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Synthesis and cardiovascular activity of a new series of cyclohexylaralkylamine derivatives related to perhexiline.

A series of 24 cyclohexylaralkylamine derivatives related to perhexiline has been synthesized and screened for cardiovascular activity. All the compounds contained an exocyclic amine which was substituted either by an alkyl, cycloalkyl, or aralkyl group. In the hope of further reducing toxicity, the synthesis of p-tolyl- and p-hydroxyphenyl derivatives 23 and 24 was undertaken. The effect of separating the cyclohexylamine moiety with respect to the aromatic nucleus has been systematically examined. The pharmacological investigations were directed to a search for compounds having an activity better than perhexiline according to the following order of criteria: (1) alpha-adrenolytic activity; (2) increase of coronary blood flow; (3) calcium antagonism. Several compounds were more potent and exhibited lower toxicity than perhexiline. Further detailed pharmacological investigations (tension time index and decreased cardiac work) have led to the selection of N,2-dicyclohexyl-2-phenethylamine (3) for clinical trials, which are now under way.