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Title:
METHOD FOR PREPARING 6-ALKYLATED STEROIDAL DERIVATIVES AND CORRESPONDING ALKYLATED 5,6,7,8-TETRAHYDRONAPHTHALENE-2(4 ALPHA.H)-ONES
Document Type and Number:
WIPO Patent Application WO/2015/063408
Kind Code:
A3
Abstract:
The present invention concerns a method for preparing certain steroidal derivatives alkylated in position 6, comprising a step of alkylating the corresponding compound halogenated in position 6 with an organometallic alkylating agent.

Inventors:
DUEZ, Stéphanie (Ludwig Maximilians Universität, Geschwister Scholl Platz 1, Munich, 80539, DE)
HAESSLEIN, Jean-Luc (54 rue La Boétie, Paris, F-75008, FR)
LHERMITTE, Frédéric (54 rue La Boétie, Paris, F-75008, FR)
QUINIO, Pauline (Ludwig Maximilians Universität, Geschwister Scholl Platz 1, Munich, 80539, DE)
Application Number:
FR2014/052740
Publication Date:
May 07, 2015
Filing Date:
October 28, 2014
Export Citation:
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Assignee:
SANOFI (54 rue La Boétie, Paris, F-75008, FR)
International Classes:
C07J5/00; C07C21/00; C07C49/637
Foreign References:
US2908696A1959-10-13
US2959602A1960-11-08
US2816902A1957-12-17
DE1059906B1959-06-25
GB926472A1963-05-15
Other References:
JOHN H. FRIED ET AL: "Alkylated Adrenal Hormones. The Synthesis of 6[alpha]-Methyl Cortical Steroids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 81, no. 5, 1 March 1959 (1959-03-01), pages 1235 - 1239, XP055124850, ISSN: 0002-7863, DOI: 10.1021/ja01514a055
ANNEN K ET AL: "17-PIVALATE IN DER PREGNANREIHE//17-PIVALATE DERIVATIVES OF PREGNANE", LIEBIGS ANNALEN DER CHEMIE, VERLAG CHEMIE GMBH. WEINHEIM, DE, vol. 4, 1 January 1983 (1983-01-01), pages 705 - 711, XP001119196, ISSN: 0170-2041
VOLKERS A A ET AL: "Alkylations of tricyclo[5.2.1.0<2,6>]deca-4,8-dien-3-one by a cuprate reaction", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 65, no. 1, 3 January 2009 (2009-01-03), pages 389 - 395, XP025712261, ISSN: 0040-4020, [retrieved on 20081017], DOI: 10.1016/J.TET.2008.10.028
LEO A. PAQUETTE ET AL: "Applications of the Squarate Ester Cascade to the Expeditious Synthesis of Hypnophilin, Coriolin, and Ceratopicanol", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 31, 1 August 2002 (2002-08-01), pages 9199 - 9203, XP055124726, ISSN: 0002-7863, DOI: 10.1021/ja020474t
H. J. RINGOLD ET AL: "STEROIDS. CXXVII. 1 6-HALO PROGESTATIONAL AGENTS", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 81, no. 13, 1 July 1959 (1959-07-01), pages 3485 - 3486, XP055125053, ISSN: 0002-7863, DOI: 10.1021/ja01522a090
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; LI, NAN ET AL: "Synthesis of 11,17,21-triacetoxy-6.alpha.-fluoro-pregn-1,4-diene- 3,20-dione", XP002739461, retrieved from STN Database accession no. 2010:1382659
LAL G SANKAR: "Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo(2.2.2)octane salts (selectfluor reagents)", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 58, no. 10, 1 January 1993 (1993-01-01), pages 2791 - 2796, XP002299135, ISSN: 0022-3263, DOI: 10.1021/JO00062A023
Attorney, Agent or Firm:
CATILLON, Marie (Patent Department54 rue La Boétie, Paris, F-75008, FR)
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