JP2008525495A5 - - Google Patents
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- Publication number
- JP2008525495A5 JP2008525495A5 JP2007548576A JP2007548576A JP2008525495A5 JP 2008525495 A5 JP2008525495 A5 JP 2008525495A5 JP 2007548576 A JP2007548576 A JP 2007548576A JP 2007548576 A JP2007548576 A JP 2007548576A JP 2008525495 A5 JP2008525495 A5 JP 2008525495A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- represented
- pharmaceutically acceptable
- acceptable salt
- compound
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229960005486 vaccine Drugs 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- -1 sodium salt compound Chemical class 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000004044 response Effects 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 235000021360 Myristic acid Nutrition 0.000 description 2
- 230000033289 adaptive immune response Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 210000002443 helper t lymphocyte Anatomy 0.000 description 2
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 description 1
- JYZJYKOZGGEXSX-ZDUSSCGKSA-N (2S)-2-hydroxytetradecanoic acid Chemical compound CCCCCCCCCCCC[C@H](O)C(O)=O JYZJYKOZGGEXSX-ZDUSSCGKSA-N 0.000 description 1
- 0 C1*2=C=C1CC2 Chemical compound C1*2=C=C1CC2 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 230000005875 antibody response Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007969 cellular immunity Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000014828 interferon-gamma production Effects 0.000 description 1
- 230000031261 interleukin-10 production Effects 0.000 description 1
- 230000004073 interleukin-2 production Effects 0.000 description 1
- 230000017307 interleukin-4 production Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63940804P | 2004-12-28 | 2004-12-28 | |
| US60/639,408 | 2004-12-28 | ||
| PCT/US2005/047017 WO2006071848A2 (en) | 2004-12-28 | 2005-12-27 | Glycolipids and analogues thereof as antigens for nk t cells |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008525495A JP2008525495A (ja) | 2008-07-17 |
| JP2008525495A5 true JP2008525495A5 (https=) | 2009-02-19 |
| JP5090928B2 JP5090928B2 (ja) | 2012-12-05 |
Family
ID=36615471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548576A Expired - Fee Related JP5090928B2 (ja) | 2004-12-28 | 2005-12-27 | Ｎｋｔ細胞に対する抗原としての糖脂質及びその類似体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7534434B2 (https=) |
| EP (1) | EP1833489A4 (https=) |
| JP (1) | JP5090928B2 (https=) |
| AU (1) | AU2005322027B2 (https=) |
| CA (1) | CA2591232C (https=) |
| WO (1) | WO2006071848A2 (https=) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9809654B2 (en) | 2002-09-27 | 2017-11-07 | Vaccinex, Inc. | Targeted CD1d molecules |
| US7645873B2 (en) * | 2003-03-20 | 2010-01-12 | The Scripps Research Institute | 6″-amino-6″-deoxygalactosylceramides |
| US20060269524A1 (en) * | 2004-02-19 | 2006-11-30 | Kibun Food Chemifa Co., Ltd. | Composition for nkt cell activation |
| US7923013B2 (en) * | 2004-12-28 | 2011-04-12 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NKT cells |
| US7534434B2 (en) | 2004-12-28 | 2009-05-19 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NK T cells |
| DE602006019759D1 (de) * | 2005-09-29 | 2011-03-03 | Torrey Pines Inst | Sulfatide zur behandlung von autoimmunkrankheiten |
| DK2056842T3 (da) | 2006-04-07 | 2013-01-14 | Univ Chicago | Modificeret galactosylceramid til behandling af cancerøse sygdomme |
| US8883745B2 (en) * | 2006-05-22 | 2014-11-11 | New York University | C—glycolipids with enhanced Th-1 profile |
| EP2040541B1 (en) * | 2006-06-30 | 2016-03-23 | The Scripps Research Institute | Adjuvants and methods of use |
| AU2008219020B2 (en) * | 2007-02-21 | 2013-08-22 | Vaccinex, Inc. | Modulation of NKT cell activity with antigen-loaded CDId molecules |
| US7960139B2 (en) | 2007-03-23 | 2011-06-14 | Academia Sinica | Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells |
| EP2144594A4 (en) * | 2007-04-13 | 2012-12-05 | Academia Sinica | ALPHA-GALACTOSYL CERAMIDE ANALOGUES AND THEIR USE IN IMMUNOTHERAPIES |
| JP5331100B2 (ja) * | 2007-04-25 | 2013-10-30 | イミュアールエックス・インコーポレーテッド | Ｎｋｔアクチベータ、ｃｄ４０アゴニスト、及び任意選択的に抗原を含んでなるアジュバント組合せと、細胞性免疫において相乗的な増強を誘導するためのその使用 |
| US8916164B2 (en) * | 2007-08-29 | 2014-12-23 | Abivax | Methods of enhancing adjuvaticity of vaccine compositions |
| EP2058011A1 (en) * | 2007-11-07 | 2009-05-13 | Wittycell | Nkt cell activating gycolipids covalently bound antigens and/or drug |
| RU2537188C2 (ru) * | 2007-12-05 | 2014-12-27 | Виттисель | Композиции и способы для усиления имунного ответа на антигены |
| AU2009268937A1 (en) | 2008-06-16 | 2010-01-14 | Aj Park | Compositions for inducing immune responses specific to Globo H and SSEA3 and uses thereof in cancer treatment |
| GB2461656B (en) * | 2008-07-11 | 2012-11-21 | Academia Sinica | Alpha-galactosyl ceramide analogues and their use as immunotherapies, adjuvants, and antiviral, antibacterial and anticancer agents |
| US7928077B2 (en) | 2008-07-11 | 2011-04-19 | Academia Sinica | Alpha-galactosyl ceramide analogs and their use as immunotherapies |
| 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 |
| JP5809560B2 (ja) * | 2008-10-08 | 2015-11-11 | アビヴァックス | インフルエンザに対して使用するためのワクチン組成物 |
| CN102325875B (zh) * | 2009-01-08 | 2018-04-10 | 阿尔伯爱因斯坦医学有限公司 | 具有细胞壁结合神经酰胺类糖脂的细菌疫苗及其应用 |
| 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 |
| US9181292B2 (en) | 2011-01-05 | 2015-11-10 | Pi-Hui Liang | Methods for preparation of glycosphingolipids and uses thereof |
| US20120288525A1 (en) | 2011-05-11 | 2012-11-15 | Chakravarty Sumana | Pharmaceutical compositions comprising attenuated plasmodium sporozoites and glycolipid adjuvants |
| US10130714B2 (en) | 2012-04-14 | 2018-11-20 | Academia Sinica | Enhanced anti-influenza agents conjugated with anti-inflammatory activity |
| IN2015KN00492A (https=) * | 2012-07-26 | 2015-07-17 | Callaghan Innovation Res Ltd | |
| WO2014031498A1 (en) | 2012-08-18 | 2014-02-27 | Academia Sinica | Cell-permeable probes for identification and imaging of sialidases |
| WO2014088432A1 (en) * | 2012-12-06 | 2014-06-12 | Callaghan Innovation Research Limited | Conjugate compounds |
| US9371352B2 (en) | 2013-02-08 | 2016-06-21 | Vaccinex, Inc. | Modified glycolipids and methods of making and using the same |
| AU2014214770B2 (en) * | 2013-02-08 | 2018-09-06 | Albert Einstein College Of Medicine Inc. | Modified glycolipids and methods of making and using the same |
| EP3013365B1 (en) | 2013-06-26 | 2019-06-05 | Academia Sinica | Rm2 antigens and use thereof |
| EP3013347B1 (en) | 2013-06-27 | 2019-12-11 | Academia Sinica | Glycan conjugates and use thereof |
| JP6486368B2 (ja) * | 2013-09-06 | 2019-03-20 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | 改変されたグリコシル基を含む糖脂質を用いたヒトｉＮＫＴ細胞の活性化 |
| US10150818B2 (en) | 2014-01-16 | 2018-12-11 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| AU2015206370A1 (en) | 2014-01-16 | 2016-07-07 | Academia Sinica | Compositions and methods for treatment and detection of cancers |
| CN106415244B (zh) | 2014-03-27 | 2020-04-24 | 中央研究院 | 反应性标记化合物及其用途 |
| CA2950415A1 (en) | 2014-05-27 | 2015-12-03 | 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 |
| CN106661099A (zh) | 2014-05-27 | 2017-05-10 | 中央研究院 | 抗her2醣抗体及其用途 |
| JP7093612B2 (ja) | 2014-05-27 | 2022-06-30 | アカデミア シニカ | Ｂａｃｔｅｒｏｉｄｅｓ由来のフコシダーゼおよびそれを使用する方法 |
| WO2015184001A1 (en) | 2014-05-28 | 2015-12-03 | 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 |
| 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 |
| JP6779887B2 (ja) | 2015-01-24 | 2020-11-04 | アカデミア シニカＡｃａｄｅｍｉａ Ｓｉｎｉｃａ | 新規なグリカンコンジュゲートおよびその使用方法 |
| EP3426693A4 (en) | 2016-03-08 | 2019-11-13 | Academia Sinica | PROCESS FOR MODULAR SYNTHESIS OF N-GLYCANES AND ARRANGEMENTS THEREOF |
| CA3034057A1 (en) | 2016-08-22 | 2018-03-01 | CHO Pharma Inc. | Antibodies, binding fragments, and methods of use |
| CN106496012B (zh) * | 2016-10-08 | 2019-03-22 | 张家港市华昌药业有限公司 | 一种α-羟基十四酸的制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5936076A (en) * | 1991-08-29 | 1999-08-10 | Kirin Beer Kabushiki Kaisha | αgalactosylceramide derivatives |
| AU687733B2 (en) | 1992-04-01 | 1998-03-05 | Rockefeller University, The | Method for in vitro proliferation of dendritic cell precursors and their use to produce immunogens |
| TW261533B (https=) * | 1992-07-16 | 1995-11-01 | Kirin Brewery | |
| AU683026B2 (en) * | 1992-10-22 | 1997-10-30 | Kirin Pharma Kabushiki Kaisha | Novel shingoglycolipid and use thereof |
| US5405772A (en) | 1993-06-18 | 1995-04-11 | Amgen Inc. | Medium for long-term proliferation and development of cells |
| AU702871B2 (en) | 1993-08-23 | 1999-03-11 | Nexell Therapeutics Inc. | (In vitro) growth of neutrophil and megakaryocyte precursors in serum-free media |
| US5663151A (en) * | 1994-03-04 | 1997-09-02 | Bristol-Myers Squibb Company | Sulfated α-glycolipid derivatives as cell adhesion inhibitors |
| US6417167B1 (en) * | 1997-02-05 | 2002-07-09 | Kirin Beer Kabushiki Kaisha | Lyophilized compositions containing shingoglycolipid and process for preparing them |
| JP3495740B2 (ja) * | 1997-04-10 | 2004-02-09 | 麒麟麦酒株式会社 | α−グリコシルセラミドを含有するＮＫＴ細胞活性化剤 |
| EP1437358B1 (en) * | 2001-08-16 | 2006-10-18 | Daiichi Asubio Pharma Co., Ltd. | Novel glycolipid and remedial agent for autoimmune disease containing the same as active ingredient |
| ES2676345T3 (es) * | 2003-02-14 | 2018-07-18 | Japan As Represented By President Of National Center Of Neurology And Psychiatry Ministry Of Health | Derivados del glicolípido, proceso para su producción, intermedios para la síntesis del mismo, y proceso para la producción de los intermedios |
| EP1784196B1 (en) * | 2004-08-27 | 2016-12-21 | Albert Einstein College Of Medicine Of Yeshiva University | Ceramide derivatives as modulators of immunity and autoimmunity |
| US7923013B2 (en) * | 2004-12-28 | 2011-04-12 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NKT cells |
| US7534434B2 (en) * | 2004-12-28 | 2009-05-19 | The Rockefeller University | Glycolipids and analogues thereof as antigens for NK T cells |
| WO2007035717A2 (en) | 2005-09-19 | 2007-03-29 | The Rockefeller University | Glycolipids and analogues thereof as antigents for nk t cells |
-
2005
- 2005-12-27 US US11/317,900 patent/US7534434B2/en not_active Expired - Fee Related
- 2005-12-27 CA CA2591232A patent/CA2591232C/en not_active Expired - Fee Related
- 2005-12-27 JP JP2007548576A patent/JP5090928B2/ja not_active Expired - Fee Related
- 2005-12-27 WO PCT/US2005/047017 patent/WO2006071848A2/en not_active Ceased
- 2005-12-27 EP EP05857215A patent/EP1833489A4/en not_active Withdrawn
- 2005-12-27 AU AU2005322027A patent/AU2005322027B2/en not_active Ceased
-
2009
- 2009-02-18 US US12/388,415 patent/US20090233875A1/en not_active Abandoned
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