3-mercapto-glutamic acid derivatives

An amino acid compound of the formula:

• ##STR139## wherein R.sup.1 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms,
• R.sup.2 represents mono-, bi- or tri-carbocyclic ring(s) containng not more than 15 carbon atoms which may be partially or fully saturated or aromatic or R.sup.2 represents heterocyclie ring selected from the group consisting of furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, furazan, pyran, pyridine, pyridazine, pyrimidine, pyrazine, indole, isoindole, benzofuran, benzothiophene, indolizine, benzimidazole, benzthiazole, benzoxazole, chromene, quinoline, isoquinoline, quinolizine, purine, indazole, quinazoline, cinnoline, quinoxaline, phthalazine, pteridine, benzodiazepine, carbazole, acridine, phenanthridine, xanthene, phenazine and phenothiazine rings which may be may be partially or fully saturated or aromatic wherein the said cabocyclic ring or heterocyclic ring represented by R.sup.2 is unsubstituted or substituted by 1 to 3 R.sup.3 s,
• R.sup.3 represents independently:
• (1) a halogen atom,
• (2) a trihalomethyl group,
• (3) a hydroxy group,
• (4) an alkyl group of 1 to 15 carbon atoms,
• (5) an alkoxy group of 1 to 4 carbon atoms,
• (6) an alkylthio, alkylsulfinyl or alkylsulfonyl group of 1 to 4 carbon atoms,
• (7) a group of the formula:
• ##STR140## in which R.sup.4 represents a hydrogen atom, a halogen atom, a trihalomethyl group, a hydroxy group, an alkyl group of 1 to 4 carbon atoms or an alkoxy group of 1 to 4 carbon atoms,
• (8) a group of the formula
• --NR.sup.5 R.sup.6
• in which R.sup.5 and R.sup.6 independently represent a hydrogen atom or an alkyl group of 1 ;
• to 4 carbon atoms,
• (9) a group of the formula
• --CO--R.sup.7
• in which R.sup.7 represents an alkyl group of 1 to 4 carbon atoms or a phenyl group substituted by R.sup.4 in which R.sup.4 is as hereinbefore defined,
• (10) a group of the formula:
• --COOR.sup.8
• in which R.sup.8 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms,
• (11) a group of the formula:
• --CONR.sup.5 R.sup.6
• in which R.sup.5 and R.sup.6 are as hereinbefore defined,
• (12) a group of the formula:
• --SO.sub.2 NR.sup.5 R.sup.6
• in which R.sup.5 and R.sup.6 are as hereinbefore defined,
• (13) a cyano group,
• (14) a nitro group, or
• (15) a group of the formula:
• --NHCO--R.sup.7,
• in which R.sup.7 is as hereinbefore defined,
• Z represents:
• (1) a hydrogen atom,
• (2) a group of the formula
• --COR.sup.9
• in which R.sup.9 represents an alkyl group of 1 to 4 carbon atoms or a phenyl group substituted by R.sup.10, in which R.sup.10 represents a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group of 1 to 4 carbon atoms or an alkoxy group of 1 to 4 carbon atoms,
• (3) a group of the formula:
• ##STR141## in which R.sup.10 is as hereinbefore defined, (4) a group of the formula:
• ##STR142## in which R.sup.11 and R.sup.12 independently represent a hydrogen atom, an alkyl group of 1 to 4 carbon atoms or a phenyl group substituted by R.sup.10, in which R.sup.10 is as hereinbefore defined, or R.sup.11 and R.sup.12 together represent an alkylene group of 4 or 5 carbon atoms and p is an integer of 1 or 2,
• (5) a group of the formula:
• ##STR143## in which each of the two R.sup.10 s are independently as hereinbefore defined,
• (6) a group of the formula:
• ##STR144## in which R.sup.10 is as hereinbefore defined and q is an integer of 1 to 4,
• (7) a group of the formula:
• ##STR145## in which R.sup.10 is as hereinbefore defined, A represents a phenyl or cycloalkyl group of 4 to 7 carbon atoms, substituted by R.sup.13, in which R.sup.13 represents a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group of 1 to 4 carbon atoms or an alkoxyl group of 1 to 4 carbon atoms, and
• m and n represent:
• (1) when m is zero, n is an integer of 1 to 4, and
• (2) when n is zero, m is an integer of 1 to 4, with the proviso that
• (i) when R.sup.1 represents a hydrogen atom, R.sup.2 represents a pyridyl group, m represents an integer of 2 and when n represents zero, Z does not represent a hydrogen atom, and
• (ii) when R.sup.2 represents a heterocyclic ring selected from the group consisting of benzthiazole, thiazole, isothiazole, benzoxazole, oxazole and isoxazole wherein the said ring represented by R.sup.2 is unsubstituted or substituted by 1 to 3 R.sup.3 s, where at least one of R.sup.3 represents:
• (1) a group of the formula:
• --NR.sup.5 R.sup.6
• in which R.sup.5 and R.sup.6 independently represent a hydrogen atom or an alkyl group of 1 to 4 carbon atoms,
• (2) a group of the formula:
• --CONR.sup.5 R.sup.6
• in which R.sup.5 and R.sup.6 are as hereinbefore defined,
• (3) a group of the formula:
• --SO.sub.2 NR.sup.5 R.sup.6
• in which R.sup.5 and R.sup.6 are as hereinbefore defined,
• (4) a cyano group,
• (5) a nitro group, or
• (6) a group of the formula:
• --NHCO--R.sup.7,
• in which R.sup.7 represents an alkyl group of 1 to 4 carbon atoms or a phenyl group substituted by a hydrogen atom, a halogen atom, a trihalomethyl group, a hydroxy group, an alkyl group of 1 to 4 carbon atoms, an alkoxyl group of 1 to 4 carbon atoms,
• Z does not represent a hydrogen atom,
• or a non-toxic salt thereof.