NEW AND USEFUL BENZAMIDINES AND METHOD OF MAKING SAME

摘要

1,267,009. Benzamidines. USV PHARMACEUTICAL CORP. 13 July, 1970 [25 July, 1969], No. 33860/70. Heading C2C. Novel compounds of Formula I (in which R is C 1-5 alkyl, cycloalkyl, phenyl, naphthyl, pyridyl, or phenyl substituted by one or more of C 1-5 alkyl, C 1-5 alkoxy, C 1-5 alkylthio, halogen and CF 3 , R1 is H, C 1-5 alkyl, C 1-5 alkoxy or halogen, each of R11 and R111 is C 1-5 alkyl, phenyl or phenyl-C 1-5 alkyl, or -NR11R111 is morpholino, pyrrolidino, piperidino, piperazino, N-methyl-piperazino or thiamorphalino, and n is 2, 3 or 4) and pharmaceutically acceptable, acid addition salts thereof, are prepared by (a) heating in an inert solvent in the presence of a base, a compound of Formula II with a compound of formula or (b) heating in an inert solvent, a compound of Formula III with a compound of Formula IV and, if desired, converting the resulting hydrochloride to the free base by treatment with ammonia in an inert solvent. The free bases may be converted to acid addition salts in known manner. N1 - phenyl - N - (4 - hydroxyphenyl) - benzamidine hydrochloride is prepared by reacting N-phenylbenzimidoyl chloride with p-aminophenol. Pharmaceutical compositions for oral or parenteral administration comprise a compound of Formula I, or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical carrier. Compounds I have hypoglycemic activity and, in certain cases, also antihistaminic activity.