Roussel Uclaf

Jean Jolly

Julien Warnant

Primo Rizzi

Jean Tessier

Jean-Pierre Demoute

Jacques Martel

Rene Heymes

Dieter Bormann

Jean A Grandadam

Charles Pavan

Jacques Bulidon

Giuseppe Gigliotti

Robert Joly

Jean Taillardat

Gaston Amiard

Walter Duerckheimer

Bernard Matra

A novel process for the preparation of syn isomers of cephalosporanic acid derivatives of the formula ##STR1## comprising reacting first in a solvent and optionally in the presence of a base, a compound of the formula ##STR2## with a compound of the formula

Process for the preparation of derivative of

Novel lactones of 2,2-dimethyl-cyclopropane-1-carboxylic acids of the formula ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 when identical are selected from the group consisting of chlorine and bromine and when at least two are different, are selected from the group consisting of fluorine, chlorine and bromine and a novel process for their preparation and a process for the preparation of cis 2,2-dimethylcyclopropane-1-carboxylic acids of the formula ##STR2##

Process for preparing

The monohydrate of 1.alpha.,25-dihydroxy-cholecalciferol having a remarkable vitamin activity and a process for its preparation.

1.alpha.,25.alpha.-Dihydroxy-cholecalciferol and methods for the

A novel process for the resolution of D,L-cis and D,L-trans 2,2-dimethyl-3-(2,2 -dihalovinyl)-cyclopropane-1-carboxylic acids of the formula ##STR1## wherein X is selected from the group consisting of fluorine, chlorine and bromine comprising salifying the said acid with an optically active base selected from the group consisting of D-ephedrine, L-ephedrine, D-N-methyl-ephedrine, L-N-methylephedrine, D-pseudo-ephedrine and L-pseudo-ephedrine to form the corresponding salt, recovering the said salt and subjecting the latter to acid hydrolysis to obtain the corresponding resolved acid which are intermediates for the synthesis of esters having a remarkable insecticidal activity.

Resolution of D,L-cis and D,L-trans

Novel lactones of cis 2,2-dimethyl-cyclopropane-1-carboxylic acids of the formula ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 when identical are selected from the group consisting of chlorine and bromine and when at least two are different, are selected from the group consisting of fluorine, chlorine and bromine and a novel process for their preparation and a process for the preparation of cis 2,2-dimethyl-cyclopropane-1-carboxylic acids of the formula ##STR2## The acids of formula IV are useful to prepare esters of elevated insecticidal activity.

Novel lactones of cis 2,2-dimethyl-cyclopropane-1-carboxylic acid and

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

The novel product, dextrorotary 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-acetonyl]-4(3H)-quinazolinon e and its non-toxic, pharmaceutically acceptable acid addition salts having anticoccidiosis activity and its preparation and use.

Novel quinazolinone

Novel stable crystalline hydrate of D form of the syn isomer of sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph- 3-eme-4-carboxylate having the formula ##STR1## which has excellent antibiotic activity against both gram negative and gram positive bacteria and a process for its preparation.

Sodium

Novel 4,5-seco-estrane-3,5,17-trione derivatives of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 3 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and K and K' are individually blocked ketones in the form of ketals which are intermediates for the preparation of therapeutically active steroids and their preparation and novel intermediates.

4,5-Seco-estrane-3,5,17-trione derivatives

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

Novel lactones of 2,2-dimethyl-cyclopropane-1-carboxylic acids of the formula ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 when identical are selected from the group consisting of chlorine and bromine and when at least two are different, are selected from the group consisting of fluorine, chlorine and bromine and a novel process for their preparation and a process for the preparation of cis 2,2-dimethyl-cyclopropane-1-carboxylic acids of the formula ##STR2##

Lactones of 2,2-dimethyl-cyclopropane-1-carboxylic acids

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.

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Fontenay-sous-Bois, France

Jean Jolly