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 (enExample) | 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 (enExample) |
| EP (1) | EP1833489A4 (enExample) |
| JP (1) | JP5090928B2 (enExample) |
| AU (1) | AU2005322027B2 (enExample) |
| CA (1) | CA2591232C (enExample) |
| WO (1) | WO2006071848A2 (enExample) |
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 |
| EP1716857A4 (en) * | 2004-02-19 | 2010-08-04 | Kibun Food Chemifa | COMPOSITION FOR ACTIVATION OF NKT CELLS |
| 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 |
| US8044029B2 (en) * | 2005-09-29 | 2011-10-25 | Torrey Pines Institute For Molecular Studies | Sulfatides for treatment of autoimmune disorders |
| PT2056842E (pt) | 2006-04-07 | 2013-01-24 | Univ Chicago | Galactosil-ceramidas modificadas para coloração e estimulação de células t assassinas naturais |
| WO2007137258A2 (en) * | 2006-05-22 | 2007-11-29 | New York University | C-glycolipids with enhanced th-1 profile |
| AU2007269299B2 (en) * | 2006-06-30 | 2013-01-17 | Brigham Young University | Adjuvants and methods of use |
| JP5357782B2 (ja) * | 2007-02-21 | 2013-12-04 | バクシネックス インコーポレーティッド | 抗原負荷ＣＤ１ｄ分子によるＮＫＴ細胞活性の調節 |
| 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 |
| WO2008133983A1 (en) | 2007-04-25 | 2008-11-06 | Immurx, Inc. | Adjuvant combinations of nkt activator, cd40 agonist, and optional antigen, the use through inducing synergistic cellular immunity |
| 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 |
| US8207135B2 (en) * | 2007-12-05 | 2012-06-26 | Wittycell | Compositions for and methods of enhancing the immune response to antigens |
| EP2303286A4 (en) | 2008-06-16 | 2011-12-28 | Academia Sinica | COMPOSITIONS FOR GENERATING IMMUNE REACTIONS SPECIFIC TO GLOBO H AND SSEA3 AND THEIR USES IN CANCER TREATMENT |
| US7928077B2 (en) | 2008-07-11 | 2011-04-19 | Academia Sinica | Alpha-galactosyl ceramide analogs and their use as immunotherapies |
| 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 |
| 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 |
| CA2739765A1 (en) * | 2008-10-08 | 2010-04-15 | Vincent Serra | Vaccine composition for use against influenza |
| PT2385980T (pt) * | 2009-01-08 | 2018-06-26 | Albert Einstein College Medicine Inc | Vacinas bacterianas com glicolípidos do tipo ceramida associados à parede celular e utilização dos mesmos |
| 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 |
| US10338069B2 (en) | 2010-04-12 | 2019-07-02 | Academia Sinica | Glycan arrays for high throughput screening of viruses |
| ES2654382T3 (es) | 2011-01-05 | 2018-02-13 | National Taiwan University | Método para la preparación de glucoesfingolípidos |
| 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 |
| CN104736550B (zh) * | 2012-07-26 | 2017-12-29 | 维多利亚联结有限公司 | 有机化合物 |
| AU2013306098A1 (en) | 2012-08-18 | 2015-02-12 | Academia Sinica | Cell-permeable probes for identification and imaging of sialidases |
| NZ708727A (en) * | 2012-12-06 | 2019-09-27 | Victoria Link Ltd | Conjugate compounds |
| CA2900524A1 (en) * | 2013-02-08 | 2014-08-14 | Albert Einstein College Of Medicine Of Yeshiva University | Modified glycolipids and methods of making and using the same |
| US9371352B2 (en) | 2013-02-08 | 2016-06-21 | Vaccinex, Inc. | Modified glycolipids and methods of making and using the same |
| US10086054B2 (en) | 2013-06-26 | 2018-10-02 | Academia Sinica | RM2 antigens and use thereof |
| WO2014210564A1 (en) | 2013-06-27 | 2014-12-31 | Academia Sinica | Glycan conjugates and use thereof |
| AU2014317889B2 (en) * | 2013-09-06 | 2020-03-05 | 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 |
| TW201620939A (zh) | 2014-01-16 | 2016-06-16 | 中央研究院 | 治療及檢測癌症之組合物及方法 |
| 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 |
| US10118969B2 (en) | 2014-05-27 | 2018-11-06 | Academia Sinica | Compositions and methods relating to universal glycoforms for enhanced antibody efficacy |
| AU2015267051B2 (en) | 2014-05-27 | 2022-03-17 | Academia Sinica | Fucosidase from bacteroides and methods using the same |
| AU2015267047A1 (en) | 2014-05-27 | 2017-01-05 | Academia Sinica | Anti-CD20 glycoantibodies and uses thereof |
| JP7062361B2 (ja) | 2014-05-27 | 2022-05-06 | アカデミア シニカ | 抗ｈｅｒ２糖操作抗体群およびその使用 |
| WO2015184001A1 (en) | 2014-05-28 | 2015-12-03 | Academia Sinica | Anti-tnf-alpha glycoantibodies and uses thereof |
| US9879042B2 (en) | 2014-09-08 | 2018-01-30 | 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 |
| 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 |
| KR102588027B1 (ko) | 2016-08-22 | 2023-10-12 | 초 파마 인크. | 항체, 결합 단편 및 사용 방법 |
| 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 (enExample) * | 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 |
| JPH09505462A (ja) | 1993-08-23 | 1997-06-03 | バクスター、インターナショナル、インコーポレイテッド | 無血清培地内での好中球前駆細胞及び巨核球前駆細胞の試験管内増殖 |
| 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 |
| ES2235324T3 (es) * | 1997-04-10 | 2005-07-01 | Kirin Beer Kabushiki Kaisha | Empleo de a-glicosilceramidas para la obtencion de un agente terapeutico para enfermedades autoinmunes. |
| US8367623B2 (en) * | 2001-08-16 | 2013-02-05 | Japan As Represented By President Of National Center Of Neurology And Psychiatry | Glycolipid and medicine for autoimmune disease containing the same as active ingredient |
| CN101165047B (zh) * | 2003-02-14 | 2010-10-20 | 国立精神神经中心主席代表的日本国 | 糖脂衍生物及其制造方法,以及其合成中间体及其制造方法 |
| KR101377116B1 (ko) * | 2004-08-27 | 2014-03-24 | 알버트 아인슈타인 컬리지 오브 메디신 오브 예쉬바 유니버시티 | 면역 및 자가면역의 조절제로서의 세라마이드 유도체 |
| 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 |
| US20090117089A1 (en) | 2005-09-19 | 2009-05-07 | The Rockefeller University | Glycolipids and analogues thereof as antigens for nk t cells |
-
2005
- 2005-12-27 JP JP2007548576A patent/JP5090928B2/ja not_active Expired - Fee Related
- 2005-12-27 EP EP05857215A patent/EP1833489A4/en not_active Withdrawn
- 2005-12-27 AU AU2005322027A patent/AU2005322027B2/en not_active Ceased
- 2005-12-27 US US11/317,900 patent/US7534434B2/en not_active Expired - Fee Related
- 2005-12-27 WO PCT/US2005/047017 patent/WO2006071848A2/en not_active Ceased
- 2005-12-27 CA CA2591232A patent/CA2591232C/en not_active Expired - Fee Related
-
2009
- 2009-02-18 US US12/388,415 patent/US20090233875A1/en not_active Abandoned
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