Patents Assigned to Labaz
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Patent number: 4520026Abstract: Novel indolizine derivatives represented by the general formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: R represents an alkyl radical having from 1 to 8 carbon atoms, or a phenyl group non-substituted or bearing one or two substituents, selected from halogen atoms and from lower alkyl and alkoxy groups,X.sub.1 represents hydrogen, chlorine, bromine, iodine, methyl or methoxy,A represents a group selected from: ##STR2## in which X.sub.2 represents hydrogen, chlorine, bromine, iodine, methyl or methoxy and X.sub.3 represents hydrogen, chlorine, bromine, iodine or methyl,R.sub.1 represents a methyl, ethyl, n-propyl or n-butyl radical,n represents an integer in the range of 2 to 6 inclusive,with the proviso that when both X.sub.2 and X.sub.3 represent hydrogen or methyl, X.sub.1 is other than hydrogen.They are effective for treating pathological syndromes of the heart and particularly angina pectoris and cardiac arrhythmias.Type: GrantFiled: June 29, 1982Date of Patent: May 28, 1985Assignee: S. A. Labaz N.V.Inventors: Gilbert Rosseels, Henri Inion
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Patent number: 4400387Abstract: Indolizine derivatives represented by the general formula: ##STR1## wherein R represents a straight- or branched-chain alkyl radical having from 1 to 8 carbon atoms, or a phenyl group non-substituted or bearing one or two substituents, which may be the same or different, selected from halogen atoms, for example fluorine, chlorine and bromine and from lower alkyl and alkoxy groups, for example methyl and methoxy and X.sub.1, X.sub.2 and X.sub.3, which may be the same or different, each represent hydrogen, chlorine, bromine or methoxy with the proviso that when they are identical X.sub.1, X.sub.2 and X.sub.3 are not simultaneously hydrogen.They possess an inhibitory activity with respect to the action of xanthine oxidase and of adenosine deaminase as well as an uricosuric action and can be used in the treatment of physiological disturbances consequent upon an excess of uric acid, upon disorders of the immunization system and as antiparasitic agents.Type: GrantFiled: June 30, 1980Date of Patent: August 23, 1983Assignee: S. A. Labaz-Sanofi N.V.Inventors: Gilbert Rosseels, Pierre Nokin
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Patent number: 4378362Abstract: Novel indolizine derivatives represented by the general formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: R represents an alkyl radical having from 1 to 8 carbon atoms, or a phenyl group non-substituted or bearing one or two substituents, selected from halogen atoms and from lower alkyl and alkoxy groups,X.sub.1 represents hydrogen, chlorine, bromine, iodine, methyl or methoxy,A represents a group selected from: ##STR2## in which X.sub.2 represents hydrogen, chlorine, bromine, iodine, methyl or methoxy and X.sub.3 represents hydrogen, chlorine, bromine, iodine or methyl,R.sub.1 represents a methyl, ethyl, n-propyl or n-butyl radical,n represents an integer in the range of 2 to 6 inclusive,with the proviso that when both X.sub.2 and X.sub.3 represent hydrogen or methyl, X.sub.1 is other than hydrogen.They are effective for treating pathological syndromes of the heart and particularly angina pectoris and cardiac arrhythmias.Type: GrantFiled: February 6, 1981Date of Patent: March 29, 1983Assignee: S.A. Labaz N.V.Inventors: Gilbert Rosseels, Henri Inion
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Patent number: 4374841Abstract: Novel pyridoxine derivatives represented by the general formula: ##STR1## in which: R represents a radical ##STR2## --CH.sub.2 --(CH.sub.2).sub.n --CH.sub.2 --OR.sub.2 or ##STR3## in which n represents 0 or 1, X and X.sub.1, which are different, represent hydrogen or methyl, Y represents hydrogen or methyl and R.sub.2 represents a phenyl group non-substituted or bearing one or two substituents selected from the group consisting of fluorine, chlorine and bromine and of the radicals methyl, ethyl, n-propyl, isopropyl and methoxy,R.sub.1 represents hydrogen or a radical of formula ##STR4## in which R.sub.3 represents a straight-chain alkyl radical having from 1 to 4 carbon atoms and pharmaceutically acceptable acid addition salts thereof.These compounds present .alpha.-antiadrenergic properties some of them also presenting .beta.-antiadrenergic, antihypertensive and central depressant effects.Type: GrantFiled: May 11, 1981Date of Patent: February 22, 1983Assignee: S. A. Labaz N.V.Inventors: Marcel Descamps, Marcel Urbain, deceased, Claire Urbain, legal representative, Jacques J. Z. Urbain, legal representative, Jean P. M. C. Urbain, legal representative, Nadine C. J. Urbain, legal representative
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Patent number: 4317768Abstract: The instant invention relates to compounds of the general formula: ##STR1## wherein R.sub.1 represents an alkyl, alkenyl, phenyl or phenylalkyl radical, R.sub.2 represents an alkyl, alkenyl or alkynyl radical, a .omega.-halogenoethyl radical, an optionally substituted benzyl radical, a phenylalkenyl radical, an optionally substituted phenyl radical, a radical of the formula R.sub.4 --O--(CH.sub.2).sub.n -- wherein n is 2, 3, or 4 and R.sub.4 represents an optionally substituted alkyl radical or a phenyl radical, R.sub.3 represents a hydrogen atom, an alkyl, alkenyl or phenyl radical.The compounds of formula I have been found to be useful as stabilizers for vinyl resins.Type: GrantFiled: November 13, 1979Date of Patent: March 2, 1982Assignee: LabazInventors: Charles Pigerol, Marie-Madeleine Chandavoine, Paul de Cointet de Fillain
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Patent number: 4299768Abstract: 1-Pyrrole- and 1-pyrrolidine-carboxylic acid derivatives corresponding to the general formula: ##STR1## in which R represents an alkyl radical having from 1 to 4 carbon atoms, preferably ethyl, and Am represents a group: ##STR2## wherein R.sub.1 represents a 3-oxo-alkyl radical ##STR3## or a 3-oxo-alkenyl radical ##STR4## and R.sub.2 represents hydrogen or R.sub.1 and R.sub.2, when they are identical, each represent hydrogen, ##STR5## R.sub.3 representing an alkyl radical having from 1 to 5 carbon atoms with the proviso that when R.sub.1 and R.sub.2 are simultaneously hydrogen, Am represents the group A.The novel derivatives are useful as intermediates for synthetizing azaprostaglandines.Type: GrantFiled: June 11, 1979Date of Patent: November 10, 1981Assignee: LABAZInventors: Charles Pigerol, Michel Schaefer, Souli Nanthavong
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Patent number: 4283420Abstract: The chemical compounds of the invention are useful as the active compound in drugs because of their anticonvulsant and/or antianoxic activity. They have the general formula ##STR1## wherein Z is a hydroxyl group; a group--OM wherein M is an alkali metal atom or an equivalent atom fraction of an alkaline-earth metal or an amino group such as --NH.sub.2, and R is a linear or branched alkyl group containing from 1 to 9 carbon atoms, and optionally substituted by one or more halogen atoms; a linear or branched alkenyl or alkynyl, alkoxyalkyl, or acylalkyl group containing from 2 to 9 carbon atoms and optionally substituted by one or more halogen atoms; an aryl or arylalkyl or aryloxyalkyl group comprising at least one aromatic radical and an alkyl chain having from 1 to 4 carbon atoms.Type: GrantFiled: April 18, 1979Date of Patent: August 11, 1981Assignee: LabazInventors: Charles Pigerol, Jean-Claude Vernieres, Pierre Eymard, Jacques Simiand, Madeleine Broll, Jean-Yves Lacolle
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Patent number: 4264773Abstract: The invention relates to 2-(4'-chloro-phenylthio)-benzonitrile, to its process of preparation and to its use for preparing 2-chlorothioxanthone.2-Chloro-thioxanthone prepared from the compound of the invention is useful as a photoinitiator for the reticulation of synthetic resins and as an intermediate for preparing pharmaceuticals.Type: GrantFiled: March 5, 1979Date of Patent: April 28, 1981Assignee: LabazInventors: Charles Pigerol, Michel Bouisset, Michel Chignac, Claude Grain
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Patent number: 4246282Abstract: .omega.-Dialkylalkanoic acid derivatives of the formula: ##STR1## in which R.sub.1 and R.sub.2, which can be the same or different, each represent an alkyl radical having from 1 to 4 carbon atoms and n represents 0, 1, 2 or 3.They possess a competitive inhibitory activity with respect to .gamma.-aminobutyric .alpha.-ketoglutaric transaminase as well as antianoxic and anticonvulsant properties and they are useful for treating central neurological disorders, whether resulting or not from cerebral ischemia, and disorders relating to the field of neuropsychiatry.Type: GrantFiled: June 7, 1979Date of Patent: January 20, 1981Assignee: LabazInventors: Michel Chignac, Claude Grain, Fernand Jammot, Charles Pigerol, Pierre L. Eymard, Madeleine Combet (epse Broll)
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Patent number: 4239893Abstract: The instant invention relates to compounds of the general formula: ##STR1## wherein R.sub.1 represents an alkyl, alkenyl, phenylalkyl radical, R.sub.2 represents a straight-chain alkyl, a straight- or branched-chain alkenyl or alkynyl radical, a .omega.-halogenoethyl radical, an optionally substituted benzyl radical, or a radical of the formula R.sub.4 --O--(CH.sub.2).sub.n --wherein n is 2, 3 or 4 and R.sub.4 represents a substituted alkyl radical.The compounds of the foregoing formula have been found to be useful as stabilizers for vinyl resins.Type: GrantFiled: November 20, 1979Date of Patent: December 16, 1980Assignee: LabazInventors: Charles Pigerol, Marie-Madeleine Chandavoine, Paul de C. de Fillain
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Patent number: 4223041Abstract: Urea derivatives of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which are the same or different, each represent a straight- or branched-chain alkyl, alkenyl or alkynyl radical having from 1 to 5 carbon atoms, R.sub.4 and R.sub.5, which are the same or different, each represent a hydrogen atom or a straight- or branched-chain alkyl, alkenyl or alkynyl radical having from 1 to 5 carbon atoms, R.sub.1, R.sub.2 and R.sub.3 being such that:(a) only one of these radicals can represent an alkenyl or alkynyl group having an unsaturated bond in the .alpha.,.beta.-position with respect to the methylurea radical, in this case, each of the other two substituents represents an alkyl radical,(b) the sum of their carbon atoms is never inferior to 4.They are useful as anxiolytic and antiagressive agents.Type: GrantFiled: October 25, 1977Date of Patent: September 16, 1980Assignee: LabazInventors: Charles Pigerol, Pierre Eymard, Jean-Claude Vernieres, Madeleine Combet epse Broll, Jean-Yves Lacolle
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Patent number: 4220793Abstract: A process for preparing 5-nitro-2-thenoic acid by oxidation of the corresponding aldehyde is described.Type: GrantFiled: November 14, 1978Date of Patent: September 2, 1980Assignee: LabazInventors: Yves Bazile, Paul de Cointet de Fillain, Charles Pigerol
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Patent number: 4219482Abstract: A process for preparing methyl-nitrothenoate and methyl-nitrofuroate by oxidation of the corresponding aldehyde is described.Type: GrantFiled: November 14, 1978Date of Patent: August 26, 1980Assignee: LabazInventors: Yves Bazile, Paul de Cointet de Fillain, Charles Pigerol
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Patent number: 4209440Abstract: This invention relates to new associations of a compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 represent a hydrogen atom, an alkyl, alkoxy or hydroxy radical and R represents a hydrogen atom or an alkyl or alkoxy radical, and of a compound of the formula: ##STR2## wherein R.sub.3 represents an alkyl, alkenyl, alkynyl or aralkyl radical or a radical of the formula R.sub.4 --O(CH.sub.2).sub.n --, wherein R.sub.4 represents an alkyl or phenyl radical and n is 2, 3 or 4.The associations according to the invention are stabilizers for vinyl resins.Type: GrantFiled: October 16, 1978Date of Patent: June 24, 1980Assignee: LabazInventors: Charles Pigerol, Marie-Madeleine Chandavoine, Paul de Cointet de Fillain
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Patent number: 4209439Abstract: Synthetic resin compositions based on vinyl polymers or copolymers are stabilized against degradation by both heat and light by the incorporation therein of a 1,4-dihydropyridine derivative represented by the general formula: ##STR1## wherein R represents a straight or branched-chain saturated or unsaturated alkyl radical containing from 9 to 22 carbon atoms. The stabilizer can be present in an amount of from 0.01 to 0.5 percent by weight, based on the vinyl resin. The vinyl resin may be, for example, polyvinyl chloride, a vinyl chloride-vinyl acetate copolymer or a vinyl chloride-vinylidene chloride copolymer. The stabilized vinyl resins can be used in the manufacture of food packaging materials and containers and also of flooring tiles and recording discs.Some of the dihydropyridine derivatives are novel compounds.Type: GrantFiled: October 12, 1978Date of Patent: June 24, 1980Assignee: LabazInventors: Charles Pigerol, Marie-Madeleine Chandavoine, Paul de Cointet Fillain
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Patent number: 4201725Abstract: Methylamine derivatives of the formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof, wherein R.sub.1 and R.sub.3 each represent a hydrogen atom or a straight- or branched-chain alkyl, alkenyl or alkynyl radical containing from 1 to 6 carbon atoms, R.sub.2 represents a straight- or branched-chain alkyl, alkenyl or alkynyl radical containing from 2 to 7 carbon atoms with the proviso that when R.sub.2 represents an alkenyl radical of the formula CH.dbd.CH--R.sub.6 or an alkynyl radical of the formula C.tbd.C--R.sub.6, in which R.sub.6 represents a hydrogen atom or a straight- or branched-chain alkyl radical of 1 to 5 carbon atoms, R.sub.1 and R.sub.3 each represent an atom of hydrogen or an alkyl radical, R.sub.4 and R.sub.5, which are the same or different, each respresent a hydrogen atom, a straight- or branched-chain alkyl, alkenyl or alkynyl radical containing from 1 to 5 carbon atoms or an .omega.-hydroxyalkyl radical containing from 2 to 5 carbon atoms or R.sub.4 and R.sub.Type: GrantFiled: March 20, 1978Date of Patent: May 6, 1980Assignee: LabazInventors: Charles Pigerol, Pierre Eymard, Jean-Claude Vernieres, Jean-Pierre Werbenec, Madeleine C. Epse Broll
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Patent number: 4186137Abstract: 3-Thienyl-acetate derivatives of the general formula: ##STR1## wherein R.sub.1 represents an alkyl, a cycloalkyl or an aralkyl radical, R.sub.2 represents hydrogen or R.sub.1 and R.sub.2, when they are taken together to form a cyclic group with the carbon atom to which they are attached, represent a polymethylene radical having from 2 to 5 carbon atoms, are prepared from a mixture consituted by a compound of the formula: ##STR2## wherein R.sub.3 has the meaning given above and an organic halide of the formula:R.sub.4 Xwherein X represents fluorine, chlorine, bromine or iodine and R.sub.4 represents an alkyl, cycloalkyl or aralkyl radical or --CH.sub.2 (CH.sub.2).sub.n X in which n is an integer in the range of from 1 to 4 inclusive and X has the meaning given above, which mixture is added to an alkali metal hydride in dimethylformamide, at a temperature between -20.degree. C. and -5.degree. C., and allowed to react, in one step, at a temperature between -20.degree. C. and -5.degree. C.Type: GrantFiled: March 17, 1977Date of Patent: January 29, 1980Assignee: LabazInventors: Charles Pigerol, Marie-Madeleine Chandavoine, Michel Chignac, Paul de Cointet de Fillain
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Patent number: 4173636Abstract: The invention relates to decahydroquinoline derivatives represented by the general formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein R.sup.1 represents an alkyl or alkoxy group, a lower dialkylamino group, an optionally substituted phenyl group, a heterocyclic group; R.sup.2 represents an alkyl group, an optionally substituted phenyl group, a naphthyl group, an unsaturated heterocyclic group, an aralkyl group or an alicyclic group; and R.sup.3 represents a substituted furyl group, an aralkyl group or a group represented by the general formula: ##STR2## wherein A represents an alkylene group; Y represents an oxygen or sulphur atom, a carbonyl, carbonyl-hydroxyimino, carbonyl-hydrazono or sulphoxide group, or a group; ##STR3## n is O or an integer of from 1 to 4, with the proviso that when n is O, Y represents a carbonyl group; and R.sup.4 and R.sup.5, which are identical or different, each represent hydrogen, a halogen atom or a methyl, methoxy or acetyl group.Type: GrantFiled: March 8, 1978Date of Patent: November 6, 1979Assignee: LabazInventor: Maurice Prost
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Patent number: RE30655Abstract: 3-Thienyl-acetate derivatives of the general formula: ##STR1## wherein R.sub.1 represents an alkyl, a cycloalkyl or an aralkyl radical, R.sub.2 represents hydrogen or R.sub.1 and R.sub.2, when they are taken together to form a cyclic group with the carbon atom to which they are attached, represent a polymethylene radical having from 2 to 5 carbon atoms, are prepared from a mixture consituted by a compound of the formula: ##STR2## wherein R.sub.3 has the meaning given above and an organic halide of the formula:R.sub.4 Xwherein X represents fluorine, chlorine, bromine or iodine and R.sub.4 represents an alkyl, cycloalkyl or aralkyl radical or --CH.sub.2 (CH.sub.2).sub.n X in which n is an integer in the range of from 1 to 4 inclusive and X has the meaning given above, which mixture is added to an alkali metal hydride in dimethylformamide, at a temperature between -20.degree. C. and -5.degree. C., and allowed to react, in one step, at a temperature between -20.degree. C. and -5.degree. C.Type: GrantFiled: June 27, 1980Date of Patent: June 23, 1981Assignee: LabazInventors: Charles Pigerol, Marie-Madeleine Chandavoine, Michel Chignac, Paul de Cointet de Fillain
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Patent number: RE31260Abstract: Process for the preparation of di-n-propyl acetonitrile of the formula: ##STR1## whereby, in a single step, sodium n-propylate in n-propanol medium is added to a reaction medium which is formed of a cyanacetate of general formula: ##STR2## in which R represents an alkyl radical having from 1 to 4 carbon atoms, and n-propyl bromide or iodide, the alkylation reaction taking place under reflux, the crude ester obtained is saponified with a 10 to 20% solution of sodium hydroxide or potassium hydroxide, the resulting salt is acidified with a strong acid, to give crude di-n-propyl cyanacetic acid, which is decarboxylated by heating at a temperature between 140.degree. C. and 190.degree. C., so as to obtain the di-n-propyl acetonitrile.Type: GrantFiled: June 27, 1980Date of Patent: May 31, 1983Assignee: LabazInventors: Michel Chignac, Claude Grain, Charles Pigerol