Aventis Pharma S.a.

Roussel Uclaf

Hoechst Marion Roussel

Patrick Roussel

Michel Vivat

Jean Buendia

Colette Colladant

John Patrick Larkin

Veronique Croco

Francis Brion

Veronique Cro-Cq

Francois Nique

Christian Moratille

Joëlle Bousquet

Crocq Veronique

The invention relates to a process for preparing compounds of formula (I): in which R, R, R, n and X are as defined in the description, and to the intermediate compounds for implementing this process.

Process and intermediates for preparing 17-halogenated 19-norsteroid compounds

Derivatives of octahydro-6,10-dioxo-6H-pyridazino &lsqb;1,2-a&rsqb; &lsqb;1,2&rsqb; diazepine-1-carboxylic acid, their preparation process and their use in the preparation of therapeutically active compounds

The invention concerns compounds of formula (I) in SR configuration or in the form of a SR&plus;SS mixture, wherein R represents a hydrogen atom, an alkyl or aralkyl radical containing up to 18 carbon atoms, the amine function being free or protected. The compounds can be used for preparing active principles for medicines.

Octahydro-6, 10-dioxo-6h-pyridazino/1,2-a/ /1,2/diazepin-1-carboxylic acid, derivatives, preparation method and use for preparing therapeutically active compounds

Process for the preparation of bicyclic compounds and the use of this process for the preparation of an ice inhibitor compound

(3,4,7,8,9,10-hexahydro-6, 10 -6H-pyridazino &lsqb;1,2-a&rsqb; &lsqb;1,2&rsqb; diazepine-1-carboxylic-acid derivatives

(3,4,7,8,9,10-hexahydro-6,10-dioxo-6H pyridazino&lsqb;1,2-A&rsqb; &lsqb;1,2&rsqb; diazepine-1-carboxylic acid derivatives

Intermediates for the compound of the formula

Process for preparing 16 &agr;-methyl-steroids

A compound of the formula ##STR1## wherein the A.sub.1 and B.sub.1 rings are as defined by the specification. The compounds are intermediates in the preparation of oxoetiocholenic acid.

17,20-epoxy steroid intermediates

A novel process for the preparation of oxoetiocholenic acid of the formula ##STR1## and intermediates therefore.

Intermediate steroid compounds

Intermediate steroid compound

A process for the preparation of a compound of the formula ##STR1##

Process for preparing 16.alpha.-methyl-steroids

The invention is drawn to a process for the preparation of oxoetiocholenic acid of the formula I ##STR1## by reacting a compound of the formula II ##STR2## with a halonitrile in the presence of a base followed by formation of a 3-ketone group. The intermediate formed is reacted with an acid of the formula HX in an anhydrous medium followed by dehydrohalogenation of the resulting compound in the presence of a base. The intermediate produced then undergoes alkaline hydrolysis followed by a conventional acid treatment to obtain the compound of formula I.

Process for the preparation of an oxoetiocholenic acid

A process for the preparation of a compound of the formula ##STR1## in which rings A and B are a remainder: ##STR2## in which the 3-ketone function is optionally protected in the form of a ketal, thioketal, hemithioketal or enol ether, or a remainder: ##STR3## wherein R is methyl or --CH.sub.2 --OR', R' is hydrogen or ether remainder or ester remainder, R.sub.1 and R.sub.2 together form a second bond, or R.sub.1 and R.sub.2 form together an epoxide in beta position, or R.sub.1 is hydrogen, ketone or .alpha.- or .beta.- hydroxy, free or protected in the form of an ether or ester and R.sub.2 is hydrogen, or R.sub.1 is hydrogen and R.sub.2 is .alpha.-hydroxy function, or R.sub.1 is .beta.-hydroxy, free or protected in the form of an ether or ester and R.sub.2 is .alpha.-fluorine or bromine and R.sub.3 is hydrogen or .alpha. or .beta. fluorine or methyl comprising reacting a compound of the formula ##STR4## in which A, B, R, R.sub.1, R.sub.2 and R.sub.3 have the above meaning with a methylation agent in the presence of a copper-based catalyst to form the 16 .alpha.-methylated enolate, hydrolyzing the latter to obtain the corresponding enol and reacting the latter with an oxidizing agent to obtain the compound of formula I.

Preparation of 16.alpha.-methyl steroids

A process for the preparation of a compound of the formula ##STR1## comprising reacting a compound of the formula ##STR2## with chlorosulfonic in an organic solvent wherein the reaction is effected at -20.degree. C. to -10.degree. C. and the temperature is then allowed to rise to 0.degree. C. to 5.degree. C.

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Thiais, France

Patrick Roussel