Title:
PROCESS TO PREPARE EPLERENONE
Document Type and Number:
WIPO Patent Application WO2003082895
Kind Code:
A3
Abstract:
The present invention involves novel intermediates, including a 7alpha-substituted steriod (II), and various novel processes which are used to prepare known intermediates useful in the production of eplerenone, a pharmaceutical agent.
Inventors:
PEARLMAN BRUCE ALLEN (US)
PADILLA AMPHLETT GREG (US)
HAVENS JEFFREY L (US)
MACKEY SONJA S (US)
WU HAIFENG (US)
PADILLA AMPHLETT GREG (US)
HAVENS JEFFREY L (US)
MACKEY SONJA S (US)
WU HAIFENG (US)
Application Number:
PCT/US2003/007793
Publication Date:
April 22, 2004
Filing Date:
March 21, 2003
Export Citation:
Assignee:
UPJOHN CO (US)
PEARLMAN BRUCE ALLEN (US)
PADILLA AMPHLETT GREG (US)
HAVENS JEFFREY L (US)
MACKEY SONJA S (US)
WU HAIFENG (US)
PEARLMAN BRUCE ALLEN (US)
PADILLA AMPHLETT GREG (US)
HAVENS JEFFREY L (US)
MACKEY SONJA S (US)
WU HAIFENG (US)
International Classes:
C07J21/00; C07C41/50; C07C43/305; C07J1/00; C07J71/00; (IPC1-7): C07J1/00
Domestic Patent References:
| WO1998025948A2 | 1998-06-18 | |||
| WO1997021720A2 | 1997-06-19 |
Foreign References:
| DE3344057A1 | 1984-06-14 | |||
| US5227375A | 1993-07-13 | |||
| US4874754A | 1989-10-17 |
Other References:
GRITSAN ET AL.: "Experimental and Quantum Chemical Study of the Reactions of 1,10-Anthraquinones with Alcohols and Amines", TETRAHEDRON, vol. 51, no. 10, 1995, pages 3061 - 3076, XP002247348
PRADHAN ET AL.: "The Dehydrogenation of steroidal delta3,5-Enol Ethers with Dichorodicyanoquinone (DDQ)", J. ORG. CHEM., vol. 29, 1964, pages 601 - 604, XP009013645
SOLO A J ET AL: "7ALPHA-ALKYLTESTOSTERONE DERIVATIVES: SYNTHESIS AND ACTIVITY AS ANDROGENS AND AS AROMATASE INHIBITORS", STEROIDS, BUTTERWORTH-HEINEMANN, STONEHAM, MA, US, vol. 40, no. 6, December 1982 (1982-12-01), pages 603 - 614, XP001088238, ISSN: 0039-128X
NICKISCH ET AL: "Stereoselective synthesis of 7.alpha.-allyl- and 7.alpha.-propylsteroids", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 29, no. 13, 1988, pages 1533 - 1536, XP002204813, ISSN: 0040-4039
DINGAS ET AL.: "Preparation de carboxyethynyl-7-steroides", COMPTES RENDUS DE L'ACADEMIE DES SCIENCES, SERIE II: MECANIQUE, PHYSIQUE, CHIMIE, SCIENCES DE LA TERRE ET DE L'UNIVERS, vol. 302, no. 11, 1986, pages 735 - 737, XP009023610
BAILEY ET AL.: "Ozonolyses of 1,2-Dibenzoylpropene and 1,2-Dibenzoylethylene. Markownikoff's Rule and the initial Atack of Ozone on an Unsaturated System", J. AM. CHEM. SOC., vol. 79, 1957, pages 3120 - 3124, XP002266403
PRADHAN ET AL.: "The Dehydrogenation of steroidal delta3,5-Enol Ethers with Dichorodicyanoquinone (DDQ)", J. ORG. CHEM., vol. 29, 1964, pages 601 - 604, XP009013645
SOLO A J ET AL: "7ALPHA-ALKYLTESTOSTERONE DERIVATIVES: SYNTHESIS AND ACTIVITY AS ANDROGENS AND AS AROMATASE INHIBITORS", STEROIDS, BUTTERWORTH-HEINEMANN, STONEHAM, MA, US, vol. 40, no. 6, December 1982 (1982-12-01), pages 603 - 614, XP001088238, ISSN: 0039-128X
NICKISCH ET AL: "Stereoselective synthesis of 7.alpha.-allyl- and 7.alpha.-propylsteroids", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 29, no. 13, 1988, pages 1533 - 1536, XP002204813, ISSN: 0040-4039
DINGAS ET AL.: "Preparation de carboxyethynyl-7-steroides", COMPTES RENDUS DE L'ACADEMIE DES SCIENCES, SERIE II: MECANIQUE, PHYSIQUE, CHIMIE, SCIENCES DE LA TERRE ET DE L'UNIVERS, vol. 302, no. 11, 1986, pages 735 - 737, XP009023610
BAILEY ET AL.: "Ozonolyses of 1,2-Dibenzoylpropene and 1,2-Dibenzoylethylene. Markownikoff's Rule and the initial Atack of Ozone on an Unsaturated System", J. AM. CHEM. SOC., vol. 79, 1957, pages 3120 - 3124, XP002266403
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