33 b) bromination reaction of a compound of formula (XII), and c) subsequent HBr elimination reaction with formation of a compound of formula (VI). The invention also provides a method for preparing alclometasone dipropionate of formula (I), which comprises the use of the compound of formula (VI) as starting product.
C07J 5/00 - Stéroïdes normaux contenant du carbone, de l'hydrogène, un halogène ou de l'oxygène, substitués en position 17bèta par une chaîne de deux atomes de carbone, p. ex. prégnane, et substitués en position 21 par seulement une unique liaison carbone-oxygène
C07J 51/00 - Stéroïdes normaux à squelette du cyclopenta[a]hydrophénanthrène non modifié non prévus dans les groupes
2.
PROCESSES FOR THE PREPARATION OF ESTETROL AND INTERMEDIATES THEREOF
A process for the preparation of a compound of formula (IIa) is described where A is a silyl protecting group, in high diastereoisomeric purity and in crystalline form, comprising the crystallization of a mixture of the compound of formula (IIa) and its isomer of formula (IIb), where A is a silyl protecting group, from an ethereal solvent. The invention also provides a process for preparing Estetrol of formula (I) in high diastereoisomeric purity, comprising the use of the compound of formula (IIa), in a crystalline form, as a starting material.
A process for the preparation of a compound of formula (IIa) is described where A is a silyl protecting group, in high diastereoisomeric purity and in crystalline form, comprising the crystallization of a mixture of the compound of formula (IIa) and its isomer of formula (IIb), where A is a silyl protecting group, from an ethereal solvent. The invention also provides a process for preparing Estetrol of formula (I) in high diastereoisomeric purity, comprising the use of the compound of formula (IIa), in a crystalline form, as a starting material.
C07J 1/00 - Stéroïdes normaux contenant du carbone, de l'hydrogène, un halogène ou de l'oxygène, non substitués en position 17bêta par un atome de carbone, p. ex. œstrane, androstane
3.
PROCESSES FOR THE PREPARATION OF ESTETROL AND INTERMEDIATES THEREOF
A process for the preparation of a compound of formula (IIa) is described where A is a silyl protecting group, in high diastereoisomeric purity and in crystalline form, comprising the crystallization of a mixture of the compound of formula (IIa) and its isomer of formula (IIb), where A is a silyl protecting group, from an ethereal solvent. The invention also provides a process for preparing Estetrol of formula (I) in high diastereoisomeric purity, comprising the use of the compound of formula (IIa), in a crystalline form, as a starting material.
C07J 1/00 - Stéroïdes normaux contenant du carbone, de l'hydrogène, un halogène ou de l'oxygène, non substitués en position 17bêta par un atome de carbone, p. ex. œstrane, androstane
C07J 51/00 - Stéroïdes normaux à squelette du cyclopenta[a]hydrophénanthrène non modifié non prévus dans les groupes
4.
PROCESS FOR THE PREPARATION OF DES-A-STEROIDS, INTERMEDIATES USEFUL FOR THE SYNTHESIS OF 9BETA,10ALFA-STEROIDS
The present invention relates to a process for the synthesis of intermediates of general formula (I): by means of a simultaneous protection and hydrogenation reaction of an intermediate of formula (II), according to the scheme below: Compounds (I) are intermediates useful for the preparation of steroidal compounds with a (9β,10α) configuration, which are an important group of molecules with known pharmacological activity.
C07J 1/00 - Stéroïdes normaux contenant du carbone, de l'hydrogène, un halogène ou de l'oxygène, non substitués en position 17bêta par un atome de carbone, p. ex. œstrane, androstane
5.
Methods for the preparation of drospirenone and intermediates thereof
The invention relates to a process for the preparation of Drospirenone in high yields and purity starting from a compound of formula 2
wherein R is a hydroxyl protective group as defined in the claims, through a sequence of oxidation, deprotection, lactonization and water elimination steps, and wherein the steps of oxidation and lactonization are performed with 1,3,5-trichloro1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (trichloroisocyanuric acid, TCCA) or 1,3-dichloro-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (dichloroisocyanuric acid, DCCA) or an alkaline metal salt thereof such as the sodium salt dihydrate (DCCA sodium salt) or 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (IBX). New synthetic intermediates useful for the synthesis of Drospirenone are disclosed, too.
A61K 31/34 - Composés hétérocycliques ayant l'oxygène comme seul hétéro-atome d'un cycle, p. ex. fungichromine ayant des cycles à cinq chaînons avec un oxygène comme seul hétéro-atome d'un cycle, p. ex. isosorbide
C07D 307/94 - Composés hétérocycliques contenant des cycles à cinq chaînons comportant un atome d'oxygène comme unique hétéro-atome du cycle condensés en spiro avec des carbocycles ou avec des systèmes carbocycliques, p. ex. griséofulvines
C07J 21/00 - Stéroïdes normaux contenant du carbone, de l'hydrogène, un halogène, ou de l'oxygène ayant un hétérocycle contenant de l'oxygène condensé en spiro avec le squelette du cyclopenta[a]hydrophénanthrène
C07J 53/00 - Stéroïdes ayant le squelette du cyclopenta[a]hydrophénanthrène modifié par condensation avec des cycles carbocycliques ou par formation d'un cycle additionnel par une liaison directe entre deux atomes de carbone cycliques
6.
METHODS FOR THE PREPARATION OF DROSPIRENONE AND INTERMEDIATES THEREOF
The invention relates to a process for the preparation of Drospirenone in high yields and purity starting from a compound of formula (2) wherein R is a hydroxyl protective group as defined in the claims, through a sequence of oxidation, deprotection, lactonization and water elimination steps, and wherein the steps of oxidation and lactonization are performed with 1,3,5-trichloro 1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (trichloroisocyanuric acid, TCCA) or 1,3-dichloro-1,3,5-triazine-2,4,6- (1H,3H,5H)-trione (dichloroisocyanuric acid, DCCA) or an alkaline metal salt thereof such as the sodium salt dihydrate (DCCA sodium salt) or 1-hydroxy - 1,2-benziodoxo1-3(1H)-one 1-oxide (IBX). New synthetic intermediates useful for the synthesis of Drospirenone are disclosed, too.
C07J 53/00 - Stéroïdes ayant le squelette du cyclopenta[a]hydrophénanthrène modifié par condensation avec des cycles carbocycliques ou par formation d'un cycle additionnel par une liaison directe entre deux atomes de carbone cycliques
A process for the preparation of Drospirenone (I) according to the scheme (A) wherein the substituent R is defined in the description. The process improves the product yield and purity by reducing the formation of undesired side-products and is particularly convenient for industrial-scale manufacturing.
C07J 53/00 - Stéroïdes ayant le squelette du cyclopenta[a]hydrophénanthrène modifié par condensation avec des cycles carbocycliques ou par formation d'un cycle additionnel par une liaison directe entre deux atomes de carbone cycliques
A process for the preparation of Drospirenone (I) according to the scheme (A) wherein the substituent R is defined in the description. The process improves the product yield and purity by reducing the formation of undesired side-products and is particularly convenient for industrial-scale manufacturing.
C07J 53/00 - Stéroïdes ayant le squelette du cyclopenta[a]hydrophénanthrène modifié par condensation avec des cycles carbocycliques ou par formation d'un cycle additionnel par une liaison directe entre deux atomes de carbone cycliques
brevets
