Title:
PREPARATION METHOD FOR INTERMEDIATE OF ECTEINASCIDIN COMPOUND
Document Type and Number:
WIPO Patent Application WO/2024/093091
Kind Code:
A1
Abstract:
The present invention provides a preparation method for preparing an intermediate of an ecteinascidin compound by taking an electrically neutral organic oxidant as a unique auxiliary agent, comprising the steps of dissolving compound A in an organic solvent, adding an electrically neutral organic oxidant, and performing a reaction at 50-70℃ for 1-25 h. The method of the present invention is simple to operate with the reagent used cheap and easy to obtain, and does not need to use other auxiliary agents such as a catalyst to assist the reaction. The method of the present invention can allow for a reaction in a water-containing system, with mild and unharsh reaction conditions, low amount of the solvent used, high yield, and small pollution to the environment, and thus is suitable for industrial production of a key intermediate of an ecteinascidin compound.
Inventors:
HUANG JINKUN (CN)
FENG CHAOYANG (CN)
WANG SHOUPING (CN)
LI HONGZHAN (CN)
WU CHENGLONG (CN)
FENG CHAOYANG (CN)
WANG SHOUPING (CN)
LI HONGZHAN (CN)
WU CHENGLONG (CN)
Application Number:
PCT/CN2023/082268
Publication Date:
May 10, 2024
Filing Date:
March 17, 2023
Export Citation:
Assignee:
CHENGDU SCIMOUNT PHARMATECH CO LTD (CN)
International Classes:
C07D515/22
Domestic Patent References:
| WO2013146970A1 | 2013-10-03 |
Foreign References:
| CN114805398A | 2022-07-29 | |||
| CN101535301A | 2009-09-16 | |||
| US20130072470A1 | 2013-03-21 | |||
| US6150568A | 2000-11-21 | |||
| CN101568532A | 2009-10-28 | |||
| CN107522698A | 2017-12-29 | |||
| CN107739387A | 2018-02-27 | |||
| CN103038240A | 2013-04-10 | |||
| CN109912629A | 2019-06-21 | |||
| CN1646539A | 2005-07-27 |
Other References:
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LEO A. PAQUETTE: "Encyclopedia of reagents for organic synthesis; Vol. 7 : Sod - Trim", WILEY , Chichester , ISBN: 978-0-470-84289-8, article VACLAV HORAK: "3,5-Di-tert-butyl-1,2-benzoquinone", XP093166388, DOI: 10.1002/047084289X.rd057.pub2
KAZUYUKI MINAGAWA; YIRONG ZHANG; TAKUYA ITO; LINQUAN BAI; ZIXIN DENG; TAIFO MAHMUD: "ValC, a New Type of C7‐Cyclitol Kinase Involved in the Biosynthesis of the Antifungal Agent Validamycin A", CHEMBIOCHEM, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 8, no. 6, 5 March 2007 (2007-03-05), Hoboken, USA, pages 632 - 641, XP072144498, ISSN: 1439-4227, DOI: 10.1002/cbic.200600528
HAIJUN DONG: "Biosynthesis of the Validamycins: Identification of Intermediates in the Biosynthesis of Validamycin A by Streptomyces hygroscopicus var. limoneus", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 123, no. 12, 1 March 2001 (2001-03-01), pages 2733 - 2742, XP093166389, ISSN: 0002-7863, DOI: 10.1021/ja003643n
YANG.M.G ET AL.: "Discovery of BMS-753426: A Potent Orally Bioavailable Antagonist of CC Chemokine Receptor 2", ACS MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 6, 25 May 2021 (2021-05-25), XP055976946, DOI: 10.1021/acsmedchemlett.1c00082
CHEN J, ET AL: "Total synthesis of ecteinascidin 743", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 128, no. 1, 11 January 2006 (2006-01-11), pages 87 - 89, XP002429041, ISSN: 0002-7863, DOI: 10.1021/ja0571794
HUOMING LI: "Research Advances in Synthesis of Trabectedin", CHEMICAL JOURNAL OF CHINESE UNIVERSITIES, JILIN DAXUE, BEIJING, CN, vol. 41, no. 10, 10 October 2020 (2020-10-10), CN , pages 2137 - 2152, XP093166393, ISSN: 0251-0790, DOI: 10.7503/cjcu20200516
LEO A. PAQUETTE: "Encyclopedia of reagents for organic synthesis; Vol. 7 : Sod - Trim", WILEY , Chichester , ISBN: 978-0-470-84289-8, article VACLAV HORAK: "3,5-Di-tert-butyl-1,2-benzoquinone", XP093166388, DOI: 10.1002/047084289X.rd057.pub2
KAZUYUKI MINAGAWA; YIRONG ZHANG; TAKUYA ITO; LINQUAN BAI; ZIXIN DENG; TAIFO MAHMUD: "ValC, a New Type of C7‐Cyclitol Kinase Involved in the Biosynthesis of the Antifungal Agent Validamycin A", CHEMBIOCHEM, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 8, no. 6, 5 March 2007 (2007-03-05), Hoboken, USA, pages 632 - 641, XP072144498, ISSN: 1439-4227, DOI: 10.1002/cbic.200600528
HAIJUN DONG: "Biosynthesis of the Validamycins: Identification of Intermediates in the Biosynthesis of Validamycin A by Streptomyces hygroscopicus var. limoneus", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 123, no. 12, 1 March 2001 (2001-03-01), pages 2733 - 2742, XP093166389, ISSN: 0002-7863, DOI: 10.1021/ja003643n
YANG.M.G ET AL.: "Discovery of BMS-753426: A Potent Orally Bioavailable Antagonist of CC Chemokine Receptor 2", ACS MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 6, 25 May 2021 (2021-05-25), XP055976946, DOI: 10.1021/acsmedchemlett.1c00082
CHEN J, ET AL: "Total synthesis of ecteinascidin 743", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 128, no. 1, 11 January 2006 (2006-01-11), pages 87 - 89, XP002429041, ISSN: 0002-7863, DOI: 10.1021/ja0571794
HUOMING LI: "Research Advances in Synthesis of Trabectedin", CHEMICAL JOURNAL OF CHINESE UNIVERSITIES, JILIN DAXUE, BEIJING, CN, vol. 41, no. 10, 10 October 2020 (2020-10-10), CN , pages 2137 - 2152, XP093166393, ISSN: 0251-0790, DOI: 10.7503/cjcu20200516
Attorney, Agent or Firm:
GAOYUNG INTELLECTUAL PROPERTY AGENCY (GENERAL PARTNERSHIP) (CN)
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