Synthesis of pyrrolidine derivatives with pharmacological activity. X. Synthesis of 1,1-diethyl- and 1,1-(epimeric)-ethylmethyl-2-methyl-4-diphenyl-methylenepyrrolidinium iodides as potential anticholinergic agents (author's transl)

Abstract

In the course of studies on the synthesis of pyrrolidine derivatives, which are analogous to Prifinium Bromide (1, 1-diethyl-2-methyl-3-diphenylmethylenepyrrolidinium bromide (1) ; Padrin[○!R], Riabal[○!R]), we prepared the ethiodide (5) of 1, 2-dimethyl-4-diphenylmethylenepyrrolidine, the methiodide (6) and the ethiodide (7) of 1-ethyl-2-methyl-4-diphenylmethylenepyrrolidine. We also present stereochemical data on diastereoisomeric quaternary pyrrolidinium salts 5 and 6, using nuclear magnetic resonance (NMR) spectroscopy. The anticholinergic action of 5, 6 and 7 was 0.13, 0.05, and 0.14, respectively in contrast to atropine which was defined as 1.00. There was no marked difference in the intensity of the action of the epimeric 1, 1-ethylmethyl compounds 5 and 6.