Title:
METHOD FOR PREPARING CHOLESTEROL, DERIVATIVE AND ANALOGUE THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/120127
Kind Code:
A1
Abstract:
The present invention relates to the field of pharmaceutical chemistry, and in particular relates to a method for preparing cholesterol, a derivative and an analogue thereof. The cholesterol derivative comprises, but is not limited to, 7-dehydrocholesterol, 25-hydroxycholesterol, 25-hydroxy-7-dehydrocholesterol and ergosterol.
Inventors:
GAN HONGXING (CN)
XIE LAIBIN (CN)
YANG XIANGXIN (CN)
XIE LAIBIN (CN)
YANG XIANGXIN (CN)
Application Number:
PCT/CN2019/126744
Publication Date:
June 24, 2021
Filing Date:
December 19, 2019
Export Citation:
Assignee:
HUNAN KEREY PHARMACEUTICAL CO LTD (CN)
International Classes:
C07J9/00
Domestic Patent References:
| WO2019105914A1 | 2019-06-06 |
Foreign References:
| US3801607A | 1974-04-02 | |||
| CN106854630A | 2017-06-16 | |||
| CN109021059A | 2018-12-18 | |||
| CN105218610A | 2016-01-06 | |||
| CN106866772A | 2017-06-20 | |||
| CN105886418A | 2016-08-24 |
Other References:
NAKAGAWA YASUO, UMEGAWA YUICHI, NONOMURA KENICHI, MATSUSHITA NAOHIRO, TAKANO TETSURO, TSUCHIKAWA HIROSHI, HANASHIMA SHINYA, OISHI : "Axial Hydrogen at C7 Position and Bumpy Tetracyclic Core Markedly Reduce Sterol's Affinity to Amphotericin B in Membrane", BIOCHEMISTRY, vol. 54, no. 2, 17 December 2014 (2014-12-17), pages 303 - 312, XP055821648, ISSN: 0006-2960, DOI: 10.1021/bi5012942
RAHUL RAY , MICHAEL F.HOLICK: "Synthesis of [3α-3H]vitamin D3 and 1α，25-dihydroxy[1β-3H]vitamin D3", METHODS IN ENZYMOLOGY, vol. 282, 31 December 1997 (1997-12-31), pages 157 - 164, XP009528509, ISSN: 0076-6879, ISBN: 9780121821838, DOI: 10.1016/S0076-6879(97)82104-0
DAUBEN, W. G.; EASTHAM, J. F. ; MICHELI, R. A.; TAKEMURA, K. H.; MANDELL, L.; CHEMERDA, J. M. : "The preparation of Δ5，7-steroidal dienes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 75, no. 13, 31 December 1953 (1953-12-31), pages 3255 - 3256, XP009528510, ISSN: 0002-7863, DOI: 10.1021/ja01109a062
JOHN M. WETZEL, MAYUMI OHNISHI, TSUYOSHI FUJITA, KOJI NAKANISHI, YOKO NAYA, HIROAKI NODA & MIYOJI SUGIURA: "Diversity in steroidogenesis of symbiotic microorganisms from planthoppers", JOURNAL OF CHEMICAL ECOLOGY, vol. 18, no. 11, 30 November 1992 (1992-11-30), pages 2083 - 2094, XP009528508, ISSN: 0098-0331
KURT SCHONAUER UND ERICH ZBIRAL: "Synthese des 7, 8-Didehydrodesmosterols", LIEBIGS ANNALEN DER CHEMIE, no. 6, 31 December 1983 (1983-12-31), pages 1031 - 1042, XP009528511, ISSN: 0170-2041, DOI: 10.1002/jlac.198319830615
SUN-SHINEYUAN: "Synthesis of 3, 4-13C2 steroids", STEROIDS, vol. 39, no. 3, 1 March 1982 (1982-03-01), pages 279 - 289, XP025217352, ISSN: 0039-874X, DOI: 10.1016/0039-128X(82)90147-7
LARRY D. GRUENKE, J. CYMERMAN CRAIG: "The synthesis of cholesterol-2,2,4,4,6-d5", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 16, no. 3, 1 January 1979 (1979-01-01), pages 495 - 500, XP055821660, ISSN: 0362-4803, DOI: 10.1002/jlcr.2580160316
J. T. EDWARD AND N. E. LAWSON: "The Conversion of Cholesterol into 10α- Cholesterol", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 35, no. 5, 31 December 1969 (1969-12-31), pages 1426 - 1430, XP055821664, ISSN: 0022-3263
FUJIMOTO G I , JACOBSON A E: "A Preparation of ß- Sitosterol", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 11, 31 December 1964 (1964-12-31), pages 3377 - 3381, XP055821673, ISSN: 0022-3263
KURATH P, CAPEZZUTO, MARGARET: "A Method for the Synthesis of C21-Labeled Cholesterol", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 31 December 1956 (1956-12-31), pages 3527 - 3529, XP055821676, ISSN: 0002-7863
LUTFUN NAHAR , ALAN B. TURNER: "Synthesis of 3β，6α-dihydroxy-5α-cholan-23-one", TETRAHEDRON, vol. 59, no. 43, 20 October 2003 (2003-10-20), pages 8623 - 8628, XP004463741, ISSN: 0040-4020, DOI: 10.1016/j.tet.2003.08.020
RAHUL RAY , MICHAEL F.HOLICK: "Synthesis of [3α-3H]vitamin D3 and 1α，25-dihydroxy[1β-3H]vitamin D3", METHODS IN ENZYMOLOGY, vol. 282, 31 December 1997 (1997-12-31), pages 157 - 164, XP009528509, ISSN: 0076-6879, ISBN: 9780121821838, DOI: 10.1016/S0076-6879(97)82104-0
DAUBEN, W. G.; EASTHAM, J. F. ; MICHELI, R. A.; TAKEMURA, K. H.; MANDELL, L.; CHEMERDA, J. M. : "The preparation of Δ5，7-steroidal dienes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 75, no. 13, 31 December 1953 (1953-12-31), pages 3255 - 3256, XP009528510, ISSN: 0002-7863, DOI: 10.1021/ja01109a062
JOHN M. WETZEL, MAYUMI OHNISHI, TSUYOSHI FUJITA, KOJI NAKANISHI, YOKO NAYA, HIROAKI NODA & MIYOJI SUGIURA: "Diversity in steroidogenesis of symbiotic microorganisms from planthoppers", JOURNAL OF CHEMICAL ECOLOGY, vol. 18, no. 11, 30 November 1992 (1992-11-30), pages 2083 - 2094, XP009528508, ISSN: 0098-0331
KURT SCHONAUER UND ERICH ZBIRAL: "Synthese des 7, 8-Didehydrodesmosterols", LIEBIGS ANNALEN DER CHEMIE, no. 6, 31 December 1983 (1983-12-31), pages 1031 - 1042, XP009528511, ISSN: 0170-2041, DOI: 10.1002/jlac.198319830615
SUN-SHINEYUAN: "Synthesis of 3, 4-13C2 steroids", STEROIDS, vol. 39, no. 3, 1 March 1982 (1982-03-01), pages 279 - 289, XP025217352, ISSN: 0039-874X, DOI: 10.1016/0039-128X(82)90147-7
LARRY D. GRUENKE, J. CYMERMAN CRAIG: "The synthesis of cholesterol-2,2,4,4,6-d5", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 16, no. 3, 1 January 1979 (1979-01-01), pages 495 - 500, XP055821660, ISSN: 0362-4803, DOI: 10.1002/jlcr.2580160316
J. T. EDWARD AND N. E. LAWSON: "The Conversion of Cholesterol into 10α- Cholesterol", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 35, no. 5, 31 December 1969 (1969-12-31), pages 1426 - 1430, XP055821664, ISSN: 0022-3263
FUJIMOTO G I , JACOBSON A E: "A Preparation of ß- Sitosterol", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 11, 31 December 1964 (1964-12-31), pages 3377 - 3381, XP055821673, ISSN: 0022-3263
KURATH P, CAPEZZUTO, MARGARET: "A Method for the Synthesis of C21-Labeled Cholesterol", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 31 December 1956 (1956-12-31), pages 3527 - 3529, XP055821676, ISSN: 0002-7863
LUTFUN NAHAR , ALAN B. TURNER: "Synthesis of 3β，6α-dihydroxy-5α-cholan-23-one", TETRAHEDRON, vol. 59, no. 43, 20 October 2003 (2003-10-20), pages 8623 - 8628, XP004463741, ISSN: 0040-4020, DOI: 10.1016/j.tet.2003.08.020
Attorney, Agent or Firm:
NTD UNIVATION INTELLECTUAL PROPERTY AGENCY LTD. (CN)
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