Potential antidepressants: 6-(Aminoalkoxy)dibenzo[b,f]thiepin-10(11H)-ones and 6-(aminoalkoxy)-10,11-dihydrodibenzo[b,f]thiepin-10-ols

Abstract

Sodium salts of 6-hydroxydibenzo[b,f]thiepin-10(11H)-one and its 2-chloro derivative were reacted with hydrochlorides of 2-dimethylaminoethyl chloride, 2-(piperidino)ethyl chloride, 3-dimethylaminopropyl chloride, and 3-(piperidino)propyl chloride in ethanol in the presence of sodium ethoxide which resulted in the title compounds IIa, IIb, IVa, Va, Vb, and VIIa. The tertiary amines IIa, IIb, and Va were partially demethylated via the carbamates VIIIa, VIIIb, and IXa to the secondary amines IIIa, IIIb, and VIa. The amino ketones IIa and Va were reduced to the amino alcohols XII and XIII. With the exception of compound Va (hydrochloride VÚFB-15 515), the products lacked completely the expected pharmacological profile of potential antidepressants.