Collect. Czech. Chem. Commun. 1989, 54, 225-228

Potential antidepressants: Synthesis of two 4-(aminoalkoxy)dibenzo[b,e]thiepin-11(6H)-ones

Irena Červená, Jiří Holubek, Emil Svátek, Jan Metyš, Martin Valchář and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Heating of 4-methoxydibenzo[b,e]thiepin-11(6H)-one with pyridine hydrochloride to 225 to 235 °C effected demethylation and gave IV. Its sodium salt reacted with 3-dimethylaminopropyl chloride in ethanol and afforded the 4-(3-dimethylaminopropoxy) compound II. The isomeric ether III was prepared via the 4-(4-bromobutoxy) compound V. Hydrochloride of II (VÚFB-17 033) inhibited mildly the binding of [3H]desipramine in rat hypothalamus, had antireserpine activity in rats, mild anticonvulsant effect, and antihypoxic effect in the test of nitrogen anoxia in mice.