Title:
GLYCOLIPID DERIVATIVES, PROCESS FOR PRODUCTION OF THE SAME, INTERMEDIATES FOR SYNTHESIS THEREOF, AND PROCESS FOR PRODUCTION OF THE INTERMEDIATES
Document Type and Number:
WIPO Patent Application WO/2004/072091
Kind Code:
A1
Abstract:
Novel glycolipid derivatives wherein the substituent of the sphingosine base moiety is alkyl having a shorter carbon chain, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl; an efficient process for mass-producing the same economically; and intermediates useful in the production thereof. Specifically, glycolipid derivatives represented by the general formula (I) are chemically synthesized: (I) wherein R3 is substituted or unsubstituted linear alkyl having 1 to 7 carbon atoms, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl; and R8 is substituted or unsubstituted alkyl having 1 to 35 carbon atoms, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl.
Inventors:
ANNOURA HIROKAZU (JP)
MURATA KENJI (JP)
YAMAMURA TAKASHI (JP)
MURATA KENJI (JP)
YAMAMURA TAKASHI (JP)
Application Number:
PCT/JP2004/001566
Publication Date:
August 26, 2004
Filing Date:
February 13, 2004
Export Citation:
Assignee:
DAIICHI SUNTORY PHARMA CO LTD (JP)
JAPAN GOVERNMENT (JP)
ANNOURA HIROKAZU (JP)
MURATA KENJI (JP)
YAMAMURA TAKASHI (JP)
JAPAN GOVERNMENT (JP)
ANNOURA HIROKAZU (JP)
MURATA KENJI (JP)
YAMAMURA TAKASHI (JP)
International Classes:
A61P37/02; C07C247/04; C07D317/28; C07H15/04; C07H15/26; (IPC1-7): C07H15/04; C07H15/26; A61K31/7032; A61P37/02; C07C247/04; C07C247/10; C07D317/28
Domestic Patent References:
| WO1994009020A1 | 1994-04-28 | |||
| WO1993005055A1 | 1993-03-18 | |||
| WO2003016326A1 | 2003-02-27 |
Other References:
MIYAMOTO KATSUICHI ET AL.: "A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells", NATURE, vol. 413, no. 6855, 4 October 2001 (2001-10-04), pages 531 - 534, XP002958968
MIYAKE SACHIKO: "NKT saibo to jikkenteki jiko men'ekisei no sekizuien", INFLAMMATION & IMMUNOLOGY, vol. 10, no. 5, 20 August 2002 (2002-08-20), pages 501 - 506, XP002980517
MIYAKE SACHIKO ET AL.: "NTK saibo toshishitsu ligand ni yoru jiko men'ekisei shikkan seigyo", KABUSHIKI KAISHA CHUNGAI IGAKUSHA, 5 December 2002 (2002-12-05), pages 71 - 77, XP002980520
AYAD TAHAR ET AL.: "A new diorganozinc-based enantio-selective access to truncated D-ribophytosphingosine", TETRAHEDRON LETTERS, vol. 44, no. 3, 13 January 2003 (2003-01-13), pages 579 - 582, XP004399526
MORITA MASAHIRO ET AL.: "Structure-activity relationship of alpha-galactosylceramides against B16-bearing mice", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, no. 12, 9 June 1995 (1995-06-09), pages 2176 - 2187, XP002919134
BROSSAY LAURENT ET AL.: "Cutting edge:structural requirements for galactosylceramide recognition by CD1-restricted NK T cells", JOURNAL OF IMMUNOLOGY, vol. 161, no. 10, 15 November 1998 (1998-11-15), pages 5124 - 5128, XP002980526
CHIU HSIN-YI ET AL.: "A facile synthesis of phyto-sphingosine from diisopropylidene-D-mannofuranose", JOURNAL OF ORGANIC CHEMISTRY, vol. 68, no. 14, 11 July 2003 (2003-07-11), pages 5788 - 5791, XP002980527
KAWANO TETSU ET AL.: "Natural killer-like non-specific tumor cell lysis mediated by specific ligand-activated Valpha14 NKT cells", PROCEEDINGS OF THE NQTURQL QCQDEMY OF SCIENCES OF THE USA, vol. 95, no. 10, 12 May 1998 (1998-05-12), pages 5690 - 5693, XP002980528
See also references of EP 1619199A4
MIYAKE SACHIKO: "NKT saibo to jikkenteki jiko men'ekisei no sekizuien", INFLAMMATION & IMMUNOLOGY, vol. 10, no. 5, 20 August 2002 (2002-08-20), pages 501 - 506, XP002980517
MIYAKE SACHIKO ET AL.: "NTK saibo toshishitsu ligand ni yoru jiko men'ekisei shikkan seigyo", KABUSHIKI KAISHA CHUNGAI IGAKUSHA, 5 December 2002 (2002-12-05), pages 71 - 77, XP002980520
AYAD TAHAR ET AL.: "A new diorganozinc-based enantio-selective access to truncated D-ribophytosphingosine", TETRAHEDRON LETTERS, vol. 44, no. 3, 13 January 2003 (2003-01-13), pages 579 - 582, XP004399526
MORITA MASAHIRO ET AL.: "Structure-activity relationship of alpha-galactosylceramides against B16-bearing mice", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, no. 12, 9 June 1995 (1995-06-09), pages 2176 - 2187, XP002919134
BROSSAY LAURENT ET AL.: "Cutting edge:structural requirements for galactosylceramide recognition by CD1-restricted NK T cells", JOURNAL OF IMMUNOLOGY, vol. 161, no. 10, 15 November 1998 (1998-11-15), pages 5124 - 5128, XP002980526
CHIU HSIN-YI ET AL.: "A facile synthesis of phyto-sphingosine from diisopropylidene-D-mannofuranose", JOURNAL OF ORGANIC CHEMISTRY, vol. 68, no. 14, 11 July 2003 (2003-07-11), pages 5788 - 5791, XP002980527
KAWANO TETSU ET AL.: "Natural killer-like non-specific tumor cell lysis mediated by specific ligand-activated Valpha14 NKT cells", PROCEEDINGS OF THE NQTURQL QCQDEMY OF SCIENCES OF THE USA, vol. 95, no. 10, 12 May 1998 (1998-05-12), pages 5690 - 5693, XP002980528
See also references of EP 1619199A4
Attorney, Agent or Firm:
Aoki, Atsushi (Ishida & Associates Toranomon 37 Mori
Bldg., 5-1, Toranomon 3-chom, Minato-ku Tokyo 23, JP)
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