WO2009059765A3 - Process for the preparation of drospirenone - Google Patents
Process for the preparation of drospirenone Download PDFInfo
- Publication number
- WO2009059765A3 WO2009059765A3 PCT/EP2008/009372 EP2008009372W WO2009059765A3 WO 2009059765 A3 WO2009059765 A3 WO 2009059765A3 EP 2008009372 W EP2008009372 W EP 2008009372W WO 2009059765 A3 WO2009059765 A3 WO 2009059765A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- drospirenone
- preparation
- androstendione
- enol
- dione
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/008—3 membered carbocyclic rings in position 15/16
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Reproductive Health (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
The present invention describes a process for the preparation of drospirenone (I) using androstendione as a starting material. In particular, androstendione protected on carbonyl group in position 3 as an enol-ether is functionalized in position 16 with a sulfoxide group and the derivative thus obtained undergoes thermal elimination in alkaline to give androsta-4,15- diene-3, 17-dione (V) which is further transformed into Drospirenone (I).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI2007A002141 | 2007-11-08 | ||
IT002141A ITMI20072141A1 (en) | 2007-11-08 | 2007-11-08 | PROCEDURE FOR THE PREPARATION OF DROSPIRENONE |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2009059765A2 WO2009059765A2 (en) | 2009-05-14 |
WO2009059765A3 true WO2009059765A3 (en) | 2009-10-15 |
Family
ID=40314693
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2008/009372 WO2009059765A2 (en) | 2007-11-08 | 2008-11-06 | Process for the preparation of drospirenone |
Country Status (2)
Country | Link |
---|---|
IT (1) | ITMI20072141A1 (en) |
WO (1) | WO2009059765A2 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8334375B2 (en) | 2009-04-10 | 2012-12-18 | Evestra, Inc. | Methods for the preparation of drospirenone |
DE102009038972A1 (en) | 2009-08-23 | 2011-06-30 | Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG, 14167 | Producing drospirenone, useful as hormonal contraceptives, by oxidatively converting hydroxy-dimethylenandrostane-one to hydroxy-dimethylenandrostan-dione, eliminating hydroxy group, followed by reacting with 1-halopropan-3-oxy |
DE102010006818A1 (en) | 2010-01-31 | 2011-08-04 | Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG, 14167 | Producing drospirenone, useful as hormonal contraceptives, by oxidatively converting hydroxy-dimethylenandrostane-one to hydroxy-dimethylenandrostan-dione, eliminating hydroxy group, followed by reacting with 1-halopropan-3-oxy |
DE102009031909B4 (en) * | 2009-07-01 | 2017-02-09 | Heyl Chemisch-Pharmazeutische Fabrik Gmbh & Co. Kg | Process for the preparation of drospirenone from prasterone |
US8921346B2 (en) * | 2010-03-16 | 2014-12-30 | Taizhou Taifa Pharmaceuticals Co., Ltd. | Preparation method of drospirenone |
CN104558091B (en) * | 2013-10-16 | 2017-07-28 | 天津金耀集团有限公司 | A kind of synthetic method of Abiraterone acetate |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1586579A1 (en) * | 2004-03-08 | 2005-10-19 | POLI INDUSTRIA CHIMICA S.p.A. | Process for the preparation of delta(15-16)-17-ketosteroids and use thereof in the synthesis of pharmacologically active compounds |
WO2006059168A1 (en) * | 2004-11-30 | 2006-06-08 | Richter Gedeon Vegyészeti Gyár Rt. | A PROCESS FOR THE PREPARATION OF 17-HYDROXY-6β,7β;15β,l6β-BISMETHYLENE-17α-PREGN-4-ENE-3-ONE-21-CARBOXYLIC ACID Ϝ-LACTONE AND KEY-INTERMEDIATES FOR THIS PROCESS |
ITMI20061802A1 (en) * | 2006-09-22 | 2008-03-23 | Antibioticos Spa | EPOXIDATION OF 17-OXO-15,16-METHYLEN STEROIDS WITH SULFOSSONUS ILIDES |
-
2007
- 2007-11-08 IT IT002141A patent/ITMI20072141A1/en unknown
-
2008
- 2008-11-06 WO PCT/EP2008/009372 patent/WO2009059765A2/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1586579A1 (en) * | 2004-03-08 | 2005-10-19 | POLI INDUSTRIA CHIMICA S.p.A. | Process for the preparation of delta(15-16)-17-ketosteroids and use thereof in the synthesis of pharmacologically active compounds |
WO2006059168A1 (en) * | 2004-11-30 | 2006-06-08 | Richter Gedeon Vegyészeti Gyár Rt. | A PROCESS FOR THE PREPARATION OF 17-HYDROXY-6β,7β;15β,l6β-BISMETHYLENE-17α-PREGN-4-ENE-3-ONE-21-CARBOXYLIC ACID Ϝ-LACTONE AND KEY-INTERMEDIATES FOR THIS PROCESS |
ITMI20061802A1 (en) * | 2006-09-22 | 2008-03-23 | Antibioticos Spa | EPOXIDATION OF 17-OXO-15,16-METHYLEN STEROIDS WITH SULFOSSONUS ILIDES |
EP1903051A2 (en) * | 2006-09-22 | 2008-03-26 | Antibioticos S.p.A. | Epoxidation of 17-oxo-15,16-methylene steroids with sulfoxonium ylides |
Non-Patent Citations (1)
Title |
---|
GROSZEK, GRAZYNA; KABAT, MAREK M.; KUREK, ALICJA; MASNYK, MAREK; WICHA, JERZY: "Cardiotonic steroids. Part 11. An improved procedure for preparation of androst-15-en-17-one derivatives", BULLETIN OF THE POLISH ACADEMY OF SCIENCES, CHEMISTRY, vol. 34, no. 7-8, 1986, pages 305 - 311, XP008104539 * |
Also Published As
Publication number | Publication date |
---|---|
ITMI20072141A1 (en) | 2009-05-09 |
WO2009059765A2 (en) | 2009-05-14 |
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