Title:
METHOD FOR PRODUCING EPIGALLOCATECHIN GALLATE CONJUGATE
Document Type and Number:
WIPO Patent Application WO/2021/187569
Kind Code:
A1
Abstract:
Provided are: a method for producing an epigallocatechin gallate conjugate; and said epigallocatechin gallate conjugate and a production intermediate thereof. This method for producing an epigallocatechin gallate conjugate represented by general formula (Id) comprises a step for reacting 2,2,2-trichloroethoxy-sulfuryl-1,2-dimethylimidazolium triflate with benzylated epigallocatechin gallate represented by general formula (v), or a step for reacting a glucuronic acid donor with the benzylated epigallocatechin gallate. [In the formulae, one among R1a and R2a represents a benzyl group and the other represents a hydrogen atom, and R1e and R2e correspond to R1a and R2a, respectively, one among R1e and R2e represents a hydrogen atom, and the other represents -SO3M (where M represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, or ammonium) or a glucuronosyl group.]
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Inventors:
IWASHITA MASAZUMI (JP)
SHIOI RYUTA (JP)
HASHIZUME KOHJIRO (JP)
MAIHARA AYAME (JP)
HAYASHI AKANE (JP)
TERASAKA SHIMPEI (JP)
NUKADA YUUKO (JP)
SHIOI RYUTA (JP)
HASHIZUME KOHJIRO (JP)
MAIHARA AYAME (JP)
HAYASHI AKANE (JP)
TERASAKA SHIMPEI (JP)
NUKADA YUUKO (JP)
Application Number:
PCT/JP2021/011133
Publication Date:
September 23, 2021
Filing Date:
March 18, 2021
Export Citation:
Assignee:
KAO CORP (JP)
International Classes:
C07D311/62; A61K31/353; A61P3/04; A61P3/06; C07B61/00
Domestic Patent References:
| WO2010067599A1 | 2010-06-17 |
Foreign References:
| KR20200005886A | 2020-01-17 | |||
| KR101822306B1 | 2018-01-25 |
Other References:
LEE, YONG-MI N ET AL.: "Conjugation with Phenylalanine Enhances Autophagy-Inducing Activity of (-)-Epigallocatechin Gallate in Hepatic Cells", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 66, no. 48, 5 December 2018 (2018-12-05), pages 12741 - 12747, XP055859390
YUJIN SEO, MI KYOUNG KIM, HYUNAH CHOO, YOUHOON CHONG: "Facile synthesis of 4″- O -alkyl-(–)-EGCG derivatives through regioselective deacetylative alkylation", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 47, no. 7, 3 April 2017 (2017-04-03), US , pages 655 - 659, XP055687793, ISSN: 0039-7911, DOI: 10.1080/00397911.2016.1278233
GREENE ET AL.: "Protective groups in organic synthesis", 2004, pages: 246 - 247
TANAKA, HIROSHI ET AL.: "Solid-Phase Synthesis of a Combinatorial Methylated(±)-Epigallocatechin Gallate Library and the Growth-Inhibitory Effects of these Compounds on Melanoma Cells", CHEMISTRY - AN ASIAN JOURNAL, vol. 5, no. 10, 4 October 2010 (2010-10-04), pages 2231 - 2248, XP055859394
YUJIN SEO, MI KYOUNG KIM, HYUNAH CHOO, YOUHOON CHONG: "Facile synthesis of 4″- O -alkyl-(–)-EGCG derivatives through regioselective deacetylative alkylation", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 47, no. 7, 3 April 2017 (2017-04-03), US , pages 655 - 659, XP055687793, ISSN: 0039-7911, DOI: 10.1080/00397911.2016.1278233
GREENE ET AL.: "Protective groups in organic synthesis", 2004, pages: 246 - 247
TANAKA, HIROSHI ET AL.: "Solid-Phase Synthesis of a Combinatorial Methylated(±)-Epigallocatechin Gallate Library and the Growth-Inhibitory Effects of these Compounds on Melanoma Cells", CHEMISTRY - AN ASIAN JOURNAL, vol. 5, no. 10, 4 October 2010 (2010-10-04), pages 2231 - 2248, XP055859394
Attorney, Agent or Firm:
THE PATENT CORPORATE BODY ARUGA PATENT OFFICE (JP)
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