Collect. Czech. Chem. Commun. 1983, 48, 163-172

Potential antidepressants: Some N-substituted derivatives of (E)-11-(3-methylaminopropylidene)-6,11-dihydrodibenzo[b,e]thiepin

Miroslav Rajšner, Jan Metyš, Jiří Holubek and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Alkylation reactions of (E)-11-(3-methylaminopropylidene)-6,11-dihydrodibenzo[b,e]thiepin (II) with alkyl bromide, propargyl bromide, 2-chloroethanol, 1-chloropropan-2-ol and 3-chloropropanol gave the N-substituted derivatives III - VII. Acylation of amino alcohols V - VII with acetyl chloride and decanoyl choride resulted in the esters VIII - XI. 6,11-Dihydrodibenzo[b,ethiepin-11-carboxylic acid was transformed via the acid chloride to the amide XIV. Out of the compounds prepared, only the amino alcohols V- VII and the ester VIII revealed in pharmacological tests the activity similar to that of tricyclic antidepressants; their activity is lower than that of prothiadene (I). The decanoates IX - XI are devoid of antireserpine activity; the attempt at finding long-acting depot antidepressant agents in this way was thus unsuccessful. The amide XIV has mild anticonvulsant activity.