Patents Assigned to LIPHA
  • 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: 4863866
    Abstract: Mutant strains of Bradyrhizobium japonicum having enhanced nodulation properties were created by transposon mutagenesis of known Bradyrhizobium japonicum strain I-110. The mutant strains grow well in a yeast-extract mannitol medium, produce extracellular polysaccharides at a level greater than the parent strain under appropriate conditions, are capable of growth on a nutirent medium containing a normally inhibitory amount of succinic acid, and contain a 21 Kdalton protein absent from the parent strain. Such strains can be used to inoculate soil in which soybean plants are grown, resulting in improved plant yields.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: September 5, 1989
    Assignee: Lipha Chemicals, Inc.
    Inventors: Robert M. Zablotowicz, Robert G. Upchurch, James M. Ligon
  • 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
  • Patent number: 4269848
    Abstract: 5-Substituted indan-2-carboxylic acids and functional derivatives thereof having inflammation-reducing properties have the general formula ##STR1## in which R is a phenyl, phenyl-lower alkenyl, phenyl-lower alkyl, phenyl substituted by at least one of the halogens, lower alkyl, lower alkoxy, acetamido, amino, lower dialkylamino, nitro, phenyl, lower alkylsulfonyl, lower dialkylaminosulfonyl and sulfamido, cyclohexyl, furyl, lower alkylfuryl, thienyl, halothienyl, lower alkylthienyl, or pyridyl group and R' is a hydroxyl, lower alkoxy, lower dialkylaminoalkoxy, cinnamoylamido lower alkoxy, 2-hydroxyethylamino, amino or lower dialkylaminoalkyl amino group. Besides the esters and amides, the functional derivatives of the acids include the pharmacologically acceptable salts of the above compounds. The compounds are also of low toxicity, have analgesic activity and exert an antipyretic effect.
    Type: Grant
    Filed: January 27, 1978
    Date of Patent: May 26, 1981
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Michel Bayssat, Francis Sautel, Jean-Claude Depin, Annie B. Matibet
  • Patent number: 4241047
    Abstract: The invention concerns a novel medicinal composition for the treatment of biliary lithiasis. The active principle of the composition is formed by the association of hymecromone (4-methyl-7-hydroxycoumarine) and chenodeoxycholic acid. The medicament is administered by oral route in a suitable pharmaceutical form.
    Type: Grant
    Filed: July 18, 1979
    Date of Patent: December 23, 1980
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Jean-Claude Lechevin, Jean-Noel Treilles
  • Patent number: 4230850
    Abstract: Novel 3-substituted-4-aminoalkoxy-5,6-condensed ring-2-pyranones are disclosed as having utility as pharmacologically active compounds, in particular vasodilatory, hypotensive, anti-ischemic and anti-tussive activity. The compounds may be 3-phenyl-4-morpholinoalkoxy-coumarins. Administration may be by the oral or parenteral route. Intermediates useful in the production of these compounds are also disclosed.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: October 28, 1980
    Assignee: LIPHA, Lyonnaise Industrielle Pharmaceutique
    Inventors: Philippe Briet, Jean-Jacques Berthelon, Jean-Claude Depin
  • Patent number: 4224341
    Abstract: 5-Substituted indan-2-carboxylic acids and functional derivatives thereof having inflammation-reducing properties have the general formula ##STR1## in which R is a phenyl, phenyl-lower alkenyl, phenyl-lower alkyl, phenyl substituted by at least one of the halogens, lower alkyl, lower alkoxy, acetamido, amino, lower dialkylamino, nitro, phenyl, lower alkylsulfonyl, lower dialkylaminosulfonyl and sulfamido, cyclohexyl, furyl, lower alkylfuryl, thienyl, halothienyl, lower alkylthienyl, or pyridyl group and R' is a hydroxyl, lower alkoxy, lower dialkylaminoalkoxy, cinnamoylamido lower alkoxy, 2-hydroxyethylamino, amino or lower dialkylaminoalkyl amino group. Besides the esters and amides, the functional derivatives of the acids include the pharmacologically acceptable salts of the above compounds. The compounds are also of low toxicity, have analgesic activity and exert an antipyretic effect.
    Type: Grant
    Filed: December 14, 1977
    Date of Patent: September 23, 1980
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Michel Bayssat, Francis Sautel, Jean-Claude Depin, Annie Betbeder Matibet
  • Patent number: 4201783
    Abstract: Substituted hexahydro benzopyrano [3,2-c] pyridines, useful as antidepressants, have the formula ##STR1## where R is hydrogen or a saturated or unsaturated, linear or branched, lower alkyl, or an aralkyl, acyl, dialkylaminoalkyl, carbonylalkyl, alkoxycarbonyl, haloalkoxycarbonyl or aryl radical; R.sub.1 is hydrogen, halogen, or lower alkoxy; R.sub.2 is hydrogen or halogen; R.sub.3 is hydrogen, halogen, lower alkyl, alkoxy nitro or amino, or forms naphthalene with R.sub.4 and the benzene ring; R.sub.4 is hydrogen, a halogen, or forms naphthalene with R.sub.3 and the benzene ring; R.sub.5 is hydrogen, lower alkyl, or aralkyl.
    Type: Grant
    Filed: June 23, 1978
    Date of Patent: May 6, 1980
    Assignee: Lipha Lyonnaise Industrielle Pharmaceutique
    Inventors: Philippe Briet, Jean-Jacques Berthelon, Jean-Claude Depin
  • Patent number: 4190665
    Abstract: Substituted arylaliphatic acids represented by the general formula ##STR1## wherein X is a nitro or amino group, may be used as drugs, in particular as an analgesic and anti-inflammatory agent.
    Type: Grant
    Filed: November 28, 1977
    Date of Patent: February 26, 1980
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Etienne Szarvasi, Didier Festal
  • Patent number: 4178388
    Abstract: Rodenticidal compositions in the form of solutions or emulsions are formed from an anticoagulant substance in a liquid aromatic hydrocarbon solvent in the presence of an emulsifier.These compositions, when diluted with water, can be used for the destruction of rodents by spraying the areas in which grow vegetables serving as foodstuffs for the rodents to be destroyed.
    Type: Grant
    Filed: September 10, 1975
    Date of Patent: December 11, 1979
    Assignee: Lipha-Lyonnaise Industrielle Pharmaceutique
    Inventor: Jean-Claude Lechevin