1-alkyl-1-azoniabicyclo[2.2.2]octane carbamate derivatives...

Details 1-alkyl-1-azoniabicyclo[2.2.2]octane carbamate derivatives... 1-alkyl-1-azoniabicyclo[2.2.2]octane carbamate derivatives...

C - Chemistry, Metallurgy

07

D

C07D 453/06 (2006.01) A61K 31/435 (2006.01) A61K 45/06 (2006.01) A61P 43/00 (2006.01) C07D 453/02 (2006.01)

Patent

CA 2470956

Carbamate of general formula (I), wherein R1, R2 and R3 are H, OH, NO2, SH, CN, F, Cl, Br, I, COOH, CONH2, (C1-C4)-alkoxycarbonyl, (C1C4)-alkylsulfanyl, (C1-C4)-alkylsulfinyl, (C1C4)-alkylsulfonyl, (C1-C4)-alkoxyl optionally substituted with one or several F, and (C1-C4)-alkyl optionally substituted with one or several F or OH; R4 is cycloalkyl, phenyl, heteroaryl or a bicyclic ring system; R5 is cycloalkyl, (C5-C10)-alkyl, a substituted (C1-C10)- alkyl; and X- is a physiologically acceptable anion. Carbamate (I) is selective M3 receptor antagonists versus M2 receptor and may be used for the treatment of urinary incontinence (particularly, the one caused by overactive bladder), irritable bowel syndrome, and respiratory disorders (particulary, chronic obstructive pulmonary disease, chronic bronchitis, asthma, emphysema, and rhinitis), as well as in ophthalmic interventions.

L'invention concerne un carbamate de formule générale (I), dans laquelle R1, R2 et R3 représentent H, OH, NO¿2?, SH, CN, F, Cl, Br, I, COOH, CONH¿2?, (C¿1?-C¿4?)-alcoxycarbonyle, (C¿1?-C¿4?)-alkylsulfanyle, (C¿1?-C¿4?)-alkylsulfinyle, (C¿1?-C¿4?)-alkylsulfonyle, (C¿1?-C¿4?)-alcoxy éventuellement substitué par un ou plusieurs F, (C¿1?-C¿4?)-alkyle éventuellement substitué par un ou plusieurs F ou OH; R4 représente cycloalkyle, phényle, hétéroaryle ou un système de noyau bicyclique; R5 représente cycloalkyle, (C¿5?-C10)-alkyle, un (C¿1?-C10)-alkyle substitué; et X représente un anion physiologiquement acceptable. Carbamate (I) représente des antagonistes sélectifs du récepteur M¿3? contre le récepteur M¿2? et peut servir dans le traitement de l'incontinence urinaire (en particulier celle causée par une vessie hyperactive), du syndrome du côlon irritable, de troubles respiratoires (en particulier la bronchopneumopathie chronique obstructive, la bronchite chronique, l'asthme, l'emphysème et la rhinite), ainsi que lors d'interventions ophtalmiques.

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