Patent ID: 6093732
Filing Date: 2000-07-25
Classification: A61P,C07D,C07F

Abstract:
A compound of formula I or a pharmaceutically acceptable salt thereof whereinA is:a) --CH.sub.2 --, orb) --NH--;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independentlya) --H,b) halo,c) --CN,d) --NO.sub.2,e) aryl,f) het,g) --OR.sup.5,h) C.sub.1-12 alkyl,i) C.sub.1-2 alkyl substituted with one to three --CN, halo, --NO.sub.2, OR.sup.5, --C(.dbd.O)R.sup.5, --COOR.sup.5, het, aryl, --SR.sup.5, --OR.sup.6, --NR.sup.7 R.sup.8, --OP(.dbd.O)(R.sup.9).sub.2, --OPH(.dbd.O)R.sup.9, --OC(.dbd.O)R.sup.10, --O-glycyl, --O-valyl or --O-lysyl,j) --Cr.tbd.CR.sup.11,k) --CH.dbd.CH--R.sup.12,l) --(CH.sub.2).sub.m --C(.dbd.O)R.sup.13,m) --SR.sup.14,n) --C(.dbd.S)R.sup.15,o) --(CH.sub.2).sub.m --SO.sub.i R.sup.13,p) --NR.sup.7 R.sup.8,q) --NHSO.sub.i R.sup.13,r) R.sup.1 and R.sup.2 taken together are het or C.sub.4-6 cycloalkyl, ors) R.sup.2 and R.sup.3 taken together are het or C.sub.4-6 cycloalkyl;R.sup.5 isa) H,b) C.sub.1-8 alkyl, optionally substituted with one to three --OH, CN, C.sub.1-4 alkoxy, halo, --NO.sub.2, het or aryl,c) aryl, ord) het;R.sup.6 isa) --SO.sub.2 C.sub.1-6 alkyl,b) --SO.sub.2 --(CH.sub.2).sub.m -aryl, orc) --SO.sub.2 --(CH.sub.2).sub.m -het;R.sup.7 and R.sup.8 are independentlya) H,b) C.sub.1-8 alkyl, optionally substituted with one to three --NO.sub.2, halo, --CN, OR.sup.5, aryl, het, C.sub.3-6 cycloalkyl, C.sub.1-6 alkynyl, C.sub.1-6 alkenyl, --SR.sup.14, orNR.sup.16 R.sup.17,c) aryl,d) het,e) --(CH.sub.2).sub.m --C(.dbd.O)OR.sup.5,f) --(CH.sub.2).sub.m --C(.dbd.O)R.sup.5, org) R.sup.7 and R.sup.8 taken together to form het;R.sup.9 isa) --OH, orb) --OC.sub.1-8 alkyl;R.sup.10 isa) H,b) C.sub.1-8 alkyl,c) --NR.sup.7 R.sup.8,d) C.sub.1-8 alkyl substituted with one to two halo, het, --NR.sup.7 R.sup.8, --COOH --O(CH.sub.2).sub.m COOH or --C(.dbd.O)N(C.sub.1-4 alkyl)(CH.sub.2).sub.n S(.dbd.O).sub.2 O.sup.- M.sup.+ ;R.sup.11 isa) C.sub.1-8 alkyl,b) C.sub.1-8 alkyl substituted with one to three --CN, halo, --NO.sub.2, --COOR.sup.5, --C(.dbd.O)R.sup.5, --SR.sup.5, aryl, --OR.sup.5, --NR.sup.7 R.sup.8, --OP(.dbd.O)(R.sup.9).sub.2, --OPH(.dbd.O)R.sup.9 --OC(.dbd.O)R.sup.10, --O-glycyl, --O-valyl or --O-lysyl orc) --(CH.sub.2).sub.m -het;R.sup.12 isa) H,b) --CN,c) C.sub.1-8 alkyl,d) C.sub.1-8 alkyl substituted with one to three --CN, halo, --NO.sub.2, --C(.dbd.O)R.sup.5, --COOR.sup.5, aryl, het, --SR.sup.5, --OR.sup.5, --NR.sup.7 R.sup.8, --OP(.dbd.O)(R.sup.9).sub.2 or --OPH(.dbd.O)R.sup.9,e) --C(.dbd.O)R.sup.5, orf) --COOR.sup.5 ;R.sup.13 isa) C.sub.1-8 alkyl,b) C.sub.1-8 alkyl substituted one to three --CN, halo, --NO.sub.2, --C(.dbd.O)R.sup.5, het, aryl, --COOR.sup.5, --SR.sup.5, --OR.sup.5 or --NR.sup.7 R.sup.8,c) het,d) aryl,e) --NR.sup.7 R.sup.8,f) OR.sup.5,g) halo;R.sup.14 isa) C.sub.1-8 alkyl, orb) C.sub.1-8 alkyl substituted with one to three --CN, halo, --NO.sub.2, --C(.dbd.O)R.sup.5, --COOR.sup.5, het, aryl, --OR.sup.5, or --NR.sup.7 R.sup.8 ;R.sup.15 isa) --NH.sub.2, orb) --NHNH.sub.2 ;R.sup.16 and R.sup.17 is independentlya) H,b) C.sub.1-4 alkyl,c) --C(.dbd.O)C.sub.1-4 alkyl, ord) --C(.dbd.O)--(CH).sub.m -aryl;aryl is phenyl or naphthyl, optionally substituted with R.sup.18 ;het is a 5-, 6- or 7-membered saturated or unsaturated heterocyclic ring having 1-3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the heteroclyclic ring is optionally fused to a benzene ring, wherein aryl, het and benzene ring are optionally substituted with R.sup.18 ;R.sup.18 isa) halo,b) --NO.sub.2,c) phenyl, optionally substituted with one to five --OH, --CN, halo, --NO.sub.2, C.sub.1-6 alkyl, het, or OC.sub.1-4 alkyl,d) C.sub.1-8 alkyl, optionally substituted with one to three halo, --CN, --NO.sub.2, aryl, --SR.sup.5, --OR.sup.5 or --NR.sup.7 R.sup.8,e) OR.sup.5, orf) --SO.sub.2 NH.sub.2 ;M is sodium, potassium or lithium atom;i is 1 or 2;m is 0, 1, 2, or 4;n is 1,2, 3 or 4;and with the following provisos:(a) where R.sup.2, R.sup.3 and R.sup.4 are each hydrogen, then R.sup.1 is other than methoxy,(b) where R.sup.4 is Cl, and R.sup.2 and R.sup.3 are each hydrogen, then R.sup.1 is other than methyl,(c) where R.sup.1 is hydrogen, R.sup.2 and R.sup.4 are each fluoro, R.sup.3 is het, then het is other than substituted piperazinyl,(d) where R.sup.1 and R.sup.3 are each hydrogen, R.sup.2 is fluoro, then R.sup.4 is other than fluoro,(e) where R.sup.2 and R.sup.4 are each hydrogen, R.sup.1 is fluoro, then R.sup.3 is other than fluoro,(f) where R.sup.1 and R.sup.3 are each hydrogen, R.sup.2 is chloro, then R.sup.4 is other than chloro,(g) where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, then R.sup.4 is not bromo,(h) where R.sup.1, R.sup.3 and R.sup.4 are each hydrogen, then R.sup.2 is not trifluoromethoxy,(i) where R.sup.1, R.sup.2 and R.sup.4 are each hydrogen, then R.sup.3 is not trifluoromethoxy, and(j) where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, then R.sup.4 is not morpholinyl.