Patent ID: 6248739
Filing Date: 2001-06-19
Classification: A61P,C07D

Abstract:
A compound of formula I, ##STR199##or a pharmaceutically acceptable salt thereof wherein,X isa) O, orb) S;W isa) R.sup.2 ;b) NR.sup.7 R.sup.8,c) OR.sup.9, ord) SO.sub.i R.sup.9 ;R.sup.1 isa) Cl,b) F,c) Br,d) CN, ore) NO.sub.2 ;R.sup.2 isa) (CH.sub.2 CH.sub.2 O).sub.m R.sup.10,b) het, wherein said het is bonded via a carbon atom,c) C.sub.1-7 alkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from a group consisting of NR.sup.7 R.sup.8, R.sup.11, CN, SO.sub.i R.sup.9, or OC.sub.2-4 alkyl which is further substituted by het, OR.sup.10, OC(.dbd.O)aryl, or NR.sup.7 R.sup.8, ord) C.sub.3-8 cycloalkyl, which may be partially unsaturated and is optionally substituted by R.sup.11, NR.sup.7 R.sup.8, SO.sub.i R.sup.9, or C.sub.1-7 alkyl optionally substituted by R.sup.11, NR.sup.7 R.sup.8, or SO.sub.i R.sup.9 ;R.sup.3 isa) H,b) halo, orc) C.sub.1-4 alkyl, optionally substituted by one to three halo;R.sup.4 isa) H,b) aryl,c) het,d) SO.sub.2 NHR.sup.12,e) CONHR.sup.12,f) NR.sup.7 R.sup.8,g) NHCOR.sup.12,h) NHSO.sub.2 R.sup.12,i) OC.sub.2-7 alkyl optionally substituted by --OH,j) SC.sub.2-7 alkyl optionally substituted by OH, ork) C.sub.1-8 alkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from a group consisting of N.sub.3, OR.sup.10, NR.sup.7 R.sup.8, halo, SO.sub.i R.sup.9, OR.sup.13 or R.sup.11 ;R.sup.5 isa) H,b) halo,c) C.tbd.CR.sup.14,d) NR.sup.7 R.sup.8,e) SO.sub.2 NHR.sup.12,f) het, org) C.sub.1-7 alkyl, optionally substituted by OH;R.sup.6 isa) H,b) halo,c) SC.sub.1-7 alkyl,e) C.sub.1-7 alkoxy, optionally substituted by one or more halo or OH, orf) C.sub.1-7 alkyl, which may be partially unsaturated and is optionally substituted by halo, NR.sup.10 R.sup.10, (CH.sub.2).sub.n OR.sup.13, R.sup.11, OC.sub.1-7 alkyl which is further substituted with het, NR.sup.7 R.sup.8, or SO.sub.i R.sup.9 ;R.sup.7 and R.sup.8 are independentlya) H,b) aryl,c) C.sub.1-7 alkyl which may be partially unsaturated and is optionally substituted by one or more substituents selected from a group consisting of NR.sup.10 R.sup.10, CONR.sup.10 R.sup.10, R.sup.11, SO.sub.i R.sup.9, halo; ord) R.sup.7 and R.sup.8 together with the nitrogen to which they are attached to form a het;R.sup.9 isa) aryl,b) het,c) C.sub.3-8 cycloalkyl, ord) C.sub.1-7 alkyl which may be partially unsaturated and optionally substituted by one or more OR.sup.10, Oaryl, het, aryl, NR.sup.10 R.sup.10, CN, SH, SO.sub.i C.sub.1-6 alkyl, SO.sub.i aryl, halo, or CONR.sup.10 R.sup.10 ;R.sup.10 isa) H, orb) C.sub.1-7 alkyl, optionally substituted by OH;R.sup.11 isa) OR.sup.10,b) Ohet,c) Oaryl,d) CO.sub.2 R.sup.10,e) het,f) aryl, org) CN;R.sup.12 isa) H,b) het,c) aryl,d) C.sub.3-8 cycloalkyl, ore) C.sub.1-7 alkyl optionally substituted by NR.sup.7 R.sup.8, or R.sup.11 ;R.sup.13 isa) (P.dbd.O)(OH).sub.2,b) (P.dbd.O)(C.sub.1-7 alkoxy).sub.2,c) CO(CH.sub.2).sub.n CON(CH.sub.3)(CH.sub.2).sub.n SO.sub.3.sup.- M.sup.+,d) an amino acid,e) C(.dbd.O)aryl,f) C(.dbd.O)C.sub.1-6 alkyl, optionally substituted by NR.sup.10 R.sup.10, org) CO(CH.sub.2).sub.n CO.sub.2 H;R.sup.14 isa) het,b) (CH.sub.2).sub.n OR.sup.13, orc) C.sub.1-7 alkyl substituted by one or more substituents selected from a group consisting of R.sup.11, OC.sub.1-7 alkyl which is further substituted with het, NR.sup.7 R.sup.8, or SO.sub.i R.sup.9 ; aryl is a phenyl radical or an ortho-fused bicyclic carbocyclic radical wherein at least one ring is aromatic;het is a four- (4), five- (5), six- (6), or seven- (7) membered saturated or unsaturated heterocyclic ring having 1, 2, or 3 heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen, which is optionally fused to a benzene ring, or any bicyclic heterocycle group;wherein any aryl is optionally substituted with one or more substituents selected from the group consisting of halo, OH, CF.sub.3, C.sub.1-6 alkoxy, and C.sub.1-6 alkyl which maybe further substituted by one to three SR.sup.10, NR.sup.10 R.sup.10, OR.sup.10, or CO.sub.2 R.sup.10 ;wherein any het is optionally substituted with one or more substituents selected from the group consisting of halo, OH, CF.sub.3, C.sub.1-6 alkoxy, oxo, oxine, and C.sub.1-6 alkyl which maybe further substituted by one to three SR.sup.10, NR.sup.10 R.sup.10, OR.sup.10, or CO.sub.2 R.sup.10 ;i is 0, 1, or 2;m is 1, 2, or 3;n is 1, 2, 3, 4, 5, or 6; andM is sodium, potassium, or lithium;With the proviso that R.sup.1 is not Cl, Br, F, or CN; whenX is O;R.sup.2 is C.sub.1-7 alkyl optionally substituted by R.sup.15 ;R.sup.3 is H, methyl, or halo;R.sup.4 is H, CONH(C.sub.1-7 alkyl), NR.sup.16 R.sup.17, or C.sub.1-7 alkyl optionally substituted by OR.sup.10, CN, COOH, or NR.sup.16 R.sup.17 ;R.sup.5 is H, halo, SO.sub.2 NHR.sup.10, NR.sup.16 R.sup.17, or C.sub.1-7 alkyl optionally substituted by OR.sup.10 ;R.sup.6 is H, halo, C.sub.1-7 alkoxy, or C.sub.1-7 alkyl optionally substituted by halo, OR.sup.10, CO.sub.2 R.sup.10 or NR.sup.16 R.sup.17 ;R.sup.15 is NR.sup.16 R.sup.17, OR.sup.10, CN, or CO.sub.2 R.sup.10 ; andR.sup.16 and R.sup.17 are independently H or C.sub.1-7 alkyl; or NR.sup.16 R.sup.17 together with the nitrogen to which they are attached form a 5- or 6-membered ring selected from pyrrolidine, piperidine, morpholine, or piperazine.