themselves optionally substituted, the phenyl and phenylalkyl radicals being optionally substituted by one or more radicals chosen from halogen atoms and hydroxyl, alkyl radicals , alkoxy, CF3, free or esterified carboxy, pyridyl and dioxol, all the alkyl and alkoxy radicals being linear or branched and containing at most 4 carbon atoms said products of formula (I) being in all the possible isomeric forms racemic, enantiomers and diastereoisomers, as well as ad salts edition with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

27) Products of formula (I) as defined in any one of the other claims in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated in any of the other claims, and R7 and R8, identical or different, are chosen from hydrogen, cycloalkyl radicals, and phenyl and heterocyclic alkyl radicals such as pyrrolidinyl, piperidyl, furyl, tetrahydrofuryl, tetrahydrofuran-2-yl, imidazolinyl, piperazinyl, indolyl, benzppyryl _. _{ppyran-8-çarbpxyiique,.} pyridyl, purinyl and morpholinyl, all these radicals being optionally substituted or else R7 and R8 form, with the nitrogen atom to which they are linked, a heterocyclic radical chosen from the pyrrolidinyl, imidazolyl, morpholinyl, piperazinyl, piperidyl, thiazolyl, diazepine radicals, spiro [4.5] decane, pyrrolyle, dihydropyrrolyle, tétrahydro-pyrrolyle, tétrahydro-pyrrolo [3, 4-c] pyrrolyle, all these radicals being all optionally substituted, all the radicals above alkyl, phenyl and heterocyclic which represent R7 and R8 or that can form R7 and R8 with the nitrogen atom to which they are linked, being optionally substituted by one or more radicals chosen from oxo radicals; cycloalkyl; CO-alkyl; -CO-furyl; hydroxyl; alkoxy; hydroxyalkoxy; alkylthio; free or esterified carboxy; optionally substituted pheny; alkyl optionally substituted with a radical chosen from hydroxyl, alkoxy, pyrrolidinyl, optionally substituted pheny and amino optionally substituted with one or two radicals chosen from alkyl and optionally substituted phenyl; amino optionally substituted with one or two identical or different radicals chosen from alkyl, hydroxyalkyl, alkoxyalkyl, CO-alkyl and phenyl itself optionally substituted; pyrrolidinyl, piperidyl, pyridyl and piperazinyl optionally substituted by one or more radicals chosen from free or esterified carboxy, alkyl, alkoxy, hydroxyl, phenylalkyl and phenyl optionally substituted, all the phenyl radicals being optionally substituted by one or more identical or different radicals chosen from halogen atoms and radicals hydroxyl, alkyl, alkoxy, CF3, free or esterified carboxy, pyridyl and dioxol, the said products of formula (I) being in all the isomeric forms _. possible racemic,. enantiomers and diastereoisomers, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).

28) Products of formula (I) as defined in any one of the other claims in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated in any of the other claims, and R7 and Identical or different R8 are chosen from the following radicals: - hydrogen; - benzopyran; - pyridyle itself optionally substituted with hydroxyl; - piperidyl optionally substituted by alkyl itself optionally substituted by pheny; - purinyl; - alkyl optionally substituted by one or more radicals chosen from hydroxyl; alkoxy; alkylthio; pyridyle; imidazolinyl; indolyl; pyrrolyl; furyl; tetrahydrofuryl; amino optionally substituted by one or two identical or different radicals chosen from alkyl, hydroxyalkyl, alkoxyalkyl and phenyl itself optionally substituted by alkyl; pyrrolidinyl itself optionally substituted by a radical alkyl; piperidyl itself optionally substituted by alkyl or phenylalkyl; piperazinyl itself optionally substituted with alkyl; phênyie optionally substituted by free or esterified dioxol or carboxy; - phenyl optionally substituted by one or more radicals chosen from alkoxy, piperidyl or piperazinyl itself optionally substituted by an alkyl radical; or R7 and R8 form with the atom. di nitrogen to which they are linked a heterocyclic radical chosen from the following radicals: imidazolyl; dihydropyrrolyl; - 1,4-dioxa-8-aza-spiro [4.5] decane; - thiazolyl; - tetrahydro-pyrrolo [3,4-c] pyrrole-2-one; - tetrahydro-pyrrolo [3, 4-c] pyrrole-1, 3-dione; - pyrrolidinyl optionally substituted by a radical chosen from pyridyl; amino itself optionally substituted by an alkyl radical and an acyl and alkyl radical itself optionally substituted by a radical chosen from hydroxyl, alkoxy, pyrrolidinyl and amino itself optionally substituted by a phenyl radical; - morpholinyl optionally substituted by one or more alkyl radicals; - piperazinyl optionally substituted by one or more identical or different radicals chosen from oxo radicals; cycloalkyl; acyl; carboxy; . pyridyle; alkyl containing at most 4 carbon atoms itself optionally substituted by a hydroxyl radical, alkoxy, hydroxyalkoxy containing at most 4 carbon atoms and phenyl itself optionally substituted by a dioxol radical; phênyie itself possibly substituted by one or more radicals chosen from halogen atoms and hydroxyl, alkoxy and CF3 radicals; - piperidyl optionally substituted by one or more substituents chosen from hydroxyl, alkyl, hydroxyalkyl and piperidyl; - diazepine or perhydro-1,4-diazepine optionally substituted with one. alkyl radical itself optionally substituted by pyrrolidinyl; said products of formula (I) being under all possible racemic, enantiomeric and diastereoisomeric isomeric forms, as well as addition salts with mineral and organic acids or with mineral and organic bases of said products formula (I).

29) Products of formula (I) as defined in any one of the other claims in which R, RI, R2, R3, R4, R5 and R6 have the meanings indicated in any of the other claims, and R7 and R8, which are identical or different, are chosen from hydrogen radicals, alkyl itself optionally substituted by a pyrrolidinyl or piperidyl radical and phenylene itself optionally substituted by one or more radicals chosen from the piperazinyl radical itself optionally substituted by an alkyl radical, . or else R7 and R8 form, with the nitrogen atom to which they are linked, a radical chosen from the following radicals: morpholinyl; thiazolyl; diazepine or perhydro-1,4-diazepine optionally substituted by an alkyl radical; 1-tetrahydro-pyrrolo [3,4-c] pyrrole-2-one; piperazinyl optionally substituted by one or more identical or different radicals chosen from oxo and alkyl radicals itself optionally substituted by a hydroxyl, alkoxy or hydroxyalkoxy radical; piperidyl optionally substituted by hydroxyl, alkyl, hydroxyalkyl or piperidyl; the alkyl and alkoxy radicals containing at most 4 carbon atoms, the said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the mineral and organic bases of the said products of formula (I).

30) Products of formula (I) as defined in the preceding claim in which: R and R6 represent a hydrogen atom,

RI represents alkyl containing at most 2 carbon atoms optionally substituted by -C0-NR7R8 or -NR7R8, R2 and R3 identical or different represent -O-alkyl containing at most 3 carbon atoms optionally substituted by -CO-NR7R8 or -NR7R8,

R7 and R8 having the meanings indicated in claim 22 or 23, said products of formula (I) being in all the possible racemic isomeric forms, enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with the mineral and organic bases of the said products of formula (I).

31) Products of formula (I) as defined in any one of the other claims in which R, RI, R2, R3, R4, R5, R6, R7 and R8 have the meanings indicated in any of the other claims , it being understood that R7 and R8 do not both represent hydrogen, the said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with acids. mineral and organic or with the mineral and organic bases of said products of formula (I).

32) Products of formula (I) as defined in any one of the other claims in which R, RI, R2, R3, R, R5 and R6 have the meanings indicated in any of the other claims, and R7 and R8 are such that either one of R7 and R8 represents hydrogen or alkyl and the other is chosen from the values of R7 and R8. as defined at_ _. One _. any of the other claims, either R7 and R8 form, with the nitrogen atom to which they are linked, a heterocyclic radical as defined in any one of the other claims, said products of formula (I) being in all the possible isomeric forms racemic , enantiomers and diastereoisomers, as well as the addition salts with mineral and organic acids or with mineral and organic bases of the said products of formula (I).

33) Products of formula (I) as defined in any one of the other claims, the names of which follow:

2- {5, 6-Dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine

2- (4- {2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2- yl) -indol-1-yl] -ethyl} -piperazin-1-yl ) -ethanol

2- (l- {2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2- yl) -indol-1-yl] -ethyl} -piperidin-4-yl ) -ethanol l - {2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] yridin-2-yl) - indol-1-yl] -ethyl} - [1,4 '] bipiperidinyl l- {2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - indol-1-yl] -ethyl} -piperidin-3-ol

2- {5, 6-Dimethoxy-1- [2- (4-methyl-perhydro-1, 4-diazepin-1- yl) -ethyl] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] yridin-2-yl) -indol- 1-yl] -1- (4-hydroxy-piperidin-1-yl) -ethanone 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) -indol - 1-yl] -l-thiazolidin-3-yl-ethanone 4- {[5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl ] -acetyl} -1-methyl-piperazin-2-one 4-Chloro-2- (5, 6-dimethoxy-1-methyl-IH-indol-3-yl) -IH- pyrrolo [2, 3-b] pyridine 2- (5,6-dimethoxy-1-methyl-1H-indol-3-yl) -lH-pyrroTό [2,3- b] pyridine-4-carbonitrile 4-chloro-2- [5,6-dimethoxy -1- (2-morpholin-4-yl-ethyl) -1H- indol-3-yl] -lH-pyrrolo [2,3-b] yridine 2- (l- {2- [3- (4-chloro -lH-pyrrolo [2,3-b] pyridin-2-yl) -5,6- dimethoxy-indol-1-yl] -ethyl} -piperidin-4-yl) -ethanol 4-chloro-2- {5 , 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -lH-indol-3-yl} -lH-pyrrolo [2,3-b] pyridine 2- {5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine-4-carbonitrile 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -5-fluoro-1H- pyrrolo [2, 3-b] pyridine 2- [5, 6-dimetho xy-1- (2-morpholin-4-yl-ethyl) -lH-indol-3- yl] -5-fluoro-1H-pyrrolo [2, 3-b] pyridine

2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - 1H-indol-3-yl} -5-fluoro-1H-pyrrolo [2, 3- b] pyridine 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - IH-indol-6-yloxy] -l-morpholin-4-yl ethanone

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - IH-indol-6-yloxy] -1- (4-methyl- [1, 4] diazepan-1-yl) - ethanone 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - IH-indol-6-yloxy] - N- [4- (4-methyl-piperazin-1-yl) -phenyl] - acetamide

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - IH-indol-6-yloxy] -1- (4-methyl-piperazin-1 -yl) -ethanone l- {4- [2- (2-Hydroxy-ethoxy) -ethyl] -piperazin-1-yl} -2- [5- Methoxy-1-methyl-3- (1H-pyrrolo [2 , 3-b] pyridin-2-yl) -IH- indol-6-yloxy] -ethanone (3aS, 6aS) -5- {2- [5-Methoxy-1-methyl-3- (IH-pyrrolo [2, 3-b] pyridin-2-yl) -IH-indol-6-yloxy] trifluoroacetate - acetyl} -hexahydro-pyrrolo [3, 4-c] pyrrol-1-one 2- {5-Methoxy-1-methyl-6- [3- (4-methyl-perhydro-1,4-diazepin-1- yl) -propoxy] -IH-indol-3-yl} -lH-pyrrolo [2,3- b] pyridine -Chloro-2- {1-methyl-5-methoxy-6- [2- (4-methyl- piperazin- -yl) -ethoxy] -lH-indόi-3-yl} -IH-pyrrolo [2, 3-b] -pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-piperidyl-pipé_ridin _r l-yl) -ethoxy] -IH-indol _7. 3-yl} _. -lH ^^ pyridine 4-Chloro-2- {5-Methoxy-1-methyl-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2 , 3-b] - pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (2-piperidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2, 3-b] - pyridine,

said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I)

34) Products of formula (I) as defined in any one of the other claims, the names of which follow:

2- {5, 6-Dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - IH-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine 2 - (4- {2- [5, 6-Dimethoxy-3- (IH-pyrrolo [2,3-b] pyridin-2- yl) -indol-1-yl] -ethyl} -piperazin-1-yl) ethanol

2- (1- {2- [5, 6-Dimethoxy-3- (IH-pyrrolo [2, 3-b] pyridin-2- yl) -indol-1-yl] -ethyl} -piperidin-4-yl ) -ethanol 1 '- {2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} - [1,4 '] bipiperidinyl 05/095399

306 l- {2- [5,6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -ethyl} -piperidin-3-ol 2- {5, 6-Dimethoxy-1- [2- (4-methyl-perhydro-1, 4-diazepin-1- yl) -ethyl] -lH-indol-3-yl} -lH-pyrrolo [2,3- b] pyridine 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol- 1-yl] -1- (4-hydroxy-piperidin-1- yl) -ethanone 2- [5, 6-Dimethoxy-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -indol- 1-yl] -l-thiazolidih-3-yl-ethanone 4 - {[5, 6-Dimethoxy-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - indol-1-yl] -acetyl} -1-methyl-piperazin-2-one 4- Chloro-2- (5,6-dimethoxy-1-methyl-IH-indol-3-yl) -1H- pyrrolo [2, 3-b] pyridine 2- (5, 6-dimethoxy-1-methyl-IH- indol-3-yl) -lH-pyrrolo [2,3- b] pyridine-4-carbonitrile 4-chloro-2- [5,6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -IH - indol-3-yl] -IH-pyrrolo [2,3-b] pyridine

2- (1- {2- [3- (4-chloro-1H-pyrrolo [2,3-b] pyridin-2-yl) -5,6- dimethoxy-indol-1-yl] -ethyl} -piperidin -4-yl) -ethanol 4-chloro-2- {5, 6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) - ethyl] -IH-indol-3-yl} -lH -pyrrolo [2, 3-b] pyridine

2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - IH-indol-3-yl} -lH-pyrrolo [2, 3-b] pyridine- -carbonitrile 2- (5, 6-dimethoxy-1-methyl-1H-indol-3-yl) -5-fluoro-1H- pyrrolo [2, 3-b] pyridine 2- [5, 6-dimethoxy-1- (2-morpholin-4-yl-ethyl) -lH-indol-3- yl] -5-fluoro-IH-pyrrolo [2, 3-b] pyridine

2- {5,6-dimethoxy-1- [2- (4-methyl-piperazin-1-yl) -ethyl] - IH-indol-3-yl} -5-fluoro-1H-pyrrolo [2, 3- b] pyridine 2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl - IH-indol-6-yloxy] -l-morpholin-4-yl- ethanone

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -

IH-indol-6-yloxy] -1- (4-methyl- [1,4] diazepan-1-yl) - ethanone

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) - IH-indol-6-yloxy] -N- [4- (4-methyl) piperazin-1-yl) -phenyl] - acetamide 05/095399

307

2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2, 3-b] pyridin-2-yl) - IH-indol-6-yloxy] -l- (4-methyl-piperazin-1 -yl) -ethanone l- {4- [2- (2-Hydroxy-ethoxy) -ethyl] -piperazin-1-yl} -2- [5- Methoxy-1-methyl-3- (1H-pyrrolo [2 , 3-b] pyridin-2-yl) -1H- indol-6-yloxy] -ethanone Trifluoroacetate from (3aS, 6aS) -5- {2- [5-Methoxy-1-methyl-3- (1H-pyrrolo [2,3-b] pyridin-2-yl) -IH-indol-6-yloxy] - acetyl} -hexâhydro-pyrrolo [3, 4-c] pyrrol-1-όhe 2- {5-Methoxy-1- methyl-6- [3- (4-methyl-perhydro-1,4-jdiazepÂn-: 1-yl) -propoxy] -IH-indol-3 ..- yl} -lH _r pyrrplo [2,3- .. ._. b] pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-methyl-piperazin-1-yl) -ethoxy] -IH-indol-3-yl} -lH-pyrrolo [2, 3-b] -pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (4-piperidyl- piperidin-1-yl) -ethoxy] -lH-indol-3- yl} -lH-pyrrolo [2,3-b] - pyridine

4-Chloro-2- {5-Methoxy-1-methyl-6- [2- (2-pyrrolidin-ethylamino) -ethoxy] -lH-indol-3-yl} -lH-pyrrolo [2,3-b] - pyridine 4-Chloro-2- {1-methyl-5-methoxy-6- [2- (2-piperidin-ethylamino) -ethoxy] -IH-indol-3-yl} -lH-pyrrolo [2, 3- b] - pyridine, said products of formula (I) being in all the possible racemic isomeric, enantiomeric and diastereoisomeric forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products formula (I).

35 - As medicaments, the products of formula (I) as defined in claims 1 to 32, as well as their prodrugs, said products of formula (I) being in all the possible isemic, racemic, enantiomeric and diastereoisomeric forms, as well as addition salts with mineral and organic acids or with pharmaceutically acceptable mineral and organic bases of the said products of formula (I). 005/095399

308

36 - As medicaments, the products of formula (I) as defined in claims 33 and 34, as well as their prodrugs, said products of formula (ï) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as addition salts with mineral and organic acids or with pharmaceutically acceptable mineral and organic bases of said products of formula (I).

37 - Pharmaceutical compositions containing, to. as active ingredient, at least one of the medicaments as defined in claims 35 and 36.

38 - Pharmaceutical compositions containing, as active principle, at least one of the medicaments as defined in claim 36.

39 - Pharmaceutical compositions as defined in the other claims containing, in addition, active principles of other chemotherapy drugs against cancer.

40 - Pharmaceutical compositions according to any one of the other claims, characterized in that they are used as medicaments, in particular for the chemotherapy of cancers.

41 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of medicaments intended to inhibit the activity of protein kinases and in particular d protein kinase.

42 - Use of products of formula (I) as defined in the preceding claim or of salts 05/095399

309 pharmaceutically acceptable of said products of formula (I) wherein the protein kinase is a protein tyrosine kinase.

43 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is chosen from the following group: CGJF1, Raf _Λ . JEGF, PDGF, VEGF ,. Tie2, _KDR, Fl.tl.-3 _^ ..FK, .. Sr.C, ... Abl, cKit, cdkl-9, Auroral-2, cdc7, Akt, Pdk, S6K, Jnk, IR, FLK- 1, FGFR1, FGFR2, FGFR3, FGFR4, FGFR5, PLK, Pyk2

44 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is chosen from the following group: IGF1, cdc7, Auroral -2, Src, Jnk, FAK, KDR, IR, Tie2

45 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is IGF1R.

46 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is in a cell culture.

47 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) in which the protein kinase is in a mammal.

48 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended for preventing or treating a disease characterized by ^" dysregulation of the activity of a protein kinase.

49 ._._- .Use ..of _ .. products. _of ... formula .... (_) .._ according to., la. The preceding claim wherein the disease to be prevented or treated is in a mammal.

50 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended for preventing or treating a disease belonging to the group next: disorders of the proliferation of blood vessels, fibrotic disorders, disorders of the proliferation of mesangial cells, metabolic disorders, allergies, asthma, thromboses, diseases of the nervous system, retinopathies, psoriasis, rheumatoid arthritis, diabetes, muscle degeneration, diseases in oncology , cancers.

51 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended to treat diseases in oncology.

52 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended to treat cancers.

53 - Use of products of formula (I) according to the preceding claim in. which the disease to be treated is cancer from solid tumors. 54 - Use of products of formula (I) according to the preceding claim wherein the disease to be treated is cancer resistant to cytotoxic agents.

55 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended to treat cancers among which cancers of the breast, stomach, colon, lungs, ovaries, uterus, brain, kidney, larynx, lymphatic system, thyroid, urogenital tract, tract including vesicle and prostate , bone cancer, pancreas, melanomas.

56 - Use of products of formula (I) according to the preceding claim in which the disease to be treated is breast, colon or lung cancer.

57 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of a medicament intended for the chemotherapy of cancers.

58 - Use of products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of medicaments intended for the chemotherapy of cancers used alone or in association.

59 - Use of. products of formula (I) as defined in any one of the other claims or of pharmaceutically acceptable salts of said products of formula (I) for the preparation of medicaments intended to be used alone or in combination with chemotherapy or radiotherapy or alternatively in combination with other therapeutic agents.

60 - Use of products of formula (I) according to the preceding claim. wherein the therapeutic agents can be commonly used anti-tumor agents.

61 - Products of formula (I) as defined in any one of the other claims as inhibitors of protein kinases, said products of formula (I) being in all the possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as addition salts with mineral and organic acids or with pharmaceutically acceptable mineral and organic bases of the said products of formula (I) as well as their prodrugs.

62 - Products of formula (I) as defined in any one of the other claims as inhibitors of

IGF1R.