1,2,4-Triazole-3-amines, their pharmaceutical compositions and method of use

Claim 1

A compound of formula (I) ##STR22## or a physiologically acceptable salt or hydrate thereof, in which R 1 represents hydrogen, C 1-14 alkyl, C 3-8 cycloalkyl, C 3-6 alkenyl, C 3-6 alkynyl, ar C 1-6 alkyl, trifluoro C 1-6 alkyl, heteroaralkyl, or C 1-6 alkyl substituted by C 3-8 cycloalkyl, hydroxy, C 1-6 alkoxy, amino, C 1-6 alkylamino or di C 1-6 alkylamino; and R 2 represents hydrogen or a C 1-4 alkyl group; or R 1 and R 2 together with the nitrogen atom to which they are attached form piperidino, morpholino, 4-methyl piperidino, pyrrolidino, hexamethyleneimino or tetrahydropyridino; Alk represents a straight or branched alkylene chain of 1 to 3 carbon atoms; Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R 5 represents hydrogen or acyl; n and m, which may be the same or different, are each 1 or 2; and R 3 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, ar C 1-6 alkyl, hydroxy C 2-6 alkyl, C 1-6 alkoxy C 2-6 alkyl or C 1-4 alkanoyloxy C 2-6 alkyl; R 7 represents hydrogen, C 1-6 alkyl, C 3-6 alkenyl, ar C 1-6 alkyl, C 1-6 alkoxy C 1-6 alkyl, acyloxy C 1-6 alkyl, C 1-6 alkylthio C 1-6 alkyl, arylthio C 1-6 alkyl, aryloxy C 1-6 alkyl, ar C 1-6 alkyloxy C 1-6 alkyl, or the group (CH 2 ) q R 6 where q is zero, 1, 2, 3, 4, 5, or 6 and the alkylene chain (CH 2 ) q may be straight or branched; and R 6 is hydroxy, C 1-6 alkoxy, nitro, heteroaryl, tetrahydropyranyloxy, or CH 2 NHC(═X)NHR 9 where X represents NCN, NSO 2 Methyl, NSO 2 Phenyl or CHNO 2 and R 9 is C 1-6 alkyl; or R 6 is the group NR 10 R 11 , where R 10 is hydrogen or C 1-6 alkyl; and R 11 is hydrogen, C 1-6 alkyl, C 3-6 alkenyl, aryl, ar C 1-6 alkyl, or heteroaralkyl, or R 11 is the group SO 2 R 12 where R 12 is C 1-6 alkyl or aryl; or R 11 is the group COR 13 where R 13 is hydrogen, C 1-6 alkyl, aryl, ar C 1-6 alkyl, C 1-6 alkoxy, halomethyl, heteroaryl, heteroaralkyl or the group NHR 14 where R 14 is hydrogen, C 1-6 alkyl, C 3-8 cycloalkyl, aryl or ar C 1-6 alkyl; or R 10 and R 11 together represent the group ═CR 15 R 16 where R 15 represents aryl or heteroaryl and R 16 represents hydrogen or C 1-6 alkyl; or R 6 is the group SO 2 R 17 in which R 17 is hydroxy, C 1-6 alkyl, aryl or the group NR 18 R 19 where R 18 and R 19 , which may be the same or different, each represents hydrogen or C 1-6 alkyl; or R 6 is the group COR 20 where R 20 is hydrogen, hydroxy, C 1-6 alkoxy, aryloxy, ar C 1-6 alkyloxy, C 1-6 alkyl, aryl, ar C 1-6 alkyl, or the group NR 21 R 22 where R 21 is hydrogen or C 1-6 alkyl optionally substituted by a hydroxy or C 1-6 alkoxy group; and R 22 is hydrogen, C 1-6 alkyl (optionally substituted by a hydroxy or C 1-6 alkoxy group), C 3-6 alkenyl, aryl, ar C 1-6 alkyl or C 3-8 cycloalkyl, or NR 21 R 22 forms a pyrrolidino ring which may be optionally substituted by hydroxy or one or two C 1-3 alkyl groups; or R 6 is the group CR 23 ═NR 24 where R 23 is hydrogen, C 1-6 alkyl, aryl or ar C 1-6 alkyl and R 24 is hydroxy, C 1-6 alkoxy, ar C 1-6 alkyloxy or --NHC(═Y)NH 2 where Y is oxygen or sulphur; or R 3 and R 7 taken together represent --CH═CH-- 2 or --(CH 2 ) 4 --; with the proviso that when the group R 6 contains a carbon atom through which it is linked to the alkylene group (CH 2 ) q then the total number of carbon atoms in the resulting chain is not greater than 6, that is, q is not greater than 5; and wherein the term aryl as a group or part of a group means phenyl or phenyl substituted with one or more C 1-3 alkyl or alkoxy groups or halogen atoms; the term acyl or the acyl portion of an acyloxyalkyl group means an aroyl, aralkanoyl or C 1-6 alkanoyl group; the term heteroaryl as a group or part of a group means thienyl, pyrrolyl, pyridyl, furyl or thiazolyl, the heteroaryl ring may be unsubstituted or substituted by C 1-3 alkyl, C 1-3 alkoxy, hydroxy C 1-6 alkyl, amino C 1-6 alkyl, C 1-6 alkylamino C 1-6 alkyl, di C 1-6 alkylamino C 1-6 alkyl or halogen, the alkyl portion of a heteroaralkyl group is a straight or barnched C 1-4 alkyl chain, and the heteroaryl ring is linked to the alkyl portion through a carbon atom.