Title:
PSEUDOGLYCOLIPID DERIVATIVE, AND SYNTHESIS INTERMEDIATE, PRODUCTION METHOD AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/102557
Kind Code:
A1
Abstract:
The present invention relates to: a compound represented by formula (I) (in the formula, X denotes -CH2- or -NH-; R1 and R3 each independently denote a substituted or unsubstituted hydrocarbon group having 5-30 carbon atoms, with any -CH2- moiety in said hydrocarbon group able to be replaced by a carbonyl group, a sulfonyl group, -O-, -S-, -COO-, -OCO-, -CONH-, -NHCO- or -NH- (however, this excludes a -CH2- adjacent to X in a case where X is -NH-); R2 denotes a hydrogen atom or a substituted or unsubstituted alkyl group having 1-6 carbon atoms, but in a case where R2 is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 carbon atom, R1 includes 1 or more substituted or unsubstituted aromatic rings, or X denotes -NH-) or a salt thereof; and a synthesis intermediate, a production method and an application of the compound.
Inventors:
KAZAMI JUNICHI (JP)
KOYAMA HIROO (JP)
TASHIRO TAKUYA (JP)
ISHII YASUYUKI (JP)
KUBO MASATO (JP)
KOYAMA HIROO (JP)
TASHIRO TAKUYA (JP)
ISHII YASUYUKI (JP)
KUBO MASATO (JP)
Application Number:
PCT/JP2021/040928
Publication Date:
May 19, 2022
Filing Date:
November 08, 2021
Export Citation:
Assignee:
RIKEN (JP)
International Classes:
C07C233/18; A61K31/133; A61K31/164; A61K31/165; A61K31/17; A61P35/00; A61P43/00; C07C213/02; C07C217/28; C07C233/22; C07C275/10
Domestic Patent References:
| WO2008102888A1 | 2008-08-28 | |||
| WO2009119692A1 | 2009-10-01 | |||
| WO2013162016A1 | 2013-10-31 | |||
| WO2004072091A1 | 2004-08-26 | |||
| WO2011096536A1 | 2011-08-11 |
Foreign References:
| JP2010523724A | 2010-07-15 | |||
| JP2008511634A | 2008-04-17 | |||
| US20100008954A1 | 2010-01-14 | |||
| KR20140019113A | 2014-02-14 | |||
| US20150010496A1 | 2015-01-08 |
Other References:
TASHIRO, T. NAKAGAWA, R. HIROKAWA, T. INOUE, S. WATARAI, H. TANIGUCHI, M. MORI, K.: "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, ELSEVIER, AMSTERDAM , NL, vol. 48, no. 19, 17 April 2007 (2007-04-17), Amsterdam , NL , pages 3343 - 3347, XP022031952, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2007.03.074
TASHIRO, T. ; NAKAGAWA, R. ; HIROKAWA, T. ; INOUE, S. ; WATARAI, H. ; TANIGUCHI, M. ; MORI, K.: "RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines", BIOORGANIC, vol. 17, no. 17, 1 September 2009 (2009-09-01), AMSTERDAM, NL, pages 6360 - 6373, XP026471116, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2009.07.025
POOJA ARORA, MANJUNATHA M. VENKATASWAMY, ANDRES BAENA, GABRIEL BRICARD, QIAN LI, NATACHA VEERAPEN, RACHEL NDONYE, JEONG JU PARK, J: "A Rapid Fluorescence-Based Assay for Classification of iNKT Cell Activating Glycolipids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 14, 13 April 2011 (2011-04-13), pages 5198 - 5201, XP055052562, ISSN: 0002-7863, DOI: 10.1021/ja200070u
Y. YOSHIGA; D. GOTO; S. SEGAWA; M. HORIKOSHI; T. HAYASHI; I. MATSUMOTO; S. ITO; M. TANIGUCHI; T. SUMIDA: "Activation of natural killer T cells by α‐carba‐GalCer (RCAI‐56), a novel synthetic glycolipid ligand, suppresses murine collagen‐induced arthritis", CLINICAL AND EXPERIMENTAL IMMUNOLOGY, vol. 164, no. 2, 10 March 2011 (2011-03-10), GB , pages 236 - 247, XP071085900, ISSN: 0009-9104, DOI: 10.1111/j.1365-2249.2011.04369.x
TAKUYA TASHIRO; TOMOKUNI SHIGEURA; HIROSHI WATARAI; MASARU TANIGUCHI; KENJI MORI: "RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines", BIOORGANIC, vol. 20, no. 14, AMSTERDAM, NL, pages 4540 - 4548, XP028502319, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2012.05.073
TASHIRO, T. ; NAKAGAWA, R. ; HIROKAWA, T. ; INOUE, S. ; WATARAI, H. ; TANIGUCHI, M. ; MORI, K.: "RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines", BIOORGANIC, vol. 17, no. 17, 1 September 2009 (2009-09-01), AMSTERDAM, NL, pages 6360 - 6373, XP026471116, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2009.07.025
POOJA ARORA, MANJUNATHA M. VENKATASWAMY, ANDRES BAENA, GABRIEL BRICARD, QIAN LI, NATACHA VEERAPEN, RACHEL NDONYE, JEONG JU PARK, J: "A Rapid Fluorescence-Based Assay for Classification of iNKT Cell Activating Glycolipids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 14, 13 April 2011 (2011-04-13), pages 5198 - 5201, XP055052562, ISSN: 0002-7863, DOI: 10.1021/ja200070u
Y. YOSHIGA; D. GOTO; S. SEGAWA; M. HORIKOSHI; T. HAYASHI; I. MATSUMOTO; S. ITO; M. TANIGUCHI; T. SUMIDA: "Activation of natural killer T cells by α‐carba‐GalCer (RCAI‐56), a novel synthetic glycolipid ligand, suppresses murine collagen‐induced arthritis", CLINICAL AND EXPERIMENTAL IMMUNOLOGY, vol. 164, no. 2, 10 March 2011 (2011-03-10), GB , pages 236 - 247, XP071085900, ISSN: 0009-9104, DOI: 10.1111/j.1365-2249.2011.04369.x
TAKUYA TASHIRO; TOMOKUNI SHIGEURA; HIROSHI WATARAI; MASARU TANIGUCHI; KENJI MORI: "RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines", BIOORGANIC, vol. 20, no. 14, AMSTERDAM, NL, pages 4540 - 4548, XP028502319, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2012.05.073
Attorney, Agent or Firm:
HIRAKI & ASSOCIATES (JP)
Download PDF: