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Paper | Regular issue | Vol 41, No. 4, 1995, pp.709-720
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6974
Synthesis of Thieno-Diltiazem Analogues

Isolde Puschmann and Thomas Erker

*Institute for Pharmaceutical Chemistry, University of Vienna, A-1090 Vienna, Althanstr.14, Austria

Abstract

The replacement of benzene by thiophene in a molecule might result in an altered metabolism of the modified drug, a different biochemical profile and/or an elimination of side effects to a certain extent. Replacement of the fused aromatic moiety in diltiazem with thiophene provides cis-4-[(2-dimethylamino)-ethyl]-4,5,6,7-tetrahydro-7-(4-methoxyphenyl)-5-oxo-thieno[2,3-b][1,4]thiaz-epin-6-yl acetate (20). The synthsis starts with the reaction of 3-nitro-2-thiophenethiol and racemic trans-(4-methoxyphenyl)glycidate. The resulting threo and erythro products are reduced, cyclized, alkylated and acetylated to give the desired compounds (20) and (21).