[The synthesis, analysis, stability and biotransformation of N-(3-methylphenyl)-N'-cyanobenzamidine and analogues (author's transl)]. / Synthese, Analytik, Stabilität und Biotransformation von N-(3-Methylphenyl)-N'-cyanbenzamidin und Analoga.

The antivirally active N-(3-methylphenyl)-N'-cyanobenzamidine (1) and some of its analogues were synthetized by the reaction of the ethyl ester of N-cyanobenzimidic acid with the corresponding arylamines. The analytical profile of 1 and of some of its analogues, which is needed for stability and biotransformation studies, was established by means of the following techniques: solubility determination, TLC, UV, IR and MS. When 1 is heated with methanolic HCl and NaOH (0.5 mol/l) for 1 h, several hydrolysis products are formed: m-toluidine, benzoic acid, benzoic acid 3-toluidide, N-(3-methylphenyl)benzamidine, N-(3-methylphenyl)-N'-carboxamidobenzamidine, benzoylurea, However, 1 is fairly stable under physiological conditions so biotransformation studies are not affected. After oral application of 1 to rats, the 3-hydroxymethyl and the 3-methyl-5-hydroxy compound as well as its glucuronide and sulphate conjugate were detected in the urine. The faeces contained considerable amounts of unchanged 1 (incomplete absorption).

[Synthesis and spectrum of pharmacologic action of aryl-arylamino- and aryl-aryliminoacetonitriles]. / Synthese und pharmakologisches Wirkungsspektrum von Aryl-arylamino- und Aryl-aryliminoacetonitrilen.

Aminoacetonitriles were synthetized from arylaldehyde, arylamine and cyanhydrogene. Their dehydrogenation led to the iminoderivatives. The compounds were evaluated for spasmolytic activity in vitro. Some aryl-arylaminoacetonitriles showed significant inhibition of the histamine-induced contraction in guinea-pig ileum and acetylcholine-induced contraction in rat ileum. Structure-activity relationships are discussed.