Laboratorios Made, S.a.

Laboratories Made, S.a.

Jorge Canals Cabiro

Cristobal M Roldan

Juan Bosch Cartes

Fernando Rabadan Peinado

Ricardo Granados Jarque

3,4,5-TRIMETHOXY-PHENYL-(1,4-DEIMETHYL-1,2,3,6-TETRAHYDRO-2-PYRIDYL)-CARBIN OL, AND ACID ADDITION SALTS THEREOF, USEFUL AS ANALGESICS, AND THEIR PREPARATION ARE DISCLOSED.

Process for the preparation of

2-(3,4,5-Trimethoxy benzyl)-3,4-dimethyl pyridine and 2-(3,4,5-trimethoxyphenyl)-(3,4-dimethyl-2-pyridyl)-ethoxy-methane and their pharmaceutically acceptable acid addition salts have analgesic properties.

Certain analgesically active substituted benzyl pyridine compounds

The compound 1,3,4-trimethyl-1-(3,4,5-trimethoxy-benzyl)-1,2,5,6-tetrahydropyridine chloride and the Hoffmann degradation thereof to produce N-Methyl-N-(3,4,5-Trimethoxybenzyl) 2,3-Dimethyl-2,4-Pentadienamine is disclosed.

The compound

There is disclosed a process for the preparation of 1,3,4-trimethyl-2-(3,4,5-trimethoxybenzyl)-1,2,5,6-tetrahydropyridine of formula ##STR1## which comprises subjecting 1,3,4-trimethyl-(3,4,5-trimethoxybenzyl)-1,2,5,6-tetrahydropyridine of formula ##STR2## to a Stevens rearrangement in the presence of a solution of phenyl-lithium in ether under reflux of the reaction mixture, and, if desired, converting the compound of formula I produced into an addition salt thereof with a pharmaceutically acceptable acid, for example hydrochloric acid, including a pharmaceutical composition utilizing as an active ingredient 1,3,4-trimethyl-2-(3,4,5-trimethoxybenzyl)-1,2,5,6-tetrahydropyridine.

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Barcelona, Spain

Jorge Canals Cabiro