Patent ID: 6326500
Filing Date: 2001-12-04
Classification: A61P,C07D

Abstract:
A compound of formula (IIc) ##STR63##or a pharmaceutically acceptable salt thereof, in whichR.sub.1 is hydrogen; halo; cyano; a cyano C.sub.1-6 alkyl group;a C.sub.1-2 alkyl group which is unsubstituted or substituted by one or more hydroxy groups;a C.sub.1-6 alkoxy group; phenoxy which is unsubstituted or substituted; phenyl which is unsubstituted or substituted; a C.sub.2-6 alkoxycarbonyl group;an amino group of formula --NR.sub.13 R.sub.14, in which R.sub.13 and R.sub.14 are independently hydrogen or a C.sub.1-4 alkyl group; or R.sub.13 and R.sub.14 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, said ring optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;a group of formula --N(R.sub.15)SO.sub.2 R.sub.16 in which R.sub.15 is hydrogen or C.sub.1-6 alkyl; and R.sub.16 is hydroxy, a C.sub.1-4 alkyl group or substituted or unsubstituted phenyl;a halogenated C.sub.1-4 alkoxy group; a halogenated C.sub.1-4 alkyl group; arylalkoxy which is unsubstituted or substituted; hydroxy;a phenyl C.sub.1-6 alkyl group which is unsubstituted or substituted; a (C.sub.2-6 alkoxycarbonyl)vinyl group;a group of formula --S(O).sub.n R.sub.7, in which R.sub.7 is a C.sub.1-4 alkyl group, and n is 0, 1 or 2; or n is 2 and R.sub.7 is a group of formula --N(R.sub.17)R.sub.18, in which R.sub.17 and R.sub.18 independently are hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group or phenyl which is unsubstituted or substituted; or R.sub.17 and R.sub.18 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;a C.sub.2-6 alkoxycarbonyl C.sub.1-6 alkyl group; a carboxy C.sub.1-6 alkyl group;a carbamoyl group of formula --CONR.sub.11 R.sub.12 or a carbamoylvinyl group of formula --CH.dbd.CH--CON(R.sub.11)R.sub.12, in each of which R.sub.11 and R.sub.12 are independently hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-8 cycloalkyl group or phenyl which is unsubstituted or substituted; or R.sub.11 and R.sub.12 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups; a group of formula --OSO.sub.2 R.sub.21, in which R.sub.21, is a C.sub.1-6 alkyl group or a phenyl group which is unsubstituted or substituted;4,5-dihydrothiazol-2-yl, 4,4-dimethyl-2-oxazolin-2-yl;or a group of formula --NR.sub.60 R.sub.61 in which R.sub.60 is hydrogen or a C.sub.1-4 alkyl group; andis a C.sub.1-6 alkanoyl group or benzoyl which is unsubstituted or substituted; orR.sub.1 is a group of formula --(O).sub.z --L.sub.3 G, wherein z is 0 or 1; L.sub.3 is a C.sub.1-4 alkylene chain which is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups; and G is a group of formula a), b), c), or d):a) --NR.sub.22 R.sub.23, whereinR.sub.22 is hydrogen or a C.sub.1-6 alkyl group; andR.sub.23 is hydrogen; a C.sub.1-6 alkyl group; a C.sub.1-6 alkanoyl group; phenylsulphonyl which is unsubstituted or substituted; benzoyl which is unsubstituted or substituted; a group of formula --CONR.sub.24 R.sub.25 whereinR.sub.24 is hydrogen, a C.sub.1-6 alkyl group or a C.sub.3-6 cycloalkyl group, andR.sub.25 is hydrogen; a C.sub.1-6 alkyl group; or phenyl which is unsubstituted or substituted; orR.sub.24 and R.sub.25 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;b) --S(O).sub.m R.sub.26, whereinm is 0, 1 or 2, andR.sub.26 is a C.sub.1-6 alkyl group or a phenyl group which is unsubstituted or substituted, orm is 2, andR.sub.26 is a group of formula --N(R.sub.17)R.sub.18 in which R.sub.17 and R.sub.18 independently are hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group or phenyl which is unsubstituted or substituted; or R.sub.17 and R.sub.18 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;c) --CONR.sub.27 R.sub.28, whereinR.sub.27 is hydrogen or a C.sub.1-6 alkyl group; andR.sub.28 is hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group, a phenyl C.sub.1-6 alkyl group in which the phenyl ring is unsubstituted or substituted, or phenyl which is unsubstituted or substituted; orR.sub.27 and R.sub.28 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;d) --OR.sub.29, whereinR.sub.29 is a C.sub.1-6 alkyl group, phenyl which is unsubstituted or substituted, a phenyl C.sub.1-6 alkyl group in which the phenyl ring is unsubstituted or substituted, a C.sub.1-6 alkanoyl group, benzoyl which is unsubstituted or substituted, a C.sub.1-6 alkylsulphonyl group, a phenylsulphonyl group which is unsubstituted or substituted; orR.sub.29 is a group of formula --L.sub.4 COR.sub.32 in which L.sub.4 is a C.sub.1-4 alkylene chain which is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups; and R.sub.32 is hydrogen, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, phenyl which is unsubstituted or substituted, or phenoxy which is unsubstituted or substituted;R.sub.2 and R.sub.3 independently are hydrogen; halo;a C.sub.1-6 alkyl group which is unsubstituted or substituted by one or more hydroxy groups; a C.sub.1-6 alkoxy group;an amino group of formula --NR.sub.13 R.sub.14 in which R.sub.13 and R.sub.14 are independently hydrogen or a C.sub.1-4 alkyl group; or R.sub.13 and R.sub.14 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;a halogenated C.sub.1-4 alkoxy group; a halogenated C.sub.1-4 alkyl group; hydroxy;a group of formula --S(O).sub.n R.sub.7 in which R.sub.7 is a C.sub.1-6 alkyl group and n is 0, 1 or 2; or n is 2 and R.sub.7 is a group of formula --N(R.sub.17)R.sub.18 in which R.sub.17 and R.sub.18 independently are hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group or phenyl which is unsubstituted or substituted; or R.sub.17 and R.sub.18 together with the nitrogen atom to which they are attached form a saturated 3- to 7-membered heterocyclic ring, optionally containing sulphur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;a group of formula --NR.sub.60 R.sub.61 in which R.sub.60 is hydrogen or a C.sub.1-6 alkyl group; andR.sub.61 is a C.sub.1-6 alkanoyl group, or benzoyl which is unsubstituted or substituted; orR.sub.1 and R.sub.2 together with the phenyl ring to which they are attached form a naphthyl group which is unsubstituted or substituted; orR.sub.2 is attached to a position on the phenyl ring adjacent to the position of attachment of L.sub.2 on the phenyl ring and L.sub.2 and R.sub.2 together with the phenyl ring to which they are attached form an indane ring which is which is unsubstituted or substituted;L.sub.2 is a C.sub.1-4 alkylene chain, a C.sub.3-6 cycloalkylene group, or a C.sub.3-4 cycloalkylidene group, each of which is unsubstituted or substitutedby one or more unsubstituted or substituted phenyl groups;by one or more C.sub.1-4 alkyl groups wherein the alkyl groups are unsubstituted or substituted by one or more hydroxy groups or by a C.sub.2-6 alkoxycarbonyl group; orby one or more C.sub.3-6 cycloalkyl groups;R.sub.6 is hydrogen, a C.sub.1-4 alkyl group which is unsubstituted or substituted by one or more hydroxy groups or by a C.sub.2-6 alkoxycarbonyl group;Q is a C.sub.1-9 alkylene chain which is uninterrupted or interrupted by oxygen or a carbonyl group, and which chain is unsubstituted or substituted by one or more hydroxy groups and/or by one or more C.sub.1-4 alkyl groups which are unsubstituted or substituted by one or more hydroxy groups;Y is an imidazole ring of formula (2), (3) or (4) ##STR64##in whichR.sub.8 is hydrogen, halo, a C.sub.1-6 alkyl group, a halogenated C.sub.1-6 alkyl group, a C.sub.1-4 alkoxy group, a halogenated C.sub.1-4 alkoxy group, a C.sub.1-4 hydroxyalkyl group, an unsubstituted or substituted phenyl group, an unsubstituted or substituted benzoyl group, an unsubstituted or substituted benzoyl C.sub.1-4 alkyl group, or a phenyl C.sub.1-4 alkyl group in which the alkyl chain is unsubstituted or substituted by one or more hydroxy groups or one or more C.sub.1-4 alkyl groups and the phenyl ring is unsubstituted or substituted;R.sub.9 and R.sub.10 independently are hydrogen; halo; a C.sub.1-6 alkyl group; a halogenated C.sub.1-6 alkyl group; a C.sub.1-4 alkoxy group; a halogenated C.sub.1-4 alkoxy group; an unsubstituted or substituted phenyl group; a C.sub.1-4 hydroxyalkyl group; a C.sub.2-6 alkoxycarbonyl group; nitro;an amino group of formula NR.sub.30 R.sub.31 in which R.sub.30 and R.sub.31 are independently hydrogen or a C.sub.1-4 alkyl group; or R.sub.30 and R.sub.31 together with the nitrogen atom to which they are attached form a pyrrolidine ring, a morpholine ring or a piperidine ring; a C.sub.1-4 alkanoyloxy C.sub.1-4 alkyl group; a cyano C.sub.1-6 alkyl group; or a group of formula g) or h):g) --L.sub.5 --NR.sub.40 R.sub.41, in whichL.sub.5 is a C.sub.1-4 alkylene chain which is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups;R.sub.40 is hydrogen or a C.sub.1-6 alkyl group, andR.sub.41 is hydrogen; a C.sub.1-6 alkyl group; a group of formula SO.sub.2 R.sub.42 in which R.sub.42 is a C.sub.1-6 alkyl group or unsubstituted or substituted phenyl;a group of formula COR.sub.43 in which R.sub.43 is a C.sub.1-6 alkyl group, unsubstituted or substituted phenyl, unsubstituted or substituted pyridyl, unsubstituted or substituted thienyl, unsubstituted or substituted furyl, unsubstituted or substituted pyrrolyl, a C.sub.1-6 alkoxy group, unsubstituted or substituted phenoxy or unsubstituted or substituted arylalkyl; ora group of formula CONR.sub.44 R.sub.45 in which R.sub.44 is hydrogen, a C.sub.1-6 alkyl group or a C.sub.3-6 cycloalkyl group, and R.sub.45 is hydrogen, a C.sub.1-6 alkyl group or unsubstituted or substituted phenyl; or R.sub.44 and R.sub.45 together with the nitrogen atom to which they are attached form a pyrrolidine ring, a piperidine ring or a morpholine ring; orh) --L.sub.7 CONR.sub.90 R.sub.91 in whichL.sub.7 is a C.sub.1-6 alkylene chain; andR.sub.90 and R.sub.91 are independently hydrogen, a C.sub.1-6 alkyl group or unsubstituted or substituted phenyl; orR.sub.90 and R.sub.91 together with the nitrogen atom to which they are attached form a pyrrolidine ring, a morpholine ring or a piperidine ring; andR.sub.19 is hydrogen, a C.sub.1-6 alkyl group, an aryl group or an aryl C.sub.1-6 alkyl group.