Patents by Inventor Alain Heymes
Alain Heymes has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 6215005Abstract: A process for the preparation of [2-(2-thienyl)-ethylamino]-(2-halogenophenyl)-acetonitriles of general formula (I) starting from 2-(2-thienyl)-ethyl-amine, alkalicyanide and o-halogeno-benzaldehyde. Compounds of general formula (I) are valuable intermediates.Type: GrantFiled: May 3, 2000Date of Patent: April 10, 2001Assignee: Sanofi-SynthelaboInventors: Alain Heymes, Bertrand Castro, Mária Bakonyi, Marianna Csatáriné Nagy, Leventéné Molnár
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Patent number: 5266711Abstract: The invention relates to a process for the preparation of 3-benzoyl benzofuran derivatives of general formula: ##STR1## wherein a benzofuran derivative of general formula: ##STR2## is reacted in situ in the presence of aluminium chloride successively with phosgene or oxalyl chloride, and then with a phenolic derivative of general formula: ##STR3## to produce a complex which is hydrolysed to form the desired compound of 3-benzoyl benzofuran.Type: GrantFiled: October 16, 1990Date of Patent: November 30, 1993Assignee: SanofiInventors: Bernard Boudet, Jean R. Dormoy, Alain Heymes
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Patent number: 5262561Abstract: Composition consisting of a mixture of (E) and (Z) isomers of esters of general formula: ##STR1## in which R represents a C.sub.1 -C.sub.4 alkyl radical, containing at least 85% of (E) isomer.A process for preparing such a composition. The use of such a composition for preparing (E)-2-propyl-2-pentenoic acid of formula: ##STR2## and also its pharmaceutically acceptable salts.Type: GrantFiled: March 13, 1992Date of Patent: November 16, 1993Assignee: Elf SanofiInventors: Andre Bousquet, Alain Heymes
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Patent number: 5132435Abstract: The invention relates to isopropyl 2-thienylglycidate of formula: ##STR1## obtained by reaction of 2-thienylcarboxaldehyde with an isopropyl haloacetate. It is employed as a synthesis intermediate in the preparation of 2-thienylacetaldoxime and of medications derived from thieno[3,2-c]pyridine.Type: GrantFiled: July 2, 1991Date of Patent: July 21, 1992Assignee: SanofiInventors: Andre Bousquet, Serge Calet, Alain Heymes
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Patent number: 5081240Abstract: The object of the invention is a process for the preparation of the trans(-) (2R,3S) diastereoisomer of the glycidic esters of general formula: ##STR1## wherein a chlorohydrin of general formula: ##STR2## is reacted with a strong organic base in a suitable solvent and at a temperature between -10.degree. C. and room temperature.Another object of the invention is intermediate compounds cis(+) (2S,3S) 1,5-benzothiazepin-4-one.Type: GrantFiled: July 12, 1990Date of Patent: January 14, 1992Assignee: SanofiInventors: Andre Bousquet, Jean-Robert Dormoy, Alain Heymes
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Patent number: 5079363Abstract: The subject of the present invention is a process for the preparation of isoquinoline derivatives in four steps wherein use is made as synthetic intermediates of organo-lithium compounds or related compounds.Type: GrantFiled: February 22, 1989Date of Patent: January 7, 1992Assignee: SanofiInventors: Michel Bouisset, Andre Bousquet, Jean-Robert Dormoy, Alain Heymes
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Patent number: 5075486Abstract: The invention relates to the preparation of di-n-propylacetonitrile, according to a process consisting in heating N-(1-propyl-n-butyl)formamide to a temperature of between 350.degree. C. and 550.degree. C. and in the absence of oxygen, in the presence of a catalyst consisting of a silica impregnated with 0.1 to 10% by weight of alkali metal cations.Type: GrantFiled: September 14, 1990Date of Patent: December 24, 1991Assignee: SanofiInventors: Michel Bouisset, Christian Forqlly, Andre Bousquet, Alain Heymes
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Patent number: 5071985Abstract: The invention relates to a process for the preparation of morphinane derivatives of general formula: ##STR1## by demethylation of 3-methoxylated compound with a sulfonic acid selected from methanesulfonic acid and trifluoromethanesulfonic acid in the presence of a sulfide.Type: GrantFiled: September 12, 1989Date of Patent: December 10, 1991Assignee: SanofiInventors: Jean-Daniel Andre, Jean-Robert Dormoy, Alain Heymes
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Patent number: 4831144Abstract: The invention relates to a process for fixing an electrophilic group in the 2-position of 1H-pyrrolo[3,2-c]pyridine N-protected in the 1-position, process which consists in protecting the 1-position in question with a labile protecting group, reacting the compound so obtained with a lithiation agent selected from a lithium amide and an alkyl lithium at a temperature between -80.degree. C. and -20.degree. C. and in the presence of tetramethylethylenediamine to obtain the corresponding 2-lithio derivative and then condensing the metal derivative so obtained at a temperature between -80.degree. C. and room-temperature with a reagent capable of giving rise to an electrophilic group to form N-protected 1H-pyrrolo[3,2-c]pyridine substituted in the 2-position by an electrophilic group.Type: GrantFiled: January 7, 1988Date of Patent: May 16, 1989Assignee: SANOFIInventors: Jean-Robert Dormoy, Alain Heymes
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Patent number: 4713485Abstract: The invention relates to a process for preparing .alpha.-hydroxy-alkanoic acids of general formula: ##STR1## in which R represents hydrogen or a lower alkyl radical and Cy represents phenyl or a heterocyclic radical, both radicals optionally comprising one or more substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl radicals and halogen atoms, process which comprises the treatment of an .alpha.,.alpha.-dihalogenated ketone of general formula: ##STR2## in which R and Cy have the same meaning as above and X represents chlorine, bromine or iodine, in the presence of an aqueous solution of an alkali metal hydroxide and a non polar organic solvent selected from an aromatic or alicyclic hydrocarbon, the treatment being carried out at a temperature between the boiling temperature of the reaction medium at atmospheric pressure and 240.degree. C. under pressure and the alkali metal so formed is then acidified to obtain the desired acid.Type: GrantFiled: November 21, 1985Date of Patent: December 15, 1987Assignee: SANOFI and Industria Chimica Prodotti FRANCIS S.p.A.Inventors: Jean-Daniel Andre, Pierre-Jean Grossi, Alain Heymes, Giovanni V. Manzaroli
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Patent number: 4675419Abstract: The invention relates to a process for preparing .alpha.-hydroxy-acids of general formula: ##STR1## in which R represents hydrogen or a lower alkyl radical and Cy represents a phenyl, naphthyl or heterocyclic radical, these latter three radicals optionally comprising one or more substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy radicals and halogen atoms, process which comprises the treatment of an .alpha.-monohalogenated ketone of general formula: ##STR2## in which R and Cy have the same meaning as above and X represents chlorine, bromine or iodine, in the presence of an aqueous solution of an alkali metal hydroxide, a non-polar organic solvent selected from an aromatic or alicyclic hydrocarbon and oxygen in excess optionally in the presence of an inert gas, the treatment being carried out at a temperature ranging from the boiling temperature of the reaction medium at atmospheric pressure and 240.degree. C.Type: GrantFiled: November 21, 1985Date of Patent: June 23, 1987Assignee: SanofiInventors: Jean-Daniel Andre, Pierre-Jean Grossi, Alain Heymes, Giovanni V. Manzaroli
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Patent number: 4625033Abstract: A process for preparing 1H-pyrrolo-[3,2-c]-pyridine or 5-aza-indole in high yield, comprising condensing 3-methyl-4-nitropyridine-1-oxide with a compound having a formula ##STR1## wherein R represents a di-loweralkylamino, morpholino, piperidino or pyrrolidino group and R.sub.1 and R.sub.2, which are the same or different, each represent a loweralkoxy group or a group R as defined; to form an enamine having a formula: ##STR2## wherein R is as define and subjecting the enamine IV to reduction cyclization; the enamines IV are new compounds.Type: GrantFiled: May 28, 1985Date of Patent: November 25, 1986Assignee: SanofiInventors: Jean-Robert Dormoy, Alain Heymes
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Patent number: 4493931Abstract: The present invention provides a multistep process for the preparation of .beta.-cyclo-substituted ethylamines of the general formula:-Ar--CH.sub.2 --CH.sub.2 --NH.sub.2 (I)in which AR is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly- substituted, wherein said compounds represent a class of intermediates which can be converted to 4,5,6,7-tetrahydro[3,2-C] or [2,3-C]pyridines wherein the latter are useful for anti-inflammatory, vasodilator or blood platelet aggregation inhibition activities.Type: GrantFiled: June 29, 1982Date of Patent: January 15, 1985Assignee: SanofiInventors: Isaac Chekroun, Alain Heymes
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Patent number: 4482718Abstract: The present invention provides a process for the preparation of 2-(thien-2-yl)- and 2-(thien-3-yl)-ethylamine derivatives of the general formula: ##STR1## in which R.sub.1, in the 2-, 3-, 4- or 5-position, is a hydrogen or halogen atom, a nitro, carboxyl, cyano or amino group, a linear or branched alkyl or alkoxy radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, the aminoethyl chain is in the 2- or 3-position, R.sub.2, R.sub.3 and R.sub.4, which are the same or different, are hydrogen atoms or heterocyclic or non-heterocyclic aromatic radicals, which are optionally mono- or polysubstituted, and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted.Type: GrantFiled: June 29, 1982Date of Patent: November 13, 1984Assignee: SanofiInventors: Isaac Chekroun, Alain Heymes
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Patent number: 4458074Abstract: The present invention provides a process for the preparation of 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]-pyridin-2-ones of the general formula: ##STR1## in which R is a hydrogen atom or a phenyl radical optionally substituted by at least one halogen atom, lower alkyl radical, lower alkoxy radical, nitro group, carboxyl group or alkoxycarbonyl radical, R' is a hydrogen atom or lower alkyl radical and n is 0 or a number of from 1 to 4, wherein a compound of the general formula: ##STR2## in which R, R' and n have the same meanings as above, is reacted with formaldehyde to give a compound of the general formula: ##STR3## in which R, R' and n have the same meanings as above, whereafter this compound is treated with dry hydrogen chloride to give the desired compound of general formula (I). The compounds are useful as anti-thrombotic agents.Type: GrantFiled: June 29, 1982Date of Patent: July 3, 1984Assignee: SanofiInventors: Andre Bouscuet, Alain Heymes
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Patent number: 4458086Abstract: The present invention provides a process for the preparation of 2-(thienyl-2)- and 2-(thienyl-3)-ethylamines of the general formula: ##STR1## in which R.sub.1, which is in the 2-, 3-, 4- or 5-position, is a hydrogen atom, a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or polysubstituted, or R.sub.1 is an alkoxy radical, a halogen atom or a nitro, carboxyl, cyano or amino group; the aminoethyl chain is in the 2- or 3-position of the thiophene nucleus; R.sub.2 is a hydrogen atom or a straight-chained or branched alkyl radical or a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly-substituted; and Ar is a heterocyclic or non-heterocyclic aromatic radical, which is optionally mono- or poly-substituted.Type: GrantFiled: June 29, 1982Date of Patent: July 3, 1984Assignee: SanofiInventors: Isaac Chekroun, Alain Heymes
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Patent number: 4439442Abstract: The object of the invention is a new naftidrofuryl salt, naftidrofuryl citrate, which is therapeutically useful because it promotes metabolism and circulatory properties and because of its vaso-active properties in the treatment of arthritis of the limbs, Reynaud's Syndrome and cerebral circulatory insufficiency.Type: GrantFiled: May 14, 1982Date of Patent: March 27, 1984Assignee: SANOFIInventors: Jacques A. Chick, Alain Heymes, Carlo Blasioli
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Patent number: 4152519Abstract: This invention relates to novel aspidospermidines being useful in synthesis and also exhibiting interesting physiological properties. A process for the preparation of the novel compounds is described and exemplified and examples of pharmaceutical compositions containing the novel compounds are given. Pharmacological test data are presented for a novel compound according to the invention.Type: GrantFiled: July 7, 1977Date of Patent: May 1, 1979Assignee: ParcorInventor: Alain Heymes
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Patent number: 4145552Abstract: A process for preparing vincamine and related alkaloids, comprising reacting a compound of formula: ##STR1## (wherein R is H or methoxy and X and Y are hydrogen or together represent a double bond between the carbon atoms to which they are bonded) with a carbanion-forming agent in a reaction medium; then introducing oxygen into the reaction medium until saturation point, a reducing agent compatible with oxygen being added to the reaction medium before the medium ceases absorbing oxygen; acidifying the mixture and extracting therefrom a mixture of compounds ##STR2##Type: GrantFiled: July 5, 1977Date of Patent: March 20, 1979Assignee: ParcorInventor: Alain Heymes
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Patent number: 4065460Abstract: This invention relates to 4,5,6,7-tetrahydro-thieno[3,2-c]-pyridine derivatives, having the formula: ##STR1## in which R.sub.1 is hydrogen or alkyl having 1-6 carbon atoms; R.sub.2 is hydrogen, an alkyl group having 1-6 carbon atoms or a phenyl or benzyl radical; R.sub.3 represents an alkyl group having 1-6 carbon atoms or a benzyl radical, and their pharmaceutically acceptable acid addition salts.Said derivatives have an anti-inflammatory and antalgic activity.Type: GrantFiled: April 6, 1976Date of Patent: December 27, 1977Assignee: ParcorInventors: Alain Heymes, Jean-Pierre Maffrand