Abstract: The present invention relates to:
a) methylbiphenyl derivatives of general formula:
in which R1 represents OH, C3-C7 alkyl or C3-C7 cycloalkyl, these compounds being in the form of individual isomers or mixtures thereof,
b) their preparation by reaction:
either of a hydroxylamine salt with an N-substituted o-(p-tolyl)benzaldimine, to give o-(p-tolyl)benzaldoxime
or of an N-substituted 2-halobenzaldimine with a p-tolylmagnesium halide in the presence of an inorganic manganese derivative, to give the compounds of formula I in which R1 represents C3-C7 alkyl or C3-C7 cycloalkyl
c) their use for the preparation of o-(p-tolyl)-benzonitrile, which is an intermediate in the synthesis of medicinal products.
Abstract: The invention concerns compounds of formula (I) wherein: A represents either a hydrogen atom or a hydroxyl group; B represents a pyrrolidin-2-yl (D) or 2-piperidyl (E), B capable of being substituted by one or two R5 groups; R1 represents a hydrogen atom, a C1-C6 alkyl, a C2-C6 alkenyl, a C1-C2 perfluoroalkyl or a C1-C6 fluoroalkyl group; R2, R3 or R4, independently of one another, represent a hydrogen atom, a C1-C6 alkyl, group or a C2-C6 alkenyl group, or R1 and R2 can together form a C1-C6 alkylene chain, or a C3-C6 alkenylene chain; R5 represents a C1-C6 alkyl group, and R6 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, C3-C6 cycloalkyl, C3-C6 cycloalkenyl or a benzyl.
Type:
Grant
Filed:
August 1, 2001
Date of Patent:
July 2, 2002
Assignee:
Sanofi-Synthelabo
Inventors:
Christophe Philippo, Alain Braun, Philippe R. Bovy
Abstract: The invention relates to 1,4-diazabicyclo[3.2.2]nonane derivatives, to pharmaceutical compositions containing them, and to methods for the treatment or prevention of disorders associated with a dysfunction of the nicotinic receptors utilizing them.
Type:
Grant
Filed:
July 16, 2001
Date of Patent:
June 18, 2002
Assignee:
Sanofi-Synthelabo
Inventors:
Alistair Lochead, Samir Jegham, Alain Nedelec, Frédéric Galli, Jean Jeunesse, Luc Even
Abstract: The subject-matter of the invention is a process for the preparation of substituted 4-methylbiphenyls of general formula:
in which R is a cyano group or a protected tetrazolyl group of formula:
in which R1, situated at the 1 or 2 position of the tetrazolyl group, is a protective group, characterized in that a halobenzene of formula:
in which Hal is a halogen atom and R has the same meaning as above, is reacted with a p-tolylmagnesium halide in the presence of a linear or branched polyether and of a catalyst comprising a transition metal.
Abstract: Pyridazino[4,5-b]indole-1-acetamide derivatives for the prevention or treatment of diseases linked to the dysfunctioning of peripheral-type benzodiazepine receptors.
Type:
Grant
Filed:
July 25, 2001
Date of Patent:
May 28, 2002
Assignee:
Sanofi-Synthelabo
Inventors:
Badia Ferzaz, Jésus Benavides, Frank Marguet, Jacques Froissant, Benoît Marabout, Yannick Evanno, Mireille Sevrin, Phikip Janiak
Abstract: The invention relates to a process for preparing (R)-(+)-3-{1-[2-(4-benzoyl-2-(3,4-difluorophenyl)-morpholin-2-yl)ethyl]-4-phenylpiperid-4-yl}-1,1-dimethylurea and the salts, solvates and/or hydrates thereof.
Type:
Grant
Filed:
June 19, 2001
Date of Patent:
May 21, 2002
Assignee:
Sanofi-Synthelabo
Inventors:
Alain Aulombard, Francoise Bernon, Sabrina Bonnefoy, Alain Burgos, Claude Cabos, Eric Lucas
Abstract: The present invention relates to cholecystokinin (CCK)-agonist substituted thiazoles of formula:
in which R1 is a substituted phenyl group, R2 is a group chosen from CH2—R7, (CH2)2—R7, S—CH2—R7, CH2—S—R7 and (C5-C8)alkyl with R7 being a (C5-C7)cycloalkyl group, and R3 is a group
with R8 being a group (CH2)nR15 or
and R15 being COOH or COO(C1-C4)alkyl. The invention also relates to a process for the preparation of the pharmaceutical compositions containing them and to their uses for the preparation of medicines.
Type:
Grant
Filed:
June 2, 2000
Date of Patent:
April 30, 2002
Assignee:
Sanofi-Synthelabo
Inventors:
Roger Brodin, Robert Boigegrain, Eric Bignon, Jean Charles Molimard, Dominique Olliero
Abstract: A method for preparing the potassium dihydrate salt of 2-[[4-(2-chlorophenyl)-2-thiazolyl]carbamoyl]indole-1-acetic acid, by reacting 2-[[4-(2-chlorophenyl)-2-thiazolyl]carbamoyl]indole-1-acetic acid or its C1-C4 alkyl esters with potassium carbonate in a two phase solvent system comprising a mixture of water and an organic solvent which is only slightly miscible with water and optionally recrystallising the precipitated intermediate solvate from water and to the potassium dihydrate salt thus obtained.
Abstract: A method of using 1,2,4-benzotriazine oxides, some of which are novel compounds, as radiosensitizers and selective cytotoxic agents is disclosed. These compounds are shown to specifically radiosensitive hypoxic tumor cells. Some are additionally disclosed to be useful as specific cytotoxic agents for these cells. They also show an unexpected ability to radiosensitize aerobic cells following or preceding a hypoxic incubation of the cells with the drug. This provides a basis for selective radiosensitization of tumors compared to normal cells. A novel method for preparing the 1,2,4-benzotriazine oxides is also disclosed.
Type:
Grant
Filed:
October 17, 1997
Date of Patent:
March 26, 2002
Assignee:
SRI International
Inventors:
William W. Lee, J. Martin Brown, Edward W. Grange, Abelardo P. Martinez, Michael Tracy, Daniel J. Pollart
Abstract: The invention relates to the use of compounds of formula
for the preparation of medicines designed for the treatment of neuronal and cerebral disorders.
The invention also relates to the compounds of formula:
a process for their preparation and the pharmaceutical compositions containing them.
Abstract: An improved process for preparing (2S)-1-[(2R,3S)-5-chloro-3-(2-chlorophenyl)-1-(3,4-dimethoxybenzenesulphonyl)-3-hydroxy-2,3 -dihydro-1H-indole-2-carbonyl]pyrrolidine-2-carboxamide by cyclization of (2S)-1-{[[4-chloro-2-(2-chlorobenzoyl)phenyl]-(3,4-dimethoxybenzenesulphonyl)amino]acetyl}pyrrolidine-2-carboxamide in the presence of an alkali metal hydroxide in a mixture of polyethylene glycol and water.
Abstract: The invention relates to the use of tetrahydropyridine derivatives of the formula
in which:
R1 is a halogen or a CF3, (C1-C4)alkyl or (C1-C4)alkoxy group;
Y is a nitrogen atom or a CH group;
Z′ and Z″ are each hydrogen or a (C1-C3)alkyl group, or one is hydrogen and the other is a hydroxyl group, or the two together are an oxo group; and
Z is:
a phenyl radical;
a phenyl radical monosubstituted by a substituent X, X being:
(a) a (C1-C6)alkyl, (C1-C6)alkoxy, (C3-C7)carboxyalkyl, (C1-C4)alkoxycarbonyl(C1-C6)alkyl, (C3-C7)carboxyalkoxy or (C1-C4)alkoxycarbonyl(C1-C6)alkoxy group;
(b) a group selected from (C3-C7)cycloalkyl, (C3-C7)cycloalkoxy, (C3-C7)cycloalkylmethyl, (C3-C7)cycloalkylamino and cyclohexenyl, it being possible for said group to be substituted by a halogen, hydroxy, (C1-C4)alkoxy, carboxy, (C1-C4)alkoxycarbonyl, amino or mono- or di-(C1-C4)alkylamino group; or
(c) a group selected from phenyl, phenoxy, phenylamino, N—(C1-C3)alkyl-phenylamino, phenylmethy
Type:
Grant
Filed:
April 18, 2000
Date of Patent:
February 5, 2002
Assignee:
Sanofi-Synthelabo
Inventors:
Bernard Bourrie, Pierre Casellas, Jean-Pierre Maffrand
Abstract: The invention relates to the use of a compound of formula (I):
for the preparation of pharmaceutical compositions for increasing the circulating, cellular and extracellular levels of TGF-&bgr;1.
Type:
Grant
Filed:
April 10, 2000
Date of Patent:
January 29, 2002
Assignee:
Sanofi-Synthelabo
Inventors:
Françoise Bono-Combie, Jacqueline Fournier, Jean Marc Herbert, Isabelle Lamarche, Umberto Guzzi
Abstract: In accordance with the present invention there is provided a method of treating a mammal having a solid tumor, the method comprising:
a) administering to the mammal an effective amount of 3-ainino-1,2,4-benzotriazine 1,4-dioxide;
b) administering to the mammal an effective amount of paclitaxel; and
c) administering to the mammal an effective amount of a platinum complex. The method provides unexpected synergistic efficacy. The invention further provides a kit for treatment of a mammalian tumor comprising 3-amino-1,2,-benzotriazine 1,4-dioxide, paclitaxel and a platinum complex.
Type:
Grant
Filed:
February 16, 2000
Date of Patent:
November 20, 2001
Assignee:
Sanofi-Synthelabo Inc.
Inventors:
Daniel L. Dexter, Paul E. Juniewicz, James B. Rake, Daniel D. Von Hoff
Abstract: The pharmaceutical formulations according to the invention contain from 0.5 to 50% by weight of a cyclic quaternary ammonium compound and pharmaceutically appropriate excipients and are formulated by wet granulation, preferably with polysorbate 80.
Type:
Grant
Filed:
July 30, 1999
Date of Patent:
October 16, 2001
Assignee:
Sanofi-Synthelabo
Inventors:
Bernard Abramovici, Xavier Boulenc, Jean-Claude Gautier, Pol Vilain
Abstract: The subject of the invention is a freeze-dried formulation consisting of an amorphous phase and a crystalline phase, which is pharmaceutically acceptable, comprising at least one nonprotein active ingredient, characterized in that it contains mannitol and alanine in a ratio R of between 0.1 and 1, R representing the mass of mannitol to the mass of alanine.
Type:
Grant
Filed:
December 9, 1998
Date of Patent:
September 4, 2001
Assignee:
Sanofi-Synthelabo
Inventors:
Colette Bouloumie, Thierry Breul, Laurence Colliere, Philippe Faure
Abstract: The present invention provides methods for treating mammalian cancer tumors, preferably solid tumors, comprising administering to a mammal in need of such treatment an effective amount of a 1,2,4-benzotriazine oxide as defined in Formula I or pharmacologically acceptable salts of said compound; and administering to the mammal from about one half hour to about twenty-four hours after administering the 1,2,4-benzotriazine oxide an effective amount of a chemotherapy agent to which the tumor is susceptible. The invention also provides kits for treatment of such tumors which comprise a chemotherapy agent and a cytotoxicity-enhancing amount of a 1,2,4-benzotriazine oxide as defined in Formula I.
Type:
Grant
Filed:
April 26, 2000
Date of Patent:
August 21, 2001
Assignee:
The Board of Trustees of Leland Stanford Junior
University
Abstract: The invention relates to the use of &bgr;3-adrenergic receptor agonists for the preparation of healing drugs and to the pharmaceutical compositions for said use.
Type:
Grant
Filed:
July 15, 1999
Date of Patent:
May 22, 2001
Assignee:
Sanofi-Synthelabo
Inventors:
André Bernat, Jean-Marc Herbert, Michèle Arnone
Abstract: The present invention relates to a pharmaceutical composition containing:
(a) a thienopyridine derivative of formula
in which R is hydrogen or a (C1-C4)alkoxycarbonyl group, or one of its pharmaceutically acceptable salts; and
(b) an HMG-CoA reductase inhibitor.