Verfahren zur Herstellung von Aminoacetylenverbindungen

The invention comprises compounds of general formula wherein R1 is a phenyl, benzyl, cyclohexyl or a -thienyl group, R2 is a phenyl or benzyl group, Z is a hydrogen atom or a hydroxy, methoxy, ethoxy or methylthio group, and Y is a di-(C1-C6) -alkylamino, piperidino, pyrrolidino or morpholino group; and their pharmacologically-acceptable acid addition salts; and their preparation by (1) reacting a compound (wherein Z may also be halogen, the product being then hydrolysed to the hydroxy compound) with formaldehyde (e.g. in the form of paraformaldehyde) and a compound H-Y, or (2) reacting a compound wherein X is a halogen atom or an alkoxy (C1-C6) radical (Z may also be halogen, the product being then hydrolysed to the hydroxy compound), with a compound R6-O-CH2-C­C-CH2Y wherein R6 is a hydrogen atom or a formyl, acetyl or propionyl group, or (3) heating and reacting an a -halo-diphenyl-acetyl halide with a compound HO-CH2-C­C-CH2-Y and treating the product with methanol or ethanol in an alkaline reaction medium and recovering the a -methoxy- or a -ethoxy-diphenyl acetate of the invention. 4-Substituted amino-2-butynol starting materials are prepared from 1-chloro-4-hydroxy-2-butyne and corresponding amines. The methyl esters of a -thienyl- and cyclohexyl-phenylglycollic acids are prepared by Fischer esterification and by hydrolysis of the ethyl ester and esterification respectively. Methyl diphenylethoxyacetate is prepared by Williamson ether synthesis. Pharmaceutical compositions.-Administration of the compounds of the invention orally (e.g. as elixirs, tablets, powders, or suspensions), topically or parenterally (intravenously or by infiltration) is mentioned. The compounds are antispasmodics and local anaesthetics.