Title:
METHOD FOR PREPARING DEHYDRODIDEMNIN B COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/274145
Kind Code:
A1
Abstract:
A method for preparing a dehydrodidemnin B compound. The method comprises: subjecting a Didemnin B compound, as represented by formula Ⅰ, and an oxidizing agent to an oxidation reaction in an organic solvent to prepare the dehydrodidemnin B compound. The method uses easily available raw materials, has simple steps, is fast and efficient, has a high yield and purity and a low cost, and is suitable for industrial scaled-up production.
Inventors:
HUANG XIN (CN)
SHAN HUANYU (CN)
WANG XUEFENG (CN)
CHEN YU (CN)
ZOU TAO (CN)
SHAO QINGLING (CN)
SHAO ZHONG (CN)
SHAN HUANYU (CN)
WANG XUEFENG (CN)
CHEN YU (CN)
ZOU TAO (CN)
SHAO QINGLING (CN)
SHAO ZHONG (CN)
Application Number:
PCT/CN2022/101504
Publication Date:
January 05, 2023
Filing Date:
June 27, 2022
Export Citation:
Assignee:
ZHEJIANG HUIDA BIOTECH CO LTD (CN)
HANGZHOU ZHONGMEIHUADONG PHARMACEUTICAL CO LTD (CN)
HANGZHOU ZHONGMEIHUADONG PHARMACEUTICAL CO LTD (CN)
International Classes:
C07K11/02; A61K38/00; A61K38/08; A61P35/00; C07K7/02
Domestic Patent References:
| WO1998017275A1 | 1998-04-30 |
Foreign References:
| US20030148933A1 | 2003-08-07 | |||
| US6030943A | 2000-02-29 | |||
| CN104650177A | 2015-05-27 | |||
| US5834586A | 1998-11-10 | |||
| CN101575363A | 2009-11-11 |
Other References:
VERA, M. D. ET AL.,: "Natural products as probes of cell biology: 20 years of didemnin research,", MEDICINAL RESEARCH REVIEWS,, vol. 22, no. 2, 8 February 2002 (2002-02-08), XP002531923, DOI: 10.1002/MED.10003
LEE JISUN, CURRANO JUDITH N., CARROLL PATRICK J., JOULLIÉ MADELEINE M.: "Didemnins, tamandarins and related natural products", NATURAL PRODUCT REPORTS, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 29, no. 3, 1 January 2012 (2012-01-01), GB , pages 404, XP093018184, ISSN: 0265-0568, DOI: 10.1039/c2np00065b
VASILAKAKI SOFIA, BARBAYIANNI EFROSINI, LEONIS GEORGIOS, PAPADOPOULOS MANTHOS G., MAVROMOUSTAKOS THOMAS, GELB MICHAEL H., KOKOTOS : "Development of a potent 2-oxoamide inhibitor of secreted phospholipase A2 guided by molecular docking calculations and molecular dynamics simulations", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 24, no. 8, 1 April 2016 (2016-04-01), AMSTERDAM, NL, pages 1683 - 1695, XP093018183, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2016.02.040
LIANG BO, RICHARD DAVID J., PORTONOVO PADMA S., JOULLIÉ MADELEINE M.: "Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 123, no. 19, 1 May 2001 (2001-05-01), pages 4469 - 4474, XP093018179, ISSN: 0002-7863, DOI: 10.1021/ja010222c
JOU, G. ET AL.,: "Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution,", THE JOURNAL OF ORGANIC CHEMISTRY,, vol. 62, no. 2, 24 January 1997 (1997-01-24), XP002085296, DOI: 10.1021/jo961932h
LASSEN KENNETH M., LEE JISUN, JOULLIÉ MADELEINE M.: "Synthetic Studies of Tamandarin B Side Chain Analogues", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 75, no. 9, 7 May 2010 (2010-05-07), pages 3027 - 3036, XP093018178, ISSN: 0022-3263, DOI: 10.1021/jo100457w
LEE JISUN, CURRANO JUDITH N., CARROLL PATRICK J., JOULLIÉ MADELEINE M.: "Didemnins, tamandarins and related natural products", NATURAL PRODUCT REPORTS, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 29, no. 3, 1 January 2012 (2012-01-01), GB , pages 404, XP093018184, ISSN: 0265-0568, DOI: 10.1039/c2np00065b
VASILAKAKI SOFIA, BARBAYIANNI EFROSINI, LEONIS GEORGIOS, PAPADOPOULOS MANTHOS G., MAVROMOUSTAKOS THOMAS, GELB MICHAEL H., KOKOTOS : "Development of a potent 2-oxoamide inhibitor of secreted phospholipase A2 guided by molecular docking calculations and molecular dynamics simulations", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 24, no. 8, 1 April 2016 (2016-04-01), AMSTERDAM, NL, pages 1683 - 1695, XP093018183, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2016.02.040
LIANG BO, RICHARD DAVID J., PORTONOVO PADMA S., JOULLIÉ MADELEINE M.: "Total Syntheses and Biological Investigations of Tamandarins A and B and Tamandarin A Analogs", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 123, no. 19, 1 May 2001 (2001-05-01), pages 4469 - 4474, XP093018179, ISSN: 0002-7863, DOI: 10.1021/ja010222c
JOU, G. ET AL.,: "Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution,", THE JOURNAL OF ORGANIC CHEMISTRY,, vol. 62, no. 2, 24 January 1997 (1997-01-24), XP002085296, DOI: 10.1021/jo961932h
LASSEN KENNETH M., LEE JISUN, JOULLIÉ MADELEINE M.: "Synthetic Studies of Tamandarin B Side Chain Analogues", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 75, no. 9, 7 May 2010 (2010-05-07), pages 3027 - 3036, XP093018178, ISSN: 0022-3263, DOI: 10.1021/jo100457w
Attorney, Agent or Firm:
BEIJING LINKTEC IP LAW FIRM (SPECIAL GENERAL PARTNERSHIP) (CN)
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