Patent ID: 6197810
Filing Date: 2001-03-06
Classification: A61P,C07D

Abstract:
A compound of the formula ##STR13##wherein the dotted line represents an optional double bond,R.sup.1, R.sup.2, R.sup.3, R.sup.1 are each independently selected from the group consisting of hydrogen, hydroxy-, (C.sub.1 -C.sub.6)alkyl-, (C.sub.1 -C.sub.6)alkoxy-, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkoxy-, ((C.sub.1 -C.sub.6)alkyl).sub.2 amino(C.sub.1 -C.sub.6)alkoxy-, (C.sub.1 -C.sub.6)alkylthio-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkythio-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkythio-, hydroxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.1 -C.sub.6)alkylamino(C.sub.1 -C.sub.6)alkyl-, ((C.sub.1 -C.sub.6)alkyl).sub.2 amino(C.sub.1 -C.sub.6)alkyl-, [(C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl]amino(C.sub.1 -C.sub.6)alkyl-, [(C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl]((C.sub.1 -C.sub.6)alkyl)amino(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl, [(C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl]amino(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl and [(C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl]((C.sub.1 -C.sub.6)alkyl)amino(C.sub.1 -C.sub.6)alkyl-; wherein each of said (C.sub.6 -C.sub.10)aryl or (C.sub.2 -C.sub.9)heteroaryl moieties of said (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkythio-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkythio-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, [(C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl]amino(C.sub.1 -C.sub.6)alkyl-, [(C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl]((C.sub.1 -C.sub.6)alkyl)amino(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl, [(C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl]amino(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl and [(C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl]((C.sub.1 -C.sub.6)alkyl)amino(C.sub.1 -C.sub.6)alkyl- are optionally substituted on any of the ring carbon atoms capable of forming an additional bond by one or more substituents per ring, most preferably one to three substituents on the terminal ring independently selected from fluoro, chloro, cyano, nitro, trifluoromethyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.6 -C.sub.10)aryloxy, trifluoromethoxy, difluoromethoxy, or (C.sub.1 -C.sub.6)alkyl;or R.sup.1 can be taken together with R.sup.2 to form a carbonyl group;or R.sup.3 can be taken together with R.sup.4 to form a carbonyl group;Q is (C.sub.1 -C.sub.6)alkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.2 -C.sub.9)heteroaryl, (C.sub.6 -C.sub.10)aryloxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryloxy(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryloxy(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryl(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.6 -C.sub.10)aryl, (C.sub.2 -C.sub.9)heteroaryl(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.2 -C.sub.9)heteroaryloxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryloxy(C.sub.6 -C.sub.10)aryl-, (C.sub.2 -C.sub.9)heteroaryloxy(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.6 -C.sub.10)aryl- or (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.2 -C.sub.9)heteroaryl-;wherein each (C.sub.6 -C.sub.10)aryl or (C.sub.2 -C.sub.9)heteroaryl moieties of said (C.sub.6 -C.sub.10)aryl, (C.sub.2 -C.sub.9)heteroaryl, (C.sub.6 -C.sub.10)aryloxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryloxy(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryloxy(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryl(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryl(C.sub.6 -C.sub.10)aryl(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.6 -C.sub.10)aryl, (C.sub.2 -C.sub.9)heteroaryl(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.6 -C.sub.10)aryl-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.2 -C.sub.9)heteroaryloxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryloxy(C.sub.6 -C.sub.10)aryl-, (C.sub.2 -C.sub.9)heteroaryloxy(C.sub.2 -C.sub.9)heteroaryl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.6 -C.sub.10)aryl- or (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy(C.sub.2 -C.sub.9)heteroaryl- is optionally substituted on any of the ring carbon atoms capable of forming an additional bond by one or more substituents per ring, preferably one to three substituents per ring, most preferably one to three substituents on the terminal ring independently selected from fluoro, chloro, bromo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, perfluoro(C.sub.1 -C.sub.3)alkyl, perfluoro(C.sub.1 -C.sub.3)alkoxy and (C.sub.6 -C.sub.10)aryloxy;with the proviso that when the dotted line is a double bond that one of R.sup.1 or R.sup.2 and one of R.sup.3 or R.sup.4 is absent;with the proviso that when one of R.sup.1 or R.sup.2 is hydroxy then the other of R.sup.1 or R.sup.2 cannot be hydroxy, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkoxy-, ((C.sub.1 -C.sub.6)alkyl).sub.2 amino(C.sub.1 -C.sub.6)alkoxy-, (C.sub.1 -C.sub.6)alkylthio, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkythio-, or (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkythio-, andwith the proviso that when one of R.sup.3 or R.sup.4 is hydroxy then the other of R.sup.3 or R.sup.4 cannot be hydroxy, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkoxy-, ((C.sub.1 -C.sub.6)alkyl).sub.2 amino(C.sub.1 -C.sub.6)alkoxy-, (C.sub.1 -C.sub.6)alkylthio, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkoxy-, (C.sub.6 -C.sub.10)aryl(C.sub.1 -C.sub.6)alkythio-, or (C.sub.2 -C.sub.9)heteroaryl(C.sub.1 -C.sub.6)alkythio-,or a pharmaceutically acceptable salt thereof.