Patent ID: 6258809
Filing Date: 2001-07-10
Classification: A61P,C07D

Abstract:
A compound of formula I: ##STR22##or a pharmaceutically acceptable salt thereof, wherein:Q is O or S(O)n;Ar is phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzthiazolyl, isoxazolyl or pyrazolyl, each optionally substituted with 1 to 4 R.sup.5 groups;R.sup.1 is independently at each occurrence H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, halo, CN, C.sub.1 -C.sub.4 haloalkyl, --NR.sup.9 R.sup.10, NR.sup.9 COR.sup.10, --OR.sup.11, SH or --S(O).sub.n R.sup.12 ;R.sup.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 cycloalkyl, halo, CN, --NR.sup.6 R.sup.7, NR.sup.9 COR.sup.10, C.sub.1 -C.sub.4 haloalkyl, --OR.sup.7, SH or --S(O).sub.n R.sup.12 ;R.sup.3 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl or C.sub.4 -C.sub.12 cycloalkylalkyl each optionally substituted with 1 to 3 substituents independently selected at each occurrence from C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, halo, C.sub.1 -C.sub.4 haloalkyl, cyano, --OR.sup.7, SH, --S(O).sub.n R.sup.13, --COR.sup.7, --CO.sub.2 R.sup.7, --OC(O)R.sup.13, --NR.sup.8 COR.sup.7, --N(COR.sup.7).sub.2, --NR.sup.8 CONR.sup.6 R.sup.7, --NR.sup.8 CO.sub.2 R.sup.13, --NR.sup.6 R.sup.7, --CONR.sup.6 R.sup.7, heteroaryl and heterocyclyl, where the heteroaryl or heterocyclyl is optionally substituted with 1 to 3 substituents independently selected at each occurrence from C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, halo, C.sub.1 -C.sub.4 haloalkyl, cyano, --OR.sup.7, SH, --S(O).sub.n R.sup.13, --COR.sup.7, --CO.sub.2 R.sup.7, --OC(O)R.sup.13, --NR.sup.8 COR.sup.7, --N(COR.sup.7).sub.2, --NR.sup.8 CONR.sup.6 R.sup.7, --NR.sup.8 CO.sub.2 R.sup.13, --NR.sup.6 R.sup.7, and --CONR.sup.6 R.sup.7 ;R.sup.5 is independently at each occurrence C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.12 cycloalkylalkyl, --NO.sub.2, halo, --CN, C.sub.1 -C.sub.4 haloalkyl, --NR.sup.6 R.sup.7, NR.sup.8 COR.sup.7, NR.sup.8 CO.sub.2 R.sup.7, --COR.sup.7 --OR.sup.7, --CONR.sup.6 R.sup.7, --CO(NOR.sup.9)R.sup.7, CO.sub.2 R.sup.7, or --S(O).sub.n R.sup.7, where C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.6 cycloalkyl and C.sub.4 -C.sub.12 cycloalkylalkyl are optionally substituted with 1 to 3 substituents independently selected at each occurrence from C.sub.1 -C.sub.4 alkyl, --NO.sub.2, halo, --CN, --NR.sup.6 R.sup.7, --NR.sup.6 R.sup.7, NR.sup.8 COR.sup.7, NR.sup.8 CO.sub.2 R.sup.7, --COR.sup.7 --OR.sup.7, --CONR.sup.6 R.sup.7, CO.sub.2 R.sup.7, --CO(NOR.sup.9)R.sup.7, or --S(O).sub.n R.sup.7 ;R.sup.6 and R.sup.7 are independently at each occurrence H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.12 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.4 alkyl)-, heteroaryl or heteroaryl(C.sub.1 -C.sub.4 alkyl)-; or NR.sup.6 R.sup.7 is piperidine, pyrrolidine, piperazine, N-methylpiperazine, morpholine or thiomorpholine;R.sup.8 is independently at each occurrence H or C.sub.1 -C.sub.4 alkyl;R.sup.9 and R.sup.10 are independently at each occurrence selected from H, C.sub.1 -C.sub.4 alkyl, or C.sub.3 -C.sub.6 cycloalkyl;R.sup.11 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or C.sub.3 -C.sub.6 cycloalkyl;R.sup.12 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;R.sup.13 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.12 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.4 alkyl)-, heteroaryl or heteroaryl(C.sub.1 -C.sub.4 alkyl)-;R.sup.13a is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.4 -C.sub.12 cycloalkylalkyl;aryl is phenyl or naphthyl, each optionally substituted with 1 to 3 substituents independently selected at each occurrence from C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, halo, C.sub.1 -C.sub.4 haloalkyl, cyano, --OR.sup.7, SH,--S(O).sub.n R.sup.13a, --COR.sup.7, --CO.sub.2 R.sup.7, --OC(O)R.sup.13a, --NR.sup.8 COR.sup.7, --N(COR.sup.7).sub.2, --NR.sup.8 CONR.sup.6 R.sup.7, NR.sup.8 CO.sub.2 R.sup.13a, --NR.sup.6 R.sup.7, and --CONR.sup.6 R.sup.7 ;heteroaryl is pyridyl, pyrimidinyl, triazinyl, furanyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzthiazolyl, isoxazolyl or pyrazolyl optionally substituted with 1 to 3 substituents independently selected at each occurrence from C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, halo, C.sub.1 -C.sub.4 haloalkyl, cyano, --OR.sup.7, SH, --S(O).sub.n R.sup.13a, --COR.sup.7, --CO.sub.2 R.sup.7, --OC(O)R.sup.13a, --NR.sup.8 COR.sup.7, --N(COR.sup.7).sub.2, --NR.sup.8 CONR.sup.6 R.sup.7, --NR.sup.8 CO.sub.2 R.sup.13a, --NR.sup.6 R.sup.7, and --CONR.sup.6 R.sup.7 ;heterocyclyl is saturated or partially saturated heteroaryl, optionally substituted with 1 to 3 substituents independently selected at each occurrence from C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, halo, C.sub.1 -C.sub.4 haloalkyl, cyano, --OR.sup.7, SH, --S(O).sub.n R.sup.13a, --COR.sup.7, --CO.sub.2 R.sup.7, --OC(O)R.sup.13a, --NR.sup.8 COR.sup.7, --N(COR.sup.7).sub.2, --NR.sup.8 CONR.sup.6 R.sup.7, --NR.sup.8 CO.sub.2 R.sup.13a, --NR.sup.6 R.sup.7, and --CONR.sup.6 R.sup.7 ; and,n is independently at each occurrence 0, 1 or 2.