3-AMINO-PYROZOLINE DERIVATIVES AND PROCESS FOR THEIR PREPARATION

摘要

Novel heterocyclic compounds are provided of formula (I) (I) wherein, Ar is pyridyl or phenyl, each of which is unsubstituted or substituted in one or two positions in the ring by the same or a different substituent, said substituent being selected from the group consisting of trifluoromethyl, fluoro, chloro, bromo and iodo: R1 is hydrogen or acyl having from 1 to 4 carbon atoms; and R4 and R5 are the same or different and each is hydrogen or alkyl having from 1 to 4 carbon atoms; or a pharmaceutically acceptable acid addition salt thereof, the compounds being selected from the group consisting of: 3-Amino-1-(3,4-dicblorophenyl)-pyrazol-2-ine, 3-Amino-1-(4-trifluoromethylphenyl)-2-pyrazoline, 3-Amino-1-(3,5-dichlorophenyl)-2-pyrazoline, 3-Amino-4-methyl-1-(3-trifluoromethylphenyl)-2-pyrazoline, 3-Amino-1-(p-fluorophenyl)-4-methyl-2-pyrazoline, 3-Amino-5-ethyl-1-phenyl-2-pyrazoline, 3-Amino-1-(m-chlorophenyl)-4-methyl-2-pyrazoline, 3-Amino-1-(p-chlorophenyl)-5-ethyl-2-pyrazoline, 3-Amino-1-(p-fluorophenyl)-5-methyl-2-pyrazoline, 3-Amino-1-(p-chlorophenyl)-4-methyl-2-pyrazoline, 3-Amino-1-(m-trifluoromethylphenyl)-pyrazol-2-ine hydrochloride, 3-Amino-1-(2,6-dichlorophenyl)pyrazol-2-ine hydro chloride monohydrate, 3-Amino-1-(m-chlorophonyl)-5-methyl-2-pyrazoline toluene p-sulphonate 3-Amino-1-(p-chlorophonyl)-5-methyl-2-pyrazoline hydrochloride, 3-Amino-1-(2-pyridyl)-2-pyrazoline, 3-Amino-1-(4-pyridyl)-2-pyrazoline, 3-Amino-1-(2-pyridyl)-2-pyrazoline hydrobromide, 3-Eutyramido-1-(3-chlorophenyl)-2-pyrazoline, 3-Butyramido-5-methyl-1-phenyl-2-pyrazoline, 3-Amino-1-(5-chloro-2-pyridyl)-2-pyrazoline, 3-Amino-1-(5-bromo-2-pyridyl)-2-pyrazoline, 3-Amino-1-(5-iodo-2-pyridyl)-2-pyrazoline, 3-Acetamido-1-(3-trifluoromethylphenyl)-2-pyrazoline. 3-Butyramido-1-(3-trifluoromethylphenyl)-2-pyrazoline, 3-Amino-1-(4-chloro-3-trifluoromethylphenyl)-2-pyrazo-line, and 3-Amino-l-(4-bromo-3-trlfluoromethylphenyl)-2-pyra2oline, the novel compounds exhlbit a potent anti-inflammatory action in mammals when administered topically