Dibenzo[b,f]-1,4-thiazepin-11(10H)-ones IIa-IIc reacted with phosphorus pentasulfide in pyridine under the formation of the thiones IIIa-IIIc which were transformed by treatment with hydrazine hydrate in 1-butanol to the hydrazine derivatives IVa-IVc. Reactions with triethyl orthoformate in ethanol in the presence of sulfuric acid effected cyclization to dibenzo[b,f]-1,2,4-triazolo[4,3-d]-1,4-thiazepine (Va) and its chloro derivatives Vb, Vc which were treated with bromine in a boiling mixture of chlorofom and pyridine and gave the 3-bromo derivatives VIa-VIc. The title compounds Ia-Ic were obtained by substitution reactions with an excess of boiling 1-methylpiperazine. An attempt at preparing an analogous 14H-dibenzo[b,g]-1,2,4-triazolo[4,3-d]-1,4-thiazocine derivative was discontinued in the stage of reaction of the thione X with hydrazine hydrate which resulted in the azine XI. Compounds Ia-Ic on intravenous administration are highly toxic and inactive in tests for CNS effects; compound Ic showed a clear anticholinergic activity.

Reactions of ethyl(2-(phenylthio)phenyl)acetimidate (X) hydrochloride with ammonia and the corresponding amines resulted in amidines V-X. Heating (2-(phenylthio)phenyl)acetonitrile with 2-aminoethylammonium toluene-4-sulfonate led to the 2-imidazoline XI. Reactions of (2-(phenylthio)phenyl)acetonitrile and the lower homologue with hydroxylamine gave the amidoximes XIII and XV; XIII was oxidized to the sulfoxide XIV. Compounds VII, XI, and XIII showed some antireserpine activity which indicates thymoleptic and antidepressant potentiality. On the other hand, none of the compounds tested did show any noteworthy affinity to the [3H]imipramine and [3H]desipramine binding sites in the rat hypothalamus.

ChemInform Abstract A large variety of title compounds such as (VI) and (VIII) are synthesized using reaction sequences generally exemplified in the scheme for (VI). Some of the 2-(methoxy-and hydroxy-phenylthio)benzylamines prepared, especially compounds (VIIIa), indicate properties of potential antidepressants being highly active and selective inhibitors of 5-hydroxytryptamine reuptake in the brain structures and having the typical antireserpine activity. The most interesting compound of the series is (VI) (hydrogen maleate VUFB-15468) which is undergoing preclinical studies. On the basis of its structure, some further compounds are prepared.

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