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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 (10-17, Kitabatake Chouhouj, Nagaokakyo-shi Kyoto 12, 61708, JP)
Murata, Kenji (2-7-21, Mitsukeyama Ibaraki-shi, Osaka 35, 56700, JP)
Yamamura, Takashi (1-6-44, Hikaricho Kokubunji-shi, Tokyo 34, 18500, JP)
Application Number:
PCT/JP2004/001566
Publication Date:
August 26, 2004
Filing Date:
February 13, 2004
Export Citation:
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Assignee:
DAIICHI SUNTORY PHARMA CO., LTD. (7-2 Kojimachi 5-chome, Chiyoda-ku, Tokyo 30, 10285, JP)
JAPAN as represented by PRESIDENT OF NATIONAL CENTER OF NEUROLOGY AND PSYCHIATRY (4-1-1, Ogawahigashicho Kodaira-shi, Tokyo 02, 18785, JP)
Annoura, Hirokazu (10-17, Kitabatake Chouhouj, Nagaokakyo-shi Kyoto 12, 61708, JP)
Murata, Kenji (2-7-21, Mitsukeyama Ibaraki-shi, Osaka 35, 56700, JP)
Yamamura, Takashi (1-6-44, Hikaricho Kokubunji-shi, Tokyo 34, 18500, JP)
International Classes:
A61P37/02; C07C247/04; C07D317/28; C07H15/04; C07H15/26; (IPC1-7): C07H15/04; A61K31/7032; A61P37/02; C07C247/04; C07C247/10; C07D317/28; C07H15/26
Domestic Patent References:
1994-04-28
1993-03-18
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, 04 October 2001, pages 531 - 534, XP002958968
MIYAKE SACHIKO: 'NKT saibo to jikkenteki jiko men'ekisei no sekizuien' INFLAMMATION & IMMUNOLOGY vol. 10, no. 5, 20 August 2002, pages 501 - 506, XP002980517
MIYAKE SACHIKO ET AL.: 'NTK saibo toshishitsu ligand ni yoru jiko men'ekisei shikkan seigyo' KABUSHIKI KAISHA CHUNGAI IGAKUSHA 05 December 2002, 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, 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, 09 June 1995, 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, 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, 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, pages 5690 - 5693, XP002980528
See also references of EP 1619199A1
Attorney, Agent or Firm:
Aoki, Atsushi (A. Aoki, Ishida & Associates Toranomon 37 Mori Bldg., 5-1, Toranomon 3-chom, Minato-ku Tokyo 23, 10584, JP)
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