KR102005003B1 - 글리코스핑고리피드의 제조 방법 및 이의 용도 - Google Patents

글리코스핑고리피드의 제조 방법 및 이의 용도 Download PDF

Info

Publication number
KR102005003B1
KR102005003B1 KR1020137020635A KR20137020635A KR102005003B1 KR 102005003 B1 KR102005003 B1 KR 102005003B1 KR 1020137020635 A KR1020137020635 A KR 1020137020635A KR 20137020635 A KR20137020635 A KR 20137020635A KR 102005003 B1 KR102005003 B1 KR 102005003B1
Authority
KR
South Korea
Prior art keywords
compound
formula
mmol
nmr
mhz
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
KR1020137020635A
Other languages
English (en)
Korean (ko)
Other versions
KR20140036147A (ko
Inventor
피-후이 리앙
Original Assignee
내셔널 타이완 유니버시티
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 내셔널 타이완 유니버시티 filed Critical 내셔널 타이완 유니버시티
Publication of KR20140036147A publication Critical patent/KR20140036147A/ko
Application granted granted Critical
Publication of KR102005003B1 publication Critical patent/KR102005003B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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

Landscapes

  • 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)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (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)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
KR1020137020635A 2011-01-05 2012-01-05 글리코스핑고리피드의 제조 방법 및 이의 용도 Active KR102005003B1 (ko)

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

Publications (2)

Publication Number Publication Date
KR20140036147A KR20140036147A (ko) 2014-03-25
KR102005003B1 true KR102005003B1 (ko) 2019-07-29

Family

ID=45688966

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020137020635A Active KR102005003B1 (ko) 2011-01-05 2012-01-05 글리코스핑고리피드의 제조 방법 및 이의 용도

Country Status (15)

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

Families Citing this family (38)

* 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
JP5986745B2 (ja) 2008-07-15 2016-09-06 アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ Ｐｔｆｅ様のアルミニウム・コート・ガラススライド上のグリカンアレイおよび関連する方法
US10087236B2 (en) 2009-12-02 2018-10-02 Academia Sinica Methods for modifying human antibodies by glycan engineering
US11377485B2 (en) 2009-12-02 2022-07-05 Academia Sinica Methods for modifying human antibodies by glycan engineering
US10338069B2 (en) 2010-04-12 2019-07-02 Academia Sinica Glycan arrays for high throughput screening of viruses
CN103068378B (zh) 2010-05-10 2016-07-06 中央研究院 具有抗流感活性的扎那米韦膦酸酯同类物及其制备方法
HK1197068A1 (en) * 2011-01-05 2015-01-02 台湾大学 Methods for preparation of glycosphingolipids and uses thereof
EP2811831B1 (en) * 2012-02-07 2018-04-11 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
WO2014031498A1 (en) 2012-08-18 2014-02-27 Academia Sinica Cell-permeable probes for identification and imaging of sialidases
WO2014031762A1 (en) 2012-08-21 2014-02-27 Academia Sinica Benzocyclooctyne compounds and uses thereof
EP2727929A1 (en) * 2012-10-30 2014-05-07 Wittycell Method of preparation of alpha galactosyl ceramides compounds
EP3013365B1 (en) 2013-06-26 2019-06-05 Academia Sinica Rm2 antigens and use thereof
WO2014210564A1 (en) 2013-06-27 2014-12-31 Academia Sinica Glycan conjugates and use thereof
US9782476B2 (en) * 2013-09-06 2017-10-10 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
CA2937123A1 (en) 2014-01-16 2015-07-23 Academia Sinica Compositions and methods for treatment and detection of cancers
WO2015148915A1 (en) 2014-03-27 2015-10-01 Academia Sinica Reactive labelling compounds and uses thereof
KR20170003720A (ko) 2014-05-27 2017-01-09 아카데미아 시니카 항-ｃｄ20 글리코항체 및 이의 용도
US10118969B2 (en) 2014-05-27 2018-11-06 Academia Sinica Compositions and methods relating to universal glycoforms for enhanced antibody efficacy
CA2950423A1 (en) 2014-05-27 2015-12-03 Academia Sinica Compositions and methods relating to universal glycoforms for enhanced antibody efficacy
KR102512592B1 (ko) 2014-05-27 2023-03-21 아카데미아 시니카 항-ｈｅｒ2 글리코항체 및 이의 용도
CN106714829A (zh) 2014-05-28 2017-05-24 中央研究院 抗TNF‑α醣抗体及其用途
CA2960712A1 (en) * 2014-09-08 2016-03-17 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
JP6956719B2 (ja) 2015-12-29 2021-11-02 オプコ・ダイアグノスティクス・リミテッド・ライアビリティ・カンパニーＯｐｋｏ Ｄｉａｇｎｏｓｔｉｃｓ，Ｌｌｃ 流体の収集のための物品
WO2017156192A1 (en) 2016-03-08 2017-09-14 Academia Sinica Methods for modular synthesis of n-glycans and arrays thereof
EP3500594A4 (en) 2016-08-22 2020-03-11 Cho Pharma Inc. ANTIBODIES, BINDING FRAGMENTS AND METHOD FOR USE
WO2019053142A1 (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
EP4274541A1 (en) * 2021-01-06 2023-11-15 Evonik Operations GmbH Hydroxy-substituted sphingolipids
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
CN117222414A (zh) 2021-03-01 2023-12-12 脱落性治疗公司 用于激活恒定自然杀伤t-细胞的化合物和用于消除炎性衰老细胞的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010006315A2 (en) * 2008-07-11 2010-01-14 Academia Sinica Alpha-galactosyl ceramide analogs and their use as immunotherapies, adjuvants, and intiviral, antibacterial, and anticancer agents

Family Cites Families (18)

* 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
EP0666268B1 (en) 1992-10-22 2000-04-19 Kirin Beer Kabushiki Kaisha Novel sphingoglycolipid and use thereof
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
US7923013B2 (en) 2004-12-28 2011-04-12 The Rockefeller University Glycolipids and analogues thereof as antigens for NKT cells
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
EP2390255B1 (en) 2006-04-03 2016-07-13 Technion Research & Development Foundation Ltd. Novel aminoglycosides and uses thereof 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
JP2010523724A (ja) 2007-04-13 2010-07-15 アカデミア シニカ α−ガラクトシルセラミド類似体およびそれらの免疫療法剤としての使用
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
HK1197068A1 (en) * 2011-01-05 2015-01-02 台湾大学 Methods for preparation of glycosphingolipids and uses thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010006315A2 (en) * 2008-07-11 2010-01-14 Academia Sinica Alpha-galactosyl ceramide analogs and their use as immunotherapies, adjuvants, and intiviral, antibacterial, and anticancer agents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Antimicrobial agents and chemotherapy, Oct. 2010, 4129-4136*

Also Published As

Publication number Publication date
IL227333A0 (en) 2013-09-30
JP6259887B2 (ja) 2018-01-10
IL227333B (en) 2018-01-31
KR20140036147A (ko) 2014-03-25
CA2854725C (en) 2019-10-22
JP6057300B2 (ja) 2017-01-11
JP2014504593A (ja) 2014-02-24
JP2017061481A (ja) 2017-03-30
CO6761397A2 (es) 2013-09-30
ES2654382T3 (es) 2018-02-13
MX2013007888A (es) 2014-09-11
US20120178705A1 (en) 2012-07-12
AU2017206277B2 (en) 2019-05-02
US20160229881A1 (en) 2016-08-11
EP2661440B1 (en) 2017-09-27
AU2017206277A1 (en) 2017-08-10
US10654880B2 (en) 2020-05-19
MX345764B (es) 2017-02-15
WO2012094540A3 (en) 2012-08-30
EP2661440A2 (en) 2013-11-13
RU2636587C2 (ru) 2017-11-24
US9181292B2 (en) 2015-11-10
CN103748103A (zh) 2014-04-23
RU2013136531A (ru) 2015-02-10
BR112013017382B1 (pt) 2021-03-16
CA2854725A1 (en) 2013-07-12
BR112013017382A2 (pt) 2016-10-04
HK1197068A1 (en) 2015-01-02
AU2012204336C1 (en) 2017-08-03
AU2012204336B2 (en) 2017-05-04
WO2012094540A2 (en) 2012-07-12
AU2012204336A1 (en) 2013-08-22

Similar Documents

Publication Publication Date Title
KR102005003B1 (ko) 글리코스핑고리피드의 제조 방법 및 이의 용도
JP3717512B2 (ja) 新規スフィンゴ糖脂質およびその使用
US8883746B2 (en) α-galactosylceramide derivatives, pharmaceutically acceptable salts thereof, preparation method and pharmaceutical composition for the immune adjuvant containing the same as an active ingredient
KR102162619B1 (ko) 유기 화합물
KR20150127030A (ko) 접합체 화합물
CA3140411C (en) Saponin conjugate and vaccine or pharmaceutical composition comprising the same
TWI595878B (zh) 製備鞘糖脂之方法及其用途
Murphy et al. R-Galactosylceramides and analogues− Important immunomodulators for use as vaccine adjuvants
TW202005977A (zh) 阿伐-選擇性唾液酸供體及其於製備唾液酸苷的用途
NZ613614B2 (en) Sphingoglycolipid compounds and uses

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20130805

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20170105

Comment text: Request for Examination of Application

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20180927

Patent event code: PE09021S01D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20190424

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20190723

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20190723

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
PR1001 Payment of annual fee

Payment date: 20220712

Start annual number: 4

End annual number: 4

PR1001 Payment of annual fee

Payment date: 20250704

Start annual number: 7

End annual number: 7

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-OTH-PR1001 (AS PROVIDED BY THE NATIONAL OFFICE)

Year of fee payment: 7