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.
Vnter Anwendung frUher beschriebener Methoden wurden sechs Ar-Monochlorderivate und das 2,8-Dichlorderivat des 10-(4-Methylpiperazino )-10, II-dihydrodibenzo[b, f]thiepins (/) synthetisiert. Ferner werden die entsprechenden 10-(2-Dimethylaminoathoxy)-Derivate XIV und drei weitere Amine dieser Gruppe (XV-XVII) beschrieben. In einigen Fallen wurden die Synthesen tiber neue Ausgangsstoffe durchgefiihrt (/1, XIX, XX); einige Nebenreaktionen (Bildung der Substanzen XVIII und XXI) werden beschrieben. Es wurde festgestellt, daB aIle beschriebenen Endprodukte eine schwachere zentral dampfende Wirkung aufweisen als die Grundsubstanz 1 (R 1 = R 2 = H) bzw. ihr 8-Chlorderivat (/, R 1 = H, R 2 = 8-CI).
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.
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