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WO2009059765A3 - Process for the preparation of drospirenone - Google Patents

Process for the preparation of drospirenone Download PDF

Info

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
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2008/009372
Other languages
French (fr)
Other versions
WO2009059765A2 (en
Inventor
Guido Galliani
Vincenzo Radaelli
Alberto Terraneo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chorisis SRL
Original Assignee
Chorisis SRL
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chorisis SRL filed Critical Chorisis SRL
Publication of WO2009059765A2 publication Critical patent/WO2009059765A2/en
Publication of WO2009059765A3 publication Critical patent/WO2009059765A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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).
PCT/EP2008/009372 2007-11-08 2008-11-06 Process for the preparation of drospirenone Ceased WO2009059765A2 (en)

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 Ceased 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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8334375B2 (en) 2009-04-10 2012-12-18 Evestra, Inc. Methods for the preparation of drospirenone
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
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
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
WO2009059765A2 (en) 2009-05-14
ITMI20072141A1 (en) 2009-05-09

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