Plurichemie Anstalt

Hovione Inter Limited

Horione Limited

Plurichenue Anstalt

Ivan Villax

Philip R Page

William Heggie

Michael B Hursthouse

Indira Ghatak

Zita Mendes

Richard Somerville

A process for the preparation of high purity flumethasone in high yield involves C3 protecting 9,11&bgr;-epoxy-17&agr;,21-dihydroxy-16&agr;-methylpregna-1,4-diene-3,20-dione,21-acetate, fluorinating at 6&agr;, removing the C3 protecting group, fluorinating the 9,11-epoxy group. The resulting flumethasone 21-acetate is treated with the methanolic potassium hydroxide in the presence of an oxidation agent, causing a simultaneous hydrolyzation and degradative oxidation, resulting in the formation of 6&agr;,9&agr;-difluoro-11&bgr;,17&agr;-dihydroxy-16&agr;-methyl-17&bgr;-carboxy-androsta-1,4-diene-3-one in high yield. Flumethasone 21-acetate is alternatively hydrolyzed to yield flumethasone free alcohol.

Process of preparation of flumethasone 21-acetate, or flumethasone and its 17-carboxyl androsten analogue

A process for the preparation of .mu.-3-carbopentazane-N.sup.1, N.sup.4 :N.sup.2, N.sup.5 -bis-[bis(triphenylphosphine)rhodium (I)] dinitrate by the reaction of tris(triphenylphosphine)nitratorhodium (I) with hydrazine in degassed methanol under an inert atmosphere.

Process for the preparation of a rhodium complex

Novel esters of 9.alpha.-fluoro- and chloro-corticosteroids of the formula ##STR1## wherein Y is chlorine or OR.sub.1, R.sub.1 and R.sub.2 represent an acyl group of 2-6 carbon atoms or a benzoyl group and where R.sub.1 and R.sub.2 can be the same or different in the same molecule, R.sub.3 is methyl or fluorine in either the .alpha.- or .beta.- orientation, X is chlorine or fluorine, and the C.sub.1  C.sub.2 bond can be saturated or not, especially those compounds of the formula ##STR2## wherein Y and R.sub.2 have the significance given above, are prepared by reacting the respective 9.beta.,11.beta.-epoxy compounds with hydrogen fluoride or chloride.

Novel 9.alpha.-fluoro- or chloro-corticosteroid esters and a process for

The present invention refers to the compounds (.mu.-hydrazine-N.sup.1 :N.sup.2)-bis[bis(triphenylphosphine)-chlororhodium (I)] and di(.mu.-hydrazine-N.sup.1 :N.sup.2)-bis[bis(triphenylphosphine)rhodium (I)] dichloride, which are homogenous hydrogenation catalysts and their application in the hydrogenation of the exocyclic methylene group of acid addition salts of 6-demethyl-6-deoxy-6-methylene-5-hydroxytetracycline (methacycline) to prepare .alpha.-6-deoxy-5-hydroxytetracycline (doxycycline).

Preparation of a new catalyst containing rhodium

The present invention refers to complexes prepared by reacting rhodium trinitrate with a suitable hydrazine and a suitable tertiary phosphine, more specifically to the compounds di(.mu.-hydrazine-N.sup.1 :N.sup.2)-bis[bis(triphenylphosphine)rhodium (I)]dinitrate and .mu.-3-carbopentazane-N.sup.1, N.sup.4 :N.sup.2, N.sup.5 -bis[bis(triphenylphosphine)rhodium (I)]dinitrate, which are homogenous hydrogenation catalysts and their application in the hydrogenation of the exocyclic methylene group of acid addition salts of 6-demethyl-6-deoxy-6-methylene-5-hydroxytetracycline (methacycline) to prepare .alpha.-6-deoxy-5-hydroxy-tetracycline (doxycycline).

Process of preparation of novel rhodium hydrogenation catalysts

A homogenous hydrogenation process of preparing 6-demethyl-6-deoxy-6 methylene-5-hydroxytetracycline using a stereospecific tertiary phosphine-hydrozino-rhodium complex catalyst.

New process for the preparation of alpha-6-deoxy-5-hydroxytetracycline

Application of catalysts containing rhodium

The present invention refers to complexes prepared by reacting rhodium trinitrate with a suitable hydrazine and a suitable tertiary phosphine, more specifically to the compounds di(.mu.-hydrazine-N.sup.1 :N.sup.2)-bis[bis(triphenylphosphine)rhodium (I)]dinitrate and .mu.-3-carbopentazane-N.sup.1,N.sup.4 :N.sup.2,N.sup.5 -bis[bis(triphenylphosphine)rhodium (I)]dinitrate, which are homogeneous hydrogenation catalysts and their application in the hydrogenation of the exocyclic methylene group of acid addition salts of 6-demethyl-6-deoxy-6-methylene-5-hydroxytetracycline (methacycline) to prepare .alpha.-6-deoxy-5-hydroxy-tetracycline (doxycycline).

Process of preparation of novel rhodium hydrogenation catalysts and

A homogeneous stereospecific rhodium complex hydrogenation catalyst is prepared using a degassed organic solvent and eventually water.

Homogeneous catalytic system and a process for the preparation of same

Stable homogeneous hydrogenation catalysts are prepared by reacting a rhodium salt or complex with a hydrazine in the presence or absence of a tertiary phosphine.

Homogeneous catalytic system comprising rhodium, hydrazine and phosphine

An improved process for the preparation of .alpha.-6-deoxytetracyclines and more particularly to the stereo specific hydrogenation of the 6-methylene group of 6-deoxy-6-demethyl-6-methylene-5-hydroxytetracyline and of its 11a-halo-analog, is described in which the catalyst is the reaction product of a rhodium salt or a complex with a hydrazine or salt thereof.

Process for the preparation of .alpha.-6-deoxytetracyclines

The 17.alpha.-monoesters and 17.alpha.,21-diesters of corticosteriods are well known and represent nowadays the most efficient group of anti-inflammatory compounds for topical application, having minimal systemic action.

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Lisbon, Portugal

Ivan Villax