Title:
PROCESS FOR PRODUCTION OF 1-HYDROXY-19-NORCYCLOVITAMIN D DERIVATIVE AND INTERMEDIATE FOR THE PRODUCTION
Document Type and Number:
WIPO Patent Application WO/2008/053961
Kind Code:
A1
Abstract:
A cyclovitamin D derivative produced from 25-hydroxyvitamin D is reacted with osmium tetraoxide or a permanganic acid salt to produce a 10,19-diolcyclovitamin D derivative. The 10,19-diolcyclovitamin D derivative is reacted with a perhalogenic acid salt or lead tetraacetate to produce a 10-oxocyclovitamin D derivative. A 1-hydroxycyclovitamin D derivative is produced from the 10-oxocyclovitamin D derivative via a cyclovitamin D derivative and a 1,10-olefincyclovitamin D derivative. The 1-hydroxycyclovitamin D derivative is subjected to solvolysis, thereby producing a 1-hydroxy-19-norvitamin D derivative. Thus, provided are: a novel process for producing a 1-hydroxy-19-norvitamin D derivative which can be used as an intermediate for the synthesis of a 1-hydroxy-19-norvitamin D derivative which is useful as a pharmaceutical agent; and an intermediate for the production.
Inventors:
TOYODA ASAKO (JP)
NAGAI HAZUKI (JP)
KONUKI KANAME (JP)
NAGAI HAZUKI (JP)
KONUKI KANAME (JP)
Application Number:
PCT/JP2007/071313
Publication Date:
May 08, 2008
Filing Date:
November 01, 2007
Export Citation:
Assignee:
MERCIAN CORP (JP)
TSUCHIDA TOSHIO (JP)
TOYODA ASAKO (JP)
NAGAI HAZUKI (JP)
KONUKI KANAME (JP)
TSUCHIDA TOSHIO (JP)
TOYODA ASAKO (JP)
NAGAI HAZUKI (JP)
KONUKI KANAME (JP)
International Classes:
C07C401/00; A61K31/59
Domestic Patent References:
| WO1990010620A1 | 1990-09-20 |
Foreign References:
| JPH03505330A | 1991-11-21 | |||
| JP2006298594A | 2006-11-02 | |||
| JPH03505330A | 1991-11-21 | |||
| JPH05221960A | 1993-08-31 | |||
| US5281731A | 1994-01-25 | |||
| US5391755A | 1995-02-21 | |||
| US4804502A | 1989-02-14 |
Other References:
ADDO J.K. ET AL.: "Synthesis and binding-analysis of 5E-[19-(2-bromoacetoxy)methyl]25-hydroxyvitamin D3 and 5E-25-hydroxyvitamin D3-19-methyl [(4-azido-2-nitro]phenyl]glycinate: novel C19-modified affinity and photoaffinity analogs of 25-hydroxyvitamin D3", STEROIDS, vol. 63, no. 4, 1998, pages 218 - 223, XP004122443
PERLMAN K.L. ET AL.: "1alpha,25-Dihydroxy-19-norvitamin D3, a novel vitamin D-related compound with potential therapeutic activity", TETRAHEDRON LETTERS, vol. 31, no. 13, 1990, pages 1823 - 1824, XP001037709
J. ORG. CHEM., vol. 45, 1980, pages 3235
TETRAHEDRON. LETT., vol. 31, 1990, pages 1823
J. ORG. CHEM., vol. 51, 1986, pages 3098
J. ORG. CHEM., vol. 51, 1986, pages 1264
J. CHEM. SOC. PERKIN TRANS., vol. 1, 1978, pages 834
J. ORG. CHEM., vol. 48, 1983, pages 1414
J. ORG. CHEM., vol. 51, 1986, pages 1269
PERLMAN K.L. ET AL.: "1alpha,25-Dihydroxy-19-norvitamin D3, a novel vitamin D-related compound with potential therapeutic activity", TETRAHEDRON LETTERS, vol. 31, no. 13, 1990, pages 1823 - 1824, XP001037709
J. ORG. CHEM., vol. 45, 1980, pages 3235
TETRAHEDRON. LETT., vol. 31, 1990, pages 1823
J. ORG. CHEM., vol. 51, 1986, pages 3098
J. ORG. CHEM., vol. 51, 1986, pages 1264
J. CHEM. SOC. PERKIN TRANS., vol. 1, 1978, pages 834
J. ORG. CHEM., vol. 48, 1983, pages 1414
J. ORG. CHEM., vol. 51, 1986, pages 1269
Attorney, Agent or Firm:
SIKs & Co. (Kyobashi-Nisshoku Bldg.8-7, Kyobashi 1-chome,Chuo-ku, Tokyo 31, JP)
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