Patent ID: 6031109
Filing Date: 2000-02-29
Classification: C07D

Abstract:
A compound represented by formula IIa ##STR63## or a pharmaceutically acceptable salt thereof, in which R.sub.1 represents hydrogen, halo, cyano, a cyano C.sub.1-6 alkyl group, a C.sub.1-12 alkyl group (unsubstituted or substituted by one or more hydroxy groups), a C.sub.1-6 alkoxy group, phenoxy (unsubstituted or substituted), phenyl (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 represent a saturated 3-7 membered heterocyclic ring which does or does not further contain sulfur, 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 represents hydrogen or C.sub.1-6 alkyl and R.sub.16 represents hydroxy, a C.sub.1-6 alkyl group or unsubstituted or substituted phenyl), a halogenated C.sub.1-4 alkoxy group, a halogenated C.sub.1-4 alkyl group, arylalkoxy (unsubstituted or substituted), hydroxy, a phenyl C.sub.1-6 alkyl group (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 represents a C.sub.1-6 alkyl group and n is 0, 1 or 2 or n is 2 and R.sub.7 represents a group of formula --N(R.sub.17)R.sub.18 in which R.sub.17 and R.sub.18 independently represent hydrogen, a C.sub.1-6 alkyl group or unsubstituted or substituted phenyl), 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 (in which R.sub.11 and R.sub.12 are independently hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group or unsubstituted or substituted phenyl or R.sub.11 and R.sub.12 together with the nitrogen atom to which they are attached represent a saturated 3-7 membered heterocyclic ring which does or does not further contain sulfur, oxygen or an additional nitrogen atom, wherein the 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 represents a C.sub.1-6 alkyl group or a phenyl group (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 represents hydrogen or a C.sub.1-6 alkyl group and R.sub.61 represents a C.sub.1-6 alkanoyl group or benzoyl (unsubstituted or substituted);a group of formula --(O).sub.z --L.sub.3 G wherein z is 0,L.sub.3 represents a C.sub.1-4 alkylene chain which is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups and G represents a group of formula a), b), c) or d):a) --NR.sub.22 R.sub.23wherein R.sub.22 represents hydrogen or a C.sub.1-6 alkyl group and R.sub.23 represents hydrogen, a C.sub.1-6 alkyl group, a C.sub.1-6 alkanoyl group, phenylsulphonyl (unsubstituted or substituted), benzoyl (unsubstituted or substituted), a group of formula --CONR.sub.24 R.sub.25 wherein R.sub.24 represents hydrogen, a C.sub.1-6 alkyl group or a C.sub.3-6 cycloalkyl group and R.sub.25 represents hydrogen, a C.sub.1-6 alkyl group or phenyl (unsubstituted or substituted) or R.sub.24 and R.sub.25 together with the nitrogen atom to which they are attached represent a saturated 3-7 membered heterocyclic ring which does or does not further contain sulfur, 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.26in which R.sub.26 represents a C.sub.1-6 alkyl group, a phenyl group (unsubstituted or substituted) and m is 0, 1 or 2 or m is 2 and R.sub.26 represents a group of formula --N(R.sub.17)R.sub.18 in which R.sub.17 and R.sub.18 independently represent hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group or unsubstituted or substituted phenyl or R.sub.17 and R.sub.18 together with the nitrogen atom to which they are attached represent a saturated 3-7 membered heterocyclic ring which does or does not further contain sulfur, 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.28in which R.sub.27 represents hydrogen or a C.sub.1-6 alkyl group and R.sub.28 represents hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-8 cycloalkyl group, a phenyl C.sub.1-6 alkyl group in which the phenyl ring is unsubstituted or substituted, or phenyl (unsubstituted or substituted) or R.sub.27 and R.sub.28 together with the nitrogen atom to which they are attached represent a saturated 3-7 membered heterocyclic ring which does or does not further contain sulfur, 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.29in which R.sub.29 represents a C.sub.1-6 alkyl group, phenyl (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 (unsubstituted or substituted), a C.sub.1-6 alkylsulphonyl group, a phenylsulphonyl group (unsubstituted or substituted), or R.sub.29 represents a group of formula --L.sub.4 COR.sub.32 in which L.sub.4 represents a C.sub.1-4 alkylene chain (unsubstituted or substituted by one or more C.sub.1-4 alkyl groups), and R.sub.32 represents hydrogen, a C.sub.1-6 alkyl group, a C.sub.1-6 alkoxy group, phenyl (unsubstituted or substituted) or phenoxy (unsubstituted or substituted);or R.sub.1 and R.sub.2 together with the phenyl ring to which they are attached represent a naphthyl group (unsubstituted or substituted);R.sub.2 and R3 independently represent hydrogen, a C.sub.1-4 alkyl group, a C.sub.1-4 alkoxy group, halo, a perhalo C.sub.1-2 alkyl group, hydroxy, cyano, a C.sub.2-6 alkoxycarbonyl group, a group of formula --S(O).sub.n R.sub.7 (in which R.sub.7 represents a C.sub.1-6 alkyl group or an aryl group and n is 0, 1 or 2), a group of formula --N(R.sub.15)SO.sub.2 R.sub.16 (in which R.sub.15 represents hydrogen or a C.sub.1-6 alkyl group and R.sub.16 represents hydrogen, a C.sub.1-6 alkyl group or unsubstituted or substituted phenyl), or a group of formula --CONR.sub.11 R.sub.12 (in which R.sub.11 and R.sub.12 are independently hydrogen, a C.sub.1-6 alkyl group, a C.sub.3-6 cycloalkyl group or unsubstituted or substituted phenyl or R.sub.11 and R.sub.12 together with the nitrogen to which they are attached represent a saturated 3-7 membered heterocyclic ring which does or does not further contain sulfur, oxygen or an additional nitrogen atom, wherein the ring is unsubstituted or substituted by one or more C.sub.1-4 alkyl groups);T represents O, S, SO, SO.sub.2, a carbonyl group or a group of formula (5) ##STR64## L.sub.2 represents a C.sub.1-4 alkylene chain, a C.sub.3-6 cycloalkylene group, or a C.sub.3-6 cycloalkylidene group, each of which is unsubstituted or substituted by one or more phenyl groups (unsubstituted or substituted), 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 a C.sub.2-6 alkoxycarbonyl group) or by one or more C.sub.3-6 cycloalkyl groups, or when T represents a carbonyl groupL.sub.2 additionally represents a C.sub.1-4 oxyalkylene chain;R.sub.6 represents hydrogen, a C.sub.1-4 alkyl group (unsubstituted or substituted by one or more hydroxy groups or by a C.sub.2-6 alkoxycarbonyl group);Q represents a C.sub.1-9 alkylene chain unsubstituted or substituted by one or more hydroxy groups and/or by one or more C.sub.1-4 alkyl groups (unsubstituted or substituted by one or more hydroxy groups) and/or in the absence or presence of oxygen or a carbonyl group;Y represents an imidazole ring of formula (1), (2), (3) or (4) ##STR65## in which R.sub.8 represents hydrogen, a C.sub.1-6 alkyl group, halo, trifluoromethyl, a C.sub.1-4 alkoxy group, a C.sub.1-4 hydroxyalkyl group, phenyl (unsubstituted or substituted), benzoyl (unsubstituted or substituted), a benzoyl C.sub.1-4 alkyl group (unsubstituted or substituted), or a phenyl C.sub.1-4 alkyl group in which the alkyl chain is unsubstituted or substituted by one or more hydroxy groups and the phenyl ring is unsubstituted or substituted;R.sub.9 and R.sub.10 independently represent hydrogen, a C.sub.1-6 alkyl group, halo, trifluoromethyl, a C.sub.1-4 alkoxy group, phenyl (unsubstituted or substituted), 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 represent a saturated 3-7 membered heterocyclic ring which does or does not further contain sulfur, 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.1-6 alkanoyloxy C.sub.1-4 alkyl group, a group of formula --L.sub.5 --NR.sub.40 R.sub.41 wherein L.sub.5 represents a C.sub.1-4 alkylene chain (unsubstituted or substituted by one or more C.sub.1-4 alkyl groups), R.sub.40 represents hydrogen or a C.sub.1-6 alkyl group, and R.sub.41 represents hydrogen, a C.sub.1-6 alkyl group, a group of formula SO.sub.2 R.sub.42 in which R.sub.42 represents a C.sub.1-6 alkyl group or phenyl (unsubstituted or substituted) or a group of formula COR.sub.43 in which R.sub.43 represents a C.sub.1-6 alkyl group, phenyl (unsubstituted or substituted), pyridyl (unsubstituted or substituted), thienyl (unsubstituted or substituted), furyl (unsubstituted or substituted) or pyrrolyl (unsubstituted or substituted), a C.sub.1-6 alkoxy group, phenoxy (unsubstituted or substituted) or arylalkyl (unsubstituted or substituted) or R.sub.41 represents a group of formula CONR.sub.44 R.sub.45 unsubstituted or substituted); andR.sub.19 represents hydrogen, a C.sub.1-6 alkyl group, aryl or an aryl C.sub.1-6 alkyl group.