Synthelabo

Guy Rossey

Isaac Chekroun

Alexander E Wick

Jose Ruiz-Montes

Antonio Ugolini

Andre Bourbon

Manuel Bedoya-Zurita

Lydia Zard

Arlette Tixidre

Abkar Vartanian

Michel Magnat

Jean-Baptiste Graux

Manuel Bedoya Zurita

Philippe Michel Manoury

Christian Hoornaert

Jean Louis Binet

Bernard M Raizon

Gerard Defosse

Helene Greciet

Didier Legroux

Marc Daumas

Najib Jabri

Bernard Gerin

A process for the preparation of ethyl 4,4,4-trifluoro-3(R)-hydroxybutanoate, wherein the ester functional group of the (S) enantiomer of ethyl (.+-.)-4,4,4-trifluoro-3-hydroxybutanoate which comprises (R) and (S) is selectively hydrolysed in aqueous medium, by means of a lipase, and the non-hydrolysed (R) enantiomer is then extracted and used in the preparation of 4,4,4-trifluoro-1,3(R)-butanediol.

Process for the resolution of ethyl

A compound of formula (1): ##STR1## in which R.sub.1 represents a 1,1-dimethylethyl, triphenylmethyl, methoxymethyl or benzyloxymethyl group; and

2-[2-(5-tetrazolyl)phenyl]-1,2-dihydroquinoline derivatives

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.

5-[(4-bromophenyl)methyl]4-pyrimidinones

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.

Triarylborane derivatives, their preparation and their use as synthesis

Derivatives of benzeneborinic acid, preparation thereof and use thereof as synthetic intermediates.

Preparation of derivatives of benzeneborinic acid

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.

2-(tetrazol-5-yl)-1,1'-biphenyl derivatives, their preparation and their

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.

Process for preparing 4-pyrimidinones

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.

Derivatives of benzeneborinic acid, preparation thereof and use thereof

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

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.

A compound which is a benzimidazole derivative of formula (I) ##STR1## in which: R.sub.1 is hydrogen or methyl,

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Voisins Le Bretonneux, France

Guy Rossey