Morpholino containing 4-arylpiperidine derivatives

Abstract

The present invention is concerned with novel 4-aryl-3/4-amino/hydroxy-piperidine derivatives of the general formula I: ##STR1## wherein R.sub.1 represents hydrogen; lower alkyl; lower aralkyl; lower acyl; aminoalkyl, wherein the alkyl moiety contains 2 to 6 carbon atoms and the amino moiety may be mono- or dialkyl substituted --(CH.sub.2).sub.n --COOH; --(CH.sub.2).sub.n --OH; ##STR2## wherein X is hydrogen or halogen and n is 1, 2, 3 or 4; one of R.sub.2 and R.sub.3 represents a cyano, or a free amino group or a derivative thereof and the other represents a free or protected hydroxyl group; or R.sub.2 represents an azido group when R.sub.3 represents a free or protected hydroxyl group, or R.sub.2 and R.sub.3 together with their associated ring carbons represent an oxazepine ring, and Ar represents an aryl group which may be substituted by lower alkyl, lower alkoxy, halogen or CF.sub.3, as well as addition salts thereof with organic or inorganic acids. Compounds of formula I generally have useful biological properties and in particular, some such compounds had been found to exhibit inter alia, significant antidepressant activity. Illustrative of compounds of formula I is 1-methyl-4-phenyl-4-acetoxy-3-(4-piperidinyl)piperidine. The present invention also provides processes for the production of, and pharmaceutical compositions containing the novel compounds of formula I.