Patents Assigned to Synthelabo
  • Patent number: 5476941
    Abstract: A compound of formula (1): ##STR1## in which R.sub.1 represents a 1,1-dimethylethyl, triphenylmethyl, methoxymethyl or benzyloxymethyl group; andR.sub.2 represents a C.sub.1 -C.sub.4 alkyl group.
    Type: Grant
    Filed: October 3, 1994
    Date of Patent: December 19, 1995
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Jose Ruiz-Montes, Guy Rossey
  • Patent number: 5472967
    Abstract: Compounds which can be expressed as tautomeric forms and having the formulas (I), (I') and (I") ##STR1## wherein R.sub.1 =a straight or branched (C.sub.1-7) alkyl group or a straight or branched (C.sub.3-9) alkenyl group or a cyclo(C.sub.3-7)alkyl(C.sub.1-6) alkyl group, R.sub.2 =an atom of hydrogen, or a straight or branched (C.sub.1-7)alkyl group, or a cyclo(C.sub.3-7)alkyl(C.sub.1-3)alkyl group, or an aryl(C.sub.1-3)alkyl group optionally substituted on the ring, or an aryloxy(C.sub.1-3)alkyl group optionally substituted on the ring, or an arylthio(C.sub.1-3)alkyl group optionally substituted on the ring, or an arylsulfonyl(C.sub.1-3)alkyl group optionally substituted on the ring, or a heteroaryl(C.sub.1-3)alkyl group optionally substituted on the ring, R.sub.3 =CO.sub.2 H, 1H-tetrazol-5-yl, NHCOR.sub.11, NHSO.sub.2 R.sub.11, CONHSO.sub.2 R.sub.11 or CONHOR.sub.12 group where R.sub.11 =a methyl, trifluoromethyl, or phenyl group optionally substituted, R.sub.
    Type: Grant
    Filed: August 24, 1994
    Date of Patent: December 5, 1995
    Assignee: Synthelabo
    Inventors: Christian Hoornaert, Marc Daumas, Michel Aletru, Jean-Claude Muller
  • Patent number: 5466706
    Abstract: Compound corresponding to the formula: ##STR1## in which X represents one or more of hydrogen, halogen, alkyl, trifluoromethyl, alkoxy, alkylthio, methylsulphonyl, cyano, ethoxycarbonyl, aminocarbonyl and carboxy, Y represents one or more of hydrogen, halogens, alkyl, trifluoromethyl, methoxy and trifluoromethoxy, R.sub.1 represents hydrogen, alkyl, phenylmethyl, 2-phenylethyl, acetyl or alkoxycarbonyl, R.sub.2 and R.sub.3 each represent hydrogen, alkyl which is optionally substituted, prop-2-enyl, prop-2-ynyl, phenyl, 1-(phenylmethyl)piperidin-4-yl, or 1-[(cyclohexen-1-yl)methyl]piperidin-4-yl, or alternatively R.sub.2 and R.sub.3 form, with the nitrogen atom carrying them, an optionally substituted heterocycle. These compounds are useful as hypnotic, anxiolytic and anticonvulsant agents.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: November 14, 1995
    Assignee: Synthelabo
    Inventors: Pascal George, Danielle De Peretti, Jocelyne Roy, Jean-Paul Schmitt, Mireille Sevrin
  • Patent number: 5457112
    Abstract: 3-(6-Quinolylmethyl)-4H-imidazol-4-one derivatives corresponding to the formula (I): ##STR1## in which R.sub.1 represents an unbranched or branched (C.sub.2 -C.sub.5) alkyl group,R.sub.2 and R.sub.3 represent, each independently of one another, either a hydrogen atom, or an unbranched or branched (C.sub.1 -C.sub.5)alkyl group, or a (CH.sub.2).sub.n -aryl group where n=0 to 3, or R.sub.2 and R.sub.3 with the imidazole ring can form a spirocyclo(C.sub.3 -C.sub.8)alkyl group,as well as their addition salts with pharmaceutically acceptable acids and bases.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: October 10, 1995
    Assignee: Synthelabo
    Inventors: Gerard Cremer, Jean Claude Muller
  • Patent number: 5455226
    Abstract: EGF (Epidermal Growth Factor)-containing pharmaceutical composition and method for the treatment of bronchopulmonary pathologies accompanied by lesions of the bronchial epithelium utilising EGF.
    Type: Grant
    Filed: December 1, 1992
    Date of Patent: October 3, 1995
    Assignees: Synthelabo, Inserm
    Inventors: Jean-Marie Zahm, Edith Puchelle, Denis Pierrot, Rachid Benali, Aline Moreau
  • Patent number: 5453430
    Abstract: Compounds of formula (I) ##STR1## wherein R represents a ##STR2## group in which R.sub.2 is a hydrogen atom, a (C.sub.1 -C.sub.4)alkoxycarbonyl group, a carboxylic group, a sodium carboxylate group, a --CH.sub.2 OR.sub.4 group R.sub.4 being a hydrogen atom or a (C.sub.1 -C.sub.4)alkyl group or a (C.sub.1 -C.sub.4)acyl group, an amide group of the formula --CONR.sub.5 R.sub.6, or a --CN.sub.4 R.sub.5 group, R.sub.5 being a hydrogen atom or a (C.sub.1 -C.sub.4)alkyl group and R.sub.6 being a hydrogen atom, a (C.sub.1 -C.sub.4)alkyl group, a hydroxy group or a (C.sub.1 -C.sub.4)alkoxy group, and R.sub.3 is a (C.sub.1 -C.sub.4)alkyl group,R.sub.1 represents either a hydrogen atom or a (C.sub.1 -C.sub.4)alkyl group,X represents either a sulphur atom, an oxygen atom or a methylene group, n=1 or 2 andAr represents either a naphthalen-1-yl group substituted by a di(C.sub.1 -C.sub.4)alkylamino group, or a 6,7-di(C.sub.1 -C.sub.4)alkoxynaphthalen-1-yl group, or a quinolin-8-yl group substituted at 3 by a (C.sub.1 -C.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: September 26, 1995
    Assignee: Synthelabo
    Inventors: Gilbert Lassalle, Thomas Purcell, Daniel Galtier, Paul H. Williams, Frederic Galli
  • Patent number: 5447928
    Abstract: Compounds of the formula ##STR1## in which Y represents hydrogen, fluorine, chlorine, methyl or methoxy, R.sub.1 represents phenyl substituted by fluorine, methyl, methoxy, trifluoromethyl or phenyl, or R.sub.1 represents 2-thienyl, R.sub.2 represents methyl, and R.sub.3 represents (C.sub.1 -C.sub.4)-alkyl, or phenyl-(C.sub.1 -C.sub.2)-alkyl optionally substituted on the ring by 2 to 3 methoxy groups, or 2-(2-pyridyl)ethyl, or R.sub.2 and R.sub.3 form, with the adjacent nitrogen, 4-phenyl(1-piperidyl), 4-phenylmethyl(1-piperidyl), 1,2,3,4-tetrahydro-2-isoquinolyl, 6-methoxy-1,2,3,4-tetrahydro-2-isoquinolyl, 5,8-dimethoxy-1,2,3,4-tetrahydro-2-isoquinolyl, 6,7-dimethoxy 1,2,3,4-tetrahydro-2-isoquinolyl, 2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl, or 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl, and X represents carbonyl or sulphonyl, and their salts are useful as neuroprotective and antiiischaemic agents.
    Type: Grant
    Filed: February 24, 1994
    Date of Patent: September 5, 1995
    Assignee: Synthelabo
    Inventors: Howard Williams, Lydia Zard, Thomas Purcell, Daniel Galtier, Jean-Claude Muller, Pascal George, Jonathan Frost, Patrick Pasau, Corinne Rousselle, Regine Bartsch
  • Patent number: 5434169
    Abstract: A compound which is a piperidine derivative of formula (I) ##STR1## in which R represents hydrogen, or unbranched or branched C.sub.1 -C.sub.6 alkyl group; andAr represents phenyl optionally substituted with one or more radicals selected from the halogens, amino, C.sub.1 -C.sub.2 alkoxy and (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.2)alkoxy, or a heteroaryl group;or a pharmaceutically acceptable acid addition salt thereof;provided that when R is hydrogen Ar is not phenyl or 4 -chlorophenyl.The compounds are useful in therapy as ligands for 5-HT.sub.3 and 5-HT.sub.4 receptors.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: July 18, 1995
    Assignee: Synthelabo
    Inventors: Samir Jegham, Itzchak Angel, Thomas Purcell, Johannes Schoemaker
  • Patent number: 5432283
    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: August 25, 1994
    Date of Patent: July 11, 1995
    Assignee: Synthelabo
    Inventors: Gerard Cremer, Pascale Goberville, Jean-Claude Muller
  • Patent number: 5430149
    Abstract: A compound represented by formula (V): ##STR1## in which R.sub.1 is selected from the group consisting of hydrogen, unbranched and branched C.sub.1-7 alkyl, unbranched and branched C.sub.3-9 alkenyl, and (C.sub.3-7)cycloalkyl(C.sub.1-6)alkyl groups, and R.sub.2 is selected from the group consisting of hydrogen, unbranched and branched C.sub.1-7 alkyl,(C.sub.3-7)cycloalkyl(C.sub.1-3)alkyl, aryl(C.sub.1-3)alkyl, aryloxy(C.sub.1-3)alkyl, arylthio(C.sub.1-3) alkyl, arylsulphonyl(C.sub.1-3)alkyl and heteroaryl (C.sub.1-3) alkyl groups.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: July 4, 1995
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Manuel Bedoya Zurita, Jose Ruiz-Montes, Guy Rossey
  • Patent number: 5420130
    Abstract: Compounds corresponding to the general formula (I) ##STR1## in which n represents 0 or 1, R.sub.1 represents a methyl group, in which case R.sub.2 represents a phenoxy(C.sub.1 -C.sub.4)alkyl group (in which the phenoxy group is optionally substituted), or else R.sub.1 and R.sub.2 together form, and with the nitrogen atom which carries them, a 4-(phenoxymethyl)piperid-1-yl group (in which the phenoxy group is optionally substituted) or a 4-phenylpiperazin-1-yl group (in which the phenyl group is optionally substituted), R.sub.3 represents a hydrogen atom or a methyl group, R.sub.4 represents a hydrogen atom and R.sub.5 represents a hydrogen atom or a group of general formula -CH.sub.2 -CH.sub.2 -NH-R.sub.6, R.sub.6 being a hydrogen atom or a tert-butyloxycarbonyl, 4-carbamoylpyrimidin-2-yl or 5-carbamoylpyrazin-2-yl group, are useful in the treatment of diseases and complaints involving hyperactivity of the .alpha.-adrenergic system at the level of the lower urinary apparatus.
    Type: Grant
    Filed: May 16, 1994
    Date of Patent: May 30, 1995
    Assignee: Synthelabo
    Inventors: Pascal George, Benoit Marabout, Jacques Froissant
  • Patent number: 5420116
    Abstract: Methods for treating disorders of the upper and lower airways, which disorders involve dehydration of the respiratory epithelium and hyperadhesion of mucus, using adenosine 5'-triphosphate disodium salt or uridine 5'-triphosphate, alone or in combination with amiloride.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: May 30, 1995
    Assignee: Synthelabo
    Inventors: Edith Puchelle, Rachid Benali, Denis Pierrot, Sophie Girod, Jean-Marie Zahm, Aline Moreau
  • Patent number: 5418241
    Abstract: The invention provides a compound which is a piperidine derivative of formula (I) ##STR1## in which R.sub.1 is hydrogen or straight or branched (C.sub.1 -C.sub.6) alkyl, R.sub.2 is hydrogen or straight or branched (C.sub.1 -C.sub.8) alkyl, Z and Z.sub.1 which may be the same or different, each is hydrogen, chlorine, hydroxyl, amino, nitro, hydroxymethyl, (C.sub.1 -C.sub.2) alkyl, (C.sub.1 -C.sub.8) alkoxy straight or branched (C.sub.1 -C.sub.5) alkoxycarbonyl or aryl (C.sub.1 -C.sub.2) alkoxy, Z is in position 4, 6 or 7 and Z and Z.sub.1 cannot both be hydrogen, or its addition salt with a pharmaceutically acceptable acid and its therapeutic application.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: May 23, 1995
    Assignee: Synthelabo
    Inventors: Samir Jegham, Gerard Defosse, Thomas Purcell
  • Patent number: 5418248
    Abstract: Compounds of the formula: ##STR1## in which R.sub.1 represents a hydroxy group, a C.sub.1 -C.sub.4 alkoxy group or an amino group of general formula --NR.sub.4 R.sub.5 in which R.sub.4 and R.sub.5 each represent, independently of each other, a hydrogen atom, a straight or branched C.sub.1 -C.sub.4 alkyl group, an allyl group or a methoxyethyl group, or alternatively --NR.sub.4 R.sub.5 represents a heterocycle containing 3 to 6 carbon atoms,Y represents a thienyl group optionally substituted by an alkyl group, andX represents a hydrogen or halogen atom,are useful as anticonvulsants and auxiolytics.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: May 23, 1995
    Assignee: Synthelabo
    Inventors: Mireille Sevrin, Claude Morel, Michel Mangane, Pascal George
  • Patent number: 5405960
    Abstract: Triarylborane derivatives corresponding to the formula (1) ##STR1## in which R either represents a group --CR.sub.1 R.sub.2 R.sub.3 where R.sub.1, R.sub.2 and R.sub.3 are each, independently of one another, a (C.sub.1 -C.sub.2)alkyl or aryl group, or represents a group --CH.sub.2 OR.sub.4 where R.sub.4 is a (C.sub.1 -C.sub.2)alkyl or benzyl group, or represents a group --Si(R.sub.5).sub.3 where R.sub.5 is a (C.sub.1 -C.sub.2)alkyl or aryl group, R being in the 1 or 2 position of the tetrazole ring, their preparation and their use as synthesis intermediates.
    Type: Grant
    Filed: August 9, 1994
    Date of Patent: April 11, 1995
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Guy Rossey, Michel Magnat
  • Patent number: 5382672
    Abstract: Derivatives of benzeneborinic acid, preparation thereof and use thereof as synthetic intermediates.
    Type: Grant
    Filed: November 19, 1993
    Date of Patent: January 17, 1995
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Jose Ruiz-Montes, Manuel Bedoya-Zurita, Guy Rossey
  • Patent number: 5380311
    Abstract: A male urinary collection catheter kit which includes a catheter which has a flexible sheath which is placed in a leaktight manner onto a penis and which is rolled up prior to being placed on the penis, a tubular-shaped part which receives the glans of the penis and which is connected to the sheath and a tube in which urine is removed and which is connected to the sheath. There is also an applicator which has a ring, the diameter of which may be varied so that it can be slipped over the tubular-shaped part, then the diameter can be reduced until the ring is caught behind the glans, then the diameter can be maintained while the virga of the penis is pulled upon to cause it to extend so that the flexible sheath can be unrolled over the penis and then the diameter can be spontaneously increased so that the applicator can be removed from the catheter.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: January 10, 1995
    Assignee: Synthelabo
    Inventor: Pierre Bailly
  • Patent number: 5380742
    Abstract: Pyrrole derivatives of formula: ##STR1## in which R.sub.1 represents a hydrogen or halogen atom, a linear or branched C.sub.1-6 alkyl group, a C.sub.3-6 alkenyl group, a C.sub.1-4 alkoxymethyl group, benzyl, a phenyl group optionally substituted by one or more halogen atoms or alkyl radicals, a CO.sub.2 R group in which R represents a linear or branched C.sub.1-4 alkyl radical, phenyl or benzyl, or a CONR'R" group in which R' and R" each represent, independently of one another, a hydrogen atom or a linear or branched C.sub.1-4 alkyl radical,R.sub.2 represents a hydrogen or halogen atom or a linear or branched C.sub.1-4 alkyl group,and R.sub.3 represents a 4,5-dihydro-1H-imidazol-2-yl or 1H-imidazol-4-yl group, and their addition salts with pharmaceutically acceptable acids are useful in therapeutics as .alpha..sub.2 -antagonists, and .alpha..sub.1 -agonists.
    Type: Grant
    Filed: November 24, 1993
    Date of Patent: January 10, 1995
    Assignee: Synthelabo
    Inventors: Mireille Sevrin, Jacques Menin, Christian Maloizel, Juan A. Diaz Martin, Ulpiano Martin Escudero Perez, Manuel Bedoya Zurita, Gregorio Del Sol Moreno, Maria D. Jimenez Bargueno, Magali Romanach Ferrer
  • Patent number: 5374735
    Abstract: Triarylborane derivatives corresponding to the formula (1) ##STR1## in which R either represents a group --CR.sub.1 R.sub.2 R.sub.3 where R.sub.1, R.sub.2 and R.sub.3 are each, independently of one another, a (C.sub.1 -C.sub.2)alkyl or aryl group, or represents a group --CH.sub.2 OR.sub.4 where R.sub.4 is a (C.sub.1 -C.sub.2)alkyl or benzyl group, or represents a group --Si(R.sub.5).sub.3 where R.sub.5 is a (C.sub.1 -C.sub.2)alkyl or aryl group, R being in the 1 or 2 position of the tetrazole ring, their preparation and their use as synthesis intermediates.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: December 20, 1994
    Assignee: Synthelabo
    Inventors: Isaac Chekroun, Guy Rossey, Michel Magnat
  • Patent number: RE34935
    Abstract: 2-Aminothiophenol is reacted with methyl (-)-(2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate, and the intermediate methyl (2S,3S)-3-[(2-aminophenyl)thio]-2-hydroxy-3-(4-methoxyphenyl)propionate is cyclized in the presence of methanesulfonic acid, in the same vessel and without isolating said intermediate product, using e.g. chlorobenzene as a solvent.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: May 9, 1995
    Assignee: Synthelabo
    Inventors: Guy Rossey, Isaac Chekroun, Antonio Ugolini, Alexander Wick, Bernard Gerin, Andre Bourbon, Jean-Baptiste Graux