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CU34115A - NEW BENCILPIRIMIDINAS - Google Patents

NEW BENCILPIRIMIDINAS

Info

Publication number
CU34115A
CU34115A CU34115A CU34115A CU34115A CU 34115 A CU34115 A CU 34115A CU 34115 A CU34115 A CU 34115A CU 34115 A CU34115 A CU 34115A CU 34115 A CU34115 A CU 34115A
Authority
CU
Cuba
Prior art keywords
group
compound
formula
amino
meaning
Prior art date
Application number
CU34115A
Other languages
Spanish (es)
Other versions
CU21022L (en
Inventor
Guido Zanetti
Gerald Rey-Bellet
Ivan Kompis
Original Assignee
Hoffmann La Roche
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CU21022L publication Critical patent/CU21022L/en
Publication of CU34115A publication Critical patent/CU34115A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Un procedimiento para la preparación de derivados de bencil-pirimidina de la fórmula general (I) en la que R1 y R2 representan cada uno, independientemente un grupo de alquilo C1-3´ alcoxilo de C1-3´ alquenilo de C2-3 o alqueniloxilo de C2-3´ Z representa un grupo nitro, amino, pirrolo, pirrolidino, piperidino, -NHR , -NHR5, -N(R4) (R5), -NH4COOR4, -NHCOOR4 , -NHCONHR3 , -NHCSNHR5, -N=N-N8R4)2, -N8NO)4 o -NR·-NH2, R4 representa un grupo de alquilo de C1-3 o alquenilo de C2-3´ R5 representa un grupo de acilo, R3 representa un átomo de hidrógeno o un grupo de alquilo de C1-3 o alquenilo de C2-3´ A representa un átomo de oxígeno enlazado a uno de los átomos de nitrógeno cíclicos y n significa cero o 1, y sus sales, cuyo procedimiento comprende a) hacer reaccionar un compuesto de la fórmula general (IIa) o bién (fórmula IIb) en donde Z representa un grupo nitro, amino, pirrolo, pirrolidino, piperidino, -NHR4, -N(R4)2´ -NHR5, -N(R4) (R5), -NR4COOR4, _NHCOOR4, -NHCONHR3, -NHCSNHR3 o -NR3NH2, el símbolo R6 representa un grupo de alquilo inferior o los dos símbolos R6 juntos representan un grupo de alquileno inferior, y representa un grupo partiente y R1, R2, R3, R4 y R5 tienen el significado indicado en esta reinvidicación 1, con guanidina, o b) hacer reaccionar un compuesto de la fórmula general (III) en la que X representa un átomo de cloro o de bromo o un grupo alquilmercapto, alquilsulfonilo o amino, con la salvedad de que uno de los símbolos X, por lo menos, tenga un significado distinto a un grupo amino, R1 y R2 tienen el significado expuesto en esta reivindicación 1, y Z tiene el significado antes expuesto en esta reivindicación, con amoníaco, o bien c) eliminar reductivamente el substitúyete designado con X1 en un compuesto de la fórmula general (IV) en la que X1 representa un átomo de cloro o de bromo o un grupo hidroxílico, R1, R2 tienen el significado expuesto en esta reivindicación 1 y Z1 tiene el significado antes expuesto en esta reivindicación, o bien d) diazoar un compuesto de la fórmula I, en donde Z representa un grupo amino, y haciendo reaccionar a continuación el producto con azida sódica, con una amina de la fórmula NH(R4)2 o con un sulfito alcalino, o bien e) tratar un compuesto de la fórmula I, en donde Z representa un grupo NHR4, con ácido nítrico, o bien f) convertir el grupo Z2 en un compuesto de la fórmula general (Va) (Vb) 0 bien (Vc) en donde R1 y R2 tienen el significado indicado en esta reivindicación 1, y Z2, que puede ser igual o diferente en las fórmulas Vb y Vc, representa un grupo convertible por reducción o hidrólisis en un grupo amino o un grupo -NHR4, en un grupo amino o un grupo -NHR4, o bien g) alquilar o alquenilar el grupo designado con Z3 en un compuesto de la fórmula general (Ia) en la que Z3 representa un grupo -NHR5 o -NHCOOR4 y R1, R2, R4 y R5 tienen el significado indicado en esta reivindicación 1, o bien h) reducir un compuesto de la fórmula I, en donde Z representa un grupo -N(NO)R4, con Zn/CH3COOH, o bien i) someter un compuesto de la fórmula I, en donde n significa cero, a N-oxidación y, si se desea, convertir un compuesto de la fórmula I obtenido en una salA process for the preparation of benzyl-pyrimidine derivatives of the general formula (I) in which R1 and R2 each independently represent a C1-3'alkyl-C1-3'alkoxy-C2-3alkenyl or alkenyloxy group. of C2-3´Z represents a nitro, amino, pyrrolo, pyrrolidino, piperidino, -NHR, -NHR5, -N (R4) (R5), -NH4COOR4, -NHCOOR4, -NHCONHR3, -NHCSNHR5, -N = N -N8R4) 2, -N8NO) 4 or -NR · -NH2, R4 represents a C1-3 alkyl or C2-3'alkenyl group R5 represents an acyl group, R3 represents a hydrogen atom or a group of C1-3alkyl or C2-3'alkenyl A represents an oxygen atom bonded to one of the cyclic nitrogen atoms and n denotes zero or 1, and its salts, the process of which comprises a) reacting a compound of the general formula (IIa) or (formula IIb) where Z represents a nitro, amino, pyrrolo, pyrrolidino, piperidino, -NHR4, -N (R4) 2´ -NHR5, -N (R4) (R5), -NR4COOR4, _NHCOOR4, -NHCONHR3, -NHCSNHR3 or -NR3NH2, the symbol R6 represents a lower alkyl group or the two symbols R6 together represent a lower alkylene group, and represents a part group and R1, R2, R3, R4 and R5 have the meaning indicated in this reinvication 1, with guanidine, or b ) reacting a compound of the general formula (III) in which X represents a chlorine or bromine atom or an alkyl mercapto, alkylsulfonyl or amino group, except that at least one of the symbols X has a meaning other than an amino group, R1 and R2 have the meaning set forth in this claim 1, and Z has the meaning set forth above in this claim, with ammonia, or c) reductively removing the substitute designated X1 in a compound of the formula general (IV) in which X1 represents a chlorine or bromine atom or a hydroxyl group, R1, R2 have the meaning set forth in this claim 1 and Z1 has the meaning set forth in this claim, or d) dia Use a compound of formula I, where Z represents an amino group, and then react the product with sodium azide, with an amine of formula NH (R4) 2 or with an alkaline sulphite, or e) treat a compound of the formula I, where Z represents a NHR4 group, with nitric acid, or f) converting the group Z2 into a compound of the general formula (Va) (Vb) 0 or (Vc) where R1 and R2 have the meaning indicated in this claim 1, and Z2, which may be the same or different in formulas Vb and Vc, represents a group convertible by reduction or hydrolysis into an amino group or a -NHR4 group, into an amino group or a group - NHR4, or g) alkylating or alkenylating the group designated with Z3 in a compound of the general formula (Ia) in which Z3 represents a group -NHR5 or -NHCOOR4 and R1, R2, R4 and R5 have the meaning indicated in this Claim 1, or h) reducing a compound of formula I, wherein Z represents a group -N (NO) R4, with Zn / CH3COOH, or b i i) subjecting a compound of formula I, where n is zero, to N-oxidation and, if desired, converting a compound of formula I obtained to a salt

CU34115A 1973-09-12 1974-09-11 NEW BENCILPIRIMIDINAS CU34115A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1305773A CH591456A5 (en) 1973-09-12 1973-09-12

Publications (2)

Publication Number Publication Date
CU21022L CU21022L (en) 1981-09-09
CU34115A true CU34115A (en) 1983-10-04

Family

ID=4388903

Family Applications (1)

Application Number Title Priority Date Filing Date
CU34115A CU34115A (en) 1973-09-12 1974-09-11 NEW BENCILPIRIMIDINAS

Country Status (28)

Country Link
JP (1) JPS6042238B2 (en)
AR (2) AR207764A1 (en)
AT (1) AT338797B (en)
BE (1) BE819773A (en)
BR (1) BR7407614D0 (en)
CA (1) CA1037476A (en)
CH (1) CH591456A5 (en)
CU (1) CU34115A (en)
DD (2) DD122785A5 (en)
DE (1) DE2443682C2 (en)
DK (1) DK135683B (en)
ES (7) ES429949A1 (en)
FI (1) FI58638C (en)
FR (1) FR2242984B1 (en)
GB (3) GB1484481A (en)
HK (1) HK181A (en)
HU (1) HU170427B (en)
IE (1) IE40523B1 (en)
IL (1) IL45510A (en)
LU (1) LU70878A1 (en)
NL (1) NL155827B (en)
NO (1) NO140858C (en)
PH (1) PH10643A (en)
PL (2) PL97757B1 (en)
SE (1) SE419443B (en)
SU (3) SU577987A3 (en)
YU (3) YU217874A (en)
ZA (1) ZA745317B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4515948A (en) * 1973-09-12 1985-05-07 Hoffmann-La Roche Inc. 2,4-Diamino-5-(4-amino and 4-dimethylamino-3,5-dimethoxy benzyl)pyrimidines
JPS5481278A (en) * 1977-10-18 1979-06-28 Wellcome Found Manufacture of triiseccaminomethane
CH639273A5 (en) * 1978-09-12 1983-11-15 Hoffmann La Roche DIURETIC MEANS.
DE3250132C2 (en) * 1981-11-09 1997-01-16 Mallinckrodt Veterinary Inc 2,4-Di:amino-5-benzyl-pyrimidine derivs. prepn.
CH664961A5 (en) * 1981-11-09 1988-04-15 Wellcome Found INTERMEDIATE PRODUCTS FOR THE SYNTHESIS OF SUBSTITUTED 2,4-DIAMINO-5-BENZYLPYRIMIDINES.
GB2180836A (en) * 1985-09-27 1987-04-08 William James Stephen Barker Sunscreen
JPH0431685Y2 (en) * 1987-06-01 1992-07-30
US4900859A (en) * 1987-12-03 1990-02-13 Hoffman-La Roche Inc. Process for 4-dimethylamino-3,5-dimethoxybenzaldehyde
CA1300166C (en) * 1987-12-03 1992-05-05 Alfredo Guerrato Process for the preparation of a benzoic acid ester

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1103931B (en) * 1957-02-21 1961-04-06 Wellcome Found Process for the preparation of 2,4-diamino-5-benzylpyrimidine derivatives
US3485840A (en) * 1964-11-12 1969-12-23 Hoffmann La Roche 2,4-diamino - 5 - (2',4',5'-substituted benzyl) pyrimidines,intermediates and processes

Also Published As

Publication number Publication date
BE819773A (en) 1975-03-11
IL45510A0 (en) 1974-11-29
IE40523B1 (en) 1979-06-20
DK135683C (en) 1977-11-14
DK468374A (en) 1975-05-12
SU571189A3 (en) 1977-08-30
AT338797B (en) 1977-09-12
JPS6042238B2 (en) 1985-09-20
SE7411382L (en) 1975-03-13
AR207764A1 (en) 1976-10-29
ES437012A1 (en) 1977-04-01
LU70878A1 (en) 1976-08-19
YU217874A (en) 1982-06-18
HU170427B (en) 1977-06-28
JPS5053385A (en) 1975-05-12
ZA745317B (en) 1975-11-26
YU37154B (en) 1984-08-31
DE2443682A1 (en) 1975-03-20
CA1037476A (en) 1978-08-29
NO140858B (en) 1979-08-20
YU301580A (en) 1983-04-27
FR2242984B1 (en) 1977-11-04
IL45510A (en) 1978-08-31
DD122785A5 (en) 1976-11-05
AU7263174A (en) 1976-02-26
ES437007A1 (en) 1977-04-01
ES437011A1 (en) 1977-04-01
AR211387Q (en) 1977-12-15
BR7407614D0 (en) 1975-07-08
DD116824A5 (en) 1975-12-12
FI58638C (en) 1981-03-10
ES437013A1 (en) 1977-04-01
HK181A (en) 1981-01-16
ES437008A1 (en) 1977-04-01
SE419443B (en) 1981-08-03
PL97757B1 (en) 1978-03-30
NL7411685A (en) 1975-03-14
IE40523L (en) 1975-03-12
DE2443682C2 (en) 1983-11-10
NO140858C (en) 1979-11-28
SU609465A3 (en) 1978-05-30
GB1484482A (en) 1977-09-01
PL99159B1 (en) 1978-06-30
FI256174A (en) 1975-03-13
SU577987A3 (en) 1977-10-25
ES429949A1 (en) 1976-10-01
FR2242984A1 (en) 1975-04-04
NL155827B (en) 1978-02-15
GB1484481A (en) 1977-09-01
YU301680A (en) 1983-04-27
CU21022L (en) 1981-09-09
GB1484483A (en) 1977-09-01
ES437009A1 (en) 1977-04-01
ATA735174A (en) 1977-01-15
CH591456A5 (en) 1977-09-15
FI58638B (en) 1980-11-28
DK135683B (en) 1977-06-06
YU37153B (en) 1984-08-31
PH10643A (en) 1977-07-22
NO743271L (en) 1975-04-07

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