AU2012204336C1 - Methods for preparation of glycosphingolipids and uses thereof - Google Patents

Methods for preparation of glycosphingolipids and uses thereof Download PDF

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Publication number
AU2012204336C1
AU2012204336C1 AU2012204336A AU2012204336A AU2012204336C1 AU 2012204336 C1 AU2012204336 C1 AU 2012204336C1 AU 2012204336 A AU2012204336 A AU 2012204336A AU 2012204336 A AU2012204336 A AU 2012204336A AU 2012204336 C1 AU2012204336 C1 AU 2012204336C1
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compound
formula
mmol
nmr
synthesis
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AU2012204336A1 (en
AU2012204336B2 (en
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Pi-Hui Liang
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National Taiwan University
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National Taiwan University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Epidemiology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
AU2012204336A 2011-01-05 2012-01-05 Methods for preparation of glycosphingolipids and uses thereof Active AU2012204336C1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2017206277A AU2017206277B2 (en) 2011-01-05 2017-07-21 Methods for preparation of glycosphingolipds and uses thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161430117P 2011-01-05 2011-01-05
US61/430,117 2011-01-05
PCT/US2012/020388 WO2012094540A2 (en) 2011-01-05 2012-01-05 Methods for preparation of glycosphingolipids and uses thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU2017206277A Division AU2017206277B2 (en) 2011-01-05 2017-07-21 Methods for preparation of glycosphingolipds and uses thereof

Publications (3)

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AU2012204336A1 AU2012204336A1 (en) 2013-08-22
AU2012204336B2 AU2012204336B2 (en) 2017-05-04
AU2012204336C1 true AU2012204336C1 (en) 2017-08-03

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AU2012204336A Active AU2012204336C1 (en) 2011-01-05 2012-01-05 Methods for preparation of glycosphingolipids and uses thereof
AU2017206277A Active AU2017206277B2 (en) 2011-01-05 2017-07-21 Methods for preparation of glycosphingolipds and uses thereof

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US (2) US9181292B2 (enExample)
EP (1) EP2661440B1 (enExample)
JP (2) JP6057300B2 (enExample)
KR (1) KR102005003B1 (enExample)
CN (1) CN103748103A (enExample)
AU (2) AU2012204336C1 (enExample)
BR (1) BR112013017382B1 (enExample)
CA (1) CA2854725C (enExample)
CO (1) CO6761397A2 (enExample)
ES (1) ES2654382T3 (enExample)
HK (1) HK1197068A1 (enExample)
IL (1) IL227333B (enExample)
MX (1) MX345764B (enExample)
RU (1) RU2636587C2 (enExample)
WO (1) WO2012094540A2 (enExample)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7960139B2 (en) 2007-03-23 2011-06-14 Academia Sinica Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells
DK2318832T3 (da) 2008-07-15 2014-01-20 Academia Sinica Glycan-arrays på PTFE-lignende aluminiumcoatede objektglas og relaterede fremgangsmåder
US11377485B2 (en) 2009-12-02 2022-07-05 Academia Sinica Methods for modifying human antibodies by glycan engineering
US10087236B2 (en) 2009-12-02 2018-10-02 Academia Sinica Methods for modifying human antibodies by glycan engineering
WO2011130332A1 (en) 2010-04-12 2011-10-20 Academia Sinica Glycan arrays for high throughput screening of viruses
DK2568976T3 (en) 2010-05-10 2016-01-11 Academia Sinica Zanamivir-phosphonate congener with the anti-influenza activity, and determining the sensitivity oseltamivir in influenza viruses
JP6057300B2 (ja) * 2011-01-05 2017-01-11 ナショナル タイワン ユニバーシティ グリコスフィンゴ脂質の調製及びその使用の方法
WO2013119857A1 (en) 2012-02-07 2013-08-15 The Regents Of The University Of California Glycosphingolipids for use in modulating immune responses
US10130714B2 (en) 2012-04-14 2018-11-20 Academia Sinica Enhanced anti-influenza agents conjugated with anti-inflammatory activity
US9914956B2 (en) 2012-08-18 2018-03-13 Academia Sinica Cell-permeable probes for identification and imaging of sialidases
JP6211084B2 (ja) 2012-08-21 2017-10-11 アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ ベンゾシクロオクチン化合物およびその使用
EP2727929A1 (en) 2012-10-30 2014-05-07 Wittycell Method of preparation of alpha galactosyl ceramides compounds
WO2014210397A1 (en) 2013-06-26 2014-12-31 Academia Sinica Rm2 antigens and use thereof
EP3013347B1 (en) 2013-06-27 2019-12-11 Academia Sinica Glycan conjugates and use thereof
EP3041484B1 (en) * 2013-09-06 2021-03-03 Academia Sinica Human inkt cell activation using glycolipids with altered glycosyl groups
US10150818B2 (en) 2014-01-16 2018-12-11 Academia Sinica Compositions and methods for treatment and detection of cancers
KR20160104727A (ko) 2014-01-16 2016-09-05 아카데미아 시니카 암의 치료 및 검출을 위한 조성물 및 방법
TWI797430B (zh) 2014-03-27 2023-04-01 中央研究院 反應性標記化合物及其用途
EP4116329A1 (en) 2014-05-27 2023-01-11 Academia Sinica Anti-her2 glycoantibodies and uses thereof
KR20170010003A (ko) 2014-05-27 2017-01-25 아카데미아 시니카 박테로이드 기원의 푸코시다제 및 이의 사용 방법
US10118969B2 (en) 2014-05-27 2018-11-06 Academia Sinica Compositions and methods relating to universal glycoforms for enhanced antibody efficacy
JP2017518989A (ja) 2014-05-27 2017-07-13 アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ 抗ｃｄ２０糖操作抗体群およびその使用
JP7063538B2 (ja) 2014-05-28 2022-05-09 アカデミア シニカ 抗ＴＮＦα糖操作抗体群およびその使用
EP3191500A4 (en) 2014-09-08 2018-04-11 Academia Sinica HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
US10495645B2 (en) 2015-01-16 2019-12-03 Academia Sinica Cancer markers and methods of use thereof
US9975965B2 (en) 2015-01-16 2018-05-22 Academia Sinica Compositions and methods for treatment and detection of cancers
AU2015378564A1 (en) 2015-01-24 2017-07-13 Academia Sinica Novel glycan conjugates and methods of use thereof
EP3374028B1 (en) * 2015-11-13 2021-05-26 La Jolla Institute for Allergy and Immunology Sphingamide compounds and methods for binding inkt cells
CA3005084A1 (en) 2015-12-11 2017-06-15 Opko Diagnostics, Llc Fluidic systems involving incubation of samples and/or reagents
HUE055156T2 (hu) 2015-12-29 2021-11-29 Opko Diagnostics Llc Folyadékgyûjtési eszköz és kapcsolódó módszerek
CN109195996A (zh) 2016-03-08 2019-01-11 中央研究院 N-聚醣及其阵列的模组化合成方法
CA3034057A1 (en) 2016-08-22 2018-03-01 CHO Pharma Inc. Antibodies, binding fragments, and methods of use
CA3075443A1 (en) * 2017-09-13 2019-03-21 Abivax Abx196 for use in the treatment of bladder cancer
CN110835361A (zh) * 2019-10-21 2020-02-25 山东大学 一类唾液酸糖基给体及其制备方法和应用
WO2021142581A1 (zh) * 2020-01-13 2021-07-22 郑州市御合源生物科技有限公司 一种糖苷化合物及其制备方法和应用
CN116669690B (zh) * 2021-01-06 2026-06-02 赢创运营有限公司 羟基取代的鞘脂
CN114805454B (zh) * 2021-01-21 2023-07-18 中国科学院生态环境研究中心 α-半乳糖神经酰胺类化合物及其制备方法和用途
EP4301374A4 (en) 2021-03-01 2025-09-10 Deciduous Therapeutics Inc COMPOUNDS FOR ACTIVATING INVARIANT NATURAL KILLER T CELLS AND METHODS OF USE IN ELIMINATING INFLAMMATORY SENESCENT CELLS
CN118459632B (zh) * 2024-04-12 2026-06-30 江南大学 一种用于聚糖固相合成的碱切除连接臂制备与应用

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0676429B2 (ja) 1987-03-09 1994-09-28 理化学研究所 ラクト系列スフィンゴ糖脂質の合成法
JP2588729B2 (ja) * 1987-10-05 1997-03-12 塩野義製薬株式会社 スフィンゴシン誘導体
ATE191916T1 (de) 1992-10-22 2000-05-15 Kirin Brewery Neues sphingolglycolipid und verwendung davon
CA2142153A1 (en) * 1994-03-04 1995-09-05 Jacques Banville Sulfated .beta.-glycolipid derivatives as cell adhesion inhibitors
JPH11269189A (ja) * 1998-03-19 1999-10-05 Nissin Food Prod Co Ltd 免疫調節作用を有する化合物
CN1405172A (zh) 2001-08-13 2003-03-26 青岛海洋大学 一种乳糖胺脂及其制备方法和应用
DE10258007B4 (de) * 2002-12-12 2006-02-09 Sanofi-Aventis Deutschland Gmbh Aromatische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel
CA2579678A1 (en) 2004-10-04 2006-04-13 Alchemia Limited Selective inhibitors
JP5090928B2 (ja) 2004-12-28 2012-12-05 ザ ロックフェラー ユニバーシティ Ｎｋｔ細胞に対する抗原としての糖脂質及びその類似体
US7923013B2 (en) 2004-12-28 2011-04-12 The Rockefeller University Glycolipids and analogues thereof as antigens for NKT cells
HUE031643T2 (en) * 2006-04-03 2017-07-28 Technion Res & Dev Foundation New aminoglycosides and their applications in the treatment of genetic disorders
US8420607B2 (en) 2006-06-30 2013-04-16 University Of Georgia Research Foundation, Inc. Anthrax carbohydrates, synthesis and uses thereof
CN101012254A (zh) * 2006-08-29 2007-08-08 中国海洋大学 一种α－半乳糖鞘糖脂的2’－OH衍生物及其制备方法
KR100868959B1 (ko) 2006-12-30 2008-11-17 재단법인서울대학교산학협력재단 알파-갈락토실세라마이드 유도체, 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는면역보조용 약학적 조성물
WO2008128207A1 (en) 2007-04-13 2008-10-23 Academia Sinica Alpha-galactosyl ceramide analogs and their use as immunotherapies
US20090137793A1 (en) 2007-11-19 2009-05-28 Academia Sinica Disaccharide compounds
US8697862B2 (en) 2008-05-16 2014-04-15 Galecto Biotech Ab Synthesis of galactoside inhibitors
US7928077B2 (en) * 2008-07-11 2011-04-19 Academia Sinica Alpha-galactosyl ceramide analogs and their use as immunotherapies
JP6057300B2 (ja) 2011-01-05 2017-01-11 ナショナル タイワン ユニバーシティ グリコスフィンゴ脂質の調製及びその使用の方法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BLANC-MUASSER, M. et al., "Triphenylmethanethiol. An useful reagent in the synthesis of 1, 2-cis-1-thioglycoses.", Tetrahedron Letters. 1990, vol. 31, no. 27, pages 3869-3870 *
DING, N. et al., "Concise synthesis of clarhamnoside, a novel glycosphingolipid isolated from the marine sponge Agela clathrodes", Carbohydrate Research. 2007, vol. 342, no. 14, pages 2003-2013 *
LEUNG, L. et al., "The Synthesis and in vivo Evaluation of 2’,2’-Difluoro KRN7000", ChemMedChem. 2009, vol. 4, pages 329-334 *
XIA, C. et al., "Roles of 3' and 4' Hydroxyls in a-Galactosylceramide Stimulation of Invariant Natural Killer T Cells", ChemMedChem. 2009, vol. 4, pages 1810-1815 *

Also Published As

Publication number Publication date
JP2017061481A (ja) 2017-03-30
US10654880B2 (en) 2020-05-19
MX2013007888A (es) 2014-09-11
HK1197068A1 (en) 2015-01-02
BR112013017382A2 (pt) 2016-10-04
RU2013136531A (ru) 2015-02-10
EP2661440A2 (en) 2013-11-13
US20120178705A1 (en) 2012-07-12
KR20140036147A (ko) 2014-03-25
RU2636587C2 (ru) 2017-11-24
ES2654382T3 (es) 2018-02-13
CA2854725A1 (en) 2013-07-12
KR102005003B1 (ko) 2019-07-29
JP2014504593A (ja) 2014-02-24
US20160229881A1 (en) 2016-08-11
MX345764B (es) 2017-02-15
CO6761397A2 (es) 2013-09-30
CA2854725C (en) 2019-10-22
WO2012094540A2 (en) 2012-07-12
BR112013017382B1 (pt) 2021-03-16
US9181292B2 (en) 2015-11-10
EP2661440B1 (en) 2017-09-27
CN103748103A (zh) 2014-04-23
JP6057300B2 (ja) 2017-01-11
WO2012094540A3 (en) 2012-08-30
AU2017206277B2 (en) 2019-05-02
AU2017206277A1 (en) 2017-08-10
IL227333A0 (en) 2013-09-30
JP6259887B2 (ja) 2018-01-10
IL227333B (en) 2018-01-31
AU2012204336A1 (en) 2013-08-22
AU2012204336B2 (en) 2017-05-04

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