Patents by Inventor Francois Clemence

Francois Clemence 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: 4530932
    Abstract: Novel 4-(1H-indol-3-yl)-.alpha.-methyl-piperidine-1-ethanol derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2, --NH.sub.2, CF.sub.3 -- and CH.sub.3 S--, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and --OH, Ar is selected from the group consisting of optionally substituted aryl and heteroaryl, the dotted line indicates the optional presence of a double bond and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable antagonistic properties toward calcium ion and antihypertensive activity and certain compounds possess .alpha. and/or .beta.-blocking properties.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: July 23, 1985
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Neil L. Brown
  • Patent number: 4518775
    Abstract: Novel compounds of the formula ##STR1## wherein X is in the 5,6,7 or 8 position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, CF.sub.3 O--, CF.sub.3 S-- and CF.sub.3 -, R.sub.1 ' is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 ' is selected from the group consisting of hydrogen or an optionally unsaturated ring able to contain one or more heteroatoms of the group consisting of --S--, --O-- and --N-- optionally substituted with one or more members of the group consisting of (a) halogens, (b) alkyl of 1 to 4 carbon atoms optionally substituted with NH.sub.2, --NHAlK or --N--(AlK).sub.2 and AlK is alkyl of 1 to 3 carbon atoms, (c) phenyl, (d) alkoxy of 1 to 4 carbon atoms, (e) --OH, (f) --CF.sub.3 and (g) --NO.sub.2 or R.sub.1 ' and R.sub.
    Type: Grant
    Filed: May 17, 1983
    Date of Patent: May 21, 1985
    Assignee: Roussel Uclaf
    Inventors: Andre Allais, Francois Clemence, Roger Deraedt, Odile Lemartret
  • Patent number: 4512997
    Abstract: Novel 4H-1,2,4-triazoles of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be in different positions of the benzene rings and are individually selected from the group consisting of hydrogen, --OH, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, --CF.sub.3, --NO.sub.2, --NH.sub.2 and --NH--AlK and ##STR2## and AlK, AlK.sub.1 and AlK.sub.2 are alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 together and/or R.sub.3 and R.sub.4 together are methylenedioxy, R is selected from the group consisting hydrogen, alkyl of 1 to 4 carbon atoms, --CH.sub.2 --COOH and --CH.sub.2 --COOAlK.sub.3 and AlK.sub.3 is alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable analgesic activity and a novel method for their preparation.
    Type: Grant
    Filed: November 17, 1983
    Date of Patent: April 23, 1985
    Assignee: Roussel Uclaf
    Inventors: Jean Meier, Francois Clemence
  • Patent number: 4501740
    Abstract: Novel 20,21-dinoreburnamenines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and .dbd.CH.sub.2, the wavy line connecting to the E ring being a single bond when R is hydrogen or alkyl of 1 to 4 carbon atoms or a double bond when R is .dbd.CH.sub.2 and the dotted line being possibly an endo carbon-carbon bond when R is hydrogen or alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts in all their possible isomers forms, racemic mixtures and optical isomers having oxygenating and cerebral vasoregulating activity of great value and a novel process and intermediates for their preparation.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: February 26, 1985
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Italo Medici, Robert Fournex, Colette Tournemine
  • Patent number: 4486438
    Abstract: Novel 4-hydroxy-3-quinoline-carboxamides of the formula ##STR1## wherein X is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --OCF.sub.3 and --SCF.sub.3, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 is selected from the group consisting of thiazolyl, 4,5-dihydro-thiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl, pyrimidinyl and tetrazolyl, all optionally substituted with alkyl of 1 to 4 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --NO.sub.2 and halogen R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl, R.sub.4 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl, R.sub.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: December 4, 1984
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Odile Le Martret, Francoise Delevallee
  • Patent number: 4450166
    Abstract: Novel N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamides of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R.sub.1 is selected from the group consisting of hydrogen, halogen, linear alkyl of 1 to 4 carbon atoms, branched alkyl of 3 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, CF.sub.3 --, CF.sub.3 O--, CF.sub.3 S-- and CH.sub.3 S-- in the 6- or 7-position and their non-toxic, pharmaceutically acceptable acid addition salts having a strong anxiolytic activity and a remarkable affinity for benzodiapines receptors and their preparation.
    Type: Grant
    Filed: June 9, 1982
    Date of Patent: May 22, 1984
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Peter F. Hunt, Odile Le Martret, Daniel Humbert
  • Patent number: 4397856
    Abstract: Novel compounds of the formula ##STR1## wherein X is in the 5,6,7 or 8 position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, CF.sub.3 O--, CF.sub.3 S-- and CF.sub.3 --, R.sub.1 ' is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 ' is selected from the group consisting of hydrogen or an optionally unsaturated ring able to contain one or more heteroatoms of the group consisting of --S--, --O-- and --N-- optionally substituted with one or more members of the group consisting of (a) halogens, (b) alkyl of 1 to 4 carbon atoms optionally substituted with NH.sub.2, --NHAlK or --N---(AlK).sub.2 and AlK is alkyl of 1 to 3 carbon atoms, (c) phenyl, (d) alkoxy of 1 to 4 carbon atoms, (e) --OH, (f) --CF.sub.3 and (g) --NO.sub.2 or R.sub.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: August 9, 1983
    Assignee: Roussel Uclaf
    Inventors: Andre Allais, Francois Clemence, Roger Deraedt, Odile Lemartret
  • Patent number: 4337353
    Abstract: Novel carboxylic acids of the formula ##STR1## wherein Z is an aliphatic hydrocarbon chain selected from the group consisting of --(CH.sub.2).sub.n -- and --CH.dbd.CH--(CH.sub.2).sub.n-2 -- where the double bond may be at any point in the chain, n is an integer from 5 to 10 and X, X.sub.1, X.sub.2 and X.sub.3 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 5 carbon atoms, alkylthio of 1 to 5 carbon atoms, CF.sub.3 --, CF.sub.3 O-- and CF.sub.3 S-- and their non-toxic, pharmaceutically acceptable organic and inorganic salts and esters having analgesic and anti-inflammatory activity and their preparation.
    Type: Grant
    Filed: February 6, 1978
    Date of Patent: June 29, 1982
    Assignee: Roussel UCLAF
    Inventors: Andre Allais, Francois Clemence, Jean Meier, Roger Deraedt
  • Patent number: 4299831
    Abstract: Novel 3-quinoline carboxamides of the formula ##STR1## wherein X' is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, straight or branched alkyl and alkoxy of 1 to 5 carbon atoms, --CF.sub.3, --SCF.sub.3 and --OCF.sub.3, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 ' is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl, pyrimidyl and tetrazolyl, all optionally substituted with alkyl of 1 to 4 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --NO.sub.2 and halogen and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic and anti-inflammatory activity and novel intermediates and process for their preparation.
    Type: Grant
    Filed: November 27, 1979
    Date of Patent: November 10, 1981
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Roger Deraedt, Andre Allais, Odile Le Martret
  • Patent number: 4294845
    Abstract: Novel racemic mixtures or optically active isomers of 1,3-benzodioxins of the formula ##STR1## wherein R.sub.1 ' is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, --NH.sub.4, aluminum, non-toxic, pharmaceutically acceptable amines, alkyl of 1 to 5 carbon atoms, 2,3-dihydroxypropanyl, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl and dialkylaminoalkyl with alkyls of 1 to 4 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and phenyl and R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen and halogen, and the non-toxic, pharmaceutically acceptable acid addition salts where R.sub.1 ' is dialkylaminoalkyl, with the proviso that R.sub.2 and R.sub.3 are not hydrogen simultaneously having hypolipemic activity and their preparation.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: October 13, 1981
    Inventors: Daniel Humbert, Francois Clemence, Michele Dagnaux
  • Patent number: 4281012
    Abstract: Novel racemates and optically active isomers and mixtures of isomers of [4H]-1,3-benzodioxin-2-carboxylic acid compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, dialkylamino alkyl with alkyls of 1 to 5 carbon atoms, alkali metal, alkaline earth metal, aluminum, --NH.sub.4, non-toxic pharmaceutically acceptable amines, 2,3-dihydroxypropanyl and (2,2-dimethyl-1,3-dioxolan-4-yl)-methyl, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.3 and R.sub.6 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, ethenyl and cyclohexyl and taken together with the carbon atom to which they are attached form cyclohexyl, R.sub.5 is selected from the group consisting of hydrogen and halogen or R.sub.1 and R.sub.2 have the above definitions, R.sub.6 is ##STR2## R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, --CF.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: July 28, 1981
    Assignee: Roussel Uclaf
    Inventors: Daniel Humbert, Francois Clemence, Michele Dagnaux
  • Patent number: 4224333
    Abstract: Novel optically active isomers or racemates of 1,3-dihydro-3-{1-[2-(2,3-dihydro-1,4-benzodioxin-2-yl)-2-hydroxyethyl]-pip eridin-4-yl}-2H-indol-2-ones of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, fluorine and alkoxy of 1 to 5 carbon atoms and R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antihypertensive activity and a novel process and intermediates for their preparation.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: September 23, 1980
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Daniel Humbert, Robert Fournex
  • Patent number: 4172137
    Abstract: Novel 5-thiazole-alkylamines of the formula ##STR1## wherein R is alkyl of 1 to 6 carbon atoms and n is a whole number of 2 to 7 and their non-toxic, pharmaceutically acceptable acid addition salts having marked antilipolytic activity.
    Type: Grant
    Filed: July 29, 1977
    Date of Patent: October 23, 1979
    Assignee: Roussel UCLAF
    Inventors: Francois Clemence, Robert Fournex
  • Patent number: 4159986
    Abstract: Novel thiophene-acetic acid derivatives of the formulae ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.1 is selected from the group consisting of lower alkyl of 1 to 4 carbon atoms and hydrogen and R.sub.2 is selected from the group consisting of hydrogen, lower alkyl of 1 to 7 carbon atoms and optionally substituted with at least one hydroxy group or an oxygen atoms-containing heterocycle,di-lower alkylamino-lower alkyl, N-heterocyclic alkyl, alkali metals, alkaline earth metals, aluminum and --H,NH (lower alkyl).sub.2 and Ar is selected from the group consisting of phenyl, optionally substituted with at least one member of the group consisting of halogen, trihalogenomethyl, lower alkyl, lower alkoxy and carboxyl, cyclohexyl, thienyl, furyl, tetrahydrofuryl and pyridyl, and in formula II, ArCO is attached to one of the positions .alpha. to the sulfur atom, which compounds have analgesic and anti-inflammatory activity and their preparations.
    Type: Grant
    Filed: September 4, 1975
    Date of Patent: July 3, 1979
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Odile Le Martret
  • Patent number: 4147790
    Abstract: Benzophenones of the formula ##STR1## wherein X.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, X.sub.2 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms, m is a whole number from 1 to 10, n is a whole number from 2 to 5 and Y is in the 2,3 or 4-position and is selected from the group consisting of hydrogen, halogen, CF.sub.3 --, CF.sub.3 O--, CF.sub.3 S--, alkyl of 1 to 8 carbon atoms and alkoxy of 1 to 8 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic activity and their preparation.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: April 3, 1979
    Assignee: Roussel Uclaf
    Inventors: Andre Allais, Francois Clemence, Roger Deraedt
  • Patent number: 4107310
    Abstract: Novel quinoline-3-carboxamides of the formula ##STR1## wherein R.sub.1 is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, --CF.sub.3, --OCF.sub.3, --SCF.sub.3, straight chain alkyl of 1 to 4 carbon atoms, branched alkyl of 3 to 5 carbon atoms and alkoxy of 1 to 4 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen and methyl, R.sub.3 is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl and imidazolyl and R.sub.4 is selected from the group consisting of hydrogen, hydroxyl, alkyl of 1 to 4 carbon atoms, phenyl and benzyl with the proviso that when R.sub.1 is in the 7 or 8-position and is halogen, --CH.sub.3, --OCF.sub.3 or --SCF.sub.3 and R.sub.4 is hydrogen, R.sub.3 is not thiazolyl, pyridinyl or oxazolyl and the non-toxic, pharmaceutically acceptable acid addition salts when R.sub.3 is imidazolyl or 4,5-dihydrothiazolyl having analgesic activity and their preparation and novel intermediates therefore.
    Type: Grant
    Filed: February 7, 1977
    Date of Patent: August 15, 1978
    Assignee: Roussel Uclaf
    Inventors: Andre Allais, Francois Clemence, Roger Deraedt, Odile Le Martret
  • Patent number: 4100291
    Abstract: Novel 1,4-benzodioxanes of the formula ##STR1## wherein R' is selected from the group consisting of hydrogen, alkoxy of 1 to 5 carbon atoms, chlorine, bromine and fluorine, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and Y and Z are hydrogen or together form a double bond in the form of their racemic mixtures or optically active isomers and their non-toxic, pharmaceutically acceptable acid addition salts having antihypertensive activity and a novel process and novel intermediates for their preparation.
    Type: Grant
    Filed: April 28, 1977
    Date of Patent: July 11, 1978
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Daniel Humbert
  • Patent number: 4078076
    Abstract: Novel pyranic derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms and cations of alkali metals, alkaline earth metals, aluminum, amines and ammonium R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and X is selected from the group consisting of hydrogen, chlorine and bromine having hypolipemic activity and reducing the level of total lipids in plasma.
    Type: Grant
    Filed: May 26, 1976
    Date of Patent: March 7, 1978
    Assignee: Roussel UCLAF
    Inventors: Francois Clemence, Daniel Humbert, Robert Fournex
  • Patent number: 4045567
    Abstract: Hypolipemiant compositions comprising an effective amount of at least one 2-alkyl-5-thiazole-carboxylic acid derivative of the formula ##STR1## wherein R is hydrogen, an alkali metal, ammonium, the monovalent residue of an organic base or a substituted or unsubstituted alkyl and where R'.sub.1 is a linear alkyl of 1 to 12 carbon atoms, and a major amount of a pharmaceutical carrier; as well as the method of reducing the amount of sanguine lipids in warm-blooded animals utilizing the above-hypolipemiant compositions.
    Type: Grant
    Filed: February 27, 1976
    Date of Patent: August 30, 1977
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Odile Le Martret
  • Patent number: 3992540
    Abstract: Novel 3-quinoline-carboxamides of the formula ##SPC1##Wherein R is selected from the group consisting of halogen, --CF.sub.3, --OCF.sub.3 and --SCF.sub.3 in the 7- or 8-position, R.sub.1 is selected from the group consisting of hydrogen and acyl of an aliphatic carboxylic acid of 2 to 4 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R.sub.2 is selected from the group consisting of thiazloyl, pyridinyl and oxazolyl and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic activity and their preparation and novel intermediates.
    Type: Grant
    Filed: July 28, 1975
    Date of Patent: November 16, 1976
    Assignee: Roussel-UCLAF
    Inventors: Francois Clemence, Roger Deraedt, Andre Allais, Odile Le Martret