Abstract: A process for the preparation of methyl (-)-(2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate, which comprises subjecting the dextrorotatory (2S,3R) enantiomer, present in a starting mixture containing both the levorotatory (2R,3S and dextrorotatory (2S,3R) enantiomers, to a transesterification reaction, in an anhydrous medium and in the presence of an enzyme which does not affect the levorotatory (2R,3S) enantiomer. The latter is an intermediate for the synthesis of compounds such as Diltiazem.
Type:
Grant
Filed:
February 13, 1991
Date of Patent:
December 8, 1992
Assignee:
Synthelabo
Inventors:
Lydia Zard, Arlette Tixidre, Guy Rossey, Alexander Wick
Abstract: A compound of formula (I) ##STR1## in which n denotes 2, 3, 4, or 5,p denotes 0 or 1,m denotes 0, 1, 2, 3, 4, or 5, andR.sub.1 denotes a hydrogen atom or a methyl group,each X, which may be identical or different to any other X if m is greater than 1, denotes fluorine, chlorine, methoxy, isopropyl or cyclopropyl,in the form of a free base or an acid addition salt.
Type:
Grant
Filed:
December 27, 1990
Date of Patent:
November 17, 1992
Assignee:
Synthelabo
Inventors:
Pascal George, Philippe Manoury, Jacques Froissant, Jean-Pierre Merly
Abstract: Anxiolytic and antipsychotic treatment is provided to patients by administering therapeutically effective amounts of N-[2-(diethylamino)-ethyl]-2-methoxy-4-[(1-H-4,5-dihydro-2-imidazolyl)-ami no]-5-chlorobenzamide, or a pharmaceutically acceptable salt thereof.
Type:
Grant
Filed:
October 31, 1991
Date of Patent:
August 25, 1992
Assignee:
Laboratoires Delagrange (Synthelabo)
Inventors:
Jacques Acher, Jean-Claude Monier, Jean-Paul Schmitt, Brenda Costall, Robert Naylor, Renee Gardaix-Luthereau
Abstract: A sustained-release pharmaceutical composition which comprises microparticles comprising an active principle, said microparticles being coated with a coating mixture comprising ethyl cellulose and an acrylic resin which is a polymerizate of acrylic and methacrylic ester, having a molecular weight of at least 100,000 and comprising units of formula: ##STR1## wherein: R.sub.1 is hydrogen or methyl,R.sub.2 is methyl or ethyl,R.sub.3 is methyl; andR.sub.4 is --CH.sub.2 --CH.sub.2 N(CH.sub.3).sub.3 Clthe resin containing 5% of trimethylammonium methacrylate chloride units by weight.
Type:
Grant
Filed:
July 26, 1990
Date of Patent:
May 12, 1992
Assignee:
Synthelabo
Inventors:
Howard Stevens, Maryvonne Chariot, Francoise Arnold, Gareth Lewis
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:
October 24, 1989
Date of Patent:
April 7, 1992
Assignee:
Synthelabo
Inventors:
Guy Rossey, Isaac Chekroun, Antonio Ugolini, Alexander Wick, Andre Bourbon, Jean-Baptiste Graux
Abstract: A benzazepine derivative which is a compound of formula (I): ##STR1## in which: each of m and n denotes the number 1, oreach of m and n denoted the number 2, orm denotes the number 3 and n denoted the number 1; andR denotes hydrogen or a group of formula --Z--R' in which Z denotes a --CO-- or --CH.sub.2 -- group and R' denotes a phenyl group which is unsubstituted or substituted with from one to three substituents selected from halogen atoms, linear or branch (C.sub.1 -C.sub.3) groups and linear or branched (C.sub.1 -C.sub.3) alkoxy groups,or a pharmacologically acceptable acid addition salt.
Type:
Grant
Filed:
February 8, 1990
Date of Patent:
March 17, 1992
Assignee:
Synthelabo
Inventors:
Pascal George, Mireille Sevrin, Michel Mangane
Abstract: A benzazepine derivative which is a compound of formula (I): ##STR1## in which each of m and n denotes the number 1, oreach of m and n denotes the number 2, orm denotes the number 3 and n denotes the number 1; and R denotes hydrogen or a group of formula --Z--R' in which Z denotes a --CO-- or --CH.sub.2 -- group and R' denotes a phenyl group which is unsubtituted or substituted with from one to three substituents selected from halogen atoms, linear or branch (C.sub.1 -C.sub.3) alkyl groups and linear or branched (C.sub.1 -C.sub.3) alkoxy groups, or a pharmacologically acceptable acid addition salt.
Type:
Grant
Filed:
July 11, 1989
Date of Patent:
January 14, 1992
Assignee:
Synthelabo
Inventors:
Pascal George, Mireille Sevrin, Michel Mangane, Jean-Pierre Merly, Dennis Bigg
Abstract: A control device for an artificial sphincter for a natural bodily passage, in particular a urinary passage, which contains a variable volume envelope. The control device includes a first chamber in the form of a balloon, a second chamber defined by two plates joined by a membrane forming a bellows, between which the balloon is accommodated, and an elastic return mechanism including at least one elastic band around the plates.
Abstract: A compound of formula (I) ##STR1## in which: X denotes hydrogen, a halogen, a trifluoromethyl group, a C.sub.1 -C.sub.4 alkyl group or a C.sub.1 -C.sub.4 alkoxy group;R.sub.1 denotes a linear or branched C.sub.2 -C.sub.8 alkyl group, a C.sub.3 -C.sub.5 cycloalkyl group or a cycloalkylmethyl group in which the cycloalkyl moiety has from 3 to 5 carbon atoms;R.sub.2 denotes hydrogen or a C.sub.1 -C.sub.4 alkyl group;R.sub.3 denotes a pyridylalkyl group; andAr denotes a phenyl group, optionally having from one to three substituents, each of which is, independently, a halogen or a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl; nitro or cyano group, or Ar denotes a naphthyl group;or a pharmacologically acceptable acid addition salt thereof.
Type:
Grant
Filed:
June 19, 1990
Date of Patent:
December 24, 1991
Assignee:
Synthelabo
Inventors:
Christian Hoornaert, Jean-Claude Muller, Nigel Beeley
Abstract: A method of anaesthetizing a subject in need of anaesthetizing, which comprises administering to the subject an anaesthetically effective amount of N-[[2-(4-ethylphenyl)-3-imidazo[1,2-a]pyridinyl]methyl] N,3-dimethylbutanamide or a pharmaceutically acceptable salt thereof.
Abstract: A compound, in the form of a pure optical isomer or a mixture thereof, of formula (I): ##STR1## in which: Z represents a group of formula --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --CH.dbd.CH--, --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.3 --, --NH-- or --N(CH.sub.3)CH.sub.2 --, in which the nitrogen is bonded to the carbonyl group;R1 represents hydrogen or a C.sub.1 -C.sub.4 alkyl group;R2 represents hydrogen or a methyl group; andR3 represents:a phenoxy group which is unsubstituted or substituted by a halogen or a methyl group,a naphthyloxy group,a phenylmethyl group substituted by a halogen or a methyl group,an unsubstituted phenylmethyl group when Z does not representa group of formula --CH.dbd.CH-- or --(CH.sub.2).sub.
Type:
Grant
Filed:
July 11, 1989
Date of Patent:
July 23, 1991
Assignee:
Synthelabo
Inventors:
Jonathan Frost, Patrick Lardenois, Jean Bertin, Alfred Saarmets, Corinne Rousselle
Abstract: 2-Aminothiophenol is reacted with (-)-(2R,3S)-2,3-epoxy-3-(4-methoxyphenyl) methylpropionate, and the intermediate (2S,3S)-3-[(2-aminophenyl)thio]-2-hydroxy-3-(4-methoxyphenyl) methylpropionate is then cyclized in the presence of methane sulfonic acid, in the same container and without isolating said intermediate product, using chlorobenzene as a solvent.
Type:
Grant
Filed:
September 14, 1989
Date of Patent:
May 7, 1991
Assignee:
Synthelabo
Inventors:
Guy Rossey, Isaac Chekroun, Antonio Ugolini, Alexander Wick, Bernard Gerin, Andre Bourbon, Jean-Baptiste Graux
Abstract: An indolone derivative is useful for the treatment of anxiety, depression and schizophrenia and is a 5HT.sub.1A agonist and 5HT.sub.2 antagonist, which is a compound of formula (I): ##STR1## in which R.sub.1 is a hydrogen or halogen atom or a (C.sub.1-4)alkyl radical,R.sub.2 is a hydrogen atom or a (C.sub.1-4)alkyl radical,R.sub.3 is a hydrogen atom, a (C.sub.1-4)alkyl radical or an S-(C.sub.1-4) alkyl radical; andR.sub.4 is a phenyl, chlorophenyl, naphthyl, 7-methoxy-1-naphthyl, 6-methoxy-1-indanyl, 2-methoxy-6-pyridyl, 3-methoxy-2-pyridyl, isoquinolyl, 7-methoxy-1-isoquinolyl, 7-methoxy-1,2,3,4-tetrahydro-1-naphthyl or 7-fluoro-1-naphthyl radical;or a pharmaceutically acceptable acid addition salt thereof.
Type:
Grant
Filed:
August 2, 1989
Date of Patent:
April 23, 1991
Assignee:
Synthelabo
Inventors:
Philippe Manoury, Jean Binet, Daniel Obitz, Gerard Defosse, Elisabeth Dewitte, Corinne Veronique
Abstract: A process for the preparation of a methyl (+)-(2S,3S)-3-[(2-aminophenyl)thio]-2-hydroxy-3-(4-methoxyphenyl)propionat e of the formula (I): ##STR1## in which X denotes hydrogen or chlorine, which process comprises reacting a 2-aminothiophenol of formula (II): ##STR2## in which X is as defined above, with methyl (-)-(2R,3S)-2,3-epoxy-3-(4-methoxyphenyl)propionate, in a 1,2-dichloroethane solvent.
Type:
Grant
Filed:
April 18, 1989
Date of Patent:
April 16, 1991
Assignee:
Synthelabo
Inventors:
Guy Rossey, Antonio Ugolini, Isaac Chekroun, Abkar Vartanian, Alexander Wick
Abstract: Phenyloxypropanolamine derivatives in the form of racemates or enantiometers, of formula (I) ##STR1## in which R is H or CH3, and their pharmaceutically acceptable salts.
Type:
Grant
Filed:
November 7, 1989
Date of Patent:
March 19, 1991
Assignee:
Synthelabo
Inventors:
Philippe Manoury, Jean Binet, Gerard Defosse
Abstract: A compound of formula (I) ##STR1## in which: X denotes hydrogen, a halogen, a trifluoromethyl group, a C.sub.1 -C.sub.4 alkyl group or a C.sub.1 -C.sub.4 alkoxy group;R.sub.1 denotes a linear or branched C.sub.2 -C.sub.8 alkyl group, a C.sub.3 -C.sub.5 cycloalkyl group or a cycloalkylmethyl group in which the cycloalkyl moiety has from 3 to 5 carbon atoms;R.sub.2 denotes hydrogen or a C.sub.1 -C.sub.4 alkyl group;R.sub.3 denotes hydrogen, a C.sub.1 -C.sub.4 alkyl group, an optionally substituted phenylalkyl group or a pyridylalkyl group;or R.sub.2 and R.sub.3 denote, together with the nitrogen to which they are attached, a pyrrolidinyl, piperidyl, morpholinyl, perhydrothiazinyl, piperazinyl or 4-methylpiperazinyl ring; andAr denotes a phenyl group, optionally having from one to three substituents, each of which is, independently, a halogen or a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.
Type:
Grant
Filed:
May 2, 1990
Date of Patent:
March 19, 1991
Assignee:
Synthelabo
Inventors:
Christian Hoornaert, Jean-Claude Muller, Nigel Beeley
Abstract: A compound which is a 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivative of formula (I) ##STR1## in which R.sub.1 denotes hydrogen; linear or branched C.sub.1 -C.sub.4 alkyl; or benzyl;R.sub.2 denotes linear or branched C.sub.1 -C.sub.6 alkyl; cyclohexyl; trichloromethyl; 1-propenyl; allyl; phenyl; 4-chlorophenyl; or benzyl:or R.sub.1 and R.sub.2 together denote a C.sub.3 -C.sub.5 aliphatic chain:X denotes halogen; C.sub.1 -C.sub.3 alkyl; methylthio; trifluoromethyl; optionally esterified carboxy of formula --COOR in which R denotes hydrogen or C.sub.1 -C.sub.6 alkyl; cyano; optionally mono- or dialkylated aminocarbonyl of formula --CONR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4 independently denote hydrogen or C.sub.1 -C.sub.4 alkyl or together denote a chain of formula --(CH.sub.2).sub.2 --Z--(CH.sub.2).sub.2 -- in which Z denotes a direct bond, oxygen, sulphur, or a divalent group of formula --CH.sub.2 --, --NH-- or --N(C.sub.1 -C.sub.4 alkyl)--; alkylamino of formula NHR.sub.5 in which R.sub.
Type:
Grant
Filed:
October 24, 1989
Date of Patent:
February 5, 1991
Assignee:
Synthelabo
Inventors:
Pascal George, Claudie Giron, Jacques Froissant
Abstract: Compositions of diltiazem and angiotensin-converting enzyme inhibitor useful for the treatment of hypertension, cardiac insufficiency and coronary insufficiency.
Type:
Grant
Filed:
May 18, 1988
Date of Patent:
January 8, 1991
Assignee:
Synthelabo
Inventors:
Icilio Cavero, Francois Elkik, Peter Hicks, Jean-Claude Muller