Roussel Uclaf

Julien Warnant

Jean Jolly

Philippe Cosquer

Italo Medici

Andre Farcilli

Jacques Prost-Marechal

Edmond Toromanoff

Robert Joly

Jacques Marechal-Prost

An improved process for the preparation of pure 9.alpha.-fluoro-16.alpha.-methyl-21-acetoxy-.DELTA..sup.1,4 -pregnadiene-11.beta.-ol-3,20-dione comprising reacting 9.alpha.-fluoro-21-acetoxy-.DELTA..sup.1,4,16 -pregnatriene-11.beta.-ol-3,20-dione with a methyl magnesium halide in the presence of a catalytic amount of a cuprous halide effecting protonation of magnesian to form 9.alpha.-fluoro-16.alpha.-methyl-21-acetoxy-.DELTA..sup.1,4 -pregnadiene-11.beta.-ol-3,20-dione, reacting the raw product with an acetylation agent to acetylate the partially deacetylated product and purifying the reacetylated product with an organic solvent, treating in solution with a peroxidation agent and then purifying again with an organic solvent.

Preparation of

Novel eburnamenine derivatives of the formula ##STR1## in the form of racemic mixtures or optically active isomers and their non-toxic, pharmaceutically acceptable acid addition salts which are oxygenators and cerebral vasoregulators of great value.

14-Imino-(15H)-eburnamine compounds, compositions, methods of use and

A novel process for the preparation of 3-oximes of the formula ##STR1## wherein R is selected from the group consisting of methyl and ethyl and R' is selected from the group consisting of hydrogen and acyl of an organic carboxylic acid of 2 to 8 carbon atoms and novel intermediates formed therein.

Novel process for the preparation of 3-oximes of steroids

A process for the preparation of an ester of chiral (A) acid with a racemic (R,S) .alpha.-cyano-3-phenoxybenzyl alcohol (B) by reacting an ester of chiral (A) acid with .alpha.-cyano-3-phenoxybenzyl alcohol of the formula ##STR1## in its optically active (R) form or (S) form or a mixture of esters of said (R) alcohol and (S) alcohol in non-equimolecular proportions with a base selected from the group consisting of ammonia, primary, secondary and tertiary amines, quaternary ammonium compounds, liquid amines of high molecular weight and a catalytic amount of a strong base in at least one solvent for the starting esters and in which the ester of racemic alcohol is soluble and recovering from the resulting solution the ester of chiral (A) acid with racemic (R,S) alcohol.

Novel racemization process

The novel esters, (R) .alpha.-cyano-3-phenoxybenzyl 2,2-dimethyl-3R-(2,2-dichlorovinyl)-cyclopropane-1R-carboxylate and (S) .alpha.-cyano-3-phenoxybenzyl 2,2-dimethyl-3R-(2,2-dichlorovinyl)-cyclopropane-1R-carboxylate, having insecticidal properties.

Insecticidal cyclopropane carboxylates

A process for the preparation of an ester of chiral (A) acid with an optically active (S) .alpha.-cyano-3-phenoxybenzyl alcohol by reacting an ester of chiral (A) acid with .alpha.-cyano-3-phenoxybenzyl alcohol of the formula ##STR1## in its optically active (R) form or a racemic (R,S) mixture or a mixture of esters of said (R) alcohol and (S) alcohol in non-equimolecular proportions designated herein as 'ester (R+S)' with a base selected from the group consisting of ammonium hydroxide, primary, secondary and tertiary amines, quaternary ammonium compounds, liquid amines of high molecular weight, ion exchange resins of a basic character and a catalytic amount of a strong base in at least one solvent in which the ester of the (R) alcohol is soluble and in which the ester of the (S) alcohol is insoluble and recovering from the resulting medium the chiral (A) acid ester of the (S) alcohol which is insoluble.

Novel inversion process

A process for the production of a .DELTA..sup.4 -gonenic steroid having the formula ##SPC1## Wherein R represents a member selected from the group consisting of hydrogen and the acyl of an organic carboxylic acid having from 1 to 18 carbon atoms, R' represents an alkyl having from 1 to 4 carbon atoms, R.sup.iv represents a member selected from the group consisting of lower alkyl, lower alkenyl or lower alkynyl, and B represents a member selected from the group consisting of two hydrogens in the 9.alpha. and 10.beta. position and a double bond which comprises the steps of reacting a 3-ketal-4,5-seco-gonane-5-one with a ketalizing agent, oxidizing the resultant 3,5-diketal-4,5-seco-gonane-17.beta.-ol, reacting the resultant 3,5-diketal-4,5-seco-gonane-17-one with an organometallic compound, hydrolyzing the resultant 3,5-diketal-17.alpha.-R.sup.iv -4,5-seco-gonane-17.beta.-ol, cyclizing the resultant 17.alpha.-R.sup.iv -4,5-seco-gonane-17.beta.-ol-3,5-dione and recovering said .DELTA..sup.4 -gonenic steroid. The novel intermediates are also part of the invention. The .DELTA..sup.4 -gonenic steroids are known compounds having steroidal properties.

Intermediates for the preparation of 17-substituted-.DELTA..sup.4

Novel intermediates for the preparation of trienic steroids which intermediates have the formula ##SPC1## Wherein R is alkyl of 1 to 4 carbon atoms and X is selected from the group consisting of aliphatic of 1 to 6 carbon atoms optionally substituted and cycloalkyl of 3 to 6 carbon atoms and Y is selected from the group consisting of =O and ethylenedioxy.

Intermediates for the preparation of trienic steroids

Process for the preparation of glaziovine by treating N-methyl bromococlaurine in an inert organic solvent with a tin hydride tri-substituted with organic radicals in the presence of a free radical promoter.

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Neuilly-sur-Seine, France

Julien Warnant