WO2006059168A1 - 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 - Google Patents

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 Download PDF

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Publication number
WO2006059168A1
WO2006059168A1 PCT/HU2005/000111 HU2005000111W WO2006059168A1 WO 2006059168 A1 WO2006059168 A1 WO 2006059168A1 HU 2005000111 W HU2005000111 W HU 2005000111W WO 2006059168 A1 WO2006059168 A1 WO 2006059168A1
Authority
WO
WIPO (PCT)
Prior art keywords
bismethylene
pregn
lactone
ene
intermediates
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/HU2005/000111
Other languages
French (fr)
Inventor
György GÁLIK
Judit Horváth
Béla SÖRÖS
Sándor MAHÓ
Zoltán Tuba
Gábor BALOGH
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.)
Richter Gedeon Vegyeszeti Gyar Nyrt
Original Assignee
Richter Gedeon Vegyeszeti Gyar RT
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 Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT
Priority to AT05797368T priority Critical patent/ATE461934T1/en
Priority to DK05797368.7T priority patent/DK1831239T5/en
Priority to AU2005311060A priority patent/AU2005311060B2/en
Priority to HK08101733.2A priority patent/HK1111168B/en
Priority to CA002585805A priority patent/CA2585805C/en
Priority to DE602005020185T priority patent/DE602005020185D1/en
Priority to SI200531003T priority patent/SI1831239T1/en
Priority to JP2007543937A priority patent/JP5129899B2/en
Priority to CN200580039861XA priority patent/CN101061132B/en
Priority to US11/719,463 priority patent/US8450476B2/en
Priority to PL05797368T priority patent/PL1831239T3/en
Priority to EP05797368A priority patent/EP1831239B8/en
Publication of WO2006059168A1 publication Critical patent/WO2006059168A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

The invention relates to a process for the preparation of 17-hydroxy-6ß,7ß;15ß,16ß- bismethylene-17a-pregn-4-ene-3-one-21-carboxylic acid ?-lactone of formula (I) as well as to key- intermediates for this process.

Description


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Claims

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PCT/HU2005/000111 2004-11-30 2005-10-11 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 Ceased WO2006059168A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
AT05797368T ATE461934T1 (en) 2004-11-30 2005-10-11 PROCESS FOR PRODUCING 17-HYDROXY-6 BETA, 7 BETA, 15 BETA,16 BETA-BISMETHYLENE-17ALPHA-PREGN-4-EN-3-ON-21-CAR ONIC ACID -LACTONE AND KEY INTERMEDIATE PRODUCTS FOR THIS PROCESS
DK05797368.7T DK1831239T5 (en) 2004-11-30 2005-10-11 Process for the preparation of 17-hydroxy-6 beta, 7 beta, 15 beta, 16 beta -bismethylene-17alpha-pregn-4-ene-3-one-21-carboxylic acid gamma-lactone and key intermediates for this process
AU2005311060A AU2005311060B2 (en) 2004-11-30 2005-10-11 A process for the preparation of 17-hydroxy-6beta,7beta;15beta,l6beta-bismethylene-17alpha-pregn-4-ene-3-one-21-carboxylic acid gamma-lactone and key-intermediates for this process
HK08101733.2A HK1111168B (en) 2004-11-30 2005-10-11 A PROCESS FOR THE PREPARATION OF 17-HYDROXY-6 ß,7ß,15 ß,16 ß -BISMETHYLENE-17α-PREGN-4-ENE-3-ONE-21-CARBOXYLIC ACID γ-LACTONE AND KEY-INTERMEDIATES FOR THIS PROCESS
CA002585805A CA2585805C (en) 2004-11-30 2005-10-11 A process for the preparation of 17-hydroxy-6.beta.,7.beta.;15.beta., 16.beta.-bismethylene-17.alpha.-pregn-4-ene-3-one-21-carboxylic acid .gamma.-lactone and key-intermediates for this process
DE602005020185T DE602005020185D1 (en) 2004-11-30 2005-10-11 PROCESS FOR PREPARATION OF 17-HYDROXY-6 BETA, 7 BETA, 15 BETA, 16 BETA-BISMETHYLENE-17ALPHA-PREGN-4HEN PRODUCTS FOR THIS PROCESS
SI200531003T SI1831239T1 (en) 2004-11-30 2005-10-11 A process for the preparation of 17-hydroxy-6 beta, 7 beta, 15 beta, 16 beta -bismethylene-17 alpha-pregn-4-ene-3-one-21-carboxylic acid lambda-lactone and key-intermediates for this process
JP2007543937A JP5129899B2 (en) 2004-11-30 2005-10-11 Process for the preparation of 17-hydroxy-6β, 7β; 15β, 16β-bismethylene-17α-pregne-4-en-3-one-21-carboxylic acid γ-lactone and important intermediates for this method
CN200580039861XA CN101061132B (en) 2004-11-30 2005-10-11 Process for the preparation of 17-hydroxy-6β,7β; 15β,16β-bis-methylene-17α-pregna-4-en-3-one-21-carboxylic acid γ-lactone and keys used in the process intermediate
US11/719,463 US8450476B2 (en) 2004-11-30 2005-10-11 Process for the preparation of 17-hydroxy-6β,7β;15β,16β-bismethylene-17α-pregn-4-ene-3-one-21-carboxylic acid γ-lactone and key intermediates for this process
PL05797368T PL1831239T3 (en) 2004-11-30 2005-10-11 A process for the preparation of 17-hydroxy-6 beta, 7 beta, 15 beta, 16 beta -bismethylene-17 alpha-pregn-4-ene-3-one-21-carboxylic acid lambda-lactone and key-intermediates for this process
EP05797368A EP1831239B8 (en) 2004-11-30 2005-10-11 A process for the preparation of 17-hydroxy-6 beta, 7 beta, 15 beta, 16 beta -bismethylene-17 alpha-pregn-4-ene-3-one-21-carboxylic acid gamma-lactone and key-intermediates for this process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HUP0402466 2004-11-30
HU0402466A HUP0402466A2 (en) 2004-11-30 2004-11-30 Industrial process for preparing 17-hydroxy-6-betha, 7-betha, 15-betha, 16-betha-bis-methylene-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid gamma lacton and the main, intermediates of the process

Publications (1)

Publication Number Publication Date
WO2006059168A1 true WO2006059168A1 (en) 2006-06-08

Family

ID=89985652

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2005/000111 Ceased WO2006059168A1 (en) 2004-11-30 2005-10-11 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

Country Status (15)

Country Link
US (1) US8450476B2 (en)
EP (1) EP1831239B8 (en)
JP (1) JP5129899B2 (en)
CN (1) CN101061132B (en)
AT (1) ATE461934T1 (en)
AU (1) AU2005311060B2 (en)
CA (1) CA2585805C (en)
DE (1) DE602005020185D1 (en)
DK (1) DK1831239T5 (en)
ES (1) ES2342781T3 (en)
HU (1) HUP0402466A2 (en)
PL (1) PL1831239T3 (en)
PT (1) PT1831239E (en)
SI (1) SI1831239T1 (en)
WO (1) WO2006059168A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1903051A3 (en) * 2006-09-22 2008-06-25 Antibioticos S.p.A. Epoxidation of 17-oxo-15,16-methylene steroids with sulfoxonium ylides
WO2009059765A3 (en) * 2007-11-08 2009-10-15 Chorisis S.R.L. Process for the preparation of drospirenone
EP2415778A1 (en) 2010-08-03 2012-02-08 Newchem S.p.A. Methods for the preparation of Drospirenone and intermediates thereof
CN102395596A (en) * 2010-03-16 2012-03-28 台州太法药业有限公司 Preparation method of drospirenone
CN114874280A (en) * 2022-06-29 2022-08-09 梯尔希（南京）药物研发有限公司 Preparation method of drospirenone impurity

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20042338A1 (en) * 2004-12-06 2005-03-06 Ind Chimica Srl PROCESS FOR THE PREPARATION OF DROSPIRENONE
DE102008026793A1 (en) * 2008-06-02 2009-12-03 Bayer Schering Pharma Aktiengesellschaft C-ring-substituted pregn-4-ene-21,17-carbolactones, as well as pharmaceutical compositions containing them
CN101768203B (en) * 2010-03-15 2012-11-28 浙江仙居君业药业有限公司 5beta, 6beta epoxy steroidal compound and preparation method thereof
CN113461767B (en) * 2020-03-31 2025-05-09 天津药业研究院股份有限公司 Synthesis method of canrenone
CN112979742B (en) * 2021-03-01 2022-07-01 泰州职业技术学院 3 alpha, 20, 20-trihydroxy-5 alpha-pregna-18-carboxylic acid-gamma-lactone and preparation method thereof
CN113512086B (en) * 2021-08-20 2022-11-29 天津信谊津津药业有限公司 Method for preparing spironolactone intermediate canrenone

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998025948A2 (en) * 1996-12-11 1998-06-18 G.D. Searle & Co. Processes for preparation of 9,11-epoxy steroids and intermediates useful therein
WO2003082894A2 (en) * 2002-03-22 2003-10-09 Pharmacia Corporation C-17 spirolactonization and 6,7 oxidation of steroids

Family Cites Families (6)

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Publication number Priority date Publication date Assignee Title
CH539621A (en) 1966-04-02 1973-07-31 Schering Ag 15 16 beta-methylene-steroids
CH510002A (en) 1968-04-22 1971-07-15 Hoffmann La Roche Hormone active steroids
DE2652761C2 (en) 1976-11-16 1985-11-21 Schering AG, 1000 Berlin und 4709 Bergkamen 15,16-methylene-spirolactones, processes for their preparation and pharmaceuticals containing them
DE3042136A1 (en) 1980-11-03 1982-06-09 Schering Ag, 1000 Berlin Und 4619 Bergkamen METHOD FOR PRODUCING 3 (BETA), 7 (BETA) -DIHYDROXY- (DELTA) (UP ARROW) 5 (UP ARROW) STEROIDS
EP0075189B1 (en) 1981-09-21 1985-08-28 Schering Aktiengesellschaft 3-beta,7-beta,15-alpha-trihydroxy-5-androsten-17-one, its 3,15-dipivalate, and its preparation
DE19633685C1 (en) 1996-08-12 1997-10-09 Schering Ag Production of drospirenone useful as steroidal agent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998025948A2 (en) * 1996-12-11 1998-06-18 G.D. Searle & Co. Processes for preparation of 9,11-epoxy steroids and intermediates useful therein
WO2003082894A2 (en) * 2002-03-22 2003-10-09 Pharmacia Corporation C-17 spirolactonization and 6,7 oxidation of steroids

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
D. BITTLER ET AL: "Synthesis of Spironenone - A Novel Highly Active Aldosterone Antagonist", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 21, no. 9, 1982, DEWILEY VCH VERLAG, WEINHEIM., pages 696 - 697, XP002365036 *
K. PETZOLDT ET AL: "A Novel Synthetic Route to the Aldosterone-Antagonist Spironenone", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 22, no. 3, 1983, DEWILEY VCH VERLAG, WEINHEIM., pages 406 - 407, XP002365035 *
NORMAN P ET AL: "CONTRACEPTIVE HORMONE REPLACEMENT THERAPY ALDOSTERONE ANTAGONIST PROGESTOGEN", DRUGS OF THE FUTURE, BARCELONA, ES, vol. 25, no. 12, December 2000 (2000-12-01), pages 1247 - 1256, XP000993474, ISSN: 0377-8282 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1903051A3 (en) * 2006-09-22 2008-06-25 Antibioticos S.p.A. Epoxidation of 17-oxo-15,16-methylene steroids with sulfoxonium ylides
WO2009059765A3 (en) * 2007-11-08 2009-10-15 Chorisis S.R.L. Process for the preparation of drospirenone
CN102395596A (en) * 2010-03-16 2012-03-28 台州太法药业有限公司 Preparation method of drospirenone
EP2415778A1 (en) 2010-08-03 2012-02-08 Newchem S.p.A. Methods for the preparation of Drospirenone and intermediates thereof
WO2012016860A1 (en) 2010-08-03 2012-02-09 Newchem S.P.A. Methods for the preparation of drospirenone and intermediates thereof
CN114874280A (en) * 2022-06-29 2022-08-09 梯尔希（南京）药物研发有限公司 Preparation method of drospirenone impurity

Also Published As

Publication number Publication date
CN101061132A (en) 2007-10-24
DE602005020185D1 (en) 2010-05-06
SI1831239T1 (en) 2010-06-30
CA2585805A1 (en) 2006-06-08
CN101061132B (en) 2011-03-30
PL1831239T3 (en) 2010-08-31
AU2005311060A1 (en) 2006-06-08
AU2005311060B2 (en) 2011-02-03
JP5129899B2 (en) 2013-01-30
EP1831239B1 (en) 2010-03-24
CA2585805C (en) 2009-12-22
HK1111168A1 (en) 2008-08-01
EP1831239B8 (en) 2010-09-15
HU0402466D0 (en) 2005-01-28
ES2342781T3 (en) 2010-07-14
DK1831239T3 (en) 2010-06-28
JP2008521876A (en) 2008-06-26
US8450476B2 (en) 2013-05-28
US20080194812A1 (en) 2008-08-14
PT1831239E (en) 2010-05-06
ATE461934T1 (en) 2010-04-15
HUP0402466A2 (en) 2006-07-28
DK1831239T5 (en) 2010-11-22
EP1831239A1 (en) 2007-09-12

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