JP2014504593A5 - - Google Patents
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- JP2014504593A5 JP2014504593A5 JP2013548554A JP2013548554A JP2014504593A5 JP 2014504593 A5 JP2014504593 A5 JP 2014504593A5 JP 2013548554 A JP2013548554 A JP 2013548554A JP 2013548554 A JP2013548554 A JP 2013548554A JP 2014504593 A5 JP2014504593 A5 JP 2014504593A5
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- Prior art keywords
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- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 37
- 238000000034 method Methods 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 7
- 108090000695 Cytokines Proteins 0.000 claims 6
- 102000004127 Cytokines Human genes 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 230000028327 secretion Effects 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- -1 lithium aluminum hydride Chemical compound 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000003550 alpha-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims 2
- 230000000259 anti-tumor effect Effects 0.000 claims 2
- 230000000840 anti-viral effect Effects 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 238000006555 catalytic reaction Methods 0.000 claims 2
- 150000002148 esters Chemical group 0.000 claims 2
- 150000002339 glycosphingolipids Chemical class 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102100037850 Interferon gamma Human genes 0.000 claims 1
- 108010074328 Interferon-gamma Proteins 0.000 claims 1
- 108010002350 Interleukin-2 Proteins 0.000 claims 1
- 108090000978 Interleukin-4 Proteins 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- 102000001708 Protein Isoforms Human genes 0.000 claims 1
- 108010029485 Protein Isoforms Proteins 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 238000010976 amide bond formation reaction Methods 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000013595 glycosylation Effects 0.000 claims 1
- 238000006206 glycosylation reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- AYNYHSGJYJNQKG-UHFFFAOYSA-N octadecane-1,3,4-triol Chemical group CCCCCCCCCCCCCCC(O)C(O)CCO AYNYHSGJYJNQKG-UHFFFAOYSA-N 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims 1
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 |
|---|---|---|---|
| JP2016209071A Division JP6259887B2 (ja) | 2011-01-05 | 2016-10-25 | グリコスフィンゴ脂質の調製及びその使用の方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014504593A JP2014504593A (ja) | 2014-02-24 |
| JP2014504593A5 true JP2014504593A5 (cg-RX-API-DMAC7.html) | 2015-02-19 |
| JP6057300B2 JP6057300B2 (ja) | 2017-01-11 |
Family
ID=45688966
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013548554A Active JP6057300B2 (ja) | 2011-01-05 | 2012-01-05 | グリコスフィンゴ脂質の調製及びその使用の方法 |
| JP2016209071A Active JP6259887B2 (ja) | 2011-01-05 | 2016-10-25 | グリコスフィンゴ脂質の調製及びその使用の方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016209071A Active JP6259887B2 (ja) | 2011-01-05 | 2016-10-25 | グリコスフィンゴ脂質の調製及びその使用の方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US9181292B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2661440B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP6057300B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102005003B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN103748103A (cg-RX-API-DMAC7.html) |
| AU (2) | AU2012204336C1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112013017382B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2854725C (cg-RX-API-DMAC7.html) |
| CO (1) | CO6761397A2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2654382T3 (cg-RX-API-DMAC7.html) |
| HK (1) | HK1197068A1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL227333B (cg-RX-API-DMAC7.html) |
| MX (1) | MX345764B (cg-RX-API-DMAC7.html) |
| RU (1) | RU2636587C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012094540A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (38)
| 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 |
| ES2442024T3 (es) | 2008-07-15 | 2014-02-07 | Academia Sinica | Matrices de glucano sobre portaobjetos de vidrio revestidos con aluminio de tipo PTFE y métodos relacionados |
| 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 |
| WO2011130332A1 (en) | 2010-04-12 | 2011-10-20 | Academia Sinica | Glycan arrays for high throughput screening of viruses |
| WO2011143262A2 (en) | 2010-05-10 | 2011-11-17 | Sinica, Academia | Zanamivir phosphonate congeners with anti-influenza activity and determining oseltamivir susceptibility of influenza viruses |
| EP2661440B1 (en) | 2011-01-05 | 2017-09-27 | National Taiwan University | Method for the preparation of glycosphingolipids |
| 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 |
| US9547009B2 (en) | 2012-08-21 | 2017-01-17 | Academia Sinica | Benzocyclooctyne compounds and uses thereof |
| 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 |
| US9981030B2 (en) | 2013-06-27 | 2018-05-29 | 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 |
| JP2017507118A (ja) | 2014-01-16 | 2017-03-16 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | がんの処置および検出のための組成物および方法 |
| US10150818B2 (en) | 2014-01-16 | 2018-12-11 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| TWI687428B (zh) | 2014-03-27 | 2020-03-11 | 中央研究院 | 反應性標記化合物及其用途 |
| CA2950423A1 (en) | 2014-05-27 | 2015-12-03 | Academia Sinica | Compositions and methods relating to universal glycoforms for enhanced antibody efficacy |
| EP3149036A4 (en) | 2014-05-27 | 2017-12-27 | Academia Sinica | Anti-cd20 glycoantibodies and uses thereof |
| US10118969B2 (en) | 2014-05-27 | 2018-11-06 | 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 |
| AU2015267044A1 (en) | 2014-05-28 | 2016-12-15 | Academia Sinica | Anti-TNF-alpha glycoantibodies and uses thereof |
| WO2016040369A2 (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 |
| KR102691114B1 (ko) | 2015-01-24 | 2024-08-01 | 아카데미아 시니카 | 신규한 글리칸 콘주게이트 및 이를 사용하는 방법 |
| WO2017083830A1 (en) * | 2015-11-13 | 2017-05-18 | La Jolla Institute For Allergy And Immunology | Sphingamide compounds and methods for binding inkt cells |
| US10852310B2 (en) | 2015-12-11 | 2020-12-01 | Opko Diagnostics, Llc | Fluidic systems involving incubation of samples and/or reagents |
| EP3397387B1 (en) | 2015-12-29 | 2021-03-24 | Opko Diagnostics, LLC | Fluid collection device and related methods |
| TW201808978A (zh) | 2016-03-08 | 2018-03-16 | 中央研究院 | N-聚醣及其陣列之模組化合成方法 |
| US10538592B2 (en) | 2016-08-22 | 2020-01-21 | Cho Pharma, Inc. | Antibodies, binding fragments, and methods of use |
| BR112020004778A2 (pt) * | 2017-09-13 | 2020-10-13 | Abivax | usos de um composto abx196 e de uma composição farmacêutica |
| 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 |
| JP7788458B2 (ja) * | 2021-01-06 | 2025-12-18 | エボニック オペレーションズ ゲーエムベーハー | ヒドロキシ置換スフィンゴ脂質 |
| 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 |
| IL305579A (en) | 2021-03-01 | 2023-10-01 | Deciduous Therapeutics Inc | Compounds for activating invariant natural killer T cells and methods for use in eliminating inflammatory senescent cells |
Family Cites Families (19)
| 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 |
| JP3717512B2 (ja) | 1992-10-22 | 2005-11-16 | 麒麟麦酒株式会社 | 新規スフィンゴ糖脂質およびその使用 |
| 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 |
| EP1797428A1 (en) | 2004-10-04 | 2007-06-20 | Alchemia Pty Ltd | Selective inhibitors |
| AU2005322027B2 (en) | 2004-12-28 | 2013-09-12 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NK Tcells |
| US7923013B2 (en) | 2004-12-28 | 2011-04-12 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NKT cells |
| DK2390255T3 (en) | 2006-04-03 | 2016-11-07 | Technion Res & Dev Foundation | 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 |
| CA2683681A1 (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 |
| ES2611206T3 (es) | 2008-05-16 | 2017-05-05 | Galecto Biotech Ab | Derivados de di-(3-deoxi-3-1H-1,2,3-triazol-1-il)-beta-D-galacto-iranosil)sulfano como inhibidores de galectina-3 |
| US7928077B2 (en) * | 2008-07-11 | 2011-04-19 | Academia Sinica | Alpha-galactosyl ceramide analogs and their use as immunotherapies |
| EP2661440B1 (en) * | 2011-01-05 | 2017-09-27 | National Taiwan University | Method for the preparation of glycosphingolipids |
-
2012
- 2012-01-05 EP EP12704939.3A patent/EP2661440B1/en active Active
- 2012-01-05 RU RU2013136531A patent/RU2636587C2/ru active
- 2012-01-05 JP JP2013548554A patent/JP6057300B2/ja active Active
- 2012-01-05 MX MX2013007888A patent/MX345764B/es active IP Right Grant
- 2012-01-05 WO PCT/US2012/020388 patent/WO2012094540A2/en not_active Ceased
- 2012-01-05 BR BR112013017382-3A patent/BR112013017382B1/pt active IP Right Grant
- 2012-01-05 US US13/344,557 patent/US9181292B2/en active Active
- 2012-01-05 HK HK14110574.7A patent/HK1197068A1/xx unknown
- 2012-01-05 CA CA2854725A patent/CA2854725C/en active Active
- 2012-01-05 KR KR1020137020635A patent/KR102005003B1/ko active Active
- 2012-01-05 ES ES12704939.3T patent/ES2654382T3/es active Active
- 2012-01-05 CN CN201280011839.4A patent/CN103748103A/zh active Pending
- 2012-01-05 AU AU2012204336A patent/AU2012204336C1/en active Active
-
2013
- 2013-07-04 IL IL227333A patent/IL227333B/en active IP Right Grant
- 2013-07-05 CO CO13159964A patent/CO6761397A2/es unknown
-
2015
- 2015-10-07 US US14/877,897 patent/US10654880B2/en active Active
-
2016
- 2016-10-25 JP JP2016209071A patent/JP6259887B2/ja active Active
-
2017
- 2017-07-21 AU AU2017206277A patent/AU2017206277B2/en active Active
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