Patent Evaluation: Amidines as Gastric Acid Secretion Inhibitors

Summary

Novelty: N-dimethoxy phenyl alkyl-N′-imidazolylphenylamidine derivatives and processes for their preparation are disclosed. These derivatives are potentially useful anti-ulcer agents.

Biology: Data are provided on inhibition of gastric secretion, inhibition of acid output and inhibition of indomethacin-induced gastric ulcers by the novel derivatives as compared with known compounds (mifentidine, famotidine, cimetidine and ranitidine). Comparable or better results than the standards are obtained.

Chemistry: The novel comopunds have the generic structure illustrated below. Specifically claimed are N-[2-(3,4-dimethoxy phenyl)ethyl]-N′-[4-(imidazol-4-yl)phenyl]formamidine (shown below) and N-[2-(3,4-dimethoxy phenyl)ethyl]-N′-[5-methyl-4-(imidazol)-4-yl) phenyl]-3,4-dimethoxy phenyl acetamidine. Seven examples illustrate the preparation of novel compounds. One method of preparation comprises reacting an N-cyano-N′-[4-(imidazol-4-yl) phenyl]amidine with a 3,4-dimethoxyphenylalkyl amine.

Structure: