Experimental antiulcer agents: N-substituted 2-(4-methyl-1-piperazinyl)acetamides as pirenzepine models and some related compounds

Abstract

Reactions of N-cyclohexyl-2-chloroacetamide, N-phenyl-2-chloroacetamide, N-(4-dimethylaminophenyl)-2-chloroacetamide, N-(2-nitrophenyl)-N-phenyl-2-chloroacetamide, its 3-nitrophenyl and 4-nitrophenyl analogues, N-(2-benzylphenyl)-2-chloroacetamide, 5-(chloroacetyl)-dibenz[b,f]azepine, and its 10,11-dihydro derivative with piperazine, 1-methylpiperazine, 2-(1-piperazinyl)ethanol, and 3-(1-piperazinyl)propanol resulted in compounds II, III, V-XV, XVIII, XXI, and XXIII, simple analogues of the antiulcer agent pirenzepine (I). Contributions to the syntheses and characterization of mianserin (XIX), bisnor analogue of imipramine (XXV), and pirenzepine (I) are presented. Two 2-aryl-2-(2-pyridyl)thioacetamides XXXVIII and XL were synthesized via nitriles XXXIX and XLI. Compounds XI (VÚFB-17 104) and XXI (VÚFB-17 113) were found to be rather effective as antiulcer agents and anticholinergics.