Indole derivatives useful as endothelin receptor antagonists

C - Chemistry – Metallurgy – 07 – D

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C07D 405/06 (2006.01) A61K 31/40 (2006.01) A61K 31/41 (2006.01) A61K 31/435 (2006.01) A61K 31/495 (2006.01) A61K 31/535 (2006.01) C07D 209/18 (2006.01) C07D 405/14 (2006.01) C07D 409/14 (2006.01) C07D 413/14 (2006.01)

Patent

CA 2253876

Compounds of formula (I), and their pharmaceutically acceptable derivatives, wherein R1 and R2 are optional substituents and independently represent C1-6 alkyl, C2-6 alkenyl [optionally substituted by CO2H or CO2(C1-6 alkyl)], C2-6 alkynyl, halogen, C1-3 perfluoroalkyl, (CH2)mAr1, (CH2)mHet1, (CH2)mCONR7R8, (CH2)mCO2R8, O(CH2)qCO2R8, (CH2)mCOR8, (CH2)mOR8, O(CH2)pOR8, (CH2)mNR7R8, CO2(CH2)qNR7R8, (CH2)mCN, S(O)nR8, SO2NR7R8, CONH(CH2)mAr1 or CONH(CH2)mHet1; R3 represents H, C1-6 alkyl, (CH2)pNR9R10, SO2R10, SO2NR9R10, (CH2)mCOR10, C2- 6 alkenyl, C2-6 alkynyl, (CH2)mCONR9R10, (CH2)mCO2R10, (CH2)pCN, (CH2)pR10 or (CH2)pOR10; R4 represents H or C1-6 alkyl; R5 represents H or OH; R6 represents phenyl optionally fused to a heterocyclic ring, the group as a whole being optionally substituted; R7-10 are fully defined herein and may independently represent Ar2 or Het2; Z represents CO2H, CONH(tetrazol-5-yl), CONHSO2O(C1-4 alkyl), CO2Ar3, CO2(C1-6 alkyl), tetrazol-5-yl, CONHSO2Ar3, CONHSO2(CH2)qAr3 or CONHSO2(C1-6 alkyl); Ar1-3 independently represent phenyl, naphthyl, or an aromatic heterocycle, which groups are optionally fused and optionally substituted; and Het1 and Het2 independently represent a non- aromatic heterocycle which is optionally substituted; are useful in the treatment of restenosis, renal failure and pulmonary hypertension.

Composés de formule (I) et leurs dérivés acceptables sur le plan pharmaceutique. Dans ladite formule, R?1¿ et R?2¿ sont des substituants optionnels et représentent indépendamment alkyle C¿1-6?, alcényle C¿2-6? [éventuellement substitué par CO¿2?H ou CO¿2?(alkyle C¿1-6?)], alcynyle C¿2-6?, halogène, perfluoroalkyle C¿1-3?, (CH¿2?)¿m?AR?1¿, (CH¿2?)¿m?Het?1¿, (CH¿2?)¿m?CONR?7¿R?8¿, (CH¿2?)¿m?CO¿2?R?8¿, O(CH¿2?)¿q?CO¿2?R?8¿, (CH¿2?)¿m?COR?8¿, (CH¿2?)¿m?OR?8¿, O(CH¿2?)¿p?OR?8¿, (CH¿2?)¿m?NR?7¿R?8¿, CO¿2?(CH¿2?)¿q?NR?7¿R?8¿, (CH¿2?)¿m?CN, S(O)¿n?R?8¿,SO¿2?NR?7¿R?8¿, CONH(CH¿2?)¿m?Ar?1¿ ou CONH(CH¿2?)¿m?Het?1¿; R?3¿ représente H, alkyle C¿1-6?, (CH¿2?)¿p?NR?9¿R?10¿, SO¿2?R?10¿, SO¿2?NR?9¿R?10¿, (CH¿2?)¿m?COR?10¿, alcényle C¿2-6?, alcynyle C¿2-6?, (CH¿2?)¿m?CONR?9¿R?10¿, (CH¿2?)¿m?CO¿2?R?10¿, (CH¿2?)¿p?CN, (CH¿2?)¿p?R?10¿ ou (CH¿2?)¿p?OR?10¿; R?4¿ représente H ou alkyle C¿1-6?; R?5¿ représente H ou OH; R?6¿ représente phényle éventuellement fusionné à un noyau hétérocyclique, le groupe dans son intégralité étant éventuellement substitué; R?7-10¿ sont intégralement définis dans la description et peuvent représenter indépendamment Ar?2¿ ou Het?2¿; Z représente CO¿2?H, CONH(tétrazol-5-yle), CONHSO¿2?O(alkyle C¿1-4?), CO¿2?Ar?3¿, CO¿2?(alkyle C¿1-6?), tétrazol-5-yle, CONHSO¿2?Ar?3¿, CONHSO¿2?(CH¿2?)¿q?Ar?3¿ ou CONHSO¿2?(alkyle C¿1-6?); Ar?1-3¿ représente indépendamment phényle, naphtyle ou un hérétocycle non aromatique dont les groupes sont éventuellement fusionnés et substitués; et Het?1¿ et Het?2¿ représentent indépendamment un hétérocycle aromatique éventuellement substitué. Les composés selon l'invention sont utiles dans le traitement de la resténose, de l'insuffisance rénale et de l'hypertension pulmonaire.

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