AU7656700A - Benzodiazepin derivatives, the production and use thereof - Google Patents

Description

0050/50761 Benzodiazepine derivatives, the preparation and use thereof The present invention relates to novel benzodiazepine derivatives, their preparation and the use as inhibitors of the enzyme poly(ADP-ribose) polymerase or PARP (EC 2.4.2.30) for producing drugs. Poly(ADP-ribose) polymerase (PARP) or, as it is also called, poly(ADP-ribose) synthase (PARS) is a regulatory enzyme which is found in cell nuclei (K. Ikai et al., J. Histochem. Cytochem. 1983, 31, 1261-1264). It is assumed that PARP is involved in the repair of DNA breaks (M.S. Satoh et al., Nature 1992, 356, 356-358). Damage or breaks in DNA strands activate the enzyme PARP which, when it is activated, catalyzes the transfer of ADP-ribose from NAD (S. Shaw, Adv. Radiat. Biol., 1984, 11, 1-69). During this, nicotinamide is released from NAD. Nicotinamide is converted back into NAD by other enzymes with consumption of the energy carrier ATP. Overactivation of PARP would accordingly result in nonphysiologically large consumption of ATP, and this leads in the extreme case to cell damage and cell death. It is known that free radicals such as superoxide anion, NO and hydrogen peroxide may lead to DNA damage in cells and thus activate PARP. The formation of large amounts of free radicals is observed in a number of pathophysiological states, and it is assumed that this accumulation of free radicals lead [sic] or contribute [sic] to the observed cell or organ damage. This includes of [sic], for example, ischemic states of organs as in stroke, myocardial infarct (C. Thiemermann et al., Proc. Nati. Acad. Sci. USA, 1997, 94, 679-683) or ischemia of the kidneys, but also reperfusion damage as occurs, for example, after lysis of myocardial infarct (see above: C. Thiemermann et al.). Inhibition of the enzyme PARP might accordingly be a means of at least partly preventing or moderating this damage. PARP inhibitors might thus represent a novel therapeutic principle for treating a number of diseases. The enzyme PARP influences the repair of DNA damage and might thus also play a part in the therapy of cancers, since a greater action potential on tumor tissue was observed (G. Chen et al. Cancer Chemo. Pharmacol. 1988, 22, 303) in combination with substances with cytostatic activity. Nonlimiting examples of tumors are leukemia, glioblassomas [sic], lymphomas, melanomas, and carcinomas of the breast and cervix.

0050/50761 -2 It has additionally been found that PARP inhibitors may show an immunosuppressant effect (D. Weltin et al. Int. J. Immunopharmacol. 1995, 17, 265-271). It has likewise been discovered that PARP is involved in immunological disorders or diseases in which the immune system plays an important part, such as, for example, rheumatoid arthritis and septic shock, and that PARP inhibitors may show a beneficial effect on the course of the disease (H. Kr6ger et al. Inflammation [sic] 1996, 20, 203-215; W. Ehrlich et al. Rheumatol. nt. 1995, 15, 171-172; C. Szabo et al., Proc. Nat/. Acad. Sci. USA 1998, 95, 3867-3872; S. Cuzzocrea et al. Eur. J. Pharmacol. 1998, 342, 67 76). PARP means for the purpose of this invention also isoenzymes of the PARP enzyme described above. In addition, the PARP inhibitor 3-aminobenzamide showed protective effects in a model of circulatory failure (S. Cuzzocrea et al., Br. J. Pharmacol. 1997, 121, 1065-1074). There is likewise experimental evidence that inhibitors of the enzyme PARP might be of benefit as agents for treating diabetes mellitus (V. Burkart et al. Nature Med. 1999, 5, 314-319). Benzodiazepines and benzodiazepinones and their derivatives represent a class of chemicals which have been widely used in organic synthesis. Derivatives of these compounds . additionally having a fused-on imidazo ring, that is to say imidazobenzodiazepinones, have scarcely been described, however. Aminodibenzodiazepinones were prepared in P.V. Khadikar et al. J. Heterocycl. Chem. 1998, 35, 675. Thus, simple derivatives having radicals such as chlorine or nitro on the benzo ring and a methyl group on the imidazo ring were prepared in Geneste et al., Eur. J. Chem. Chim. [sic] Ther. 1978, 13, 53. In M.J. Kukla et al., J. Med. Chem. 1991, 34, 3187, a dihydroimidazobenzodiazepinone was prepared as intermediate for active substances said to have an anti-HIV effect. The compounds of the general compound [sic] I according to this invention have not previously been described and are accordingly novel. It has additionally been found, surprisingly, that benzodiazepine derivatives having a fused-on ring are very effective inhibitors of the enzyme PARP.

0050/50761 -3 The present invention describes novel benzodiazepine derivatives of the general formulae [sic] I which are potent PARP inhibitors. The present invention relates to substituted benzodiazepine derivatives of the general formula I X i H N- A

R

1 B N in which A can be a C-C 3 chain where each carbon atom may also carry one or two of the following substituents: C-C 4 -alkyl, OH, 0-C-C 4 -alkyl, COOH, COO-C-C 4 -alkyl and phenyl or one C atom may also carry an =0 group, and X1 can be S, O and NH, and R' is hydrogen, chlorine, fluorine, bromine, iodine, branched and unbranched Cr-C6 alkyl, OH, nitro, CF 3 , CN, NR 1 R 12 , NH-CO-R 13 , O-C-C 4 -alkyl, where R" and R' 2 are, independently of one another, hydrogen or C-C 4 -alkyl, and R 3 is hydrogen,

C-C

4 -alkyl, C-C 4 -alkyl-phenyl or phenyl, and B can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by one R 4 and a maximum of 3 different or identical R 5 radicals, and one or two carbon or sulfur atoms may also carry one or two =O groups, such as, for example, keto groups, sulfones or sulfoxides, or is a radical L,-Y-Mw in which L can be a straight-chain or branched, saturated or unsaturated carbon chain of 1 to 8 C atoms, it being possible for each carbon atom to be substituted by one or two R4 radicals and a maximum of two different or 0050/50761 -4 identical R 5 radicals, and M has, independently of L, the same meaning as L, and Y is a bond, or can be S, 0 or NRa, where R 3 can be hydrogen, branched and unbranched C 1

-C

6 -alkyl, C1-C 4 -alkyl-phenyl, phenyl, and v can be 0 and 1, and w can be 0 and 1, and when Y is a bond, R 4 and R 5 are not both hydrogen, and when B is L,-Y-M., R' is not chlorine or NO 2 , and

R

4 is hydrogen and -(D)p-(E)s-(F')q -G 1

-(F

2 )r-(G 2

)-G

3 , where D can be S, NR43 and O E can be phenyl, _C--O ,

-SO

2 -, -SO 2 NH-, -NHCO-, -CONH-, NHSO 2 -, -NHCOCH 2

X

4 , and

X

4 can be S, O or NH, and

F

1 can be a straight-chain or branched saturated or unsaturated carbon chain of 1 to 8 C atoms, and

F

2 has, independently of F', the same meaning as F', G1 is a bond or can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 0050/50761 -5 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by a maximum of 3 different or identical R 5 radicals, and one or two carbon or sulfur atoms may also carry one or two =0 groups, and

G

2 is NR 41

R

42 and N No R N R7 N r_ - R9 R7 R7R 7 N N - N N 0 or a bond, and

G

3 can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by a maximum of 3 different or identical radicals R 5 , and one or two carbon or sulfur atoms may also carry one or two =0 groups, or is hydrogen, and p can be 0 and 1 and s can be 0 and 1 and q can be 0 and 1 and r can be 0 and 1 and R4 can be hydrogen, C-C 6 -alkyl, it being possible for each carbon atom also to carry up to two R 6 radicals, phenyl which may also carry a maximum of two R 6 radicals, 0050/50761 -6 and (CH 2 )t-K and R42 can be hydrogen, C-C 6 -alkyl, -CO-R 8 , C0 2

-R

8 , SO 2

NH

2 , S0 2

-R

8 , -(C=N)-R 8 [sic] and -(C=N)-NHR 8 [sic] and R43 can be hydrogen and C-C 4 -alkyl and t can be 1, 2, 3, 4 and K can be NR"R 12 , NR"-C-C 4 -alkyl-phenyl, pyrrolidine, piperidine, 1,2,5,6 tetrahydropyridine, morpholine, homopiperidine, piperazine, which may also be substituted by an alkyl radical C-C 6 -alkyl, and homopiperazine which may also be substituted by an alkyl radical Cr-C 6 -alkyl, and

R

5 can be hydrogen, chlorine, fluorine, bromine, iodine, OH, nitro, CF 3 , CN, NR 1 R,

NH-CO-R

13 , C1-C 4 -alkyl-CO-NH-R 13 , COR 8 , Co-C 4 -alkyl-O-CO-R 13 , C1-C4 alkyl-phenyl, phenyl, C02-Cl-C 4 -alkyl, and branched and unbranched

C

1

-C

6 alkyl, O-C 1

-C

4 -alkyl, S-C 1 -C4-alkyl, it being possible for each C atom of the alkyl chains to carry up to two R 6 radicals, and for the alkyl chains also to be unsaturated, and

R

6 can be hydrogen, chlorine, fluorine, bromine, iodine, branched and unbranched

C-C

6 -alkyl, OH, nitro, CF 3 , CN, NR"R1 2 , NH-CO-R1 3 , O-C-C 4 -alkyl, R 7 can be hydrogen, Cr-C 6 -alkyl, phenyl, it being possible for the ring also to be substituted by up to two R 71 radicals, and an amine NR"R' 2 or a cyclic saturated amine which has 3 to 7 members, and may also be substituted by an alkyl radical Cr-C 6 -alkyl, and homopiperazine which may also be substituted by an alkyl radical 0l-C 6 -alkyl, and where the radicals R", R 12 and R1 3 in K, R 5 , R 6 and R 7 may, independently of one another, assume the same meaning as for R', and R 7 can be OH, CriC 6 -alkyl, O-CriC 4 -alkyl, chlorine, bromine, iodine, fluorine, CF 3 , nitro, NH 2 , and

R

8 can be Cr-C 6 -alkyl, CF 3 , phenyl, Cr1C4-alkyl-phenyl, it being possible for the ring 0050/50761 -7 also to be substituted by up to two R 81 radicals, and R81can be OH, C-C 6 -alkyl, O-C 1

-C

4 -alkyl, chlorine, bromine, iodine, fluorine, CF 3 , nitro, NH 2 , and R9 can be hydrogen, C 1

-C

6 -alkyl, C 1

-C

4 -alkyl-phenyl, C0 2

-C

1

-C

4 -alkyl-phenyl, C02

C

1

-C

4 -alkyl, S0 2 -phenyl, COR 8 and phenyl, it being possible for the phenyl rings also to be substituted by up to two R 91 radicals, and R91 can be OH, C 1

-C

6 -alkyl, O-Cl-C 4 -alkyl, chlorine, bromine, iodine, fluorine, CF 3 , nitro, NH 2 , and their tautomeric forms, possible enantiomeric and diastereomeric forms, and prodrugs thereof. Preferred compounds of the formula I are those where A is a C2 chain, which may be substituted, and X' is 0, and

R

1 is hydrogen. Preferred compounds of the formula I are those as indicated above, in which B can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by one R 4 and a maximum of 3 different or identical R 5 radicals, and one or two carbon or sulfur atoms may also carry one or two =0 groups. Particularly preferred radicals for B are: B phenyl, cyclohexyl, piperidine, pyridine, pyrimidine, pyrrole, pyrazole, thiophene, furan, oxazole, naphthalene, piperazine, quinoline, pyrazine, which may also be 0050/50761 -8 substituted by one R4 or a maximum of 2 R 5 . Very particularly preferred compounds of the formula I are those where

R

4 [lacuna] hydrogen or Do, 1

-F

1 o, 1

-G

2

-G

3 with G 3 equal to hydrogen and D [lacuna] 0 and NR 4 3 , where R 4 3 is hydrogen and C 1

-C

3 -alkyl and

F

1 [lacuna] C 2

-C

4 -alkyl. Additional particularly preferred compounds of the formula I are those where B is L,-Y Mw where v is 0, and w is1,and Y is a bond, and M can be a straight-chain or branched carbon chain of 2 to 8 C atoms, which contains at least one double bond, it being possible for each carbon atom to be substituted by one or two R 4 radicals and a maximum of two different or identical

R

5 radicals, and

R

1 is hydrogen, and R 4 is Do,,-F'o, 1

-G'-G

2

-G

3 with G 3 equal to hydrogen, and D is 0 and NR 43 , where R 43 is hydrogen and C 1

-C

3 -alkyl and F' is C 2

-C

4 -alkyl. The use of compounds of the general formula I for producing medicines with a PARP inhibiting effect is likewise claimed, with R', X' and A having the same meaning as above, and it being possible for B to be hydrogen and a C 1

-C

6 alkyl chain. The compounds of the formula I can be employed as racemates, as enantiomerically 0050/50761 -9 pure compounds or as diastereomers. If enantiomerically pure compounds are required, they can be obtained, for example, by carrying out a conventional racemate resolution with the compounds of the formula I or their intermediates using a suitable optically active base or acid. Alkyl chains may in each case be branched or unbranched. Unbranched alkyl chains are preferred. The invention thus also relates to compounds which are mesomers or tautomers of compounds of the formula I. The invention further relates to the physiologically tolerated salts of the compounds I, which can be obtained by reacting compounds I with a suitable acid or base. Suitable acids and bases are listed, for example, in Fortschritte der Arzneimittelforschung, 1966, Birkhuser Verlag, volume 10, pages 224-285. These include, for example, hydrochloric acid, citric acid, tartaric acid, lactic acid, phosphoric acid, methanesulfonic acid, acetic acid, formic acid, maleic acid, fumaric acid etc., and sodium hydroxide, lithium hydroxide, potassium hydroxide and tris. Prodrugs mean compounds which are metrabolized [sic] in vivo to compounds of the general formula 1. Typical prodrugs are phosphates, carbamates of amino acids, esters and others. The benzodiazepine derivatives I according to the invention can be prepared in various ways, as outlined in synthesis schemes 1-3. The possible methods of synthesis are essentially already known or are based on analogous routes which are known.

0050/50761 - 10 Synthesis scheme 1 CHO R 1 0 B NH II

NH

2 N A H RI 0 NH N N-A B Condensation of the aldehyde 11 with diamines Ill results in the benzimidazole 1, this preferably being done in polar solvents such as ethanol or dimethylformamide and [sic] addition of acids such as acetic acid at elevated temperature, ordinarily 80-120*C. It is beneficial for the reaction to add weak oxidizing agents such as, for example, copper(ll) salts which are added, for example, as aqueous solutions. [lacuna] RI COO-Alkyl COOH X I + H B B N

H

2 N N- A IV V H III

R

1 X H I N HN N-A H B 0 As an alternative to the aldehydes il shown in scheme 1, it is also possible to employ benzoic [sic] acids such as V (see scheme 2) or benzonitriles [sic] such as VII (see 0050/50761 - 11 scheme 3) in place of the aldehyde. Reaction of these derivatives takes place in analogy to the preparation of [sic] the substituted aldehydes 11. Starting from V the condensation to 11 takes place in two stages. Firstly, the benzoic [sic] acid V is reacted with the aniline Ill in a peptide-like coupling to give the amide VI. This is carried out under conventional 5 conditions which are listed, for example, in Houben-Weyl, Methoden der Organischen Chemie, 4th Edition, E5, chapter V, and C.R. [sic] Larock, Comprehensive Organic Transformations, VCH Publisher, 1989, pages 972 et seq. The ring closure takes place [sic] to the benzimidazole then takes place at elevated temperature, for example 60 to 180 0 C, with or without solvents such as dimethylformamide, with the addition of acids D such as acetic acid or directly in acetic acid itself. [lacuna] R1 CN X 1 i H N B N N- A

H

2 N N-A VII H IIi B 5 Reaction of the diamine Ill with a nitrile VII likewise takes place under conventional conditions. This may entail the use of solvents such as dimethylformamide with the addition of acids or else the use of polyphosphoric acid at elevated temperature such as 60 to 2000C. It is, however, also possible to use the conventional methods for preparing amidines from benzonitriles as described in Houben-Weyl, Methoden der organischen Chemie, E5, pages 1304 et seq., J. Amer. Chem. Soc. 1957, 427 and J. Org. Chem. 1987, 1017. Compounds Ill are synthesized as shown in scheme 4 by reacting a substituted nitrobenzoic ester IX with a suitable diamine in a polar solvent such as dimethylformamide in the presence of a base such as potassium carbonate at 1000C to 150 0 C, preferably at 110 0 C to 1300C, in particular at about 120 0 C, followed by hydrogenation in the presence of a suitable catalyst such as 10% palladium on carbon.

0050/50761 - 12 Scheme 4 C0 2

R

2 H A N- A 1) H 2 N NH 2 I-NH N0 2 2) H 2 - Pd/C NH2 Ix Y = Halogen The invention additionally relates to the intermediates of the formula Ill X H H N-A NH

R

1 NH2 in which A is a C1C3 chain it being possible for each carbon atom also to carry one or two of the following substituents: C1-C 4 -alkyl, OH, O-C,-C 4 -alkyl, CO 2 H, C0 2 -Cl C4-alkyl and phenyl or one C atom may also carry an =0 group, and

X

1 and R' have the meanings stated in the previous claims [sic], excluding the compounds 9-amino-3-methyl-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one, 9-amino-3-methyl-3,4-dihydro-1 H-1,4-benzodiazepine-2,5-dione, 6,8-diamino-2,4-(1 H,3H)-quinazolinedione, 8-amino-2,4-(1 H,3H)-quinazolinedione and the salts thereof. Additionally a process for preparing compounds of the formula IlIl and their salts, where 2-halo-3-nitrobenzoic esters are reacted with a suitable diamine in a polar solvent in the presence of a base, and then the nitro group is hydrogenated with hydrogen in the presence of a suitable catalyst, 0050/50761 -13 and the use of compounds of the formula Ill in the synthesis of PARP inhibitors. The substituted benzodiazepine derivatives I contained in the present invention are inhibitors of the enzyme poly(ADP-ribose) polymerase or PARP (EC 2.4.2.30). The inhibitory effect of the substituted benzodiazepine derivatives I can be determined using an enzyme assay which has already been disclosed in the literature, with a K being determined as a gauge of the effect. The benzodiazepine derivatives I were measured in this way for an inhibitory effect on the enzyme poly(ADP-ribose) polymerase or PARP (EC 2.4.2.30). The substituted benzodiazepine derivatives of the general formulae [sic] I are inhibitors of poly(ADP-ribose) polymerase (PARP) or, as it is also called, poly(ADP-ribose) synthase (PARS) and can thus be used for the treatment and prophylaxis of diseases associated with an increased activity of these enzymes. The compounds of the formulae [sic] I can be employed to produce drugs for treating damage following ischemias and for the prophylaxis of expected ischemias in various organs. The present benzodiazepine derivatives of the general formula I can accordingly be used for the treatment and prophylaxis of neurodegenerative disorders occurring after ischemia, trauma (craniocerebral trauma), massive bleeding, subarachnoid hemorrages and stroke, and of neurodegenerative disorders such as multi-infarct dementia, Alzheimer's disease, Huntington's disease and of epilepsies, in particular of generalized epileptic seizures such as, for example, petit mal and tonoclonic seizures and partial epileptic seizures such as temporal lope [sic], and complex partial seizures, and further for the treatment and prophylaxis of damage to the heart after cardiac ischemias and damage to the kidneys after renal ischemias, for example of acute renal insufficiency caused by drug therapies such as, for example, associated with cyclosporin treatment, of acute kidney failure or of damage occurring during and after a kidney transplant. The compounds of the general formulae [sic] I can further be used for treatment of acute myocardial infarct and damage occurring during and after medical lysis thereof (for example with TPA, reteplase, streptokinase or mechanically with a laser or Rotablator) and of microinfarcts during and after heart valve replacement, aneurysm resections and heart transplants. The present benzodiazepine derivatives I can likewise be used for 0050/50761 -14 treatment of a [sic] revascularization of critically narrowed coronary arteries, for example in PCTA [sic] and bypass operations, and critically narrowed peripheral arteries, for example leg arteries. In addition, the benzodiazepine derivatives I can be beneficial in the treatment of tumors and metastasis thereof, and be used for treating inflammations and rheumatic disorders such as, for example, rheumatoid arthritis, and for the treatment of diabetes mellitus, for the treatment of multiorgan failure, for example associated with septic shock, and for the treatment of ARDS ("acute respiratory distress syndrome [lacuna] shock lung). The pharmaceutical preparations according to the invention contain a therapeutically effective amount of the compounds I in addition to conventional pharmaceutical excipients. For local external use, for example, in dusting powders, ointments or sprays, the active substances can be present in the usual concentrations. The active substances are ordinarily present in an amount of 0.001 to 1% by weight, preferably 0.001 to 0.1% by weight. For internal use, the preparations are administered in single doses. From 0.1 to 100 mg are given per kg of body weight in a single dose. The preparation may be administered in one or more doses each day, depending on the nature and severity of the disorders. Appropriate for the required mode of administration, the pharmaceutical preparations according to the invention comprise conventional carriers and diluents, in addition to the active substance. For local external use, it is possible to use pharmaceutical excipients such as ethanol, isopropanol, ethoxylated castor oil, ethoxylated hydrogenated castor oil, polyacrylic acid, polyethylene glycol, polyethylene glycol stearate, ethoxylated fatty alcohols, liquid paraffin, petrolatum and wool fat. Examples suitable for internal use are lactose, propylene glycol, ethanol, starch, talc and polyvinylpyrrolidone. It is also possible for antioxidants such as tocopherol and butylated hydroxyanisole, and butylated hydroxytoluene, flavor-improving additives, stabilizers, emulsifiers and lubricants to be present. The substances present in the preparation in addition to the active substance, and the substances used in the production of the pharmaceutical preparations are toxicologically acceptable and compatible with the particular active substance. The pharmaceutical 0050/50761 -15 preparations are produced in a conventional way, for example by mixing the active substance with other [sic] conventional carriers and diluents. The pharmaceutical preparations can be administered in various ways, for example 5 orally, parenterally such as intravenously by infusion, subcutaneously, intraperitoneally and topically. Thus, possible presentations are tablets, emulsions, infusion and injection solutions, pastes, ointments, gels, cremes, lotions, dusting powders and sprays. Pharmacological example: Inhibition of the enzyme poly(ADP-ribose) polymerase or PARP (EC 2.4.2.30) A 96-well microtiter plate (Flacon [sic]) is coated with histones (type Il-AS; SIGMA H7755). For this purpose, histones are dissolved in a concentration of 50 gg/ml in carbonate buffer (0.05 M NaHCO 3 ; pH 9.4). The individual wells of the microtiter plates are each incubated with 100 pl of this histone solution overnight. The histone solution is then removed, and the individual wells are incubated with 200 pl of a 1 % strength BSA (bovine serum albumine [sic]) solution in carbonate buffer at room temperature for 2 hours. This is followed by washing three times with washing buffer (0.05% Tweenl0 in PBS). For the enzyme reaction, 50 pla of the enzyme reaction solution (5 pl of reaction buffer (1 M tris-HCI pH 8.0, 100 mM MgC 2 , 10 mM DTT), 0.5 Il of PARP (c = 0.22 pg/pl), 4 i of activated DNA (SIGMA D-4522, 1 mg/ml in water), 40.5 pl of H 2 0) are preincubated in each well with 10 pl of an inhibitor solution for 10 minutes. The enzyme reaction is started by adding 40 pl of a substrate solution (4 til of reaction buffer (see above), 8 pl of NAD solution (100 pM in H 2 0), 28 pll of H 2 0). The reaction time is 20 minutes at room temperature. The reaction is stopped by washing three times with washing buffer (see above). This is followed by incubation at room temperature with a specific anti-poly(ADP-ribose) antibody for one hour. The antibodies used were a [sic] "10H" monoclonal anti-poly(ADP-ribose) antibodies (Kawamaitsu H et al. (1984) Monoclonal antibodies to poly(adenosine diphosphate ribose) recognize different structures. Biochemistry 23, 3771-3777). It is likewise possible to use polyclonal antibodies. The antibodies were employed in a 1:5000 dilution in antibody buffer (1% BSA in PBS; 0.05% Tween20). Washing three times with washing buffer is followed by incubation at room temperature with the secondary antibody for one hour. In this case the monoclonal antibody used was an anti-mouse IgG coupled to peroxidase (Boehringer Mannheim), and the rabbit antibody was an anti-rabbit IgG coupled to peroxidase (SIGMA A-6154), 0050/50761 -16 each in a 1:10,000 dilution in antibody buffer. After washing three times with washing buffer, the color reaction is carried out using 100 il/well color reagent (SIGMA, TMB mixture, T8540) at room temperature for about 15 min. The color reaction is stopped by adding 100 plu of 2 M H 2

SO

4 . Measurement is carried out immediately thereafter (450 nm versus 620 nm; "Easy Reader" EAR340AT ELISA plate reader, SLT-Labinstruments, Austria). The IC50 of an inhibitor to be measured is the concentration of inhibitor at which a half-maximum change in color concentration occurs. Examples Example 1 2-(4-(4-Methylpiperazin-1 -yl)phenyl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one a) 9-Nitro-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] 24 g (0.11 mol) of methyl 2-chloro-3-nitrobenzoate were dissolved in 250 ml of dimethylformamide. 15.4 g (0.11 mol) of potassium carbonate and 22.3 ml (0.33 mol) of ethylenediamine were successively added, and the mixture was heated at 1200C for 3 hours. The mixture was then concentrated to half the volume in vacuo, and the residue was poured into water, whereupon the product precipitated. 19.7 g of the product were obtained. b) 9-Amino-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] 1.7 g of 10% palladium/carbon were added to 19 g (91.7 mmol) of the intermediate 1a in 500 ml of ethanol, and it was then hydrogenated with hydrogen. The mixture was then filtered. The filtrate was concentrated in vacuo, and the residue was recrystallized from isopropanol/ether. The crystals which separated out were filtered off with suction. 14.4 g of the product were obtained. c) 2-(4-(4-Methylpiperazin-1 -yl)phenyl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one 2.0 g (11.3 mmol) of the intermediate 1b and 2.8 ml (45.15 m [sic]) of concentrated acetic acid were dissolved in 200 ml of methanol and, at room temperature, a solution of 3.0 g (14.7 mmol) of 4-(4-methylpiperazin-1 yl)benzaldehyde in 50 ml of methanol was added dropwise. The mixture was stirred at room temperature for 1 hour. Then 2.9 g (14.7 mmol) of copper(ll) 0050/50761 -17 acetate dissolved in 100 ml of water were added dropwise, and the mixture was refluxed for 30 minutes. During this time, in parallel a solution of 4.1 g (17 mmol) of sodium sulfide x 9 H 2 0 in 70 ml of water and a solution of 17 ml of 1 M hydrochloric acid in 50 ml of water were added. After cooling, the resulting precipitate was filtered off with suction, and the filtrate was concentrated in vacuo. The resulting residue was partitioned between aqueous sodium bicarbonate solution and ethyl acetate. The organic phase was separated off, dried and concentrated in vacuo. The residue was crystallized from ethyl acetate/ether. 2.4 g of the product were obtained. 1 H-NMR (D 6 -DMSO): 8 = 2.2 (3H), 2.5 (4H), 3.3 (4H), 3.5 (2H), 4.4 (2H), 7.1 (2H), 7.3 (1H), 7.7-7.9 (4H) and 8.4 (1H) ppm. [M' = 361] Example 2 2-(4-Nitrophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one The product was obtained in analogy to the method in 1c from 9-amino-1,2,3,4 tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] and 4-nitrobenzaldehyde. 1 H-NMR (D 6 -DMSO): S = 3.6 (2H), 4.5 (2H), 7.4 (1H) and 7.9-8.6 (7H) ppm. [M* = 3081 Example 3 2-(4-(2-N,N-Diethylaminoeth-1 -yloxy)phenyl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one The product was obtained in analogy to the method in 1c from 9-amino-1,2,3,4 tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] and 4-(2-N,N-diethylaminoeth-1-yloxy) benzaldehyde. 1 H-NMR (D 6 -DMSO): 6 = 1.0 (6H), 2.6 (4H), 2.8 (1H), 3.5 (2H), 4.1 (2H), 4.5 (2H), 7.1 (2H), 7.4 (1H), 7.7-7.9 (4H) and 8.4 (1H) ppm. [M' = 378] 0050/50761 - 18 The following further examples were prepared in analogy to the above methods: Example 4 2-(4-(2-Piperidin-1-yleth-1-yloxy)phenyl)-5,6-dihydroimidazo [4,5,1 -jk]-[1,4]benzodiazepin-7(4H)-one The product was obtained in analogy to the method in 1c from 9-amino-1,2,3,4 tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] and 4-(2-piperidin-1 -yleth-1 yloxy)benzaldehyde. 'H-NMR (D 6 -DMSO): 8 = 1.3-1.6 (6H), 2.5 (4H), 2.7 (2H), 3.6 (2H), 4.2 (2H), 4.5 (2H), 7.1 (2H), 7.4 (1H), 7.7-7.9 (4H) and 8.4 (1H) ppm. [M* = 390] Example 5 2-(4-(N-(2-N,N-Diethylaminoeth-1-yl)-N-methylamino)phenyl)-5,6 dihydroimidazo[4,5,1-jk]-[1,4]benzodiazepin-7(4H)-one The product was obtained in analogy to the method in 1c from 9-amino-1,2,3,4 tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] and 4(N-(2-N,N-diethylaminoeth-1-yl) N-methylamino)benzaldehyde. 1 H-NMR (D 6 -DMSO): 8 = 0.9 (6H), 2.5 (6H), 3.0 (3H), 3.4-3.6 (4H), 4.45 (2H), 6.8 (2H), 7.3 (1H), 7.6-7.9 (4H) and 8.45 (1H) ppm. [M' = 391] Example 6 2-(4-(4-(tert-Butyloxycarbonyl)piperazin-1-yl)phenyl)-5,6 dihydroimidazol[4,5,1-jk]-[1,4]benzodiazepin-7(4H)-one [sic] The product was obtained in analogy to the method in 1c from 9-amino-1,2,3,4 tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] and 4-(4-(tert-butyloxy carbonyl)piperazin-1-yl)benzaldehyde.

0050/50761 -19 1 H-NMR (D 6 -DMSO): 8 = 1.4 (9H), 3.3 (4H), 3.4-3.6 (6H), 4.45 (2H), 7.1 (2H), 7.3 (1H), 7.7-7.9 (4H) and 8.4 (1 H) ppm. [M* = 447] 5 Example 7 2

-(

4

-(

4 (tert-Butyloxycarbonyl)homopiperazin-1-yl)phenyl)-5,6-dihydroimidazol[4,5,1 jk]-[1,4]benzodiazepin-7(4H)-one [sic] The product was obtained in analogy to the method in 1c from 9-amino-1,2,3,4 tetrahydro-5H-1,4-benzodiazepin-5-ones [sic] and 4 -(4-(tert-butyloxy carbonyl)homopiperazin-1 -yl)benzaldehyde. 'H-NMR (D 6 -DMSO): 8 = 1.2-1.3 (9H), 1.8-1.9 (2H), 3.2-3.8 (1OH), 4.45 (2H), 6.9 (2H), 7.3 (1H), 7.7 (2H), 7.8 (2H) and 8.4 (1H) ppm. [M* =461] Example 8 2-(4-(Homopiperazin-1-yl)phenyl)-5,6-dihydroimidazol[4,5,1-jk]-[1,4]benzodiazepin 7(4H)-one [sic] The product was prepared from the product from Example 7 in analogy to Example 9. [M* = 361] Example 9 2-(4-(Piperazin-1-yl)phenyl-5,6- dihydroimidazo[4,5,1-jk]- [1,4]benzodiazepin-7(4H) one trihydrochloride 0.5 g of Example 6 was added to 30 ml of isopropanolic hydrogen chloride solution at room temperature and stirred for several hours. The mixture was then concentrated in vacuo, and the resulting residue was recrystallized from ethanol. The product was obtained as trihydrochloride. 'H-NMR (D 6 -DMSO): 8 = 3.2-3.8 (1OH), 4.5 (2H), 7.2 (2H), 7.5-8.0 (5H), 8.6 (1H) and 9.6 (broad) ppm.

0050/50761 -20 [M* = 347] Example 10 2-(4-Aminophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one x 2 HCI [M' = 280] Example 11 2 -(Piperidin-4-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one x HCI [M* = 271] Example 12 2-(1 -n-Propylpiperidin-4-yl)-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one x HCI [M' = 313] Example 13 2-(1 -Benzylpiperidin-4-yl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4] benzodiazepin-7(4H)-one x HCI [M* = 361] Example 14 2 -(Pyridin-4-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one x HCI [M' = 265] Example 15 2-(Thien-3-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4-)-one x HCI [M* = 270] Example 16 2 -(Quinolin-3-yl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4]benzodiazepin 7(4H)-one x HCI [M' = 315] 0050/50761 -21 Example 17 2-(Naphth-2-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M' = 313] Example 18 2-(1 H-Im idazol-1 -yl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4]benzo diazepin-7(4H)-one x HCI [M' = 330] Example 19 2-(4-(3-Formylpyrrol-1 -yl)phenyl)-5,6-dihydroimidazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M' = 356] Example 20 2-(4-(3-Trifluoroacetam idomethylpyrrol- 1 -yl)phenyl)-5,6-di hydroimidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one x HCI [M' = 453] Example 21 2-(4-(4-(Piperidin-1 -yl)piperidin-1 -yl)phenyl)-5,6-dihydro imidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one x 2 HCI [M' = 432] Example 22 2-(4-(3-(Piperidin-1 -ylmethyl)pyrrol-1 -yl)phenyl)-5,6-dihydro imidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one x HCI [M* = 427] Example 23 2-(4-(3-Aminomethylpyrrol-1 -yl)phenyl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one x HCI [M' = 358] Example 24 2-(3-(2-(N,N-Dimethylamino)eth-1 -yl)-4-nitrophenyl)-5,6-di- 0050/50761 -22 hydroimidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one x HCI [M* = 380] Example 25 5 5,6-Dihydroimidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one [M* = 187] Example 26 2-(Pyrazin-2-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one x HCI [M+ = 2661 Example 27 2-(2-(tert-Butyloxycarbonylaminomethyl)thiazol-4-yl)-5,6-di hydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M* = 399] Example 28 2-(2-(Aminomethyl)thiazol-4-yl)-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one x HCI [M* = 300] Example 29 2-(2-fluoro-4-(pyridin-4-yl)phenyl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M' = 358] Example 30 2-(1 -(1 -Methylpiperidin-4-yl)piperidin-4-yl)-5,6-dihydro imidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one x 2 HCI [M* = 369] Example 31 2-[(2)-1-(4-Fluorophenyl)-2-(pyridin-3-yl)ethenyl]-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M' = 384] 0050/50761 -23 Example 32 2-(1 -Benzylpiperidin-3-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M' = 360] Example 33 2-(1 -Phenylcyclopent-1 -yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M' = 331] Example 34 2-(1 -Phenylcyclohex-1 -yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M* = 345] Example 35 6-(4-(Aminomethyl)cyclohex-1 -yl)-5,6-dihydroimidazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M* = 298] Example 36 2-[(E)-2-(Pyridin-4-yl)ethenyl]-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one [M* = 290] Example 37 2-[3-Cyanophenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 288] Example 38 2-(2-Phenyl-1 H-imidazol-4-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 329] Example 39 2-[2-(4-Methylphenyl)-1,3-oxazol-4-yl]-5,6-dihydroimidazo- 0050/50761 -24 [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 344] Example 40 2-[1 -(4-Fl uorophenyl)-5-methyl- 1 H-pyrazol-4-yi]-5,6-dihydro imidazo[4,5, 1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 361] Example 41 2-fl-(4-Chlorophenyl)-1 H-pyrazol-5-yl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 3631 Example 42 2-(3-Propyl-5-isoxazolyl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 296] Example 43 2-[1-(4-Methoxyphenyl)-1 H-pyrrol-3-yl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 358] Example 44 2- (1,2,5-Trimethyl- 1H-pyrrol-3-yl)-5,6-dihydroimidazo [4,5,1 -jk][1 ,4]benzodiazepin-7(4H)-one [M*-1 = 294] Example 45 2-(4-Benzoyl-1-methyl-1 H-pyrrol-2-yl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 370] Example 46 2

-{

4 -Methyl-5-[4-(trifluoromethyl)phenyl]-3-isoxazoly}-5,6-di hydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 4121 0050/50761 -25 Example 47 2-(5-Methyl-2-furyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 267] Example 48 2-[1 -(2-Chlorophenyl)-5-(trif luoromethyl)- 1 H-pyrazol-4-yl] 5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 431] Example 49 2-(5-Methyl-1 H-imidazol-4-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 267] Example 50 2-(1 -Methyl-1 H-pyrazol-4-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 267] Example 51 2-(1 -Methyl-1 H-indol-3-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 316] Example 52 2-{6-f(4-Chlorophenyl)thio]imidazo[2,1 -b][1,3]thiazol-5-yl) 5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 4511 Example 53 2-[1-(4-Chlorophenyl)-1 H-pyrrol-3-yl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 363] Example 54 0050/50761 -26 2-[2-(4-Fluorobenzoyl)- 1 -benzof uran-5-yl]-5,6-dihydroimidazo. [4,5,1 -jk][ 1,4lbenzodiazepin-7(4H)-one [M'-1 = 4251 Example 55 2 -(2,5-Dibromo-3-thienyl)-5,6-dihydroim idazo[4,5, 1 -jk][1 ,4]benzo diazepin-7(4H)-one [M'-1 = 4271 Example 56 2-(2-Phenyl- 1,3-oxazol-4-yl)-5, 6-dihydroim idazo[4,5, 1 -jkj[1 ,4] benzodiazepin-7(4H)0-one [M+-1 = 330] Example 57 2 -(6-Methyl-2-pyridinyl)-5,6-dihydroimidazo[4,5,1 -jk][1 ,4]benzo diazepin-7(4h)-one [M'-1 = 278] Example 58 2-( 1,5- Dim ethyl-3-oxo-2-phenyl-2,3-dihydro- 1 H-pyrazol-4-yI) 5, 6-dihydroim idazo[4,5, 1 -jk][1 ,4]benzodiazepin-7(4H-)-one [M'-1 = 373] Example 59 2-[1 -(Benzylam inocarbonyl methy) pyrrol2yj-5,6-ihydr 0 im idazo [4,5,1 -jk][1 ,4]-benzodiazepin-7(4H)-one [M'-1 = 3991 Example 60 2-( 1-Phenyl- 1 H-pyrazol-4-yl)-5,6-dihydroim idazo[4,5, 1-jk][1 ,4] benzodiazepin-7(4H)-one [M+-1 = 329] Example 61 2-[1 -( 3 -Cyano- 4 -methoxypyridin-2-yl)pyrrol-2y]-..,6.rihydro imidazo[4,5, 1 -jk][1 ,4]-benzodiazepin-7(4H)-one 0050/50761 -27 [M*-1 = 384] Example 62 2-{1 -[(4-Methylphenyl)sulfonyl]-1 H-indol-3-yl}-5,6-dihydro imidazo[4,5,1 -jk][1, 4]benzodiazepin-7(4H)-one [M*-1 = 456] Example 63 2-(5-Methoxy-1 H-indol-3-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H-one [M*-1 = 332] Example 64 2-[4-Bromo-1 -(4-chlorobenzyl)-1 H-pyrazol-5-yl]-5,6-dihydro imidazo[4,5, 1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 456] Example 65 2-[1-(4-Methylphenyl)-1 H-pyrrol-2-yl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-l = 342] Example 66 2 -(5-Chloro-3-methyl- 1 -phenyl-1 H-pyrazol-4-yl)-5,6-dihydro imidazo[4,5,1 -jk][1, 4 ]benzodiazepin-7(4H)-one [M*-l = 377] Example 67 2-[4-(4-Chlorobenzoyl)-1-methyl-1 H-pyrrol-2-yl]-5,6-dihydro imidazo[4,5, 1 -jk][1, 4 ]benzodiazepin-7(4H-one [M*-1 = 404] Example 68 2 -[4-(Diethylamino)phenyl]-5,6-dihydroimidazo[4,5, 1 -jk][1,4] benzodiazepin-7(4-O.one [M*-1 = 334] 0050/50761 -28 Example 69 2-(4-Methoxy- 1 -naphthyl)-5,6-dihydroimidazo[4,5,1 -jk][1 ,4]benzo diazepin-7(4H)-one M+1= 343] Example 70 2

-(

4 -Methoxy-2,5-dimethylphenyl)..S6-dihydroim idazo[4,5, 1 -jk] [1 ,4lbenzodiazepin-7(4H).one [M+-1 = 321] Example 71 2

-[

3

-(

4 -Chlorophenoxy)phenyl]..5,6-dihydroim idazo[4,5, 1 -jk][ 1,4] benzodiazepin-7(4-I-one [M+-1 = 389] Example 72 2-[4-(Methylthio)phenyl].5, 6-dihydroim idazo[4,5, 1 -jk][1 ,4] benzodiazepin-7(4H)O-one [M+-1 = 309] Example 73 2-[4-(Acetyloxy)phenyl]-5,s6-dihydroim idazo[4,5, 1 -jk][1 ,4jbenzo diazepin-7(4H)-one [M+-1 = 321] Example 74 2

-[

2 ,5-Bis(trifuorom ethyl) phenylj5, 6-dihydroim idazo[4,5, 1-jk] [1 ,4lbenzodiazepin-7(4H)-one [M'-1 = 399] Example 75 2

-(

2

,

3 -Dimethoxyphenyl)-5,6-dihydroim idazo[4,5, 1 -jk][1 ,4]benzo diazepin-7(4H)-one [M+-1 = 323] Example 76 2-(2-Methylphenyl)-5, 6-dihydroim idazo[4,5, 1 -jk][1 ,4]benzo- 0050/50761 -29 diazepin-7(4H)-one [M*-1 = 277] Example 77 5 2-[4-(Benzyloxy)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 369] Example 78 0 2-(2-Chloro-6-fluorophenyl)-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 315] Example 79 5 2-(2-Ethoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 307] Example 80 D 2-(4-Isopropylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 305] Example 81 5 2-(6-Nitro-1,3-benzodioxol-5-yl)-5,6-dihydroimidazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 352] Example 82 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 321] Example 83 2-[4-(Dimethylamino)-1 -naphthyl]-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 3551 0050/50761 - 30 Example 84 2-[4-(Difluoromethoxy)phenyl]-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one 5 [M*-1 = 329] Example 85 2-(3,7-Dichloro-8-quinolinyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one a [M*-1 = 383] Example 86 2-[4-Chloro-3-(trifluoromethyl)phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one 5 [M*-1 = 365] Example 87 2-(1 -tert-Butyl-1 H-pyrazol-4-yl)-5,6-dihydroimidazo[4,5, 1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 309] Example 88 2-(4-Chloro-5-nitro-1 -benzothien-2-yl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 398] Example 89 2-[1-(4-Phthalimidobutan-1-yl)indol-3-yl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 503] Example 90 2-(3-Isobutyl-5-isoxazolyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 310] Example 91 0050/50761 - 31 2-[1 -(4-Methoxyphenyl)-5-(trifluoromethyl)- 1 H-pyrazol-4-yl] 5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 427] 5 Example 92 2-[2-(Dimethylam ino)- 1,3-thiazol-5-yl]-5,6-dihydroim idazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 313] ) Example 93 2-[3-(4-tert-Butylphenyl)-5-isoxazoly]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 386] Example 94 2-[1 -(4-Chlorophenyl)-3,5-dimethyl- 1 H-pyrazol-4-yl]-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 391] Example 95 2-(3-Chlorophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 297] Example 96 2-(3-Fluorophenyl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 281] Example 97 2-(3-Phthalimidophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 408] Example 98 2 -{4-[3-Chloro-5-(trifluoromethyl)-2-pyridinyl]phenyl}-5,6-di hydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 442] 0050/50761 - 32 Example 99 2-[5-(6-Methylnicotinamido)-2-chlorophenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]-benzodiazepin-7(4H)-one [M*-1 = 431] Example 100 2-(4-tert-Butoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 335] Example 101 4-(7-Oxo-4,5,6,7-tetrahydroimidazo[4,5,1 -jk][1,4]benzodiazepin 2-yl)benzonitrile [M*-1 = 288] Example 102 2-[3-(Trifluoromethoxy)phenyl]-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 347] Example 103 2 -[3-(3,5-Dichlorophenoxy)phenyl]-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 423] Example 104 2

-(

3 -Bromo-4,5-dimethoxyphenyl)-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 402] Example 105 2-[5-(Allyloxy)- 1,3-dimethyl- 1 H-pyrazol-4-yl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 337] Example 106 0050/50761 - 33 2-{2-[3-(Trifluoromethyl)anilino]phenyl}-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 422] 5 Example 107 2-[2-(2-Phenylethyl)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 367] ) Example 108 2-(3-Benzoylphenyl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 367] i Example 109 2-(4-Acetamidophenyl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 320] Example 110 2-(1,3-Benzodioxol-5-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 307] Example 111 2-(5-Aminosulfonyl-2,4-dichlorophenyl)-5,6-dihydroimidazo-[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 411] Example 112 2-(2-Benzoyloxymethylphenyl)-5,6-dihydroimidazo[4,5,1 -jk]-[1,4]benzodiazepin-7(4H) one [M*-1 = 397] Example 113 2-(2-N,N-Diethylaminocarbonyl-3,6-difluor-phenyl)-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one 0050/50761 - 34 [M+-1 = 398] Example 114 2

-(

2 -(N-2,2,2-Trifluoracetam ido)phenyI)-5,6-dihydroimidazo [4,5,1 -jkj--[1 , 4 ]benzodiazepin-7(4H)-one [M+-1 = 374] Example 115 2

-[

4 -(Trifluoromnethyl) phenyll.5,6dihydroim idazo[ 4 5

,

1 -jk[ 1, ,4] benzodiazepin-7(4" -one [M+-1 = 331] Example 116 2

-[

2 -Fl uoro-4-(trifluoromnethyl) phenyll]5,6-dihydroim idazo [4,5,1 -jk][1 , 4 Ibenzodiazepin-7(4H-..one [M+-1 = 349] Example 117 2 -(3-Chloro-4-methoxyphenyl)-5, 6-dihydroim idazo[4,5, 1 -jk][1 ,4] benzodiazepin-7(4 -one [M+-l = 327] Example 118 2 -(3-Bromo-4-fluorophenyl)-5, 6-dihydroimidazo[4,5, 1 -jk][1 ,4] benzodiazepin-7(4h)..one [M+-1 = 360] Example 119 2-(2, 5-Dim ethyl- 1 -phenyl-1 H-pyrrol-3-y)-5,6-dihydroimidazo [4,5,1 -jk][ 1, 4 ]benzodiazepin-7(4H).-one [M'-1 = 356] Example 120 2 -[4-(2,4-Dichlorobenzoyl)-1 1-methyl-i H-pyrrol-2-yl]-5,6-dihydro. imidazo[4,5, 1 -jk][1 , 4 Ibenzodiazepin-7(4HM-one [M+- 1 = 439] 0050/50761 -35 Example 121 2-[1 -(2-Fluorophenyl)-1 H-pyrrol-2-yl]-5,6..dihydroimidazo. [4,5,1 -jk][l , 4 lbenzodiazepin-7(4H).one [M+-1 = 346] Example 122 2

-(

3 ,5-Dimethoxyphenyl)..56dihydroim idazo[4,5, 1 -jk][1 ,4]benzo diazepin-7(4M--one [M+-1 = 323] Example 123 2

-(

4 -Bromo-2-fluorophenyl)..5,6-dihydroim idazo[4,5, 1-jk][1 ,4] benzodiazepin-7(4H).one [M'-1 = 360] Example 124 2 -(2-Chloro-4-fluorophenyl)-5,6-dihydroim idazo[4,5, 1 -jkj[1 ,4] benzodiazepin-7(4H)-one [M+-1 = 315] Example 125 2

-II

2 -(Benzyloxy)-3-methoxyphenyJ..5,6-dihydroim idazo[4,5, 1 -jk] [1 , 4 Ibenzodiazepin-7(4h)-one [M+-1 = 399] Example 126 2

-(

2

,

4 -Diethoxy-3-methylphenyl).5,6-dihydroim idazo[4,5, 1-jk] [1 , 4 lbenzodiazepin-7(4h)..one [M+-1 = 365] Example 127 2 -(5-Bromo-2,4-dimethoxyphenyl).5,6-dihydroimidazo[4,5, 1-k] [1, 4 ]benzodiazepin7(4" one [M+-1 = 402] Example 128 2

-[

4 -(Dimethylamino)2.methoxyphenyl] 6 dihydimidazo- 0050/50761 -36 [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 336] Example 129 5 2-[2-Chloro-5-(trifluoromethyl)phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 3661 Example 130 3 2-(3,5-Dimethylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 291] Example 131 5 2-[4-Fluoro-2-(trifluoromethyl)phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 349] Example 132 2-(5-Bromo-2-fluorophenyl)-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 360] Example 133 i 2-[4-(1 -Pyrrolidinyl)phenyl]-5,6-dihydroimidazo[4,5,1 -jk] [1,4]benzodiazepin-7(4-)-one [M*-1 = 332] Example 134 2-(4-Isopropoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 3211 Example 135 2-(3,5-Dibromophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 4211 0050/50761 -37 Example 136 2 -[4-(Benzyloxy)-2-methoxyphenyl]-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one 5 [M*-1 = 399] Example 137 2-[3-Fluoro-4-(trif I uoromethyl)phenyl]-5,6-dihydroim idazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 349] Example 138 2-[5-(4-Nitrophenyl)-2-furyl]-5,6-dihydroimidazo[4,5,1-jk] [1,4]benzodiazepin-7(4H)-one [M-1 = 374] Example 139 2-(3-Acetyloxyphenyl)-5,6-dihydroimidazo[4,5, 1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 321] Example 140 2-[2-(tert-Butylthio)phenyl]-5,6-dihydroimidazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 351] Example 141 2-[2-Fl uoro-5-(trifluoromethyl)phenyl]-5,6-dihydroim idazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 349] Example 142 2-(3,4-Dimethylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 291] Example 143 0050/50761 -38 2-[4-(Ethylthio)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H) -one [M*-1 = 323] 5 Example 144 2-{4-[(Trifluoromethyl)thio]phenyl}-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 363] Example 145 2-{2-[(4-Chlorophenyl)thio]phenyl}-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 406] i Example 146 2-(4-Chloro-3-fluorophenyl)-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 316] Example 147 2-(2-(4-Ethoxycarbony-piperidin-1 -yl)-thiazol-5-yl)-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 425] Example 148 2-{1,3-Dimethyl-5-[4-(trifluoromethyl) phenoxy]- 1 H-pyrazol-4-yl} 5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 441] Example 149 2-{1 -Methyl-3-(trifl uoromethyl)-5-[3-(trifl uoromethyl)phenoxy] 1 H-pyrazol-4-yl}-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 495] Example 150 2-[2-(4-Benzyl-1 -piperazinyl)-1,3-thiazol-5-yl]-5,6-dihydro- 0050/50761 -39 imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 444] Example 151 5 2-(5-Isopropyl-2-methylcyclohexyl)-5,6-dihydroimidazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 325] Example 152 D 2-(6,6-Dimethylbicyclo[3. 1.1 ]hept-2-yl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 309] Example 153 5 2-[5-(3-Nitrophenyl)-2-furyl]-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 374] Example 154 2-(2,5-Dimethoxytetrahydro-3-furanyl)-5,6-dihydroim idazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 317] Example 155 i 2-(2-Thienyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 269] Example 156 2-(1,3-Thiazol-2-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 270] Example 157 2-(4-Methoxycyclohexyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 299] 0050/50761 -40 Example 158 2

-(

3 ,5-Dimethoxy-2-methoxycarbonylphenyl)-5,6-dihydroimidazo- [4,5,1 -jk][1,4] benzodiazepin-7-(4H)-one [M*-1 = 381] Example 159 2-{5-[1 -Methyl-3-(trifluoromethyl)-1 H-pyrazol-5-yl]-2-thienyl} 5,6-dihydroimidazo[4,5,1 -jk][ 1,4]benzodiazepin-7(4H)-one [M*-1 = 417] Example 160 2

-(

2 -Fluoro-5-methoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 311] Example 161 2-(4-Butylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 319] Example 162 2-[2-(Trifluoromethoxy)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 347] Example 163 2-(4-Quinolinyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 314] Example 164 2-(2-Quinolinyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 314] Example 165 0050/50761 -40 Example 158 2-(3,5-Dimethoxy-2-methoxycarbonylphenyl)-5,6-dihydroimidazo- (3> [4,5,1-jk][1,4] benzo'Iiazepin-7-(4H)-one 5 [M-1 = 381] Example 159 2-{5-[1 -Methyl-3-(trifluoromethyl)-1 H-pyrazol-5-yl]-2-thienyll 5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one ) [M*-1 = 417] Example 160 2-(2-Fluoro-5-methoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one 5 [M*-1 = 311] Example 161 2-(4-Butylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 319] Example 162 2-[2-(Trifluoromethoxy)phenyl]-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 347] Example 163 2-(4-Quinolinyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 314] Example 164 2-(2-Quinolinyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 314] Example 165 0050/50761 -41 2 -(2-Chloro-3-quinolinyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 348] 5 Example 166 2-[4-(1 H-Pyrrol-1 -yl)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 328] Example 167 2-(1 H-Indol-6-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 302] Example 168 2-[4-(1,1 -Dioxo-1,2-thiazinan-2-yl)-phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 396] Example 169 2-(1,3-Benzothiazol-6-yl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 320] Example 170 2-(2,3-Dihydro-1-benzofuran-5-y)-5,6-dihydroimidazo[4,5,1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 305] Example 171 2

-(

4 -(2-(2-Furylmethylthio)acetamido)phenyl)-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 432] Example 172 2 -{[5-( 2 -Fluorobenzoyl)-2-thienyl]methyl}-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one 0050/50761 - 42 [M*-1 = 405] Example 173 2-(2-(2-Acetamidopyridin-5-ylthio)pyridin-5-yl)-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 430] Example 174 2 -(4-(N-(3,4-Dioxo-2-ethoxy-1-cyclobuten-1-yl)amino)phenyl-5,6-dihydroimidazo [4,5,1 -jk][1,4]-benzodiazepin-7(4H)-one [M+-1 = 4021 Example 175 2

-[(

2 -Quinoxalinylthio)methyl]-5,6-dihydroimidazo[4,5,1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 3611 Example 176 2-[4-(Methylamino)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 2921 Example 177 2-(5-(4-Aminosulfonylphenyl)furan-2-yl)-5,6-dihydroimidazo-[4,5,1-jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 408] Example 178 2-{2,5-Dimethyl- 1 -[4-(trifluoromethyl)phenyl]-1 H-pyrrol-3-yl} 5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 4241 Example 179 2-{1-[(2,4-Difluorophenyl)sulfonyl]-1H-pyrrol-2-yl}-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 428] 0050/50761 -43 Example 180 2-{1 -[2,6-Dichloro-4-(trifl uoromethyl)phenyl]-2,5-dimethyl 1 H-pyrrol-3-yl}-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one 5 [M*-1 = 493] Example 181 2-[5-(Phenylethynyl)-2-thienyl]-5,6-dihydroimidazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one 0 [M*-1 = 3691 Example 182 2-{5-[2-(Trifluoromethoxy)phenyl]-2-furyl}-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one 5 [M*-1 = 413] Example 183 2-(5-(2-Methoxycarbonylthiophen-3-yl)furan-2-yl)-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one a [M*-1 = 393] Example 184 2-(2,5-Dimethylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one 5 [M*-1 = 291] Example 185 2-(4-Methoxycarbonylphenyl)-5,6-dihydroimidazo[4,5,1 -jk]-[1,4]benzodiazepin-7(4H) one [M*-1 = 321] Example 186 2-(4-Methylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one 5 [M*-1 = 277] Example 187 0050/50761 -44 2-(3,4-Difluorophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 299] 5 Example 188 2-(4-Fluorophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 281] ) Example 189 2-(3-Chloro-4-fluorophenyl)-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 315] Example 190 2-(3-Bromo-4-methoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 372] Example 191 2-[4-(Trifluoromethoxy)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 374] Example 192 2-(2,5-Difluorophenyl)-5,6-dihydroimidazo[4,5,1-jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 299] Example 193 2-[4-(1,1,2,2-Tetrafluoroethoxy)phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 379] Example 194 2-[4-Fluoro-3-(trifluoromethyl)phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one 0050/50761 -45 [M*-1 = 349] Example 195 2-(4-Cyanophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo 5 diazepin-7(4H)-one [M*-1 = 288] Example 196 2-(3-Bromo-4-fluorophenyl)-5,6-dihydroimidazo[4,5,1-jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 360] Example 197 2-(4-tert-Butyl-2-methylphenyl)-5,6-dihydroim idazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 333] Example 198 2-[4-(1 -Methoxy-1 -methylethyl)phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 335] Example 199 2-(4-Bromophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin 7(4H)-one [M*-1 = 342] Example 200 2-[4-(3,4-Dichlorophenoxy)phenyl]-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 424] Example 201 2-[4-(2-Propynyloxy)phenyl]-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 317] 0050/50761 -46 Example 202 2-{4-[Chloro(difluoro)methyl]phenyl}-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 3471 5 Example 203 2-(4-Benzoylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 367] Example 204 2-(4-Ethylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 291] Example 205 2-(2-Hydroxy-5-methylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one [M*-1 = 293] Example 206 2-[4-(2,6-Difluorobenzoyl)-1-methyl-1 H-pyrrol-2-yl]-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 406] Example 207 2-[4-(3-Chlorobenzoyl)-1-methyl-1 H-pyrrol-2-yl]-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 404] Example 208 2-(2-Ethoxy-1 -naphthyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 357] Example 209 2

-[

2 -(Benzyloxy)-4,5-dimethoxyphenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one 0050/50761 -47 [M*-1 = 429] Example 210 2-{4-[(2-Chloroethyl) (ethyl)am ino]-2-methylphenyl}-5,6-dihydro imidazo[4,5,1-jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 382] Example 211 2-(4,5-Dimethoxy-2-methylphenyl)-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 337] Example 212 2-(7-Methyl-2-naphthyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 327] Example 213 2-(2,4-Dimethoxy-5-methylphenyl)-5,6-dihydroim idazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 337] Example 214 2-(3-Benzoyl-2,4-dichlorophenyl)-5,6-dihydroim idazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 436] Example 215 2-(6-Chloro-1,3-benzodioxol-5-yl)-5,6-dihydroimidazo[4,5, 1-jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 341] Example 216 2-[4-(Benzyloxy)-3,5-dimethoxyphenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 429] 0050/50761 -48 Example 217 2-(3,4-Diethoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 3511 5 Example 218 2-(2-((Pyridin-2-yl)aminocarbonyl)eth-1-yl)-5,6-dihydro im idazo[4,5,1 -jk][ 1,4]benzodiazepin-7(4H)-one [M*-1 = 335] Example 219 2-(3-((Pyridin-2-yl)aminocarbonyl)prop-1-yl)-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 349] Example 220 2-((1,3-Dimethyl-3,7-dihydro-2,6-dioxo-1 H-purin-8-yl)methyl-5,6 dihydroimidazo[4,5,1 -jk]-[1,4]benzodiazepin-7(4H)-one [M*-1 = 379] Example 221 2-(2-((Thiazol-2-yl)aminocarbonyl)eth-1-yl)-5,6-dihydroimidazo-[4,5, 1 jk][1,4]benzodiazepin-2-yl)-7(4H)-one [M*-1 = 341] Example 222 2-{2-[(1,3-Dimethyl-1 H-pyrazol-5-yl)amino]phenyl}-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 372] Example 223 2

-(

2 -(4-Chlorophenyl)methylthio-3-cyanopyridin-6-yl)-5,6-dihydro imidazo-[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 445] Example 224 2-(4-tert-Butylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo- 0050/50761 -49 diazepin-7(4H)-one [M*-1 = 319] Example 225 2-{2,5-Dimethyl-1 -[3-(trifluoromethyl)phenyl]-1 H-pyrrol-3-yl} 5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 424] Example 226 2-(5-Chloro-3-methyl-1 -phenyl-1 H-pyrazol-4-yl)-5,6-dihydro imidazo[4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 377] Example 227 2-[2,5-Bis(trifluoromethyl)phenyl]-5,6-dihydroim idazo[4,5,1 -jk] [1,4]benzodiazepin-7(4H)-one [M*-1 = 399] Example 228 2-[4-(4-tert-Butyl-1, 3 -thiazol-2-yl)phenyl]-5,6-dihydroimidazo [4,5,1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 402] Example 229 2-(3-Cyano-4-N,N-dimethylamino-2-fluorophenyl)-5,6-dihydro imidazo-[4,5, 1 -jk][1,4]benzodiazepin-7(4H)-one [M*-1 = 349] Example 230 2-(6-Methoxy-2-naphthyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 343] Example 231 2-(4-Isobutylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo diazepin-7(4H)-one [M*-1 = 319] 0050/50761 -50 Example 232 2-(3-Bromo-4-methoxyphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4] benzodiazepin-7(4H)-one 5 [M*-1 = 372] The following compounds according to the invention can be prepared in analogy to the methods described above: 1. 2-(4-(4-n-propylpiperazin-1 -yl)phenyl)-5,6-dihydroimidazo-[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 2. 2-(4-(4-isopropylpiperazin-1 -yl)phenyl)-5,6-dihydroimidazo-[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 3. 2-(4-(4-benzylpiperazin-1 -yl)phenyl)-5,6-dihydroimidazo-[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 4. 2-(4-(4-n-butylpiperazin-1 -yl)phenyl)-5,6-dihydroimidazo-[4,5,1 jk][1,4]benzodiazepin-7(4H)-one 5. 2-(4-(4-ethylpiperazin-1 -yl)phenyl)-5,6-dihydroimidazo-[4,5,1 jk][1,4]benzodiazepin-7(4H)-one 6. 2-(4-(2-N,N-dimethylaminoeth-1 -yloxy)phenyl)-5,6-dihydro-imidazo[4,5, 1 k][1,4]benzodiazepin-7(4H)-one 7. 2-(4-(2-pyrrolidin-1 -yleth-1 -yloxy)phenyl)-5,6-dihydroimid-azo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 8. 2-(4-(2-piperazin-1 -yleth-1 -yloxy)phenyl)-5,6-dihydro-imidazo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 9. 2-(4-(2-(4-methylpiperazin-1 -yl)eth-1 -yloxy)phenyl)-5,6-dihydroimidazo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 10. 2-(4-(2-(4-propylpiperazin-1 -yl)eth-1 -yloxy)phenyl)-5,6-dihydroimidazo[4,5, 1- 0050/50761 -51 jk][1 ,4lbenzodiazepin-7(4H)-one 11. 2-(4-(2-(4-ethylpiperazin-i -yI)eth-1 -yloxy)phenyl)-5,6-dihydroimidazo[45,1 j k][ 1,4]benzodiazepin-7(4H) -one 12. 2 -(4-(2-(4-benzylpiperazin- 1 -yI)eth- 1 -yloxy)phenyl)-5,6-dihydroim idazo[4,5, 1 jk][1 ,4]benzodiazepin-7(4H)-one 13. 2-(4-(2-(4-acetam idopiperazin- 1 -yI)eth-1 -yloxy)phenyl)-5, 6-dihydroim idazo[4,5, 1 jk][ 1,4]benzodiazepin-7(4H)-one 14. 2-(4-(2-(4-benzam idopiperazin- 1 -yI)eth- 1 -yloxy)phenyl)-5,6-dihydroim idazo[4,5, 1 jk][1 ,4]benzodiazepin-7(4H)-one 15. 2 -(4-(4-methylhomopiperazin- 1 -yI)phenyl)-5,6-dihydroim idazo-[4,5, 1 jk][1 ,4lbenzodiazepin-7(4H)-one 16. 2-(4-(4-benzylhomopiperazin- 1 -yI)phenyl)-5, 6-dihydroim idazo-[4,5, 1 jk][1 ,4]benzodiazepin-7(4H)-one 17. 2-(4-(4-n-butylhomopiperazin-i -yI)phenyl)-5, 6-dihydro-im idazo[4,5, 1 jk][1 ,4lbenzodiazepin-7(4H)-one 18. 2-(4-(4-ethylhomopiperazin- 1 -yI)phenyl)-5,6-dihydroim idazo-[4,5, 1 jk][1 ,4]benzodiazepin-7(4H)-one 19. 2-(4-methoxyphenyI)-,6-dihydroim idazo[4,5, 1 -jkj[ 1,4] benzo-diazepin-7(4H) -one 20. 2-(4-chlorophenyl)-5,6-dihydroim idazo[4,5, 1 -jkj[1 ,4lbenzo-diazepin-7(4H)-one 21. 2-(4-am inophenyl)-5,6-dihydroim idazo[4,5, 1 -jkj[1 ,4]benzo-diazepin-7(4H)-one 22. 2

-(

4 -isopropylphenyl)-5,6-dihydroimidazo[4,5,1 -jk] 1 ,4]-benzodiazepin-7(4H)-one 23. 2-(3-chlorophenyl)-5,6-dihydroim idazo[4,5, 1 -jk][1 ,4]benzo-diazepin-7(4H)-one 24. 2-(3-methylphenyl)-5,6-dihydroim idazo[4,5, 1 -jk][1 ,4]benzo-diazepin-7(4H)-one 0050/50761 -52 25. 2-(3-phenylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo-diazepin-7(4H)-one 26. 2-(3-isopropylphenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]-benzodiazepin-7(4H)-one 27. 2-(3-fluorophenyl)-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo-diazepin-7(4H)-one 28. 2-piperidin-4-yl-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo-diazepin-7(4H)-one 29. 2-(1 -ethylpiperidin-4-yl)-5,6-dihydroim idazo[4,5,1 -jk]-[1,4]benzodiazepin-7(4H) one 30. 2-(1 -n-propylpiperidin-4-yl)-5,6-dihydroimidazo[4,5,1 -jk]-[1,4]benzodiazepin 7(4H)-one 31. 2-(1 -isopropylpiperidin-4-yI)-5,6-dihydroimidazo[4,5,1 -jk]-[1,4]benzodiazepin 7(4H)-one 32. 2-pyridin-4-yI-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodi-azepin-7(4H)-one 33. 2-pyridin-2-yi-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodi-azepin-7(4H)-one 34. 2-thien-2-yl-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo-diazepin-7(4H)-one 35. 2-indol-5-yl-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodi-azepin-7(4H)-one 36. 2-indol-2-yI-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodi-azepin-7(4H)-one 37. 2-quinolin-3-yI-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo-diazepin-7(4H)-one 38. 2-isoquinolin-1 -yl-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo-diazepin-7(4H)-one 39. 2-quinoxalin-2-yl-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzo-diazepin-7(4H)-one 40. 2-naphth-2-yl-5,6-dihydroimidazo[4,5,1 -jk][1,4]benzodi-azepin-7(4H)-one 41. 2-(2-(N,N-dimethylamino)eth-1 -ylamino)phenyl)-5,6-dihydro-imidazo[4,5,1

-

0050/50761 - 53 k][1,4]benzodiazepin-7(4H)-one 42. 2-(2-(N,N-diethylamino)eth-1 -ylamino)phenyl)-5,6-dihydro-imidazo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 5 43. 2-(2-piperidin-1 -yleth-1 -ylamino)phenyl)-5,6-dihydroimid-azo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 44. 2-(2-pyrrolidin-1 -yleth-1 -ylamino)phenyl)-5,6-dihydroimid-azo[4,5, 1 D jk][ 1,4]benzodiazepin-7(4H)-one 45. 2-(3-(N, N-dimethylamino)prop-1 -ylamino)phenyl)-5,6-dihydro-imidazo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 5 46. 2-(3-(N, N-diethylam ino)prop- 1 -ylamino)phenyl)-5,6-dihydro-imidazo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 47. 2-(3-piperidin-1 -ylprop-1 -ylamino)phenyl)-5,6-dihydroimid-azo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 48. 2-(3-pyrrolidin-1-ylprop-1 -ylamino)phenyl)-5,6-dihydro-imidazo[4,5, 1 jk][1,4]benzodiazepin-7(4H)-one 49. 2-cyclohexyl-5,6-dihydroimidazo[4,5,1 -jkj[1,4]benzodi-azepin-7(4H)-one 50. 2-(cis-4-aminocyclohex-1 -yl)-5,6-dihydroimidazo[4,5,1 -jk]-[1,4]benzodiazepin 7(4H)-one 51. 2-(4-methoxycyclohex-1 -yl)-5,6-dihydroimidazo[4,5,1 -jkj-[1,4]benzodiazepin 7(4H)-one 52. 2-phenyl-5,6-dihydroimidazo[5,4,1 -jk][1,4]benzodiazepin-7(4H)-one 53. 2-(3-aminophenyl)-5,6-dihydroimidazo[5,4,1 -jk][1,4]benzo-diazepin-7(4H)-one 54. 2-(4-NN-dimethylaminomethylphenyl)-5,6-dihydroimidazo-[5,4, 1 jk][1,4]benzodiazepin-7(4H)-one 0050/50761 -54 55. 2-(4-(2-NN-dimethylam inoeth-1 -yI)phenyl)-5,6-dihydro-imidazo[54,1 jk][1 ,4]benzodiazepin-7(4H)-one 5 56. 2 -(4-hydroxyphenyl)-5,6-dihydroim idazo[5,4, 1 -jkj[1 ,4]benzo-diazepin-7(4h)-one 57. 2-(4-pyrrolidinemethylphenyl)-5,6-dihydroim idazo[5,4, 1 -jk]-[1 ,4lbenzodiazepin 7(4H)-one 58. 2 -(2-methylthiophenyl)-5,6-dihydroim idazo[5,4, 1 -jk][ 1,4I-benzodiazepin-7(4)-. one 59. 2 -(4-carboxyphenyl)-5,6-dihydroim idazo[5,4, 1 -jk][1 ,4]benzo-diazepin-7(4H)-one 60. 2

-(

3 ,5-bis(trifluoromethy)pheny)5,6-dihydroim idazo-[5,4, 1 jkj[1 ,4lbenzodiazepin-7(4H)-one 61. 2-(4-tert-butylphenyl)-5, 6-dihydroimidazo[5,4, 1 -jk][ 1,4]-benzodiazepin-7(4M -one 62. 2

-(

3 -(morpholin-4-ylmethyl)phenyl).5,6..dihydroim idazo-j5,4, 1 -jk][1 ,4]benzo diazepin-7(4H)-one

Claims (19)

1. A compound of the formula I X1 H N- A N R1 N B in which A can be a 0,-C 3 chain where each carbon atom may also carry one or two of the following substituents: C-C 4 -alkyl, OH, O-CI-C 4 -alkyl, COOH, COO-C-C 4 -alkyl and phenyl or one C atom may also carry an =0 group, and X1 can be S, 0 and NH, and R' is hydrogen, chlorine, fluorine, bromine, iodine, branched and unbranched Cl-C 6 -alkyl, OH, nitro, CF 3 , CN, NR"R 12 , NH-CO-R 13 , O-C-C 4 -alkyl, where R" and R 12 are, independently of one another, hydrogen or C-C 4 alkyl, and R 13 is hydrogen, C-C 4 -alkyl, C-C4-alkyl-phenyl or phenyl, and B can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by one R 4 and a maximum of 3 different or identical R 5 radicals, and one or two carbon or sulfur atoms may also carry one or two =0 groups, or is a radical Lv-Y-M. in which L can be a straight-chain or branched, saturated or unsaturated carbon chain of 1 to 8 C atoms, it being possible for each carbon atom to be substituted by one or two R 4 radicals and a maximum of two different or identical R 5 radicals, and 0050/50761 -56 M has, independently of L, the same meaning as L, and Y is a bond, or can be S, 0 or NR , where R 3 can be hydrogen, branched and unbranched C1-C 6 -alkyl, C1-C 4 -alkyl-phenyl, phenyl, and v can be 0 and 1, and w can be 0 and 1, and when Y is a bond, R 4 and R 5 are not both hydrogen, and when B is Lv-Y-M,, R 1 is not chlorine or NO 2 , and R 4 is hydrogen and -(D)p-(E)-(F')q -G'-(F 2 )r-(G 2 )-G 3 , where D can be S, NR43 and O E can be phenyl, -SO 2 -, -SO 2 NH-, -NHCO-, -CONH-, NHSO 2 -, -NHCOCH 2 X 4 , and x4 can be S, 0 or NH, and F1 can be a straight-chain or branched saturated or unsaturated carbon chain of 1 to 8 C atoms, and F 2 has, independently of F', the same meaning as F', G1 is a bond or can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated 0050/50761 -57 mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by a maximum of 3 different or identical R 5 radicals, and one or two carbon or sulfur atoms may also carry one or two =0 groups, and G 2 is NR 4 1 R 4 2 and R7 R7 R7 R N R7 N N N N- R 9 R 7 R7 R7 R N N N N 0 or a bond, and G can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by a maximum of 3 different or identical radicals R 5 , and one or two carbon or sulfur atoms may also carry one or two =0 groups, or is hydrogen, and p can be0and1and s can be 0 and 1 and q can be 0 and 1 and r canbe0and1and R 4 can be hydrogen, C 1 -C 6 -alkyl, it being possible for each carbon atom also 0050/50761 -58 to carry up to two R radicals, phenyl which may also carry a maximum of two R 6 radicals, and (CH 2 )-K and R 42 can be hydrogen, CI-C 6 -alkyl, -CO-R 8 , C0 2 -R , SO 2 NH 2 , S0 2 -Ra, -(C=N)-R 8 [sic] and -(C=N)-NHR 8 [sic] and R 43 can be hydrogen and C-C 4 -alkyl and t can be 1, 2, 3, 4 and K can be NR"R' 2 , NR"-C-C 4 -alkyl-phenyl, pyrrolidine, piperidine, 1,2,5,6 tetrahydropyridine, morpholine, homopiperidine, piperazine, which may also be substituted by an alkyl radical C-C 6 -alkyl, and homopiperazine which may also be substituted by an alkyl radical C-C 6 -alkyl, and R 5 can be hydrogen, chlorine, fluorine, bromine, iodine, OH, nitro, CF 3 , CN, NR"R 12 , NH-CO-R1 3 , Cr-C 4 -alkyl-CO-NH-R 13 , COR 8 , Co-C4 alkyl-O-CO-R13, C1-C4-alkyl-phenyl, phenyl, CO2-Cl-C 4 -alkyl, and branched and unbranched C1-C 6 -alkyl, O-C 1 -C 4 -alkyl, S-Ci-C 4

7-alkyl, it being possible for each C atom of the alkyl chains to carry up to two R 6 radicals, and for the alkyl chains also to be unsaturated, and, R can be hydrogen, chlorine, fluorine, bromine, iodine, branched and unbranched C-C 6 -alkyl, OH, nitro, CF 3 , CN, NR'R 12 , NH-CO-R 13 , 0-Cr C 4 -alkyl, R can be hydrogen, C-C 6 -alkyl, phenyl, it being possible for the ring also to be substituted by up to two R ' radicals, and an amine NR"R1 2 or a cyclic saturated amine which has 3 to 7 members and may also be substituted by an alkyl radical CI-C 6 -alkyl, and homopiperazine which may also be substituted by an alkyl radical C-C6-alkyl, and where the radicals R", R 12 and R' 3 in K, R 5 , R 6 and R 7 may, independently of one another, assume the same meaning as for R', and R 71can be OH, C-C 6 -alkyl, O-C-C 4 -alkyl, chlorine, bromine, iodine, fluorine, CF 3 , nitro, NH 2 , and 0050/50761 - 59 R 8 can be C-C 6 -alkyl, CF 3 , phenyl, C-C 4 -alkyl-phenyl, it being possible for the ring also to be substituted by up to two R 8 1 radicals, and 5 R81 can be OH, C-C 6 -alkyl, O-C-C 4 -alkyl, chlorine, bromine, iodine, fluorine, CF 3 , nitro, NH 2 , and R9 can be hydrogen, Cr C 6 -alkyl, C-C 4 -alkyl-phenyl, C0 2 -Cr C4-alkyl-phenyl, C0 2 -C-C 4 -alkyl, S0 2 -phenyl, COR 8 and phenyl, it being possible for the ) phenyl rings also to be substituted by up to two R 91 radicals, and R 9 1 can be OH, C-C 6 -alkyl, O-C-C 4 -alkyl, chlorine, bromine, iodine, fluorine, CF 3 , nitro, NH 2 , and its tautomeric forms, possible enantiomeric and diastereomeric forms, and prodrugs thereof. 2. A compound of the formula I as claimed in claim 1, where A is a C2 chain, which may be substituted, and X 1 is 0, and R' is hydrogen. 3. A compound of the formula I as claimed in either of claims 1 or 2, in which B can be an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 15 carbon atoms, an unsaturated, saturated or partially unsaturated mono-, bi- or tricyclic ring with a maximum of 14 carbon atoms and 0 to 5 nitrogen atoms, 0 to 2 oxygen atoms or 0 to 2 sulfur atoms, each of which may also be substituted by a maximum of 3 different or identical R9 radicals, and one or two carbon or sulfur atoms may also carry one or two =0 groups. 4. A compound of the formula I as claimed in claim 3, where 0050/50761 - 60 B [lacuna] phenyl, cyclohexyl, piperidine, pyridine, pyrimidine, pyrrole, pyrazole, thiophene, furan, oxazole, naphthalene, piperazine, quinoline, pyrazine, each of which may also be substituted by one R4 or a maximum of 2 R 5 . 5. A compound of the formula I as claimed in claim 4, where R 4 is hydrogen or Do,1-F 1 o,-G 2 -G 3 with G 3 equal to hydrogen, and D [lacuna] 0 and NR 43 , where R 43 is hydrogen and C-C 3 -alkyl and F' [lacuna] C 2 -C 4 -alkyl. 6. A compound of the formula I as claimed in either of claims 1 or 2, in which B is Lv-Y-M., where v is 0, and w is 1, and Y is a bond, and M can be a straight-chain or branched carbon chain of 2 to 8 C atoms which contains at least one double bond, it being possible for each carbon atom to be substituted by one or two R 4 radicals and a maximum of two different or identical R 5 radicals, and R' is hydrogen, and R 4 is Do, 1 -F'o, 1 -G'-G 2 -G 3 , with G 3 equal to hydrogen, and D is 0 and NR 43 , where R43 is hydrogen and C1-C 3 -alkyl and F 1 is C2-C 4 -alkyl. 7. A drug comprising one or more compounds of the formula I as claimed in any of claims 1 to 6 in addition to conventional carriers and excipients. 0050/50761 - 61 8. The use of compounds of the formula I as claimed in any of claims 1 to 6 or of the formula I where R 1 , X 1 and A have the meaning as above, and B can be hydrogen and a C-C 6 -alkyl chain, for producing drugs with a PARP-inhibiting effect.

9. The use of compounds of the formula I as claimed in claim 8 for producing drugs for treating neurodegenerative disorders and neuronal damage.

10. The use as claimed in claim 8 for treating neurodegenerative disorders and neuronal damage caused by ischemia, trauma or massive bleeding.

11. The use as claimed in claim 8 for treating stroke and craniocerebral trauma.

12. The use as claimed in claim 8 for treating Alzheimer's disease Parkinson's disease and Huntington's disease.

13. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment or prophylaxis of damage due to ischemias.

14. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of epilepsies, in particular of generalized epileptic seizures, such as, for example, petit mal and tonoclonic seizures and partial epileptic seizures, such as temporal lope [sic], and complex partial seizures.

15. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of damage to the kidneys after renal ischemia, damage caused by drug therapy such as, for example, during cyclosporie [sic] therapy, and for treatment during and after kidney transplants.

16. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of damage to the heart following cardiac ischemia.

17. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of microinfarcts such as, for example, during and after heart valve replacement, aneurysm resections and heart transplants. 0050/50761 - 62 18. The use of compounds of the formula I as claimed in claim 8 for producing drugs for treatment in cases of revasculariation [sic] of critical [sic] narrowed coronary arteries such as, for example, in PTCA and bypass operations or of critically narrowed peripheral arteries, especially leg arteries.

19. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of acute myocardial infarct and of damage during and after medical or mechanical lysis thereof.

20. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of tumors and metastasis thereof.

21. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of sepsis of multiorgan failure such as, for example, during septic shock and of acute respiratory distress synchrome [sic].

22. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of immunological disorders such as inflammations and rheumatic disorders such as, for example, rheumatoid arthritis.

23. The use of compounds of the formula I as claimed in claim 8 for producing drugs for the treatment of diabetes mellitus.

24. A compound of the formula Ill X H N- A NH NH 2 in which A is a C 1 -C 3 chain it being possible for each carbon atom also to carry one or two of the following substituents: C1-C 4 -alkyl, OH, O-C1-C 4 -alkyl, CO 2 H, C0 2 -Cl-0 4 -alkyl and phenyl or one C atom may also carry an =0 group, and 0050/50761 -63 X' and R 1 have the meanings stated in the previous claims, excluding the compounds 5 9-amino-3-methyl-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin 5-one, 9-amino-3-methyl-3,4-dihydro-1 H-1,4-benzodiazepine-2,5-dione, 6,8-diamino-2,4-(1 H,3H)-quinazolinedione, 8-amino-2,4-(1 H,3H)-quinazolinedione, and the salts thereof.

25. A process for preparing compounds of the formula IlIl and salts thereof, wherein 2-halo-3-nitrobenzoic esters are reacted with a suitable diamine in a polar solvent in the presence of a base, and then the nitro group is hydrogenated with hydrogen in the presence of a suitable catalyst.

26. The use of compounds of the formula Ill in the synthesis of PARP inhibitors.