Title:
PREPARATION METHOD FOR AND APPLICATION OF DEMETHYLENEBERBERINE
Document Type and Number:
WIPO Patent Application WO/2021/129783
Kind Code:
A1
Abstract:
Disclosed are a preparation method for and an application of demethyleneberberine. The preparation method comprises the following steps: adding berberine hydrochloride to xylene, then adding trifluoromethanesulfonic acid, stirring at room temperature to carry out reaction, then adding hydrochloric acid until no more yellow precipitate is produced, filtrating the reaction solution, washing the obtained precipitate, recrystallizing the washed precipitate by using ethanol, then converting same into a hydrochloride by using a strong base anion exchange resin, and concentrating to then obtain yellow solid demethyleneberberine. The present invention achieves the high-efficiency preparation of demethyleneberberine, the synthesis route yield is high, the conditions are mild, the reagents used are less toxic and low in cost, and separation and purification are simple and convenient, thus the present invention can be used for large-scale preparation. The present invention also finds for the first time that demethyleneberberine has the effect of inhibiting MAO-B enzyme activity, indicating that demethyleneberberine has development potential in preventing and treating Parkinson's disease and other diseases caused by abnormal MAO-B enzyme activity.
Inventors:
TAO CHENG (CN)
WU ZHENGZHI (CN)
CHEN JIAN (CN)
LIANG SHAOYU (CN)
LIU ZHANYAN (CN)
LIU JIEREN (CN)
WU ZHENGZHI (CN)
CHEN JIAN (CN)
LIANG SHAOYU (CN)
LIU ZHANYAN (CN)
LIU JIEREN (CN)
Application Number:
PCT/CN2020/139230
Publication Date:
July 01, 2021
Filing Date:
December 25, 2020
Export Citation:
Assignee:
SHENZHEN INST GERIATRICS (CN)
WU ZHENGZHI (CN)
WU ZHENGZHI (CN)
International Classes:
C07D455/03; A61K31/4375; A61P25/16
Foreign References:
| CN104672310A | 2015-06-03 | |||
| CN1314347A | 2001-09-26 | |||
| CN109293655A | 2019-02-01 | |||
| CN100999522A | 2007-07-18 |
Other References:
CHENG TAO, SHENG-QUAN HU, JIAN CHEN, YUAN-JI CHEN, KE-HUAN SUN, GUO-ZHEN CUI, MIN MA, ZHENG-ZHI WU: "Highly Efficient Synthesis and Monoamine Oxidase B Inhibitory Profile of Demethyleneberberine, Columbamine and Palmatine", NEUROCHEMISTRY INTERNATIONAL, vol. 139, 22 July 2020 (2020-07-22), XP055823802, DOI: 10.1016/j.neuint.2020.104807
HUO LI, GAN YONGJUN, SHEN YI, ZHOU HUI, LI QINGENG: "Synthesis of Rotundine", CHINESE JOURNAL OF PHARMACEUTICALS, 1 January 2012 (2012-01-01), pages 323, XP055629146
LIU ZHAN-JIANG, HUANG PEI-QIANG: "Biomimetic Enantioselective Total Synthesis of (−)-Robustanoids A and B and Analogues", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 84, no. 9, 3 May 2019 (2019-05-03), pages 5627 - 5634, XP055823804, ISSN: 0022-3263, DOI: 10.1021/acs.joc.9b00573
HUO LI, GAN YONGJUN, SHEN YI, ZHOU HUI, LI QINGENG: "Synthesis of Rotundine", CHINESE JOURNAL OF PHARMACEUTICALS, 1 January 2012 (2012-01-01), pages 323, XP055629146
LIU ZHAN-JIANG, HUANG PEI-QIANG: "Biomimetic Enantioselective Total Synthesis of (−)-Robustanoids A and B and Analogues", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 84, no. 9, 3 May 2019 (2019-05-03), pages 5627 - 5634, XP055823804, ISSN: 0022-3263, DOI: 10.1021/acs.joc.9b00573
Attorney, Agent or Firm:
SHINY INTELLECTUAL PROPERTY FIRM (CN)
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