Patents Assigned to Labaz
  • Patent number: 4170643
    Abstract: Novel aminoglycoside-aminocyclitol derivatives corresponding to the general formula: ##STR1## wherein R.sub.1 and R.sub.2, which are different, represent hydrogen or CH.sub.2 NH.sub.2 and R is selected from the group consisting of: ##STR2## wherein R.sub.3 represents NH.sub.2 or OH and R.sub.4 represents ##STR3## wherein R.sub.5 represents hydrogen or methyl and the pharmaceutically acceptable acid addition salts thereof.They are useful as antibiotics.
    Type: Grant
    Filed: April 13, 1977
    Date of Patent: October 9, 1979
    Assignee: Labaz
    Inventors: Stephan Gero, Daniel Mercier, Alain Olesker, Andre Cier
  • Patent number: 4155929
    Abstract: 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: Grant
    Filed: May 10, 1978
    Date of Patent: May 22, 1979
    Assignee: Labaz
    Inventors: Michel Chignac, Claude Grain, Charles Pigerol
  • Patent number: 4139634
    Abstract: Indole derivatives of the formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl radical, R.sub.2 and R.sub.3, which are the same or different, each represent a hydrogen atom, a methyl or ethyl radical, a benzyl radical or represent together a pentamethylene, hexamethylene, oxydiethylene or N-methylaminodiethylene chain, forming thus a cycle with the nitrogen atom, R.sub.4 represents a phenyl, 2', 4'-dimethyl-phenyl, isopropyl, cyclopropyl, 1-methyl-cyclopropyl, cyclopentyl or cyclohexyl radical, R.sub.5 represents a hydrogen atom, a branched- or straight-chain alkyl radical containing from 1 to 3 carbon atoms, a methylthio or ethylthio radical or a straight-chain acyl radical containing from 2 to 6 carbon atoms, R.sub.6 represents a hydrogen atom or a halogen atom, a methyl, methoxy, hydroxy, carboxy, nitro, amino, methylamino or dimethylamino radical, R.sub.7 represents a hydrogen atom or a halogen atom and n is 1 or 2, with the proviso that two at least of the groups R.sub.5, R.sub.
    Type: Grant
    Filed: May 20, 1977
    Date of Patent: February 13, 1979
    Assignee: Labaz
    Inventors: Charles Pigerol, Paul DE Cointet de Fillain, Pierre Eymard, Jean-Pierre Werbenec, Madeleine Broll
  • Patent number: 4134909
    Abstract: The invention relates to new compounds of the general formula : ##STR1## wherein X represents a hydrogen or halogen atom, R.sub.1 and R.sub.2, which are the same or different, each represent a hydrogen atom or a methoxy radical and R.sub.3 represents an alkyl or aryl radical, with the proviso that at least one of the substituents R.sub.1 and R.sub.2 is not a hydrogen atom.The compounds of formula I are useful for preparing stabilizers for thermoplastic resins.
    Type: Grant
    Filed: June 29, 1977
    Date of Patent: January 16, 1979
    Assignee: Labaz
    Inventors: Charles Pigerol, Paul DE Cointet de Fillain, Yves Bazile, Michel Chignac, Claude Grain
  • Patent number: 4129572
    Abstract: 2-Phenyl-indole derivatives of the general formula: ##STR1## wherein R.sub.1 represents a hydroxy radical, a branched- or straight-chain alkyloxy group containing from 1 to 12 carbon atoms, an allyloxy or propargyloxy radical, a cylcoalkyloxy radical containing from 5 to 7 carbon atoms or a benzyloxy radical, R.sub.2 represents a hydroxy radical, an ethoxy, methylsulphonyloxy, benzenesulphonyloxy or toluenesulphonyloxy group and R.sub.3 represents a hydrogen atom, a hydroxy radical or a methoxy group. The said 2-phenyl-indole derivatives are useful in particular as stabilizers of polymers and co-polymers of vinyl chloride.
    Type: Grant
    Filed: July 1, 1977
    Date of Patent: December 12, 1978
    Assignee: Labaz
    Inventors: Charles Pigerol, Paul DE Cointet de Fillain, Yves Bazile
  • Patent number: 4127607
    Abstract: Process for preparing di-n-propyl acetamide of the formula: ##STR1## whereby di-n-propyl acetonitrile is hydrolyzed by means of 80% sulphuric acid aqueous solution in the proportion of 2 to 2.5 g of dilute acid/g of nitrile, at a temperature between 80.degree. C and 130.degree. C to obtain the desired amide.
    Type: Grant
    Filed: May 25, 1977
    Date of Patent: November 28, 1978
    Assignee: Labaz
    Inventors: Michel Chignac, Claude Grain, Charles Pigerol
  • Patent number: 4127609
    Abstract: Cyclohexanediol derivatives of the general formula: ##STR1## wherein R.sub.1 and R.sub.2, which are identical, each represent a N.sub.3 or NH.sub.2 group, and the acid addition salts of the derivative containing two NH.sub.2 groups.These compounds are useful as intermediate products for the preparation, for example, of synthetic antibiotics.
    Type: Grant
    Filed: January 22, 1976
    Date of Patent: November 28, 1978
    Assignee: Labaz
    Inventors: Andre Cier, Stephan Gero, Alain Olesker, Jean Leboul
  • Patent number: 4127604
    Abstract: Process for the preparation of di-n-propyl acetic acid of formula: ##STR1## and its non-toxic alkali and alkaline earth metal salts whereby in a single stage, sodium n-propylate in n-propanol medium is added to a reaction medium formed of a cyanacetic ester 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 or potassium hydroxide, the salt thus obtained is acidified with a strong acid, to give the crude di-n-propyl cyanacetic acid, which is decarboxylated by heating at a temperature between 140.degree. and 190.degree. C, to provide the di-n-propyl acetonitrile, the di-n-propyl acetonitrile obtained is hydrolysed by means of an aqueous solution of 75 to 80% sulphuric acid at a temperature of 80.degree.-140.degree.
    Type: Grant
    Filed: May 25, 1977
    Date of Patent: November 28, 1978
    Assignee: Labaz
    Inventors: Michel Chignac, Claude Grain, Charles Pigerol
  • Patent number: 4124710
    Abstract: The invention relates to acetamidoxime derivatives represented by the general formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein R.sub.1 represents a branched- or straight-chain alkyl group containing from 1 to 4 carbon atoms or a phenyl group, A represents one of the groups: ##STR2## R.sub.2 represents an amino group such as, for example, a dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, pyrrolidino, morpholino, piperidino or heptamethyleneimino group or a 1-piperazino group substituted in the 4-position by a straight-chain alkyl group containing from 1 to 4 carbon atoms, X represents a hydrogen or chlorine atom or a methoxy group and n is the integer 2 or 3.The compounds of formula I have been found to be potentially useful in the treatment of disorders of arterial pressure.
    Type: Grant
    Filed: December 9, 1976
    Date of Patent: November 7, 1978
    Assignee: Labaz
    Inventors: Marcel Descamps, Alex Areschka
  • Patent number: 4117151
    Abstract: The present invention is concerned with novel sulfonamide compounds of the general formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof, wherein Ar represents an optionally substituted phenyl group or a saturated heterocyclic group, Am represents a dialkylamino group or a saturated heterocyclic group, A represents a 3-benzofuryl or 3-benzo[b] thienyl group, substituted in the 2-position by a lower alkyl group and optionally substituted in the 5-position by a halogen atom or a lower alkoxy group, and n is the integer 2 or 3.Said compounds are effective for treating certain pathological or otherwise abnormal conditions of the heart and more particularly angina pectoris.
    Type: Grant
    Filed: March 2, 1977
    Date of Patent: September 26, 1978
    Assignee: Labaz
    Inventors: Marcel Descamps, Charles Goldenberg
  • Patent number: 4115401
    Abstract: Prostaglandin derivatives corresponding to the general formula: ##STR1## wherein R.sub.1 represents hydrogen, methyl or ethyl, R.sub.2, R.sub.3 and R.sub.4, which are the same or different, each represent hydrogen or methyl and R is selected from the groups consisting of: ##STR2## in which R.sub.5 represents hydrogen, methyl or ethyl, R.sub.6 represents methyl, ethyl or acetyl and R.sub.7 and R.sub.8, when they are different, each represent hydrogen or a branched- or straight-chain alkyl group having from 1 to 7 carbon atoms or R.sub.7 and R.sub.8, when they are identical, each represent hydrogen or a straight-chain alkyl group having from 1 to 3 carbon atoms with the provisos that:When both R.sub.7 and R.sub.8 represent hydrogen, R.sub.5 is methyl or ethyl,When R.sub.5 represents methyl and R.sub.2, R.sub.3, R.sub.4, R.sub.7 and R.sub.8 all represent hydrogen then R.sub.1 is ethyl,The said prostaglandin derivatives being in the form of a mixture of isomers or of an individual isomer.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: September 19, 1978
    Assignee: Labaz
    Inventors: Souli Nanthavong, Charles Pigerol, Pierre Eymard, Jacques Simiand
  • Patent number: 4113736
    Abstract: The present invention relates to new stabilizers of polymers and co-polymers of vinyl chloride corresponding to the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6, which are the same or different, represent:R.sub.1 = a hydrogen atom or a branched- or straight-chain alkyloxy group containing from 1 to 12 carbon atoms,R.sub.2 = a hydrogen atom, a branched-or straight-chain alkyl group containing from 1 to 3 carbon atoms or a branched- or straight-chain alkyloxy group containing from 1 to 12 carbon atoms,R.sub.3 and R.sub.5 = a hydrogen atom, a hydroxy group, a branched- or straight-chain alkyl group containing from 1 to 3 carbon atoms or a branched- or straight-chain alkyloxy group containing from 1 to 12 carbon atoms,R.sub.4 = a hydrogen atom, a hydroxy group, a branched- or straight-chain alkyl group containing from 1 to 3 carbon atoms or a branched- or straight-chain alkyloxy group containing from 2 to 12 carbon atoms,R.sub.
    Type: Grant
    Filed: March 17, 1976
    Date of Patent: September 12, 1978
    Assignee: S. A. Labaz
    Inventors: Charles Pigerol, Paul DE Cointet de Fillain, Souli Nanthavong
  • Patent number: 4108865
    Abstract: Thiophene compounds of formula: ##STR1## wherein R.sub.1 represents an alkyl radical containing 1 to 4 carbon atoms, a cycloalkyl, cycloalkenyl or aralkyl radical, R.sub.2 represents an atom of hydrogen or a methyl radical with the proviso that when R.sub.2 represents methyl R.sub.1 represents alkyl, or R.sub.1 and R.sub.2, when they are taken together, represent, with the carbon atom to which they are attached, a cyclopolymethylene radical having from 3 to 6 carbon atoms, whereby a reaction medium comprising a solvent and a compound of the general formula: ##STR2## wherein R.sub.3 represents an atom of alkali metal, and R.sub.4 represents an atom of hydrogen or of alkali metal is treated at a temperature between -20.degree. and +80.degree. C with the appropriate quantity of a halide of the general formula:R.sub.5 X IIIin which X represents an atom of fluorine, chlorine, bromine, or iodine and R.sub.
    Type: Grant
    Filed: March 1, 1976
    Date of Patent: August 22, 1978
    Assignee: Labaz
    Inventors: Charles Pigerol, Paul de Cointet DE Fillain, Claude Grain, Jacques Le Blay
  • Patent number: 4103012
    Abstract: Novel indolizine derivatives of the general formula: ##STR1## and pharmaceutically acceptable acid addition salts thereof, wherein R represents a branched- or straight-chain alkyl radical having from 1 to 5 carbon atoms, a phenyl radical, a mono-fluoro-, mono-chloro- or mono-bromo-phenyl, a di-fluoro-, di-chloro- or di-bromo-phenyl radical, a methoxy-phenyl radical or a methyl-phenyl radical optionally substituted on the aromatic moiety by an atom of fluorine, chlorine or bromine and R.sub.1 and R.sub.2, which are different, represent a hydrogen atom or a group of the formula: ##STR2## wherein R.sub.3 and R.sub.4 which are identical, each represent a hydrogen atom or a methyl radical, Am represents a dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, morpholino, piperidino, pyrrolidino or 4-methyl-piperazino group and n is an integer in the range of from 2 to 6 inclusive.
    Type: Grant
    Filed: February 16, 1977
    Date of Patent: July 25, 1978
    Assignee: Labaz
    Inventors: Jean Gubin, Gilbert Rosseels
  • Patent number: 4096112
    Abstract: New stabilizers for polymers of vinyl chloride, the said stabilizers being 2-phenyl-indole derivatives corresponding to the formula: ##STR1## wherein R.sub.1 and R.sub.2, which are the same or different, each represent a branched- or straight-chain alkyl group containing from 1 to 12 carbon atoms, a cyclohexyl radical, a branched- or straight-chain alkyloxy group containing from 1 to 12 carbon atoms, a benzyloxy radical, a hydroxy radical or R.sub.1 and R.sub.2 represent together an alkylenedioxy radical containing from 1 to 3 carbon atoms, R.sub.3 represents a hydrogen atom, a methyl or methoxy radical, with the proviso that one at least of the substituents R.sub.1 or R.sub.2 does not represent an alkyl radical.
    Type: Grant
    Filed: December 29, 1976
    Date of Patent: June 20, 1978
    Assignee: Labaz
    Inventors: Charles Pigerol, Marie-Madeleine Chandavoine, Paul de Cointet DE Fillain, Souli Nanthavong
  • Patent number: 4057644
    Abstract: 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 represent 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: Grant
    Filed: July 22, 1976
    Date of Patent: November 8, 1977
    Assignee: Labaz
    Inventors: Charles Pigerol, Pierre Eymard, Jean-Claude Vernieres, Jean-Pierre Werbenec, Madeleine Broll
  • Patent number: 4057530
    Abstract: New stabilizers of polymers and co-polymers of vinyl chloride, the said stabilizers being 2-phenyl-indole derivatives corresponding to the formula: ##STR1## wherein R represents a phenyl radical, an amino group, optionally substituted by an acetyl or benzoyl radical, a mercapto group, optionally substituted by a branched-or straight-chain alkyl group containing from 1 to 12 carbon atoms or by a cyclohexyl radical, a carboxyl radical, a radical represented by the formula:R.sub.1 O--wherein R.sub.1 represents a hydrogen atom, an isopropyl, carboxymethyl, carbethoxymethyl, carbethoxyisopropyl, acetyl, docosanoyl, benzoyl, benzyl, or allyl radical or a branched-or straight-chain alkyl radical containing from 6 to 12 carbon atoms.
    Type: Grant
    Filed: June 2, 1975
    Date of Patent: November 8, 1977
    Assignee: Labaz
    Inventors: Charles Pigerol, Paul DE Cointet de Fillain, Souli Nanthavong, Jacques Le Blay
  • Patent number: 4048334
    Abstract: 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.tbd.CH--R.sub.4 or an alkynyl radical of the formula C=C--R.sub.4, in which R.sub.4 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.1, R.sub.2 and R.sub.3 being such that no compound of formula I possesses more than 13 carbon atoms.They are useful for treating Parkinson's disease and for correcting extra-pyramidal disturbances provoked by neuroleptics.
    Type: Grant
    Filed: August 22, 1975
    Date of Patent: September 13, 1977
    Assignee: Labaz
    Inventors: Charles Pigerol, Pierre Eymard, Jean-Claude Vernieres, Jean-Pierre Werbenec
  • Patent number: 4032660
    Abstract: Acetoxime derivatives of formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which may be the same or different, each represent a branched- or straight-chain alkyl radical having from 1 to 4 carbon atoms or R.sub.1 and R.sub.2, when they are taken together, represent with the carbon atom to which they are attached, a cyclohexyl group, are useful for treating disturbances of the mental functions including anxiety and as anticonvulsants.
    Type: Grant
    Filed: June 5, 1975
    Date of Patent: June 28, 1977
    Assignee: Labaz
    Inventors: Georges Marcel Taillandier, Jean-Louis Alain Benoit-Guyod, Andre Louis Boucherle, Pierre Luc Eymard, Madeleine Broll
  • Patent number: 4026925
    Abstract: 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=CH--R.sub.4 or an alkynyl radical of the formula C.tbd.C--R.sub.4, in which R.sub.4 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.1, R.sub.2 and R.sub.3 being such that no compound of formula I possesses more than 13 carbon atoms.They are useful for treating Parkinson's disease and for correcting extra-pyramidal disturbances provoked by neuroleptics.
    Type: Grant
    Filed: May 15, 1975
    Date of Patent: May 31, 1977
    Assignee: Labaz
    Inventors: Charles Pigerol, Pierre Eymard, Jean-Claude Vernieres, Jean-Pierre Werbenec