Industriale Chimica S.r.l.

Industriale Chimca S.r.l.

Roberto Lenna

Francesco Barbieri

Claudio Delfrate

Francesca Costantino

Riccardo Di Brisco

Silvia Piuri

Andrea Vanossi

Andrea Fasana

Maria Giovanna Luoni

Johannes Bernardus Maria Rewinkel

Juan B Rodriguez

Javier Alberto Ramirez

Davide Rigamonti

Jerry Ortiz

Silvio Pirovano

Maria Julieta Comin

Tea Borelli

Jerry David Ortiz Blacio

Maurizio Montoro

Luigi Panza

Cristina Ghidoli

Daniele Giudici

Lorenzo Menna

Edoardo Mariani

Monica Noseda

Roberto Di Brisco

Javier Ramirez

Juan Bautista Rodriguez

The present invention refers to a process for preparing (3α,5α)-hydroxy-3-methyl-pregnan-20-one, a compound also known as Ganaxolone, having the formula below: (I):

Process for preparing (3α,5α)-3-hydroxy-3-methyl-pregnan-20-one (Ganaxolone)

The present invention relates to a new process for the synthesis of 3α-hydroxy-5α-pregnan-20-one, commonly known as brexanolone, wherein the corresponding cyclic 20-ketal or cyclic 20-thioketal compound of formula (IV) is deprotected with the use or iodine in an organic solvent: (I).

Process for the preparation of 3α-hydroxy-5α-pregnan-20-one (brexanolone)

The present invention to a process for the preparation of the sodium salt of 4-[[(1R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-1-phenylethyl]-amino]-butanoic acid, compound also known as Elagolix sodium salt, having the formula (I) reported below:

Process for the synthesis of the sodium salt of 4-[[(1R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-[[2-fluoro-6-(trifluoromethyl)-phenyl]methyl]-3,6-dihydro-4-methyl-2.6-dioxo-1(2H)-pyrimidinyl]-1-phenylethyl]amino]-butanoic acid (elagolix sodium salt) and intermediates of said process

A process for the synthesis of &#x3b2;-hydroxy 3-17-(1H-benzimidazol-1-yl)androsta-5,16-diene is described, a compound also known as Galeterone and used in the treatment of prostate cancer, having the formula (6). 

Process for the preparation of 3&#x3b2;-hydroxy-17-(1H-benzimidazol-1-YL) androsta-5,16-diene

The present invention refers to a new process for the synthesis of (9&#x3b2;,10&#x3b1;)-pregn-4-ene-3,20-dione, commonly known as retroprogesterone, having the formula (1) shown below. 

Process for the preparation of 9 beta,10 alpha-progesterone (retroprogesterone)

The present invention relates to a new process for the synthesis of 17&#x3b2;-hydroxy-des-A-androst-9,10-en-5-one, the compound of the following formula (1), which can be used as an intermediate in the synthesis of retroprogesterones.

Process for the preparation of 17&#x3b2;-hydroxy-des-A-androst-9,10-en-5-one

A process is described wherein, by employing 17&#x3b1;-(3-hydroxypropyl)-6&#x3b2;,7&#x3b2;;15&#x3b2;,16&#x3b2;-dimethylene-5&#x3b2;-androstane-3&#x3b2;,5,17&#x3b2;-triol (II) as starting product, in a single stage reaction there is obtained drospirenone, (I), a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic action, that is useful for preparing pharmaceutical compositions with contraceptive action. 

Process for the preparation of drospirenone

The present invention relates to a novel process for the synthesis of abiraterone and in particular abiraterone acetate, a compound of formula (I) reported below: having pharmacological activity suitable for slowing down the progression of advanced stage prostate cancer. The process is characterized by the fact that the intermediate triflation step is carried out on prasterone (DHEA) or its 3-acetate using Ar&#x2014;N(OTf)as the triflation reagent, but where Ar is not phenyl, and by the fact that the base used in this step is an alkali metal alcoholate. 

Process for the preparation of abiraterone or abiraterone acetate

The present invention relates to a novel process for the synthesis of abiraterone, and in particular of abiraterone acetate, compound of formula (I) reported below: N O (I) which has pharmacological activity useful for slowing down the progression of prostate cancer at an advanced stage. The process is characterized by an intermediate step wherein DHEA-acetate is triflated using Ar&#x2014;N(OTf)as the triflation reagent. 

Process for the preparation of abiraterone and abiraterone acetate

An improved process for the preparation of intermediate (V) through the elimination of a molecule of water from intermediate (IV) is described. Intermediate (V) is a key molecule for the synthesis of eplerenone, a synthetic steroid with pharmacological activity used in the treatment of chronic pathological conditions, including hypertension.

Process for the preparation of 7 &#x3b1;-(methoxycarbonyl)-3-OXO-17alpha-pregn-4,9(11)-dien-21,17-carbolactone, a useful intermediate for the synthesis of molecules with pharmacological activity

A process is disclosed wherein, using either 17a-(3-hydroxypropyl)-6p,7p;15p,16p-dimethylene-5p-androstane-3p,5,17p-triol (II) or 3&#x3b2;,5^&#xef;I^&#x3ba;^-6&#x3b2;,7&#x3b2;;15&#x3b2;,16&#x3b2;-dimethylene-5&#x3b2;,17&#x3b1;-pregnane-21,17-carbolactone (III) as starting material, through a single-step reaction it is obtained drospirenone (I), a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic activity, useful for preparing pharmaceutical compositions with contraceptive action. 

There is described a process for the industrial synthesis of 11-methylene-18-methyl-estr-4-en-3,17-dione, a compound having the structure formula (I) depicted below: (Formula I) (I) useful as intermediate compound in the synthesis of the progestin compounds Desogestrel and Etonogestrel. 

Process for preparing 11-methylene-18-methyl-estr-4-en-3, 17-dione, useful as intermediate compound for the synthesis of molecules having pharmacological activity

It is described of a process for the preparation of drospirenone, the compound of formula 1 shown below, a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic activity, useful for preparing pharmaceutical compositions having contraceptive action, starting from 17&#x3b1;-(3-hydroxypropyl)-6&#x3b2;,7&#x3b2;;15&#x3b2;,16&#x3b2;-dimethylene-5&#x3b2;-androstane-3&#x3b2;,5,17&#x3b2;-triol. 

A process is described, comprising the oxidation of 17&#x3b1;-(3-hydroxypropyl)-6&#x3b2;,7&#x3b2;,15&#x3b2;,16&#x3b2;-dimethylen-5&#x3b2;-androstan-3&#x3b2;,5,17&#x3b2;-triol, for the preparation of drospirenone, a synthetic steroid with progestogenic, antimineralocorticoid and antiandrogenic activity, useful for preparing pharmaceutical compositions with contraceptive action.

A process is described for the preparation on an industrial scale of N-[2-(8S)-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propionamide, ramelteon, having the structure illustrated below: 

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S. Giorgio su Legnano, Italy

Roberto Lenna