Title:
15-OXOSTEROID COMPOUND AND METHOD FOR PRODUCING SAME
Document Type and Number:
WIPO Patent Application WO/2018/147345
Kind Code:
A1
Abstract:
Provided is a method by which a compound, which is useful as an intermediate and in which an oxo group is introduced specifically at the 15-position of a steroid skeleton, can be produced at a high yield without involving a complex procedure. A 15-oxosteroid compound represented by formula (1), which is useful as an intermediate, is produced by reacting a compound represented by formula (2) with an oxidizing agent (a hypervalent iodine compound or the like) and a co-oxidizing agent (a peroxide or the like). (In the formulae: R1 to R3 may be the same as, or different from, each other, and each denote a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group or a haloalkoxy group; R4 denotes a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acyl group or an alkoxycarbonyl group; R5 denotes a hydrogen atom, an alkyl group or an acyl group; R6 denotes a hydrogen atom, an alkyl group, an acyl group or a sulfonyl group; and X denotes an oxygen atom (O) or a methylene group (CH2).)
Inventors:
TAKENAKA YOSUKE (JP)
ISOMURA NORIHITO (JP)
ASAGARASU AKIRA (JP)
UCHIDA HIROSHI (JP)
ISOMURA NORIHITO (JP)
ASAGARASU AKIRA (JP)
UCHIDA HIROSHI (JP)
Application Number:
PCT/JP2018/004295
Publication Date:
August 16, 2018
Filing Date:
February 08, 2018
Export Citation:
Assignee:
ASKA PHARM CO LTD (JP)
International Classes:
C07J73/00; C07J75/00
Foreign References:
| JPH01199993A | 1989-08-11 | |||
| JP2001503732A | 2001-03-21 | |||
| JP2591640B2 | 1997-03-19 |
Other References:
ZHAO, Y. ET AL.: "An Unexpected Oxidation of Unactivated Methylene C-H Using DIB/TBHP Protocol", ORGANIC LETTERS, vol. 13, no. 16, 2011, pages 4308 - 4311, XP055532950, ISSN: 1523-7060
OGAWA, S. ET AL.: "Osmiumporphyrin-catalyzed oxyfunctionalization and isomerization of natural (5 beta ) -bile acids with tert-butyl hydroperoxide", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2007, no. 21, 2007, pages 3555 - 3563, XP055624915, ISSN: 1434-193X, DOI: 10.1002/ejoc.200700158
IIDA, T. ET AL.: "Potential bile acid metabolites. 25. Synthesis and chemical properties of stereoisomeric 3a, 7a, 16-and3a, 7alpha 15-trihydroxy-5beta-cholan-24-oic acids", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 50, no. 10, 2002, pages 1327 - 1334, XP002569736, ISSN: 0009-2363, DOI: 10.1248/cpb.50.1327
CHEM. PHARM. BULL., vol. 41, no. 5, 1993, pages 870 - 875
ORG. LETT., vol. 13, no. 16, 2011, pages 4308 - 4311
ORG. LETT. VOL., vol. 13, no. 16, 2011, pages 4308 - 4311
CHEM. PHARM. BULL., vol. 40, no. 4, 1992, pages 935 - 941
See also references of EP 3581577A4
OGAWA, S. ET AL.: "Osmiumporphyrin-catalyzed oxyfunctionalization and isomerization of natural (5 beta ) -bile acids with tert-butyl hydroperoxide", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2007, no. 21, 2007, pages 3555 - 3563, XP055624915, ISSN: 1434-193X, DOI: 10.1002/ejoc.200700158
IIDA, T. ET AL.: "Potential bile acid metabolites. 25. Synthesis and chemical properties of stereoisomeric 3a, 7a, 16-and3a, 7alpha 15-trihydroxy-5beta-cholan-24-oic acids", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 50, no. 10, 2002, pages 1327 - 1334, XP002569736, ISSN: 0009-2363, DOI: 10.1248/cpb.50.1327
CHEM. PHARM. BULL., vol. 41, no. 5, 1993, pages 870 - 875
ORG. LETT., vol. 13, no. 16, 2011, pages 4308 - 4311
ORG. LETT. VOL., vol. 13, no. 16, 2011, pages 4308 - 4311
CHEM. PHARM. BULL., vol. 40, no. 4, 1992, pages 935 - 941
See also references of EP 3581577A4
Attorney, Agent or Firm:
KUWATA Mitsuo et al. (JP)
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