Laboratorios Made, S.a.

Laboratories Made, S.a.

Ricardo Granados Jarque

Fernando Rabadan Peinado

Juan Bosch Cartes

Cristobal M Roldan

Jorge Canals Cabiro

Cristobal Martinez Roldan

Mercedes A Domingo

Mercedes Alvarez Domingo

Rosa Llobera Jimenez

Francisco L Calahorra

2,5-Dimethyl-benzo[b]thieno[2,3-f]morphan and the precursors thereof, 2-(3-benzo[b]thienylmethyl)-1,4-dimethyl-1,2,3,6-tetrahydropyridine and 2-(3-benzo[b]-thienylmethyl)-1,4-dimethyl-1,2,5,6-tetrahydropyridine, useful as analgesic agents, are disclosed.

2,5-Dimethyl-benzo[b]-thieno[2,3-f]morphan and precursors thereof

2,5-dimethyl-benzo [b] thiene [3,2-f] morphan and 2-(2-benzo [b] thienyl-methyl)-1,4-dimethyl-1,2,3,6-tetrahydropyridine or their pharmacologically acceptable acid addition salts are useful as analgesic agents.

2,5-Dimethyl-benzo(b) thiene (3,2-f) morphan and precursor thereof

Furfural is reacted with 2-bromo-3,4-dimethylpyridine in an ether solution of butyl-lithium at about -15.degree. C. in an inert atmosphere to form 2-furyl-(3,4-dimethyl-2-pyridyl)-carbinol, having analgesic properties.

2-Furyl-(3,4-dimethyl-2-pyridyl)-carbinol

2-Cyano-4-methylpyridine is reacted in an inert atmosphere with an ethereal solution of freshly prepared 2-furoyl-lithium followed by acid hydrolysis to form 2-(2-furoyl)-4-methylpyridine which is then reacted with methyl iodide to form 2-(2-furoyl)-1,4-dimethylpyridinium iodide. Both furoyl compounds exhibit thermal and chemical analgesic properties.

2-(2-Furoyl)-4-methylpyridine and its methyl iodide quaternary salt

3-Thienyl-3-methyl-4-pentyl-2-pyridyl-ketone of the formula: ##STR1## useful as an analgesic and a process for its preparation are disclosed.

3-Thienyl-3-methyl-4-pentyl-2-pyridyl-ketone

Alpha-2,5,9-trimethyl-benzo [b]thiene [2,3-f]morphan and 2-(3-benzo[b]thienylmethyl)-1,3,4-trimethyl-1,2,5,6-tetrahydropyridine or their pharmacologically acceptable acid addition salts are useful as analgesic agents.

Alpha-2,5,9-trimethyl-benzo(b)thiene(2,3-f)morphan and precursor thereof

The compound 1,4,4a-trimethyl-1,2,4a,4b,9a,10a-hexahydro-10H benzo �b! thieno �2',3':4,3! cyclopent �1,2-b!-pyridine of the formula: ##STR1## or a pharmaceutically acceptable acid addition salt thereof is disclosed as an analgesic compound.

1,4,4A-Trimethyl-1,2,4a,-4b,9a,10a-hexahydro-10H-benzo �b! thieno

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

Ricardo Granados Jarque