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).

  • Patent number: 6215005
    Abstract: 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: Grant
    Filed: May 3, 2000
    Date of Patent: April 10, 2001
    Assignee: Sanofi-Synthelabo
    Inventors: Alain Heymes, Bertrand Castro, Mária Bakonyi, Marianna Csatáriné Nagy, Leventéné Molnár
  • Patent number: 5266711
    Abstract: 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: Grant
    Filed: October 16, 1990
    Date of Patent: November 30, 1993
    Assignee: Sanofi
    Inventors: Bernard Boudet, Jean R. Dormoy, Alain Heymes
  • Patent number: 5262561
    Abstract: 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: Grant
    Filed: March 13, 1992
    Date of Patent: November 16, 1993
    Assignee: Elf Sanofi
    Inventors: Andre Bousquet, Alain Heymes
  • Patent number: 5132435
    Abstract: 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: Grant
    Filed: July 2, 1991
    Date of Patent: July 21, 1992
    Assignee: Sanofi
    Inventors: Andre Bousquet, Serge Calet, Alain Heymes
  • Patent number: 5081240
    Abstract: 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: Grant
    Filed: July 12, 1990
    Date of Patent: January 14, 1992
    Assignee: Sanofi
    Inventors: Andre Bousquet, Jean-Robert Dormoy, Alain Heymes
  • Patent number: 5079363
    Abstract: 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: Grant
    Filed: February 22, 1989
    Date of Patent: January 7, 1992
    Assignee: Sanofi
    Inventors: Michel Bouisset, Andre Bousquet, Jean-Robert Dormoy, Alain Heymes
  • Patent number: 5075486
    Abstract: 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: Grant
    Filed: September 14, 1990
    Date of Patent: December 24, 1991
    Assignee: Sanofi
    Inventors: Michel Bouisset, Christian Forqlly, Andre Bousquet, Alain Heymes
  • Patent number: 5071985
    Abstract: 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: Grant
    Filed: September 12, 1989
    Date of Patent: December 10, 1991
    Assignee: Sanofi
    Inventors: Jean-Daniel Andre, Jean-Robert Dormoy, Alain Heymes
  • Patent number: 4831144
    Abstract: 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: Grant
    Filed: January 7, 1988
    Date of Patent: May 16, 1989
    Assignee: SANOFI
    Inventors: Jean-Robert Dormoy, Alain Heymes
  • Patent number: 4713485
    Abstract: 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: Grant
    Filed: November 21, 1985
    Date of Patent: December 15, 1987
    Assignee: SANOFI and Industria Chimica Prodotti FRANCIS S.p.A.
    Inventors: Jean-Daniel Andre, Pierre-Jean Grossi, Alain Heymes, Giovanni V. Manzaroli
  • Patent number: 4675419
    Abstract: 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: Grant
    Filed: November 21, 1985
    Date of Patent: June 23, 1987
    Assignee: Sanofi
    Inventors: Jean-Daniel Andre, Pierre-Jean Grossi, Alain Heymes, Giovanni V. Manzaroli
  • Patent number: 4625033
    Abstract: 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: Grant
    Filed: May 28, 1985
    Date of Patent: November 25, 1986
    Assignee: Sanofi
    Inventors: Jean-Robert Dormoy, Alain Heymes
  • Patent number: 4493931
    Abstract: 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: Grant
    Filed: June 29, 1982
    Date of Patent: January 15, 1985
    Assignee: Sanofi
    Inventors: Isaac Chekroun, Alain Heymes
  • Patent number: 4482718
    Abstract: 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: Grant
    Filed: June 29, 1982
    Date of Patent: November 13, 1984
    Assignee: Sanofi
    Inventors: Isaac Chekroun, Alain Heymes
  • Patent number: 4458086
    Abstract: 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: Grant
    Filed: June 29, 1982
    Date of Patent: July 3, 1984
    Assignee: Sanofi
    Inventors: Isaac Chekroun, Alain Heymes
  • Patent number: 4458074
    Abstract: 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: Grant
    Filed: June 29, 1982
    Date of Patent: July 3, 1984
    Assignee: Sanofi
    Inventors: Andre Bouscuet, Alain Heymes
  • Patent number: 4439442
    Abstract: 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: Grant
    Filed: May 14, 1982
    Date of Patent: March 27, 1984
    Assignee: SANOFI
    Inventors: Jacques A. Chick, Alain Heymes, Carlo Blasioli
  • Patent number: 4152519
    Abstract: 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: Grant
    Filed: July 7, 1977
    Date of Patent: May 1, 1979
    Assignee: Parcor
    Inventor: Alain Heymes
  • Patent number: 4145552
    Abstract: 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: Grant
    Filed: July 5, 1977
    Date of Patent: March 20, 1979
    Assignee: Parcor
    Inventor: Alain Heymes
  • Patent number: 4065460
    Abstract: 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: Grant
    Filed: April 6, 1976
    Date of Patent: December 27, 1977
    Assignee: Parcor
    Inventors: Alain Heymes, Jean-Pierre Maffrand