Potential antidepressants: 10-Amino-2-chloro-10,11-dihydrodibenzo[b,f]thiepins

Abstract

Reduction of N-(2-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yl)formamide with lithium aluminium hydride resulted in the methylamino compound IV. The dimethylamino compound V was obtained by methylation of 10-amino-2-chloro-10,11-dihydrodibenzo[b,f]thiepin with formic acid and aqueous formaldehyde. Substitution reactions of 2,10-dichloro-10,11-dihydrodibenzo[b,f]thiepin with a series of primary and secondary amines afforded the title compounds VI to XXVIII. The bases were transformed to salts and pharmacologically tested. Only the pyrrolidino compound IX (hydrogen succinate VÚFB-15 551) showed a clear pharmacological profile of a potential antidepressant.