Title:
METHOD FOR PREPARING CODEINE AND DERIVATIVE AND INTERMEDIATE THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/164889
Kind Code:
A1
Abstract:
Disclosed are a method for preparing codeine and a derivative and intermediate thereof. Simple, cheap and easily-available commercially available compounds are used as starting materials in the present invention, various intermediates that are required for the preparation of codeine and a derivative thereof, i.e., intermediates shown in formulas (I) - (VI), are synthesized sequentially by means of various reactions such as Suzuki-Miyaura cross-coupling reaction, Mitsunobu reaction and Heck reaction, and then, codeine, deoxycodeine, norcodeine and other derivatives are prepared using these intermediates, respectively. The method for preparing codeine and a derivative and intermediate thereof provided by the present invention has a short synthesis route and high yield, and various intermediate compounds involved in the synthesis process all can be prepared on a gram scale.
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Inventors:
WHITE LORENZO VALENTINO (AU)
BANWELL MARTIN GERHARDT (AU)
LAN PING (CN)
HE YUTAO (CN)
HU NAN (CN)
BANWELL MARTIN GERHARDT (AU)
LAN PING (CN)
HE YUTAO (CN)
HU NAN (CN)
Application Number:
PCT/CN2022/079056
Publication Date:
September 07, 2023
Filing Date:
March 03, 2022
Export Citation:
Assignee:
UNIV JINAN (CN)
International Classes:
C07C271/08; C07C269/06; C07D221/22; C07D307/77; C07D489/02
Domestic Patent References:
| WO1996016063A1 | 1996-05-30 |
Foreign References:
| CN109666030A | 2019-04-23 |
Other References:
LI, JING ET AL.: "Formal Synthesis of (±)-Morphine", CHEMISTRY-AN ASIAN JOURNAL, vol. 8, no. 6, 18 March 2013 (2013-03-18), XP072418333, ISSN: 1861-4728, DOI: 10.1002/asia.201300139
VARIN, M. ET AL.: "Diastereoselective total synthesis of (±)-codeine", CHEMISTRY-A EUROPEAN JOURNAL, vol. 14, no. vol. 22, 18 June 2008 (2008-06-18), XP071827356, ISSN: 0947-6539, DOI: 10.1002/chem.200800744
UCHIDA, K. ET AL.: "Total synthesis of (±)-morphine", HETEROCYCLES, vol. 77, no. 2, 25 September 2008 (2008-09-25), ISSN: 0385-5414
STORK, G. ET AL.: "Regiospecific and Stereoselective Syntheses of (±)-Morphine, Codeine, and Thebaine via a Highly Stereocontrolled Intramolecular 4 + 2 Cycloaddition Leading to a Phenanthrofuran System", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, no. 32, 22 July 2009 (2009-07-22), XP055355231, ISSN: 0002-7863, DOI: 10.1021/ja9038505
TROST BARRY M., WEIPING TANG, F. DEAN TOSTE: "Divergent Enantioselective Synthesis of (-)-Galanthamine and (-)-Morphine", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, no. 42, 24 September 2005 (2005-09-24), pages 14785 - 14803, XP093087577
KENJI UCHIDA, SATOSHI YOKOSHIMA, TOSHIYUKI KAN, TOHRU FUKUYAMA: "Total synthesis of (±)-morphine", HETEROCYCLES, JAPAN INSTITUTE OF HETEROCYCLIC CHEMISTRY, JP, vol. 77, no. 2, 1 January 2009 (2009-01-01), JP , pages 1219 - 1234, XP009548349, ISSN: 0385-5414, DOI: 10.3987/COM-08-S(F)103
VARIN, M. ET AL.: "Diastereoselective total synthesis of (±)-codeine", CHEMISTRY-A EUROPEAN JOURNAL, vol. 14, no. vol. 22, 18 June 2008 (2008-06-18), XP071827356, ISSN: 0947-6539, DOI: 10.1002/chem.200800744
UCHIDA, K. ET AL.: "Total synthesis of (±)-morphine", HETEROCYCLES, vol. 77, no. 2, 25 September 2008 (2008-09-25), ISSN: 0385-5414
STORK, G. ET AL.: "Regiospecific and Stereoselective Syntheses of (±)-Morphine, Codeine, and Thebaine via a Highly Stereocontrolled Intramolecular 4 + 2 Cycloaddition Leading to a Phenanthrofuran System", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, no. 32, 22 July 2009 (2009-07-22), XP055355231, ISSN: 0002-7863, DOI: 10.1021/ja9038505
TROST BARRY M., WEIPING TANG, F. DEAN TOSTE: "Divergent Enantioselective Synthesis of (-)-Galanthamine and (-)-Morphine", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, no. 42, 24 September 2005 (2005-09-24), pages 14785 - 14803, XP093087577
KENJI UCHIDA, SATOSHI YOKOSHIMA, TOSHIYUKI KAN, TOHRU FUKUYAMA: "Total synthesis of (±)-morphine", HETEROCYCLES, JAPAN INSTITUTE OF HETEROCYCLIC CHEMISTRY, JP, vol. 77, no. 2, 1 January 2009 (2009-01-01), JP , pages 1219 - 1234, XP009548349, ISSN: 0385-5414, DOI: 10.3987/COM-08-S(F)103
Attorney, Agent or Firm:
GUANGZHOU HUIHANG PATENT AGENCY (GENERAL PARTNERSHIP) (CN)
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