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 - Normal steroids containing carbon, hydrogen, halogen, or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane, and substituted in position 21 by only one singly bound oxygen atom
C07J 51/00 - Normal steroids with unmodified cyclopenta[a]hydrophenanthrene skeleton not provided for in groups
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 - Normal steroids containing carbon, hydrogen, halogen, or oxygen, not substituted in position 17 beta by a carbon atom, e.g. oestrane, 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 - Normal steroids containing carbon, hydrogen, halogen, or oxygen, not substituted in position 17 beta by a carbon atom, e.g. oestrane, androstane
C07J 51/00 - Normal steroids with unmodified cyclopenta[a]hydrophenanthrene skeleton not provided for in groups
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 - Normal steroids containing carbon, hydrogen, halogen, or oxygen, not substituted in position 17 beta by a carbon atom, e.g. oestrane, 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 - Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
C07D 307/94 - Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
C07J 21/00 - Normal steroids containing carbon, hydrogen, halogen, or oxygen, having an oxygen-containing hetero ring spiro-condensed with the cyclopenta[a]hydrophenanthrene skeleton
C07J 53/00 - Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by condensation with carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms
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 - Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by condensation with carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms
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 - Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by condensation with carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms
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 - Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by condensation with carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms
patents
