Title:
NOVEL METHOD FOR PREPARING INOTODIOL
Document Type and Number:
WIPO Patent Application WO/2021/194244
Kind Code:
A1
Abstract:
The present invention relates to a novel method for preparing Inotodiol. The method differs in terms of process from existing methods for preparing Inotodiol, and produces a high yield of Inotodiol. Therefore, the method can be useful for the preparation and mass production of Inotodiol.
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Inventors:
KIM SOONG-HYUN (KR)
KO EUN BI (KR)
SONG MINSOO (KR)
PARK GA YOUNG (KR)
LEE EUNHYE (KR)
BAE SERI (KR)
KANG JIHEE (KR)
PARK YOOJIN (KR)
CHOI YOUJEONG (KR)
KO EUN BI (KR)
SONG MINSOO (KR)
PARK GA YOUNG (KR)
LEE EUNHYE (KR)
BAE SERI (KR)
KANG JIHEE (KR)
PARK YOOJIN (KR)
CHOI YOUJEONG (KR)
Application Number:
PCT/KR2021/003622
Publication Date:
September 30, 2021
Filing Date:
March 24, 2021
Export Citation:
Assignee:
DAEGU GYEONGBUK MEDICAL INNOVATION FOUND (KR)
International Classes:
C07J75/00; C07J5/00; C07J9/00; C07J13/00
Other References:
ALAIN AMANN , GUY OURISSON, BANG LUU: "A Novel Stereospecific Synthesis of 22-Hydroxylated Triterpenes and Steroids: Syntheses of 22R-Hydroxylanosterol and 22R-Hydroxydesmosterol", SYNTHESIS, vol. 1987, no. 8, 1 January 1987 (1987-01-01), pages 696 - `700, XP055853657, DOI: 10.1055/s-1987-28048
SCHAUDER J R , KRIEF A: "Regio and sterochemically controlled ring opening of epoxides with Grignard reagents. Stereocontrolled synthesis of the steroid side chains. First stereoselective hemisynthesis of 20S isolanosterol", TETRAHEDRON LETTERS, vol. 23, no. 42, 1 January 1982 (1982-01-01), pages 4389 - 4392, XP002485957, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)85609-9
MATHIAS C LU , FORTUNE KOHEN , R E COUNSELL: "Hypocholesterolemic agents. 8. Synthesis of 25-azadihydrolanosterol and derivatives", JOURNAL OF MEDICINAL CHEMISTRY, vol. 14, no. 2, 1 January 1971 (1971-01-01), US, pages 136 - 138, XP002325659, ISSN: 0022-2623, DOI: 10.1021/jm00284a013
BOAR R. B., LEWIS D. A., MCGHIE J. F.: "Epoxides of lanosterol and some related compounds", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, 1 January 1972 (1972-01-01), Cambridge, UK, pages 2231 - 2235, XP055853665, ISSN: 0300-922X, DOI: 10.1039/p19720002231
BARTLETT WILLIAM R, JOHNSON WILLIAM S, PLUMMER MARK S, SMALL VERNON R: "Cationic Cyclization of a Substrate Having an Internal Acetylenic Bond. Synthesis of Euphol and Tirucallol1", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 55, 1 January 1990 (1990-01-01), pages 2215 - 224, XP055853668
SUNDEN, H. ; IBRAHEM, I. ; CORDOVA, A.: "Direct organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes", TETRAHEDRON LETTERS, vol. 47, no. 1, 2 January 2006 (2006-01-02), Amsterdam , NL, pages 99 - 103, XP025005006, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2005.10.128
TETRAHEDRON, vol. 30, 1974, pages 977 - 986
CHEM. PHARM. BULL., vol. 31, no. 3, 1983, pages 907 - 911
See also references of EP 4130020A4
SCHAUDER J R , KRIEF A: "Regio and sterochemically controlled ring opening of epoxides with Grignard reagents. Stereocontrolled synthesis of the steroid side chains. First stereoselective hemisynthesis of 20S isolanosterol", TETRAHEDRON LETTERS, vol. 23, no. 42, 1 January 1982 (1982-01-01), pages 4389 - 4392, XP002485957, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)85609-9
MATHIAS C LU , FORTUNE KOHEN , R E COUNSELL: "Hypocholesterolemic agents. 8. Synthesis of 25-azadihydrolanosterol and derivatives", JOURNAL OF MEDICINAL CHEMISTRY, vol. 14, no. 2, 1 January 1971 (1971-01-01), US, pages 136 - 138, XP002325659, ISSN: 0022-2623, DOI: 10.1021/jm00284a013
BOAR R. B., LEWIS D. A., MCGHIE J. F.: "Epoxides of lanosterol and some related compounds", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, 1 January 1972 (1972-01-01), Cambridge, UK, pages 2231 - 2235, XP055853665, ISSN: 0300-922X, DOI: 10.1039/p19720002231
BARTLETT WILLIAM R, JOHNSON WILLIAM S, PLUMMER MARK S, SMALL VERNON R: "Cationic Cyclization of a Substrate Having an Internal Acetylenic Bond. Synthesis of Euphol and Tirucallol1", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 55, 1 January 1990 (1990-01-01), pages 2215 - 224, XP055853668
SUNDEN, H. ; IBRAHEM, I. ; CORDOVA, A.: "Direct organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes", TETRAHEDRON LETTERS, vol. 47, no. 1, 2 January 2006 (2006-01-02), Amsterdam , NL, pages 99 - 103, XP025005006, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2005.10.128
TETRAHEDRON, vol. 30, 1974, pages 977 - 986
CHEM. PHARM. BULL., vol. 31, no. 3, 1983, pages 907 - 911
See also references of EP 4130020A4
Attorney, Agent or Firm:
LEE, Won Hee (KR)
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