N-`4-(2-IMINO-PYRROLIDIN-1-YL)PHENYL

Compounds of the formula I where D is absent or denotes -CH=N-CH=CH-, -NH-N=CH-, -O-N=CH- or -CH2-CH2-CH2-CH2-, and where, if D is present, a monosubstitution by NH2 may additionally occur on D,R1 denotes H or CH2NH2,W denotes -OC(R2a)2- or -NR2C(R2a)2-,R2a denotes H, A' or Ar',A' denotes alkyl having 1, 2, 3, 4, 5 or 6 C atoms and where 1-7 H atoms may be replaced by F,Ar' denotes phenyl or benzyl, each of which is unsubstituted or mono- or disubstituted by Hal,Y denotes phenylene which is unsubstituted or mono- or disubstituted by A, Cl or F,T denotes piperidin-1-yl, pyrrolidin-1-yl, 1H-pyridin-1-yl, morpholin-4-yl, piperazin-1-yl, 1,3-oxazolidin-3-yl, 2H-pyridazin-2-yl, azepan-1-yl, 2-azabicyclo[2.2.2]octan-2-yl, each of which is monosubstituted by =NR2b, =S or =NOR2b,R2b denotes H, -CH2CH2NA'2, OH or OA",A" denotes methyl, ethyl, propyl, isopropyl or butyl, and pharmaceutically usable salts, solvates and stereoisomers thereof, including mixtures thereof in all ratios.

Compounds according to Claim 1, selected from the group 2-(3-aminomethylphenylamino)-N-[3-chloro-4-(2-hydroxy-iminopyrrolidin-1-yl)phenyl]-2-phenylacetamide;2-(3-aminomethylphenylamino)-N-(3-chloro-4-(2-iminopyrroli-din-1-yl)phenyl]-2-phenylacetamide;2-(1-aminoisoquinolin-7-yloxy)-N-[4-(2-methoxyiminopiperi-din-1-yl)phenyl]-4-methylvaleramide;2-(1-aminoisoquinolin-7-yloxy)-N-[4-(2-iminopiperidin-1 -yl)-phenyl]-4-methylvaleramide;2-(3-aminomethylphenylamino)-N-[3-methyl-4-(2-hydroxy-iminopiperidin-1-yl)phenyl]-2-(2-fluorophenyl)acetamide;2-(3-aminomethylphenylamino)-N-[3-methyl-4-(2-iminopiperi-din-1-yl)phenyl]-2-(2-fluorophenyl)acetamide;2-(3-aminomethylphenylamino)-N-[3-chloro-4-(2-hydroxy-iminopyrrolidin-1-yl)phenyl]-2-(2-fluorophenyl)acetamide;2-(3-aminomethylphenylamino)-N-[3-chloro-4-(2-iminopyrroli-din-1-yl)phenyl]-2-(2-fluorophenyl)acetamide;2-(1-aminoisoquinolin-7-yloxy)-N-[3-methyl-4-(2-iminopiperi-din-1-yl)phenyl]-4-methylvaleramide;2-(3-aminomethylphenylamino)-N-[3-trifluoromethyl-4-(2-aza-bicyclo[2.2.2]octan-3-imino-2-yl)phenyl]-2-(2-fluorophenyl)acetamide;2-(3-aminomethylphenylamino)-N-[3-trifluoromethyl-4-(2-aza-bicyclo[2.2.2]octan-3-hydroxyimino-2-yl)phenyl]-2-(2-fluorophenyl)-acetamide;2-( 1-aminoisoquinolin-7-yloxy)-N-[3-methyl-4-(2-methoxy-iminopiperidin-1-yl)phenyl]-4-methylvaleramide;2-(3-aminomethylphenylamino)-N-[3-fluoro-4-(2-iminopyrroli-din-1-yl)phenyl]-2-(2-chlorophenyl)acetamide;2-(3-aminomethylphenylamino)-N-[3-methyl-4-(2-iminopyrrolidin-1-yl)phenyl]-2-(2-fluorophenyl)acetamide;2-(3-aminomethylphenylamino)-N-[3-chloro-4-(2-iminopyrrolidin-1-yl)phenyl]-2-(2-chlorophenyl)acetamide;2-(3-aminobenzo[d]isoxazol-5-ylamino)-N-[3-chloro-4-(2-iminopyrrolidin-1-yl)phenyl]-2-phenylacetamide;2-(1-aminoisoquinolin-7-yloxy)-N-[4-(2-iminopyrrolidin-1-yl)-phenyl]-4-methylvaleramide;2-(1-aminoisoquinolin-7-yloxy)-N-[4-(2-methoxyiminopyrrolidin-1-yl)phenyl]-4-methylvaleramide;2-(3-aminomethylphenylamino)-N-[3-methyl-4-(2-(2-dimethyl-aminoethylimino)pyrrolidin-1-yl)phenyl]-2-(2-chloro)phenylacet-amide;2-(5-amino-5,6,7,8-tetrahydronaphthalen-2-yloxy)-N-[4-(3-imino-2-azabicyclo[2.2.2]oct-2-yl)-3-methylphenyl]-2-phenylacet-amide;2-(5-amino-5,6,7,8-tetrahydronaphthalen-2-yloxy)-2-(2-fluorophenyl)-N-[4-(3-imino-2-azabicyclo[2.2.2]oct-2-yl)-3-methylphenyl]-acetamide; and pharmaceutically usable salts, solvates and stereoisomers thereof, including mixtures thereof in all ratios.

Process for the preparation of compounds of the formula I according to Claims 1-2 and pharmaceutically usable salts, solvates and stereoisomers thereof, characterised in thata) for the preparation of a compound of the formula I in which W denotes -OC(R2a)2- or -NR2aC(R2a)2-, a compound of the formula II in which Z denotes OH or NHR2a and R1, R2a and D have the meanings indicated in Claim 1, with the proviso that any further OH and/or amino group present is protected, is reacted with a compound of the formula III         L-C(R2a)2-CONH-Y-T     III in which L denotes Cl, Br or I and R2a, Y and T have the meanings indicated in Claim 1, and, where appropriate, a protecting group is subsequently removed,b) for the preparation of a compound of the formula I, a compound of the formula IV in which L denotes Cl, Br, I or a free or reactively functionally modified OH groupand R1, D and W have the meanings indicated in Claim 1, with the proviso that any further OH and/or amino group present is protected, is reacted with a compound of the formula V         Z'-Y-T     V in which Z' denotes NH2 and Y and T have the meanings indicated in Claim 1, and, where appropriate, a protecting group is subsequently removed,c) and/or in that a radical T and/or R1 in a compound of the formula I is converted into another radical T and/or R1 by, for example, i) converting a sulfanyl compound into an imino compound,ii) removing an amino-protecting group, and/or a base or acid of the formula I is converted into one of its salts.

Compounds of the formula I according to one or more of Claims 1 to 2 as inhibitors of coagulation factor Xa.

Compounds of the formula I according to one or more of Claims 1 to 2 as inhibitors of coagulation factor VIIa.

Medicaments comprising at least one compound of the formula I according to one or more of Claims 1 to 2 and/or pharmaceutically usable salts, solvates and stereoisomers thereof, including mixtures thereof in all ratios, and optionally excipients and/or adjuvants.

Medicaments comprising at least one compound of the formula I according to one or more of Claims 1 to 2 and/or pharmaceutically usable salts, solvates and stereoisomers thereof, including mixtures thereof in all ratios, and at least one further medicament active ingredient.

Use of compounds according to one or more of Claims 1 to 2 and/or physiologically acceptable salts and solvates thereof for the preparation of a medicament for the treatment of thromboses, myocardial infarction, arteriosclerosis, inflammation, apoplexy, angina pectoris, restenosis after angioplasty, claudicatio intermittens, migraine, tumours, tumour diseases and/or tumour metastases.

Set (kit) consisting of separate packs of (a) an effective amount of a compound of the formula I according to one or more of Claims 1 to 2 and/or pharmaceutically usable salts, solvates and stereoisomers thereof, including mixtures thereof in all ratios, and(b) an effective amount of a further medicament active ingredient.

Use of compounds of the formula I according to one or more of Claims 1 to 2 and/or pharmaceutically usable salts, solvates and stereoisomers thereof, including mixtures thereof in all ratios, for the preparation of a medicament for the treatment of thromboses, myocardial infarction, arteriosclerosis, inflammation, apoplexy, angina pectoris, restenosis after angioplasty, claudicatio intermittens, migraine, tumours, tumour diseases and/or tumour metastases, in combination with at least one further medicament active ingredient.

Intermediate compounds of the formula VI in which R denotes H, F, Cl or A',A' denotes alkyl having 1-6 C atoms, where 1-7 H atoms may be replaced by F,n denotes 3, 4 or 5, and salts thereof.