Title:
ESTERIFIED α-GALACTOSYLCERAMIDE
Document Type and Number:
WIPO Patent Application WO/2010/030012
Kind Code:
A1
Abstract:
Disclosed are a novel esterified α-galactosylceramide which is effective for the treatment of cancer or the like, and a pharmaceutical preparation comprising the esterified α-galactosylceramide. Specifically disclosed is a compound represented by formula (I) [wherein R1 represents a hydrocarbon group having 1 to 30 carbon atoms; R2 represents a hydrocarbon group having 1 to 20 carbon atoms; R3 represents a hydrogen atom, or a hydrocarbon group having 1 to 5 carbon atoms; and R4 and R5 independently represent a hydrogen atom, or a hydrocarbon group having 1 to 5 carbon atoms, or R4 and R5 may together form a bivalent hydrocarbon group having 1 to 5 carbon atoms, and R4 and R5 may, together with the adjacent ethylenedioxy, form a cyclic structure] or a salt thereof.
Inventors:
SHIOZAKI MASAO (JP)
TASHIRO TAKUYA (JP)
MORI KENJI (JP)
NAKAGAWA RYUSUKE (JP)
WATARAI HIROSHI (JP)
TANIGUCHI MASARU (JP)
TASHIRO TAKUYA (JP)
MORI KENJI (JP)
NAKAGAWA RYUSUKE (JP)
WATARAI HIROSHI (JP)
TANIGUCHI MASARU (JP)
Application Number:
PCT/JP2009/065963
Publication Date:
March 18, 2010
Filing Date:
September 11, 2009
Export Citation:
Assignee:
RIKEN (JP)
SHIOZAKI MASAO (JP)
TASHIRO TAKUYA (JP)
MORI KENJI (JP)
NAKAGAWA RYUSUKE (JP)
WATARAI HIROSHI (JP)
TANIGUCHI MASARU (JP)
SHIOZAKI MASAO (JP)
TASHIRO TAKUYA (JP)
MORI KENJI (JP)
NAKAGAWA RYUSUKE (JP)
WATARAI HIROSHI (JP)
TANIGUCHI MASARU (JP)
International Classes:
C07H15/06; A61K31/7032; A61K31/7048; A61P35/00; A61P37/04; A61P43/00; C07H15/26
Domestic Patent References:
| WO1994009020A1 | 1994-04-28 | |||
| WO2003105769A2 | 2003-12-24 | |||
| WO1994009020A1 | 1994-04-28 | |||
| WO2008102888A1 | 2008-08-28 |
Foreign References:
| JP2007531768A | 2007-11-08 | |||
| JP2008511634A | 2008-04-17 | |||
| JP2006117582A | 2006-05-11 | |||
| JP2006519878A | 2006-08-31 | |||
| US20050222048A1 | 2005-10-06 | |||
| DE10128250A1 | 2001-12-20 | |||
| US20070238673A1 | 2007-10-11 |
Other References:
PASSACANTILLI,P. ET AL.: "Neighboring-group participation in nitrile-forming Beckmann fragmentation reactions: Synthesis of enantiopure (E)-2,3-Di-0-substituted-5-methoxy- pent-4-ene-nitriles and their conversion into pyranosylamines", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, pages 5083 - 5091, XP008136122
PASSACANTILLI,P. ET AL.: "A highly efficient and stereocontrolled synthesis of 2-deoxy-1,5- thioanhydro-L-hexitols from D-glycals in a tandem nucleophilic displacement reaction", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, pages 3097 - 3104, XP008136123
CILIBERTI,E. ET AL.: "Glycals in organic synthesis: a systematic strategy for the preparation of uncommon piperidine 1,2-dideoxy- L-azasugars and 2-deoxy-1,5-anhydro-L-hexitols", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, pages 1463 - 1473, XP008136124
GRAZIANI,A. ET AL.: "2-Deoxy-disaccharide approach to natural and unnatural glycosphingolipids synthesis", TETRAHEDRON: ASYMMETRY, vol. 11, no. 19, 2000, pages 3921 - 3937, XP004219743
PASSACANTILLI,P. ET AL.: "Oxime-based methods for synthesis of stereodefined acyclic polyfunctionalized 5-azido-nitriles and 5-substituted isoxazoles from carbohydrate derivatives", TETRAHEDRON, vol. 60, no. 31, 2004, pages 6453 - 6459, XP004527554
REIKO,T,LEE. ET AL.: "Preparation of some (1-6)-linked disaccharides, and their derivatives suitable for protein modification", CARBOHYDRATE RESEARCH, vol. 101, 1982, pages 39 - 47, XP008136125
KAWANO,T. ET AL.: "CDld-restricted and TCR- mediated activation of Val4 NKT cells by glycosylceramides", SCIENCE, vol. 278, no. 5343, 1997, pages 1626 - 1629, XP002175772
TAKUYA,TASHIRO. ET AL.: "RCAI-56, a carbocyclic analogue of KRN7000: its synthesis and potent activity for natural killer (NK) T cells to preferentially produce interferon-y", TETRAHEDRON LETTERS, vol. 48, May 2007 (2007-05-01), pages 3343 - 3347, XP022031952
See also references of EP 2336144A4
PROC. NATL. ACAD. SCI. USA, vol. 95, 1998, pages 5690 - 5693
J. IMMUNOL., vol. 155, 1995, pages 2972 - 2983
J. IMMUNOL., vol. 161, 1998, pages 3271 - 3281
NAT. IMMUNOL., vol. 4, 2003, pages 1164 - 1165
BIOCHIM. BIOPHYS. ACTA, 1973, pages 315 - 335
SCIENCE, vol. 278, 1997, pages 1626 - 1629
J. MED. CHEM., vol. 38, 1995, pages 2176 - 2187
ANGEW. CHEM. INT. ED. ENGL., vol. 43, 2004, pages 3818 - 3822
ORG. LETT., vol. 8, 2006, pages 3375 - 3378
ORG. LETT., vol. 6, 2004, pages 4077 - 4080
J. EXP. MED., vol. 198, 2003, pages 1631 - 1641
TETRAHEDRON LETT., vol. 48, 2007, pages 3343 - 3347
BIOL. PHARM. BULL., vol. 18, 1995, pages 1487 - 1491
BIOORG. MED. CHEM., vol. 5, 1997, pages 2245 - 2249
BIOORG. MED. CHEM., vol. 6, 1998, pages 1905 - 1910
TETRAHEDRON, vol. 61, 2005, pages 1855 - 1862
0. PLETTENBURG, V. BODMER-NARKEVITCH, C-H. WONG, J. ORG. CHEM., vol. 67, 2002, pages 4559 - 4564
S. ROY, A. CHAKRABORTY, R. GHOSH, CARBOHYDR. RES., vol. 343, 2008, pages 2523 - 2529
T. J. LUCAS ET AL., CARBOHYDR. RES., vol. 39, 1975, pages 39 - 45
K. MURATA, T. TOBA, K. NAKANISHI, B. TAKAHASHI, T. YAMAMURA, S. MIYAKE, H. ANNOURA, J. ORG. CHEM., vol. 70, 2005, pages 2398 - 2401
J. C. TADAV, S. PAMU, D. C. BHUNIA, S. PABBERAJA, SYNLETT., 2007, pages 992 - 994
J. MULLER, M. BRUNNBAUER, M. SCHMIDT, A. TERFORT, SYNTHESIS, 2005, pages 998 - 1004
C-H, WONG ET AL., J. ORG. CHEM, vol. 67, 2002, pages 4559 - 4564
PASSACANTILLI,P. ET AL.: "A highly efficient and stereocontrolled synthesis of 2-deoxy-1,5- thioanhydro-L-hexitols from D-glycals in a tandem nucleophilic displacement reaction", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, pages 3097 - 3104, XP008136123
CILIBERTI,E. ET AL.: "Glycals in organic synthesis: a systematic strategy for the preparation of uncommon piperidine 1,2-dideoxy- L-azasugars and 2-deoxy-1,5-anhydro-L-hexitols", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, pages 1463 - 1473, XP008136124
GRAZIANI,A. ET AL.: "2-Deoxy-disaccharide approach to natural and unnatural glycosphingolipids synthesis", TETRAHEDRON: ASYMMETRY, vol. 11, no. 19, 2000, pages 3921 - 3937, XP004219743
PASSACANTILLI,P. ET AL.: "Oxime-based methods for synthesis of stereodefined acyclic polyfunctionalized 5-azido-nitriles and 5-substituted isoxazoles from carbohydrate derivatives", TETRAHEDRON, vol. 60, no. 31, 2004, pages 6453 - 6459, XP004527554
REIKO,T,LEE. ET AL.: "Preparation of some (1-6)-linked disaccharides, and their derivatives suitable for protein modification", CARBOHYDRATE RESEARCH, vol. 101, 1982, pages 39 - 47, XP008136125
KAWANO,T. ET AL.: "CDld-restricted and TCR- mediated activation of Val4 NKT cells by glycosylceramides", SCIENCE, vol. 278, no. 5343, 1997, pages 1626 - 1629, XP002175772
TAKUYA,TASHIRO. ET AL.: "RCAI-56, a carbocyclic analogue of KRN7000: its synthesis and potent activity for natural killer (NK) T cells to preferentially produce interferon-y", TETRAHEDRON LETTERS, vol. 48, May 2007 (2007-05-01), pages 3343 - 3347, XP022031952
See also references of EP 2336144A4
PROC. NATL. ACAD. SCI. USA, vol. 95, 1998, pages 5690 - 5693
J. IMMUNOL., vol. 155, 1995, pages 2972 - 2983
J. IMMUNOL., vol. 161, 1998, pages 3271 - 3281
NAT. IMMUNOL., vol. 4, 2003, pages 1164 - 1165
BIOCHIM. BIOPHYS. ACTA, 1973, pages 315 - 335
SCIENCE, vol. 278, 1997, pages 1626 - 1629
J. MED. CHEM., vol. 38, 1995, pages 2176 - 2187
ANGEW. CHEM. INT. ED. ENGL., vol. 43, 2004, pages 3818 - 3822
ORG. LETT., vol. 8, 2006, pages 3375 - 3378
ORG. LETT., vol. 6, 2004, pages 4077 - 4080
J. EXP. MED., vol. 198, 2003, pages 1631 - 1641
TETRAHEDRON LETT., vol. 48, 2007, pages 3343 - 3347
BIOL. PHARM. BULL., vol. 18, 1995, pages 1487 - 1491
BIOORG. MED. CHEM., vol. 5, 1997, pages 2245 - 2249
BIOORG. MED. CHEM., vol. 6, 1998, pages 1905 - 1910
TETRAHEDRON, vol. 61, 2005, pages 1855 - 1862
0. PLETTENBURG, V. BODMER-NARKEVITCH, C-H. WONG, J. ORG. CHEM., vol. 67, 2002, pages 4559 - 4564
S. ROY, A. CHAKRABORTY, R. GHOSH, CARBOHYDR. RES., vol. 343, 2008, pages 2523 - 2529
T. J. LUCAS ET AL., CARBOHYDR. RES., vol. 39, 1975, pages 39 - 45
K. MURATA, T. TOBA, K. NAKANISHI, B. TAKAHASHI, T. YAMAMURA, S. MIYAKE, H. ANNOURA, J. ORG. CHEM., vol. 70, 2005, pages 2398 - 2401
J. C. TADAV, S. PAMU, D. C. BHUNIA, S. PABBERAJA, SYNLETT., 2007, pages 992 - 994
J. MULLER, M. BRUNNBAUER, M. SCHMIDT, A. TERFORT, SYNTHESIS, 2005, pages 998 - 1004
C-H, WONG ET AL., J. ORG. CHEM, vol. 67, 2002, pages 4559 - 4564
Attorney, Agent or Firm:
TAKASHIMA, HAJIME (JP)
Takashima 1 (JP)
Takashima 1 (JP)
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