Substituted 4-amino-2-arylcyclopenta[d]pyrimidines, their preparation, their use and pharmaceutical preparations comprising them

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Quick Facts

Patent No.: US 7,138,398
App. No.: 10/660,489
Granted: Nov 21, 2006
Kind: B2

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Abstract

The present invention relates to compounds of formula (I) wherein R 1 , R 2 and R 3 have the meanings given in the claims. Said compounds are valuable active agents in medicaments for the treatment and prophylaxis of diseases, for example cardiovascular diseases such as hypertension, angina pectoris, heart failure, thrombosis and atherosclerosis. The compounds of formula (I) are able to modulate the body's own production of cyclic guanosine monophosphate (cGMP) and are generally suitable for the treatment and prophylaxis ofisorders associated with an impaired cGMP balance. The invention also relates to methods for producing compounds of formula (I), to their use in the treatment and prophylaxis of the above diseases and in the preparation of medicaments for such diseases, and to pharmaceutical preparations containing the compounds of formula (I).

Claims (82)

1. A compound of formula I,

wherein one of R 1 and R 2 is selected from the group consisting of

(C 1 –C 8 )-alkyl, wherein the (C 1 –C 8 )-alkyl is unsubstituted or substituted by at least one identical or different substituents chosen from hydroxyl, (C 1 –C 4 )-alkoxy, (C 1 –C 4 )-alkyl-S(O) m —, unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl and unsubstituted or substituted pyridyl; and

(C 3 –C 9 )-cycloalkyl, wherein the (C 3 –C 9 )-cycloalkyl is unsubstituted or substituted by at least one identical or different substituents chosen from (C 1 –C 4 )-alkyl, hydroxyl, amino and unsubstituted or substituted benzyl, and

wherein the other one of R 1 and R 2 is hydrogen, and

wherein the radicals phenyl, naphthyl, pyridyl and benzyl contained in the radicals R 1 or R 2 are unsubstituted or substituted in the aromatic ring by at least one identical or different substituents chosen from halogen, (C 1 –C 4 )-alkyl, phenyl, CF 3 , NO 2 , OH, —O—(C 1 –C 4 )-alkyl, —O—(C 2 –C 4 )-alkyl-O—(C 1 –C 4 )-alkyl, (C 1 –C 2 )-alkylenedioxy, NH 2 , —NH—(C 1 –C 4 )-alkyl, —N((C 1 –C 4 -alkyl) 2 , —NH—CHO, —NH—CO—(C 1 –C 4 )-alkyl, —CN, —CO—NH 2 , —CO—NH—(C 1 –C 4 -alkyl, —CO—N((C 1 –C 4 )-alkyl) 2 , —CO—OH, —CO—O—(C 1 –C 4 )-alkyl, —CHO and —CO—(C 1 –C 4 )-alkyl,

wherein R 3 is aryl but cannot be unsubstituted phenyl;

wherein aryl is chosen from phenyl, naphthyl and heteroaryl, and wherein said phenyl, naphthyl, and heteroaryl is unsubstituted or substituted by at least one identical or different substituents chosen from halogen, (C 1 –C 4 )-alkyl, phenyl, CF 3 , NO 2 , OH, —O—(C 1 –C 4 )-alkyl, —O—(C 2 –C 4 )-alkyl-O—(C 1 –C 4 )-alkyl, (C 1 –C 2 )-alkylenedioxy, NH 2 , —NH—(C 1 –C 4 -alkyl, —N((C 1 –C 4 )-alkyl) 2 , —NH—CHO, —NH—CO—(C 1 –C 4 )-alkyl, —CN, —CO—NH 2 , —CO—NH—(C 1 –C 4 )-alkyl, —CO—N((C 1 –C 4 -alkyl) 2 , —CO—OH, —CO—O—(C 1 –C 4 )-alkyl, —CHO and —CO—(C 1 –C 4 )-alkyl;

wherein heteroaryl is chosen from a radical of a monocyclic 5-membered aromatic heterocycle, a radical of a monocyclic 6-membered aromatic heterocycle, a radical of a bicyclic 8-membered aromatic heterocycle, a radical of a bicyclic 9-membered aromatic heterocycle, and a radical of a bicyclic 10-membered aromatic heterocycle, each of which contain at least one identical or different ring heteroatoms chosen from N, O and S; and

m is 0, 1 or 2;