Abstract: 1,2-diacylamino-1,2-di(4-pyridil)ethanes of general formula: ##STR1## where R is a saturated or unsaturated alkyl group, a homocyclic or heterocyclic aromatic ring, with or without substituents, or a saturated or unsaturated cycloalkyl. Said compounds are useful as analgesic. A process for preparing such products is also described.
Type:
Grant
Filed:
March 10, 1980
Date of Patent:
September 8, 1981
Assignee:
Laboratorios Made, S.A.
Inventors:
Miguel F. Brana, Maria L. Lopez Rodriguez, Jose M. Castellano Berlanga, Jose L. Soto Camara, Cristobal Martinez Roldan
Abstract: N-substituted-3-substituted naphthalimides are prepared by reacting 3-substituted naphthalic acid with a compound having a primary amino group. The naphthalimides possess cytotoxic properties.
Type:
Grant
Filed:
June 2, 1978
Date of Patent:
May 20, 1980
Assignee:
Laboratorios Made, S.A.
Inventors:
Miguel F. Brana, Antonio M. Sanz, Rafael P. Alvarez-Ossorio, Cristobal M. Roldan, Cristina R. Fernandez de Gamboa
Abstract: 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.
Type:
Grant
Filed:
January 23, 1978
Date of Patent:
December 18, 1979
Assignee:
Laboratorios Made, S.A.
Inventors:
Ricardo Granados Jarque, Mercedes Alvarez Domingo, Juan Bosch Cartes, Cristobal Martinez Roldan, Fernando Rabadan Peinado
Abstract: 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.
Type:
Grant
Filed:
October 6, 1978
Date of Patent:
November 13, 1979
Assignee:
Laboratorios Made, S.A.
Inventors:
Ricardo Granados Jarque, Juan Bosch Cartes, Rosa Llobera Jimenez, Cristobal Martinez Roldan, Fernando Rabadan Peinado
Abstract: 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.
Type:
Grant
Filed:
October 6, 1978
Date of Patent:
November 6, 1979
Assignee:
Laboratorios Made, S.A.
Inventors:
Ricardo G. Jarque, Juan B. Cartes, Rosa L. Jimenez, Cristobal M. Roldan, Fernando R. Peinado
Abstract: 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.
Type:
Grant
Filed:
February 2, 1978
Date of Patent:
October 23, 1979
Assignee:
Laboratorios Made, S.A.
Inventors:
Ricardo G. Jarque, Mercedes A. Domingo, Juan B. Cartes, Cristobal M. Roldan, Fernando R. Peinado
Abstract: Compounds having the formula ##STR1## wherein Y is 2-dimethylaminoethyl, 2-diethylaminoethyl, 2-(N-pyrrolidino)ethyl or 2-(N-piperidino)ethyl. The compounds are prepared by reacting 3-nitronaphthalic acid, or corresponding anhydride, with the corresponding primary amine. The compounds possess cytostatic and raticide properties.
Type:
Grant
Filed:
September 19, 1977
Date of Patent:
March 27, 1979
Assignee:
Laboratorios Made, S.A.
Inventors:
Cristobal M. Roldan, Miguel F. Brana, Jose M. C. Berlanga
Abstract: 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.
Type:
Grant
Filed:
March 14, 1978
Date of Patent:
March 20, 1979
Assignee:
Laboratorios Made, S.A.
Inventors:
Ricardo G. Jarque, Mercedes A. Domingo, Juan Bosch Cartes, Cristobal M. Roldan, Fernando R. Peinado
Abstract: 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.
Type:
Grant
Filed:
April 29, 1975
Date of Patent:
June 14, 1977
Assignee:
Laboratorios Made, S.A.
Inventors:
Juan Bosch Cartes, Jorge Canals Cabiro, Ricardo Granados Jarque, Cristobal Martinez Roldan, Fernando Rabadan Peinado
Abstract: 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.
Type:
Grant
Filed:
March 1, 1976
Date of Patent:
June 7, 1977
Assignee:
Laboratorios Made, S.A.
Inventors:
Ricardo Granados Jarque, Juan Bosch Cartes, Jorge Canals Cabiro, Cristobal Martinez Roldan, Fernando Rabadan Peinado
Abstract: 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.
Type:
Grant
Filed:
April 29, 1975
Date of Patent:
January 4, 1977
Assignee:
Laboratorios Made, S.A.
Inventors:
Ricardo Granados Jarque, Juan Bosch Cartes, Jorge Canals Cabiro, Cristobal Martinez Roldan, Fernando Rabadan Peinado
Abstract: Compounds having the formula ##EQU1## wherein R is 2-picolyl, 3-picolyl or 4-picolyl. The compounds are prepared by reacting dipropylacetic acid, or the corresponding chloride or anhydride, with 2-picolylamine, 3-picolylamine or 4-picolylamine. The compounds possess anti-convulsant and barbiturate potentiation properties.
Type:
Grant
Filed:
October 24, 1974
Date of Patent:
April 20, 1976
Assignee:
Laboratorios Made, S.A.
Inventors:
Christobal Martinez Roldan, Miguel Fernandez Brana, Jose Maria Castellano Berlanga