3-amino-pyrozoline derivatives and process for their...

C - Chemistry – Metallurgy – 07 – D

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C07D 401/04 (2006.01) C07D 213/04 (2006.01)

Patent

CA 1150266

ABSTRACT OF THE DISCLOSURE Novel heterocyclic compounds are provided of formula (I) (I) Image wherein, Ar is pyridyl or phenyl, each of which is unsub- stituted or substituted in one or two positions in the ring by the same or a different substituent, said sub- stituent 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 pharma- ceutically 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

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