Patents Assigned to Lipha, Lyonnaise Industrielle Pharmaceutique
  • Patent number: 5489592
    Abstract: Novel 3,4-dihydro-4-oxo-3(prop-2-enyl)-1-phtalazineacetic acids and derivatives of formula (I) ##STR1## in which R.sub.1 R.sub.2 and R.sub.3 are the same or different and stand for H, a halogen or a linear or branched aliphatic, saturated or unsaturated radical, substituted or not by at least one halogen or R.sub.4 residue such as defined below, except when R.sub.4 is H; R.sub.4 and R.sub.5 are the same or different and stand for H, a linear or branched aliphatic radical, saturated or unsaturated, an aryl or heteroaryl radical, said radicals being substituted or not by at least one grouping such as fluorine, chlorine, bromine, methyl or trifluoromethyl, where R.sub.4 and R.sub.5 do not simultaneously denote H; R.sub.6 stands for hydroxy or alkoxy radical; R.sub.
    Type: Grant
    Filed: June 20, 1994
    Date of Patent: February 6, 1996
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Francois Collonges, Herve Dumas, Philippe Durbin, Daniel Guerrier
  • Patent number: 5476846
    Abstract: The present invention concerns new substituted sulfonamides, and the physiologically acceptable salts, complexes, esters and amides thereof, represented by the formula ##STR1## which is defined herein. Said compounds find application as anti-thrombotic and anti-asthmatic medicines.
    Type: Grant
    Filed: November 17, 1994
    Date of Patent: December 19, 1995
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Claude Lardy, Daniel Guerrier, Gilles Chavernac, Francois Collonges
  • Patent number: 5387709
    Abstract: The present invention concerns new substituted sulfonamides, and the physiologically acceptable salts possibly in the form of complexes, esters and amides thereof, represented by the formula: ##STR1##
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: February 7, 1995
    Assignee: Lipha Lyonnaise Industrielle Pharmaceutique
    Inventors: Claude Lardy, Daniel Guerrier, Gilles Chavernac, Francois Collonges
  • Patent number: 5338849
    Abstract: These compounds correspond to the formula ##STR1## in which one of the groups X.sub.1 to X.sub.4 represents nitrogen and the others a CH radical,R.sub.1 and R.sub.2 represent H, halogen, alkyl, hydroxymethyl, alkyloxymethyl, dialkylaminoalkyl, dialkylaminoalkyloxymethyl, carboxyl, ethyl carboxylate, piperidino, alkenyl, cycloalkyl, cycloalkenyl, alkylthio, benzyl, phenyl, thiophene or pyridine, optionally substituted,R.sub.3 and R.sub.4 represent H, halogen, alkyl, cycloalkyl, alkoxy or alkylthio,R.sub.5 and R.sub.6 denote H, alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl or alkylthioalkyl, or together form alkylene or alkyleneoxyalkylene chains,R.sub.7 denotes H, alkyl or cycloalkyl; one of the radicals R.sub.5 to R.sub.7 can also denote optionally substituted phenyl or benzyl,R.sub.8 represents H, alkyl, cycloalkyl or optionally substituted phenyl or benzyl,R.sub.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: August 16, 1994
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Didier Festal, Denis Descours, Jacques Decerprit
  • Patent number: 5219859
    Abstract: The invention relates to indole derivatives of formula 1, ##STR1## in which: R.sub.1 and R.sub.2 represent H, alkyl, alkenyl, cycloalkyl, N-alkylamino- or N,N-dialkylaminoalkyl, benzyl, pyridylmethyl or phenyl, optionally substituted,R.sub.3 and R.sub.4 represent H, halogen, alkyl, alkoxy, alkylthio, CF.sub.3, NO.sub.2, N-alkylamino or N,N-dialkylamino, benzyl or phenyl, optionally substituted,R.sub.5 represents H, alkyl, cycloalkyl or optionally substituted benzyl,R.sub.6 denotes an alkyl, phenyl or heterocyclic radical, optionally substituted,Z denotes the bivalent radicals --(CH.sub.2).sub.n --C(R.sub.7 R.sub.8)--(CH.sub.2).sub.p --, --CH=CH--C(R.sub.7 R.sub.8)-- in which n=0--2, p=0--2 and n+p.ltoreq.2, R.sub.7 and R.sub.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: June 15, 1993
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Didier Festal, Denis Descours, Robert Bellemin, Jacques Decerprit
  • Patent number: 5183924
    Abstract: Derivatives of benzocycloalkenyldihydroxyalkanoic acids, inhibitors of HMG CoA reductase, antagonists of thromboxane A.sub.2 receptors and antifungals, denoted by the formula I ##STR1## in which X=CH.sub.2, O or S; R.sub.1 and R.sub.2, identical or different, =H, C.sub.1-3 alkyl or together form a --(CH.sub.2).sub.n -- chain (n=4,5) optionally substituted symmetrically by one or two C.sub.1-3 alkyl radicals.R.sub.3 and R.sub.4, identical or different, =H, CF.sub.3, halogen (Cl, F, Br), C.sub.1-5 N,N-dialkylamino, C.sub.1-4 alkyl, C.sub.1-5 -alkoxy, C.sub.1-3 alkylthio, or phenyl optionally substituted by at most substituents which may be identical or different and may denote C.sub.1-3 alkyl or C.sub.1-3 alkoxy radicals or halogens (F, Cl), it being understood that when one of R.sub.3 and R.sub.4 denotes the radicals: CF.sub.3, N,N-dialkylamino, C.sub.6 H.sub.5 or substituted phenyl, it is present at the vertices 3', R' or 5' according to formula 1 and the other denotes a hydrogen atom.R.sub.5 and R.sub.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: February 2, 1993
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Didier Festal, Jean-Yves Nioche, Denis Descours, Robert Bellemin, Jacques Decerprit
  • Patent number: 5167949
    Abstract: The present invention relates to 4(3H)-pteridinones represented by the formula: ##STR1## in which X is an oxygen atom or a sulphur atom, Y is a hydrogen atom, a lower alkyl radical, especially a methyl radical, at the 6-position or a hydroxyl group at the 7-position, R.sub.1 is a hydrogen atom, a lower alkyl radical, a substituted or unsubstituted phenyl radical, a benzyl radical, a methoxymethyl group, an acetyl group, a 2-acetoxyethyl group or a 2,2,2-trifluoroethyl group and R.sub.2 is a hydrogen atom or a lower alkyl radical, especially a methyl radical. Application of these compounds as anti-allergic drugs.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: December 1, 1992
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Gerard Ferrand, Herve Dumas, Jean-Claude Depin, Yvette Quentin
  • Patent number: 5116954
    Abstract: Substituted six-membered benzo-fused heterocycles of the formula (I) ##STR1## in which: X=0, NH, S.fwdarw.(O).sub.n (n=0 or 2);R.sub.1 is phenyl, phenyl substituted by methoxy, hydroxy, chlorine, fluorine, diethylaminoethoxy, phenoxy, 2-methyl-4-thiazolyl, 2-amino-4-thiazolyl, phenyl, amino, nitro, terbutyl, carboxymethyl, acetamido, dimethyltriazenyl, benzoyl, hexyl, undecyl, trifluoromethyl, carbamoyl; or R.sub.1 is trifluoromethyl, pyridyl-2,pyridyl-4;R.sub.2 is H, methoxy, hydroxy; orR.sub.1 and R.sub.2 are --CH.dbd.CH--CH.dbd.CH--;R.sub.3 and R.sub.4 are methoxy, hydroxy, fluorine or form a fused benzene ring;CR.sub.5 R.sub.6 R.sub.7 is carboxymethyl, --CH.sub.2 --PO.sub.3 H,--CH.sub.2 --PO(oET).sub.2, 4-methylpiperazinyl, aminomethyl,3-4-5-trimethoxyphenylaminomethyl, acetyl, bromoacetyl, hydroxyethyl, acetoxyethyl, mercaptomethyl, acetylthiomethyl, methoxy-carbopnylthiomethyl, --CH--CONH.sub.2, ##STR2## substituted thiazolyl, subsituted furanone, imidazo(1,2-a)pyridinyl, indolizinyl, or R.sub.4 and R.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: May 26, 1992
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
  • Patent number: 5082859
    Abstract: Derivatives of benzocycloalkenyldihydroxyalkanoic acids, inhibitors of HMG CoA reductase, antagonists of thromoboxane A.sub.2 receptors and antifungals, denoted by the formula I ##STR1## in which X=CH.sub.2, O or S; R.sub.1 and R.sub.2, identical or different, =H, C.sub.1-3 alkyl or together from a --(CH.sub.2).sub.n -- chain (n=4,5) optionally substituted symmetrically by one or two C.sub.1-3 alkyl radicals.R.sub.3 and R.sub.4, identical or different, =H, CF.sub.3, halogen (Cl, F, Br), C.sub.1-5 N,N-dialkylamino, C.sub.1-4 alkyl, C.sub.1-5 -alkoxy, C.sub.1-3 alkylthio, or phenyl optionally substituted by at most two substitutents which may be identical or different and may denote C.sub.1-3 alkyl or C.sub.1-3 alkoxy radicals or halogens (F, Cl), it being understood that when one of R.sub.3 and R.sub.4 denotes the radicals: CF.sub.3, N,N-dialkylamino, C.sub.6 H.sub.5 or substituted phenyl, it is present at the vertices 3', 4'or 5' according to formula 1 and the other denotes a hydrogen atom.R.sub.5 and R.sub.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: January 21, 1992
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Didier Festal, Jean-Yves Nioche, Denis Descours, Robert Bellemin, Jacques Decerprit
  • Patent number: 5001134
    Abstract: The present invention relates to piperidines denoted by the formula: ##STR1## in which X is the 4-fluorobenzoyl, 2-(4-fluorophenyl)-1,3-dioxolan-2-yl or 6-fluoro-1,2-benzisoxazol-3-yl group, Y is a hydrogen atom or the hydroxyl group, m is an integer between 0 and 4 inclusive, n is 0 or 1, Q is a nitrogen atom or the methine group; when Q is a nitrogen atom, R is the cyano group or the carbamoyl group; when Q is the methine group, R is the nitro group; R.sup.1 and R.sup.2 may be identical or different and are hydrogen, a lower alkyl radical, the phenyl radical, the 2,2,2-trifluoroethyl group or the 2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl group; or the NR.sup.1 R.sup.2 structural unit is the piperidino radical or the 4-(4-fluorobenzoyl)-1-piperidinyl group.Application of these compounds as antihypertensive medications.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: March 19, 1991
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Gerard Ferrand, Herve Dumas, Jean-Claude Depin, Gilles Chavernac
  • Patent number: 4957927
    Abstract: 1-[(diarylmethoxy)alkyl]pyrrolidines and piperidines represented by the following formula: ##STR1## wherein X is hydrogen or a fluorine atom, Alk is a linear-chain or branched alkyl group having two or three carbon atoms; R.sub.1 and R.sub.2 are hydrogen or a linear-chain or branched alkoxy radical having 1 to 4 carbon atoms; n is 4 or 5.The compounds can be used as cardiovascular medicines.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: September 18, 1990
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Gerard Ferrand, Jacques Barbanton, Jean-Claude Depin, Gilles Chavernac
  • Patent number: 4783533
    Abstract: The invention concerns [oxo-4-4H-[1]-benzopyran-8-yl]-alcanoic acids and their derivatives, their manufacture, represented by the formula. ##STR1## where AR is hydrogen, a phenyl radical which may or may not be substituted thenyl, furyl, naphthyl, a lower alkyl, cycloalkyl, aralkyl radical; B is a linear or branched lower alkyl radical, either saturated or ethylinically unsaturated; R.sub.1 is hydrogen or a phenyl radical; X is hydrogen or a lower alkyl or alkoxy radical and n=1, as well as salts, esters, aminoesters and amides.Compounds and their derivatives may be used as medicines, in particular in the control of tumors.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: November 8, 1988
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
  • Patent number: 4652583
    Abstract: Naftidrofuryl can be used to prepare a pharmaceutical which promotes the regeneration of nerve fibers. A neurologically active quantity of N,N-2-diethylaminoethyl-tetrahydro-alpha-(1-naphthylmethyl)-2-furanpropano ate or an addition salt thereof is incorporated in an excipient or an inert, nontoxic, pharmaceutically acceptable vehicle.
    Type: Grant
    Filed: April 17, 1986
    Date of Patent: March 24, 1987
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Michel Mosnier, Marcel Grand
  • Patent number: 4649153
    Abstract: 5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acids represented by the formula: ##STR1## in which Ar is a phenyl or thienyl group, optionally substituted, or a furyl group; R is a lower alkyl radical, are useful as anti-inflammatory and analgesic medicines.
    Type: Grant
    Filed: June 20, 1985
    Date of Patent: March 10, 1987
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Gerard Ferrand, Jacques Barbanton, Jean-Claude Depin
  • Patent number: 4602034
    Abstract: The invention concerns: (oxo-4-4H-(1)-benzopyran-8-yl) alkanoic acids and their derivatives, their manufacture, represented by the formula: ##STR1## where Ar is hydrogen, a phenyl radical which may or may not be substituted, thenyl, furyl, naphthyl, a lower alkyl, cycloalkyl, aralkyl radical; B is a linear or branched lower alkyl radical, either saturated or ethylinically unsaturated; R.sub.1 is hydrogen or a phenyl radical; X is hydrogen or a lower alkyl or alkoxy radical and n=1, as well as salts, esters, aminoesters and amides.Compounds and their derivatives may be used as medicines, in particular in the control of tumors.
    Type: Grant
    Filed: November 6, 1984
    Date of Patent: July 22, 1986
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Philippe Briet, Jean-Jacques Berthelon, Francois Collonges
  • Patent number: 4585786
    Abstract: The invention relates to hydroxy-4-2H-1-benzothiopyran-2-ones, represented by the following formula: ##STR1## in which, when R.sub.1 is hydrogen, R and AR' can form a tetrahydronaphtyl cycle; R and R.sub.1 can form a carbonyl group; R is a hydroxyl group when R.sub.1 is hydrogen; AR is a biphenyl or phenoxyphenyl group, which is substituted or non-substituted by a halogen, and AR' is a substituted or non-substituted phenyl group which may form with R a tetrahydronaphtyl cycle or a thienyl group. These compounds have interesting properties and may be used in particular as rodenticides.
    Type: Grant
    Filed: March 27, 1985
    Date of Patent: April 29, 1986
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventor: Jean-Jacques Berthelon
  • Patent number: 4554273
    Abstract: Disclosed are 2-amino-5-phenyl-1,3-benzodiazepines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, halogen, alkyl, or alkoxy; R.sub.2 being able to occupy any of the possible positions on the aromatic ring; R.sub.3 is hydrogen or alkyl; and R.sub.4 is hydrogen, alkyl, cycloalkyl, arylalkyl, heteroarylalkyl, dialkylaminoethyl, dialkylaminopropyl, (1-ethyl-2-pyrrolidino) methyl, dialkylamino, alkoxycarbonyl or cyano; or R.sub.3 and R.sub.4 form, with the adjacent nitrogen atom, a heterocycle having 5 to 7 side chains, optionally containing another heteroatom selected from oxygen, sulfur or nitrogen, this latter being able to be substituted by an alkyl group. The majority of the compounds are obtained by condensation of the corresponding 2-methylthio benzodiazepine hydroiodide with an appropriate amine. The compounds are useful as antidepressants.
    Type: Grant
    Filed: February 7, 1984
    Date of Patent: November 19, 1985
    Assignee: Lipha Lyonnaise Industrielle Pharmaceutique
    Inventors: Michel Bayssat, Gerard Ferrand, Jean-Claude Depin
  • Patent number: 4552878
    Abstract: This invention relates to benzo- and thieno-triazine-1,2,3 ones-4 represented by the formula ##STR1## in which m is 2, 3 or 4, X is the vinylene group --CH.dbd.CH-- or a sulfur atom; R.sub.1 and R.sub.2 can be alike or different and are hydrogen, halogen, a lower alkyl radical, lower alkoxy radical or trifluoromethyl radical; when X is --CH--CH-- n is 0, 1 or 2 and R is hydrogen, halogen, a lower alkyl radical, lower alkoxy radical or nitro group; when X is a sulfur atom, R is hydrogen or constitutes a --CH.sub.2 --.sub.4 chain between the two open positions of the thiophenic ring. The compounds are useful as antidepressant drugs.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: November 12, 1985
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Gerard Ferrand, Herve Dumas, Michel Bayssat, Jean-Claude Depin
  • Patent number: 4512994
    Abstract: Long-acting forms of theophylline for use in treating asthma comprise theophylline associated with a compound of the substituted cinnamamide type of the general formula ##STR1## wherein R is hydrogen, a hologen or an acetyl radical; R.sub.1 is hydrogen or the methyl radical; R.sub.2 is ##STR2## wherein R.sub.3 is hydrogen or the methyl radical; or R.sub.1 and R.sub.2 together with the adjacent nitrogen tom form the 2,2-dimethyl-3-oxazolidinyl group.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: April 23, 1985
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Michel Bayssat, Maryse Belleville, Marcel Grand
  • Patent number: 4310536
    Abstract: Compositions having rodenticidal activity are disclosed which are constituted by a solution of a compound having anti-coagulant activity and which is an indane dione or a 4-hydroxycoumarin, preferably chlorophacinone, diphacinone, bromadiolone or coumachlor, in a glycol in admixture with a volatile co-solvent, preferably acetone or dichloromethane, which increases the solvent activity of the glycol for the anti-coagulant compound. The composition is stable and may be applied to solid or liquid baits or used to form trail poisons.
    Type: Grant
    Filed: December 14, 1977
    Date of Patent: January 12, 1982
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Eugene Boschetti, Jean-Claude Lechevin