ES325829A2 - A procedure for producing derivatives of 17 exoyohimban or aloyohimbane. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

Improvements introduced in the object of the main Patent No. 279,152, issued September 28, 1962, by: A process for producing 17-oxoyohimban derivatives or alloyohimban, substituted in 18-methylene, of the formula: ** (See formula) ** wherein: (1) R is a hydrogen atom and R1 is a n-butyl, tert-butyl, lower cycloalkyl, pyridyl, lower alkyl substituted by pyridyl, lower alkyl substituted by lower alkoxy group in which the lower alkyl part contains from 2 to 4 carbon atoms, or lower alkyl substituted by di (lower alkyl) -amino; or (2) R and R1 are each an n-propyl group; or (3) R and R1 together with the nitrogen atom form a heterocyclic group consisting of a 4-substituted piperazino group of the formula: ** (See formula) ** wherein R is phenyl, lower alkyl having from 2 to 6 carbon atoms, lower alkoxycarbonyl or a side chain of the formula: ** (See formula) ** wherein n is an integer from 1 to 4, or a 4-substituted piperidino group of the formula: ** (See formula) ** or of the formula: ** (See formula) ** wherein n is an integer from 1 to 4 and R3 is cyano, acetamidomethyl, lower alkoxy, lower alkanoyl, lower alkanoyl-oxy, lower alkoxycarbonyl or a side chain of the formula: ** (See formula) ** wherein n is an integer from 1 to 4, and pharmaceutically acceptable non-toxic acid addition salts thereof, characterized by: (a) condensing a yohim-ban-17-one or alloyohimban-17-one with a lower alkyl formate in the presence of a Claisen type condensation reagent to form the corresponding 18-hydroxymethylene derivative, (b) condensing the thus-formed hydroxymethylene derivative with a primary or secondary amine, to thereby produce the product of formula I, (c) and, if desired, forming the acid addition salts of the above. (Machine-translation by Google Translate, not legally binding)