Synthesis and Antiinflammatory and Analgesic Properties of 2-Amino-1 H-benzimidazole and 1,2-Dihydro-2-iminocycloheptimidazole Derivatives

Abstract

(3) and (4) were synthesized and evaluated for antiinflammatory and analgesic activities. The compounds in the series 3 were synthesized via phenylthioureas (6) or (12). Most of 4 were synthesized by two methods. One was the reaction of carbodiimides (14) with (method A). The other was the reaction of guanidines (15) with (method B). Some of the compounds 3 and 4 exhibited potent antiinflammatory and analgesic activities when compared to timegadine (1) or tiaramide hydrochloride (HC1) (17). It was of interest that (4e) showed superior analgesic activity to timegadine or tiaramide HC1 (ED50 = 1.7 mg/kg p.o. in the acetic acid-induced writhing test, ED30 = 14.0 mg/kg p.o. in Randall-Selitto method) in spite of no effect on prostaglandin E2 synthesis. © 1993, The Pharmaceutical Society of Japan. All rights reserved.