Synthelabo

Alexander E Wick

Jonathan Reid Frost

Guy Rossey

Isaac Chekroun

Antonio Ugolini

Jean Bertin

Patrick Andre Lardenois

Bernard Gaudilliere

Jean Rousseau

Regis Dupont

Bernard M Raizon

Jean Montel

Veronique Andrieu

Andre Bourbon

Abkar Vartanian

Jean-Baptiste Graux

Jean Louis Binet

Salomon Z Langer

Lydia Zard

Arlette Tixidre

Johannes Schoemaker

Louis Henrion

Maria C Renones

Bernard Gerin

Jean P Thenot

The present invention provides a piperidine derivative of formula (I) ##STR1## in which R represents a straight- or branched-chain (C.sub.1 -C.sub.19)alkyl group, a straight- or branched-chain (C.sub.2 -C.sub.19)alkenyl group, a (C.sub.3 -C.sub.6)cycloalkyl group, a cycloalkylmethyl group in which the cycloalkyl moiety has from three to six carbon atoms, a phenyl group which is optionally substituted by a halogen atom or a phenyl methyl group which is optionally substituted by a halogen atom, or an addition salt thereof, in the form of an optically pure enantiomer or of a mixture of enantiomers, a process for making them and their therapeutic application.

Alpha-(4-chlorophenyl)-4-[(4-fluorphenyl)-methyl]piperidine-1-ethanol

Pharmaceutical compositions which comprises a core comprising alfuzosin hydrochloride which core is coated with a coating whose dissolution is pH-dependent and applications to the preparation of sustained-release dosage compositions which are unable for a once-daily oral administration.

Sustained-release compositions of alfuzosin hydrochloride

A pharmaceutical preparation intended for transdermal administration contains alfusozin [(N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydr o-2-furancarboxamide] or a salt thereof and a mixture composed of water, at least one organic solvent and at least one absorption promoter.

Transdermal pharmaceutical composition

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.

Process for the preparation of methyl

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.

Method for preparing

Process for the preparation of compounds of the general formula (I) ##STR1## wherein R is hydrogen or (C.sub.1-4)alkyl.

Process for the preparation of propionic acid derivatives

Ifenprodil and its analogues are useful for the treatment of psychoses such as schizophrenia.

Method of treatment of psychotic disorders

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.

Method of preparing

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.

Compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, halogen, trifluoromethyl, alkyl, hydroxyl, alkyoxy, benzyloxy, alkanoyloxy, or benzoyloxy, or when R.sub.2 is hydroxyl or methoxy in the 4-position and R.sub.3 is hydrogen, R.sub.1 may also represent hydroxymethyl carbamoyl or alkoxycarbonyl,

Therapeutically useful 1-phenyl-2-piperidinoalkanol derivatives

Diphenylazomethine derivatives of formula (I) ##STR1## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is an --OH,--OM (M=alkaline metal or alkaline earth metal), --NH.sub.2 or --O(C.sub.1-4 alkyl) group, and which are in the form of cis or trans isomers or mixtures thereof, have central nervous system activity and can be used as antidepressants and anticonvulsants.

Unsaturated diphenylazomethine derivatives, their preparation and

Compounds of general formula (I) ##STR1## wherein R1 represents a phenyl, halophenyl, methylphenyl, ethylphenyl, methoxyphenyl, trifluoromethylphenyl or naphthyl group, R2 represents hydrogen or a methyl or phenyl group, and R3 represents hydrogen or a benzyl group, except compounds in which R1 is a phenyl or 4-fluorophenyl group, R2 is hydrogen and R3 is hydrogen or a benzyl group, and their pharmaceutically acceptable acid addition salts have useful anti-depressant and anti-ischaemic properties.

Furo 3,2-c pyridine derivatives and their use in treating depression and

Process for preparing diphenylazomethines of formula (II) ##STR1## by decarboxylation of diphenylazomethines of formula (I) ##STR2## in which X.sub.1 and X.sub.2 each denote, independently of each other, a hydrogen atom or a halogen atom or a methyl radical,

Preparation of diphenylazomethines

Pyridine derivatives of the general formula (I) ##STR1## in which X is --O-- or --NH--, R.sub.1 is a phenyl group optionally substituted by one or two halogen atoms or a methyl, ethyl, trifluoromethyl, methoxy or phenyl group or, when R.sub.2 is not a benzyl group, an amino group, or is a naphthyl or benzodioxanyl group, and R.sub.2 is hydrogen or a benzyl group, or when X is --O--, R.sub.2 can also be a methyl or ethyl group, and their pharmaceutically acceptable acid addition salts are useful as antianoxics.

Anti-anoxic furo- or pyrrolo-pyridine compounds and pharmaceutical

New 3-phenoxypropan-2-ol derivatives of the formula: ##STR1## wherein R represents a cycloalkyl radical having 5 or 6 carbon atoms, X represents an oxygen atom or a bond, and R' represents the isopropyl or tert.-butyl radical, have been found to be useful in therapy, and more particularly in the treatment of cardiovascular diseases and glaucoma.

Growing community of inventors

Saint Nom La Breteche, France

Alexander E Wick