RU2636587C2 - Способы получения гликосфинголипидов и их применение - Google Patents
Способы получения гликосфинголипидов и их применение Download PDFInfo
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- RU2636587C2 RU2636587C2 RU2013136531A RU2013136531A RU2636587C2 RU 2636587 C2 RU2636587 C2 RU 2636587C2 RU 2013136531 A RU2013136531 A RU 2013136531A RU 2013136531 A RU2013136531 A RU 2013136531A RU 2636587 C2 RU2636587 C2 RU 2636587C2
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- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
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| 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 |
| 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 |
| CA2835489C (en) | 2010-05-10 | 2018-03-06 | Chi-Huey Wong | Zanamivir phosphonate congeners with anti-influenza activity and determining oseltamivir susceptibility of influenza viruses |
| CA2854725C (en) | 2011-01-05 | 2019-10-22 | National Taiwan University | 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 |
| US9914956B2 (en) | 2012-08-18 | 2018-03-13 | Academia Sinica | Cell-permeable probes for identification and imaging of sialidases |
| CA2883168A1 (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 |
| WO2014210397A1 (en) | 2013-06-26 | 2014-12-31 | Academia Sinica | Rm2 antigens and use thereof |
| WO2014210564A1 (en) | 2013-06-27 | 2014-12-31 | Academia Sinica | Glycan conjugates and use thereof |
| KR102298172B1 (ko) * | 2013-09-06 | 2021-09-06 | 아카데미아 시니카 | 변화된 글리코실 그룹을 갖는 당지질을 사용한 인간 iNKT 세포 활성화 |
| CA2937123A1 (en) | 2014-01-16 | 2015-07-23 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| US10150818B2 (en) | 2014-01-16 | 2018-12-11 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| 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 |
| US10118969B2 (en) | 2014-05-27 | 2018-11-06 | Academia Sinica | Compositions and methods relating to universal glycoforms for enhanced antibody efficacy |
| AU2015267045B2 (en) | 2014-05-27 | 2021-02-25 | Academia Sinica | Anti-HER2 glycoantibodies and uses thereof |
| FI3149045T3 (fi) | 2014-05-27 | 2023-03-20 | Academia Sinica | Koostumuksia ja menetelmiä, jotka liittyvät yleisglykoformeihin vasta-aineiden parannettua tehokkuutta varten |
| US20150344585A1 (en) | 2014-05-27 | 2015-12-03 | Academia Sinica | Anti-cd20 glycoantibodies and uses thereof |
| US11332523B2 (en) | 2014-05-28 | 2022-05-17 | Academia Sinica | Anti-TNF-alpha glycoantibodies and uses thereof |
| TWI745275B (zh) | 2014-09-08 | 2021-11-11 | 中央研究院 | 使用醣脂激活人類ｉＮＫＴ細胞 |
| US9975965B2 (en) | 2015-01-16 | 2018-05-22 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| US10495645B2 (en) | 2015-01-16 | 2019-12-03 | Academia Sinica | Cancer markers and methods of use thereof |
| 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 |
| US10852310B2 (en) | 2015-12-11 | 2020-12-01 | Opko Diagnostics, Llc | Fluidic systems involving incubation of samples and/or reagents |
| CA3006882C (en) | 2015-12-29 | 2023-11-28 | Opko Diagnostics, Llc | Fluid collection device and related methods |
| JP2019515876A (ja) | 2016-03-08 | 2019-06-13 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | Ｎ−グリカンおよびそのアレイのモジュール合成のための方法 |
| TWI764917B (zh) | 2016-08-22 | 2022-05-21 | 醣基生醫股份有限公司 | 抗體、結合片段及使用方法 |
| JP7214718B2 (ja) * | 2017-09-13 | 2023-01-30 | アビバックス | 膀胱癌の治療に使用するためのａｂｘ１９６ |
| 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 |
| US20240092728A1 (en) * | 2021-01-06 | 2024-03-21 | 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 |
| JP2024512318A (ja) | 2021-03-01 | 2024-03-19 | ディシジュアス セラピューティクス， インコーポレイテッド | インバリアントナチュラルキラーｔ細胞を活性化するための化合物および炎症性老化細胞の排除における使用の方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008128062A1 (en) * | 2007-04-13 | 2008-10-23 | The Rockefeller University | Glycolipids and analogues thereof as antigens for nk t cells |
| RU2340622C2 (ru) * | 2002-12-12 | 2008-12-10 | Санофи-Авентис Дойчланд Гмбх | Новые ароматические фторгликозидные производные, содержащие эти соединения лекарственные средства, и их применение |
Family Cites Families (17)
| 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 |
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| 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 |
| CN101036057A (zh) | 2004-10-04 | 2007-09-12 | 阿尔卡米亚有限公司 | 选择性抑制剂 |
| US7534434B2 (en) | 2004-12-28 | 2009-05-19 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NK T cells |
| WO2007113841A2 (en) * | 2006-04-03 | 2007-10-11 | 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 |
| 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 |
| EP2679595B1 (en) | 2008-05-16 | 2016-12-28 | Galecto Biotech AB | Di-(3-deoxy-3-1H-1,2,3-triazol-1-yl)-beta-D-galacto-pyranosyl)sulfane derivatives as galectin-3 inhibitors |
| US7928077B2 (en) * | 2008-07-11 | 2011-04-19 | Academia Sinica | Alpha-galactosyl ceramide analogs and their use as immunotherapies |
| CA2854725C (en) * | 2011-01-05 | 2019-10-22 | National Taiwan University | Methods for preparation of glycosphingolipids and uses thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2340622C2 (ru) * | 2002-12-12 | 2008-12-10 | Санофи-Авентис Дойчланд Гмбх | Новые ароматические фторгликозидные производные, содержащие эти соединения лекарственные средства, и их применение |
| WO2008128062A1 (en) * | 2007-04-13 | 2008-10-23 | The Rockefeller University | Glycolipids and analogues thereof as antigens for nk t cells |
Non-Patent Citations (2)
| Title |
|---|
| Kun-Hsien Lin et al. Antimicrobial Agents an Chemotherapy, 2010, 4129-4136. * |
| Matthias Trappeniers et al. ChemMedChem, 2008, 3, 1061-1070. * |
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| BR112013017382B1 (pt) | 2021-03-16 |
| JP2014504593A (ja) | 2014-02-24 |
| JP6259887B2 (ja) | 2018-01-10 |
| JP2017061481A (ja) | 2017-03-30 |
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