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.

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.

Die Thiophenole (I) reagieren mit dem Nitril (II) zu den Arylthjoacetonitrilen (III), die in die Titelverbindungen (IV) bzw. deren Hydro‐ Chloride übergeführt werden.

Nucleophilic substitution reactions of a series of thio-substituted fluoroarenes with 1-methyl-4-piperidinol, 1-benzyl-4-piperidinol, and 1-methyl-4-phenyl-4-piperidinol in the presence of sodium hydride in dimethylformamide gave the title compounds V-XI and XIII. The salts of these bases were pharmacologically tested and salts of compounds V, XI, and XIII showed in behavioural tests properties which are indicative of antidepressant activity.

Substituted N,N-Dimethyl-3-(phenylthio)-and -4-(phenylthio) benzylamines.-Twelve selected derivatives of 3-phenylthio-and 4phenylthiobenzylamine are synthesized in order to determine the influence of the structural manipulation (positional isomerism) on the biological activity. The most interesting compound (IXa) shows affinity to cholinergic and 5-HT2 serotonin receptors in the rat brain and some properties considered to be indicative of antidepressant activity. -(SINDELAR, K.; KMONICEK, V.; HRUBANTOVA, M.; POLIVKA, Z.; Collect. Czech. Chem. Commun. 57 (1992) 1, 194-203; Res. Inst. Pharm. Biochem., 130 60 Prague 3, CSFR; EN)