Heterocyclic-substituted indoles and pharmaceutical compositions containing them

Claim 1

A compound of the formula: ##STR12## wherein R 1 is hydrogen, methyl, ethyl, isopropyl or phenyl; R 2 is a heterocyclic five-membered ring containing 1 to 4 heteroatoms or a heterocyclic six-membered ring containing 1 to 4 heteroatoms selected from the group consisting of pyrrole, furan, thiophene, pyrazole, imidazole, thiazole, oxazole, triazole, tetrazole, thiadiazole, oxadiazole, pyridine, N-oxypyridine, pyrazine, N,N-dioxypyrazine, pyrimidine, N,N-dioxypyrimidine, pyridazine, oxazine, thiazine, triazine and tetrazine, said five- and six-membered rings optionally being substituted by one or more C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, hydroxyl, nitro, amino, halogen or cyano groups; or R 2 is a phenyl ring of the formula: ##STR13## wherein R 3 , R 4 and R 5 are the same or different and each represents: hydrogen; C 1 -C 5 alkyl-sulphonyloxy; trifluoromethanesulphonyloxy; C 1 -C 5 alkyl-sulphonyamino; trifluoromethanesulphonylamino; N-C 1 -C 5 -alkyl-C 1 -C 5 -alkyl-sulphonylamino; N-C 1 -C 5 -alkyl-trifluoromethanesulphonylamino; C 1 -C 5 -alkyl-sulphenylmethyl; C 1 -C 5 -alkyl-sulphinylmethyl; C 1 -C 5 -alkylsulphonylmethyl; a carbonyl group substituted by hydroxyl, C 1 -C 5 alkoxy, amino, C 1 -C 5 alkylamino oor di-C 1 -C 5 -alkyl-amino; a sulphonyl group substituted by amino, C 1 -C 5 alkylamino or di-C 1 -C 4 -alkyl-amino; a morpholino-, pyrrolidino-, piperidino-, or hexamethyleneimino-sulphonyl radical; C 1 -C 5 alkylcarbonylamino; amino-carbonylamino; C 1 -C 5 alkyl-aminocarbonylamino; C 1 -C 5 alkylthio; C 1 -C 5 alkylsulphinyl; C 1 -C 5 alkylsulphonyl; nitro; halogen; amino; hydroxyl; C 1 -C 5 -alkyl; C 1 -C 5 alkoxy; C 2 -C 5 alkenyloxy; C 2 -C 5 alkynyloxy; cyano-C 1 -C 5 -alkoxy; carboxy-C 1 -C 5 -alkoxy; C 1 -C 5 -alkoxy-carbonyl-C 1 -C 5 -alkoxy; di-C 1 -C 5 -alkylamino; 1-imidazolyl; trifluoromethyl; or cyano; A is a heterocyclic radical selected from the group consisting of 3-oxo-2,3-dihydro-6-pyridazinyl, 5-alkyl-3-oxo-2,3-dihydro-6-pyridazinyl, 3-oxo-2,3,4,5-tetrahydro-6-pyridazinyl, 5-alkyl-3-oxo-2,3,4,5-tetrahydro-6-pyridazinyl, 5-hydroxyalkyl-3-oxo-2,3,4,5-tetrahydro-6-pyridazinyl, 3-cyano-6-alkyl-2-oxo-1,2-dihydro-5-pyridinyl, 3-aminocarbonyl-6-alkyl-2-oxo-1,2-dihydro-5-pyridinyl, 6-alkyl-2-oxo-1,2-dihydro-5-pyridinyl, 3-amino-6alkyl-2-oxo-1,2-dihydro-5-pyridinyl, 3-hydroxy-6-alkyl-2-oxo-1,2-dihydro-5-pyridinyl, 3-oxo-2H-3,4-dihydro-1,4-thiazin-6-yl, 6-oxo-1,6-dihydro-1,2,4-triazin-3-yl, 6-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl, 5-oxo-4,5-dihydro-6H-1,3,4-oxadiazin-2-yl, 5-oxo-4,5-dihydro-6H-1,3,4-thiadiazin-2-yl, 3-oxo-2,3-dihydroo-1,2,4-triazin-6-yl, 3-oxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl, 2-oxo-2,3-dihydro-6H-1,3,4-oxadiazin-5-yl, 2-oxo-2,3-dihydro-6H-1,3,4-thiadiazin-5-yl, 5-alkyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazin-6-yl, 2-oxo-1,2-dihydro-5-pyrimidinyl, 4-alkyl-2-oxo-1,2-dihydro-5-pyrimidinyl, 2-oxo-1,2-dihydro-5-pyrazinyl, 3-alkyl-2-oxo-1,2-dihydro-5-pyrazinyl, 6-alkyl-2-oxo-1,2-dihydro-5-pyrazinyl, 4,4-dialkyl-5-oxo-4,5-dihydro-3-pyrazolyl, 2-oxo-4-pyrrolidinyl, 3-alkyl-2-oxo-4-pyrrolidinyl, 5-oxo-4,5-dihydro-1,2,4-triazol-3-yl, 4-alkyl-5-oxo-4,5-dihydro-1,2,4-triazol-3-yl, 2-oxo-2,3-dihydro-4(5)-imidazolyl and 5(4)-alkyl-2-oxo-2,3-dihydro-4(5)-imidazolyl; X is a valency bond or a C 1 -C 4 alkylene or vinylene group, a tautomer thereof or a physiologically acceptable salt thereof with an inorganic or organic acid.