Patents Assigned to Synthelabo
  • Patent number: 5373023
    Abstract: The invention provides compounds which are tetrahydronaphthalene derivatives of the formula (I) ##STR1## wherein R.sub.1 represents a halogen atom, a cyano group, a nitro group, an unbranched (C.sub.1 -C.sub.6) alkoxy group, a (C.sub.1 -C.sub.6 cycloalkyl) (C.sub.1 -C.sub.2 alkoxy) group or an aryl (C.sub.1 -C.sub.2 alkoxy) group,R.sub.2 represents a (C.sub.1 -C.sub.4) alkyl group, an aryl group optionally substituted with at least one methoxy group, a pyridyl group or a benzodioxanyl group,R.sub.3 represents a hydrogen atom or a (C.sub.1 -C.sub.2) alkyl group, and n=0 to 3, or are addition salts with pharmaceutically acceptable acids. The compounds of the invention have anti-ischaemic activity.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: December 13, 1994
    Assignee: SYNTHELABO
    Inventors: Paul Howard Williams, Christian Hoornaert, Jean Claude Muller
  • Patent number: 5371227
    Abstract: The present invention provides a compound which is a quinoline derivative of the formula (I) ##STR1## in which R.sub.1 represents either 1H-tetrazol-5-yl, or CO.sub.2 H,R.sub.2 represents either (C.sub.1-7)alkyl or (C.sub.2-6)alkenyl,R.sub.3 and R.sub.4 represent, independently of each other, hydrogen, halogen, cyano group, (C.sub.1-7)alkyl, (C.sub.3-7)cycloalkyl(C.sub.1-4)alkyl, aryl, aryl(C.sub.1-4)alkyl, aryl(C.sub.2-6)alkenyl, --(CH.sub.2).sub.m --COR.sub.5 in which m=0 to 4 and R.sub.5 represents hydrogen, --OH, --(C.sub.1-6)alkoxy, or --NR.sub.7 R.sub.8, R.sub.7 and R.sub.8 representing, independently of each other, hydrogen or --(C.sub.1-4)alkyl group, or a --(CH.sub.2).sub.n --R.sub.6 group in which n=1 to 4 and R.sub.6 represents --OH, --(C.sub.1-6)alkoxy, --(C.sub.1-4)alkoxy --(C.sub.1-4)alkoxy, or (C.sub.3-7)cycloalkyl(C.sub.1-4)alkoxy group, or a pharmaceutically acceptable salt thereof and their therapeutic applications.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: December 6, 1994
    Assignee: Synthelabo
    Inventors: Gerard Cremer, Pascale Goberville, Jean-Claude Muller
  • Patent number: 5371233
    Abstract: Compounds corresponding to the formula (I) ##STR1## in which X represents dibromomethyl, formyl, (C.sub.1-4)alkyl, or a group CH(OR.sub.5).sub.2 or CH(OH)OR.sub.5, wherein the or each R.sub.5 is hydrogen (C.sub.1-3)alkyl or the two R.sub.5 's in the case of CH(OR.sub.5).sub.2 are linked to provide a 1,3-dioxolane or 1,3-dioxane ring, and Y represents hydrogen, 1,1-dimethylethyl, triphenylmethyl, trimethylstannyl, tributylstannyl, (1,1-dimethylethyl)dimethylsilyl, (1,1-dimethylethyl)diphenylsilyl, 2-cyanoethyl, or a group CH.sub.2 OR.sub.6 wherein R.sub.6 is methyl, phenylmethyl, 1,1-dimethylethyl, 2,2,2-trichloroethyl, benzyloxycarbonyl or 2,2,2-trichloroethyloxycarbonyl, Y being in position 1 or 2 on the tetrazole ring. The compounds of formula (I) are useful as intermediates in the synthesis of compounds possessing therapeutic activity.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: December 6, 1994
    Assignee: Synthelabo
    Inventors: Marc Daumas, Christian Hoornaert, Isaac Chekroun, Manuel Bedoya-Zurita, Jose Ruiz-Montes, Guy Rossey, Helene Greciet
  • Patent number: 5330985
    Abstract: A compound which is a pyrimidine-4-carboxamide derivative of the general formula (I) ##STR1## in which n is 0 or 1, m is 0 or 1,R.sub.1 represents a methyl group whenR.sub.2 represents a phenoxy(C.sub.1 -C.sub.4)alkyl group (in which the phenoxy group optionally carries 1 or 2 substituents selected from halogen atoms and methoxy groups), orR.sub.1 and R.sub.2 form together with the nitrogen atom to which they are attached a 4-phenoxypiperidin-1-yl group (in which the phenoxy group optionally carries 1 or 2 substituents selected from halogen atoms and methoxy groups), a phenoxymethylpiperidin-1-yl group (in which the phenoxy group optionally carries 1 or 2 C.sub.1 -C.sub.4 alkyl groups) or a 4-phenylpiperazin-1-yl group (in which the phenyl group optionally carries 1 or 2 substituents selected from halogen atoms and methoxy groups), and R.sub.3 represents a hydrogen atom or only when n is 1 a hydroxyl group or a methoxy group, or is an addition salt thereof with an acid, is useful as an .alpha.
    Type: Grant
    Filed: July 1, 1993
    Date of Patent: July 19, 1994
    Assignee: Synthelabo
    Inventors: Pascal George, Benoit Marabout, Jacques Froissant, Jean Pierre Merly
  • Patent number: 5318551
    Abstract: An applicator for an external urinary collection catheter. The catheter has a flexible sheath intended to be applied in a leaktight manner onto the penis of a patient. The sheath is connected to a tubular shaped part (for receiving the glans) which itself is connected to a tube for removing urine. The sheath is rolled on itself prior to its application. The applicator has a tubular body intended to surround, at least partially, the part for receiving the glans. The body has at least two controllable jaws. One end of each of the jaws is integral with an annular support, and the other free end of each of the jaws has a radially internal projection intended to hook behind the glans and to hold the latter during the unrolling of the flexible sheath on the penis.
    Type: Grant
    Filed: May 3, 1993
    Date of Patent: June 7, 1994
    Assignee: Synthelabo
    Inventor: Marin Di Cristo
  • Patent number: 5312920
    Abstract: A process for preparing a compound represented by formula ##STR1## by deprotecting a compound represented by formula (VII) ##STR2## in which R.sub.1 represents an unbranched or branched C.sub.1-7 alkyl, unbranched or branched C.sub.3-9 alkenyl, or (C.sub.3-7)cycloalkyl(C.sub.1-6)alkyl, and R.sub.2 represents hydrogen, unbranched or branched C.sub.1-7 alkyl, (C.sub.3-7)cycloalkyl(C.sub.1-3)alkyl, aryl(C.sub.1-3)alkyl optionally substituted on the ring-system, aryloxy(C.sub.1-3)alkyl optionally substituted on the ring-system, arylthio(C.sub.1-3)alkyl optionally substituted on the ring-system, arylsulphonyl(C.sub.1-3)alkyl optionally substituted on the ring-system, and heteroaryl(C.sub.1-3)alkyl optionally substituted on the ring-system.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: May 17, 1994
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Manuel Bedoya Zurita, Jose Ruiz-Montes, Guy Rossey
  • Patent number: 5280030
    Abstract: A compound which is a piperidine derivative of general formula (I) ##STR1## in which R.sub.1 represents a hydrogen atom, a linear or branched (C.sub.1-6)alkyl group or a cyclo(C.sub.3-8)alkyl group, X represents an oxygen atom, a sulphur atom or a group of general formula N--R.sub.3 in which R.sub.3 is a hydrogen atom, or a linear or branched (C.sub.1-8)alkyl, cyclo(C.sub.3-6)alkyl, cyclo(C.sub.3-6)alkylmethyl, (C.sub.1-4)alkoxy-(C.sub.1-4)alkyl, phenyl, pyridin-4-yl, pyridin-3-yl, pyridin-4-ylmethyl or pyridin-3-ylmethyl group and Z represents a hydrogen or fluorine atom and acid addition salts thereof with pharmaceutically acceptable acids, can be used for the treatment and prevention of disorders in which 5-HT receptors are involved.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: January 18, 1994
    Assignee: Synthelabo
    Inventors: Samir Jegham, Gerard DeFosse, Thomas Purcell, Johannes Schoemaker
  • Patent number: 5278312
    Abstract: Derivatives of benzeneborinic acid corresponding to the formula (1) ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 represent, each independently of the others, either a (C.sub.1 -C.sub.2)alkyl group or an aryl group, the group --CR.sub.1 R.sub.2 R.sub.3 being in position 1 or 2 of the tetrazole ring, preparation thereof, and method of use as synthetic intermediates.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: January 11, 1994
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Jose Ruiz-Montes, Manuel Bedoya-Zurita, Guy Rossey
  • Patent number: 5272157
    Abstract: Compounds of general formula (I) ##STR1## in which n is 1 or 2;R represents a linear or branched C.sub.1 -C.sub.3 -alkyl group; andX represents at least one substituent chosen from hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -alkoxy, in the form of a free base or an acid addition salt thereof, and their therapeutic application.
    Type: Grant
    Filed: November 17, 1992
    Date of Patent: December 21, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Jacques Froissant, Mireille Sevrin
  • Patent number: 5262405
    Abstract: A composition for use in the treatment of the obstruction of air ways comprising one or more phospholipids, alone or in association with excipients. This composition can be used in a method of treating the obstruction of air ways in a patient.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: November 16, 1993
    Assignees: Synthelabo, Inserm
    Inventors: Sophie Girod-Vaquez, Edith Puchelle, Claude Galabert, Jean-Marie Zam, Denis Pierrot
  • Patent number: 5254560
    Abstract: A compound which is a carboxamide derivative of general formula (I) ##STR1## in which R represents a hydrogen atom, a methyl group or a phenoxyalkyl group of general formula ##STR2## in which X represents one or more substituents independently chosen from hydrogen, fluorine, chlorine, methyl, 1-methylethyl and methoxy andn is 2 or 3,m is 0 or 1 andp is 1 or 2 such that m+p=2q is 0 or 1, andR.sub.1 represents a hydrogen atom or a methyl group,or a pharmaceutically acceptable acid addition salt thereof. Process for their preparation and their therapeutic use.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: October 19, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Christian Maloizel, Benoit Marabout, Jean-Pierre Merly
  • Patent number: 5246939
    Abstract: A compound which is a 2-aminopyrimidine carboxamide derivative represented by formula (I) ##STR1## in which X represents hydrogen, fluorine, chlorine, methyl, 1-methylethyl or methoxy, with the proviso that more than one substituent X may be present in which case each X may be the same or different,n represents 2 or 3,m represents 1, in which case p represents 1, or elsem represents 0, in which case p represents 2,q represents 0 or 1, andR.sub.1 represents a hydrogen atom;or a pharmaceutically acceptable acid addition salt thereof.A compound of formula (I) has .alpha..sub.1 -adrenergic receptor antagonist activity and is useful as a therapeutic substance.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: September 21, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Christian Maloizel, Benoit Marabout, Jean-Pierre Merly
  • Patent number: 5244894
    Abstract: Compounds corresponding to the general formula (I) ##STR1## in which n=2 or 3, X=H, F, Cl or OCH.sub.3, R=H or CH.sub.3, R.sub.1 =H or CH.sub.3, R.sub.2 =alkyl, hydroxyalkyl, (hydroxy)(methoxy)alkyl, dimethoxyalkyl, 2-(aminosulphonyl)ethyl, 2-(methylsulphonyl)ethyl, 2-(methylsulphonylamino)ethyl, aminocarbonylmethyl which is optionally substituted by nitrogen, phenylethyl which is optionally substituted, pyrimidinylaminoalkyl or arylcaronylaminoalkyl, or else R.sub.1 and R.sub.2 form, with the nitrogen which carries them, a piperidine, morpholine, thiomorpholine or piperazine ring, optionally substituted by nitrogen. Use in therapeutics.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: September 14, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Philippe Manoury, Benoit Marabout, Jacques Froissant, Jean-Pierre Merly
  • Patent number: 5244901
    Abstract: The present invention provides a compound which is a 4-pyrimidinecarboxamide derivative of general formula (I) ##STR1## in which X represents one or more substituents independently chosen from fluorine, chlorine, methoxy and cyclopropyl,R.sub.1 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, andR.sub.2 represents a hydrogen atom or a methyl group, or a pharmaceutically acceptable acid addition salt thereof; their preparation and their application in therapy.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: September 14, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Jacques Froissant, Arlette Tixidre
  • Patent number: 5229392
    Abstract: A compound which is a 2-aminopyrimidine-4-carboxamide derivative represented by general formula (I) ##STR1## in which m represents 2 or 3,n represents 2 or 3,R.sub.1 represents hydrogen or methyl, andX represents a substituent selected from the group consisting of hydrogen, fluorine, chlorine, methoxy, ethoxy, methyl and 1-methylethyl, with the proviso that more than one substituent X may be present in which case each X may be the same or different, or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: July 20, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Philippe Manoury, Michel Mangane, Jean-Pierre Merly
  • Patent number: 5212181
    Abstract: A compound which is an ethanol or ethanone derivative of general formula (I) ##STR1## in which X represents CO or CHOH, or is an addition salt thereof with an acid, and, when X represents CHOH, is in the form of a pure enantiomer or a mixture of enantiomers, can be used for the treatment and prevention of cerebral disorders.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: May 18, 1993
    Assignee: Synthelabo
    Inventors: Jonathan Frost, Patrick Lardenois
  • Patent number: 5210086
    Abstract: A compound which is a 2-aminopyrimidine-4-carboxamide derivative, of the general formula (I) ##STR1## in which m is 0 or 1,p is 0 or 1,q is 1 or 2,n is 2 or 3,R.sub.1 represents a hydrogen atom or a methyl group, and X represents at least one substituent selected from hydrogen, fluorine, chlorine, methoxy, methyl, isopropyl,or a pharmaceutically acceptable addition salt thereof, its preparation and use in therapy.
    Type: Grant
    Filed: October 1, 1991
    Date of Patent: May 11, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Christian Maloizel, Benoit Marabout
  • Patent number: 5192797
    Abstract: A compound which is a 2-aminoalkyl-5-arylalkyl-1,3-dioxane of general formula (I) ##STR1## in which m represents 0 or 1;n represents 1, 2, 3 or 4;R.sub.1 represents hydrogen or methyl;R.sub.2 represents hydrogen, methyl or an alkanoyl group of the general formula COR' in which R' represents a hydrogen atom or a linear or branched C.sub.1 -C.sub.4 -alkyl group, or an alkoxycarbonyl group of the general formula COOR" in which R" represents a linear or branched C.sub.1 -C.sub.4 -alkyl group; and Ar represents either a phenyl group optionally carrying one or two substituents selected from halogen, C.sub.1 -C.sub.4 alkyl, methoxy and trifluoromethyl, or a naphthalen-1-yl or naphthalen-2-yl group optionally carrying a substituent selected from halogen, methyl, methoxy and cyclopropylmethoxy groups,in the form of a cis- or trans-stereoisomer, and in the form of a free base or an acid addition salt thereof and its therapeutic use.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: March 9, 1993
    Assignee: Synthelabo
    Inventors: Bernard Raizon, Yannick Evanno, Odette LeGalloudec
  • Patent number: 5192763
    Abstract: [(1-Arylpyrrolidin-2-yl)methyl]piperazine compounds corresponding to the formula ##STR1## in which Z denotes a group of formula N-R.sub.1 in which R.sub.1 is either a hydrogen atom or a C.sub.1-3 alkyl group or a group of formula Ar--C.sub.n H.sub.2n in which n denotes 0, 1 or 2 and Ar denotes a phenyl group optionally substituted by one or more halogen atoms and/or C.sub.1-3 alkyl or C.sub.1-3 alkoxy radicals, or a group of formula COR.sub.2 in which R.sub.2 denotes the CH.sub.3, C.sub.6 H.sub.5, CH.sub.2 C.sub.6 H.sub.5 or OC.sub.2 H.sub.5 group and their salts of addition to pharmaceutically acceptable acids. The compounds are useful for the treatment of neurological disorders.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: March 9, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Jacques Menin, Jean-Pierre Merly, Dennis Bigg, Daniel Obitz, Michel Peynot, Corinne Veronique
  • Patent number: 5179108
    Abstract: Compounds of general formula (I) ##STR1## in which n is 1 or 2;R represents a linear or branched C.sub.1 -C.sub.3 -alkyl group; andX represents at least one substituent chosen from hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -alkoxy, in the form of a free base or an acid addition salt thereof, and their therapeutic application.
    Type: Grant
    Filed: March 6, 1991
    Date of Patent: January 12, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Jacques Froissant, Mireille Sevrin