JP2010514758A5 - - Google Patents
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- JP2010514758A5 JP2010514758A5 JP2009543946A JP2009543946A JP2010514758A5 JP 2010514758 A5 JP2010514758 A5 JP 2010514758A5 JP 2009543946 A JP2009543946 A JP 2009543946A JP 2009543946 A JP2009543946 A JP 2009543946A JP 2010514758 A5 JP2010514758 A5 JP 2010514758A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- dihydroxy
- formula
- pyran
- 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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- -1 aryl alkyl C 5 Chemical compound 0.000 claims description 30
- 125000003277 amino group Chemical group 0.000 claims description 22
- VQFKFAKEUMHBLV-BYSUZVQFSA-N 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQFKFAKEUMHBLV-BYSUZVQFSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000003368 amide group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims description 4
- FKVMWDZRDMCIAJ-UHFFFAOYSA-N undecanamide Chemical compound CCCCCCCCCCC(N)=O FKVMWDZRDMCIAJ-UHFFFAOYSA-N 0.000 claims description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 230000028327 secretion Effects 0.000 claims description 3
- 108090000695 Cytokines Proteins 0.000 claims description 2
- 102000004127 Cytokines Human genes 0.000 claims description 2
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 2
- 210000004443 dendritic cell Anatomy 0.000 claims description 2
- YRIDQLUIJWIYTQ-CMKFUXGOSA-N n-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-11-hydroxyundecanamide Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](NC(=O)CCCCCCCCCCO)CO[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O YRIDQLUIJWIYTQ-CMKFUXGOSA-N 0.000 claims description 2
- BLEPUQBZGDNRHC-CMKFUXGOSA-N n-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-11-sulfanylundecanamide Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](NC(=O)CCCCCCCCCCS)CO[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O BLEPUQBZGDNRHC-CMKFUXGOSA-N 0.000 claims description 2
- VBYGAGMOQCNOGC-HVXYMDBUSA-N n-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-12-hydroxydodecanamide Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](NC(=O)CCCCCCCCCCCO)CO[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O VBYGAGMOQCNOGC-HVXYMDBUSA-N 0.000 claims description 2
- LTHCSWBWNVGEFE-UHFFFAOYSA-N octanamide Chemical compound CCCCCCCC(N)=O LTHCSWBWNVGEFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 229960005486 vaccine Drugs 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 150000002254 galactosylceramides Chemical class 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 description 10
- 0 C*([n]1nnc(SS=*)c1)=C Chemical compound C*([n]1nnc(SS=*)c1)=C 0.000 description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 108090000978 Interleukin-4 Proteins 0.000 description 2
- QPGGZMQVQYITSV-DATVVERSSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-2-(4-heptyltriazol-1-yl)-3,4-dihydroxyoctadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C([C@@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)N1N=NC(CCCCCCC)=C1)O[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O QPGGZMQVQYITSV-DATVVERSSA-N 0.000 description 1
- RNDXMEKYKSSAMK-IUAYPLKUSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-2-(4-hexadecyltriazol-1-yl)-3,4-dihydroxyoctadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 RNDXMEKYKSSAMK-IUAYPLKUSA-N 0.000 description 1
- JFQQZWBTSXQLTC-DHSWYTMZSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-2-(4-hexyltriazol-1-yl)-3,4-dihydroxyoctadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C([C@@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)N1N=NC(CCCCCC)=C1)O[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O JFQQZWBTSXQLTC-DHSWYTMZSA-N 0.000 description 1
- AVDUUWCJJJVSKA-IAYFSJKOSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-3,4-dihydroxy-2-(4-pentacosyltriazol-1-yl)octadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 AVDUUWCJJJVSKA-IAYFSJKOSA-N 0.000 description 1
- YLAIBGQPPXWHSD-WGUQISDVSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-3,4-dihydroxy-2-(4-tetracosyltriazol-1-yl)octadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 YLAIBGQPPXWHSD-WGUQISDVSA-N 0.000 description 1
- KCRBJQLTYCOVMS-JYWCXLKKSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-3,4-dihydroxy-2-(4-tricosyltriazol-1-yl)octadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 KCRBJQLTYCOVMS-JYWCXLKKSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- XUHWMOZKLZBMMU-UHFFFAOYSA-N 4-(6-phenylhexyl)-2H-triazole Chemical compound C1(=CC=CC=C1)CCCCCCC=1N=NNC=1 XUHWMOZKLZBMMU-UHFFFAOYSA-N 0.000 description 1
- LRICDRQZYJXCKY-UHFFFAOYSA-N C1(=CC=CC=C1)CCCCCCCC=1N=NNC1 Chemical compound C1(=CC=CC=C1)CCCCCCCC=1N=NNC1 LRICDRQZYJXCKY-UHFFFAOYSA-N 0.000 description 1
- YFFHTFRKLOPKKB-UHFFFAOYSA-N C1(=CC=CC=C1)CCCCCCCCC=1N=NNC1 Chemical compound C1(=CC=CC=C1)CCCCCCCCC=1N=NNC1 YFFHTFRKLOPKKB-UHFFFAOYSA-N 0.000 description 1
- 102100037850 Interferon gamma Human genes 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020060139200A KR100868959B1 (ko) | 2006-12-30 | 2006-12-30 | 알파-갈락토실세라마이드 유도체, 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는면역보조용 약학적 조성물 |
| KR10-2006-0139200 | 2006-12-30 | ||
| PCT/KR2007/006889 WO2008082156A1 (en) | 2006-12-30 | 2007-12-27 | Alpha-galactosylceramide derivatives, pharmaceutically acceptable salts thereof, preparation method and pharmaceutical composition for the immune adjuvant containing the same as an active ingredient |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010514758A JP2010514758A (ja) | 2010-05-06 |
| JP2010514758A5 true JP2010514758A5 (enExample) | 2012-08-02 |
| JP5167273B2 JP5167273B2 (ja) | 2013-03-21 |
Family
ID=39588766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009543946A Active JP5167273B2 (ja) | 2006-12-30 | 2007-12-27 | αガラクトシルセラミド誘導体、その薬学的に許容可能な塩、その製造方法及びそれを有効成分として含む免疫補助用薬学的組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8883746B2 (enExample) |
| EP (1) | EP2102225A4 (enExample) |
| JP (1) | JP5167273B2 (enExample) |
| KR (1) | KR100868959B1 (enExample) |
| CN (2) | CN101573369A (enExample) |
| WO (1) | WO2008082156A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8916164B2 (en) | 2007-08-29 | 2014-12-23 | Abivax | Methods of enhancing adjuvaticity of vaccine compositions |
| US8207135B2 (en) | 2007-12-05 | 2012-06-26 | Wittycell | Compositions for and methods of enhancing the immune response to antigens |
| US7928077B2 (en) * | 2008-07-11 | 2011-04-19 | Academia Sinica | Alpha-galactosyl ceramide analogs and their use as immunotherapies |
| CA2739765A1 (en) | 2008-10-08 | 2010-04-15 | Vincent Serra | Vaccine composition for use against influenza |
| KR20110045545A (ko) * | 2009-10-27 | 2011-05-04 | 서울대학교산학협력단 | 신규 알파-갈락토실세라마이드 유도체, 이의 약학적으로 허용 가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 면역보조용 약학적 조성물 |
| JP5669215B2 (ja) | 2010-02-05 | 2015-02-12 | 独立行政法人理化学研究所 | 新規合成糖脂質およびその用途 |
| ES2654382T3 (es) * | 2011-01-05 | 2018-02-13 | National Taiwan University | Método para la preparación de glucoesfingolípidos |
| KR101307331B1 (ko) * | 2012-02-01 | 2013-09-10 | 서울대학교산학협력단 | 신규 알파-갈락토실세라마이드 유도체, 이의 약학적으로 허용 가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 면역보조용 약학적 조성물 |
| US10227290B2 (en) * | 2012-02-07 | 2019-03-12 | The Regents Of The University Of California | Glycosphingolipids for use in modulating immune responses |
| JP6233890B2 (ja) * | 2012-08-03 | 2017-11-22 | 国立研究開発法人理化学研究所 | 水酸化ｋｒｎ７０００類縁体及びその用途 |
| KR101969129B1 (ko) * | 2012-08-03 | 2019-04-15 | (주)스파크바이오파마 | 알파-갈락토실세라마이드 유사체, 이의 제조방법 및 이를 포함하는 면역조절 이상으로 인한 질환의 치료 또는 예방용 약학적 조성물 |
| JP2015531384A (ja) | 2012-10-03 | 2015-11-02 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | インバリアントｎｋｔ細胞アゴニストを用いたインフルエンザ後の細菌重複感染の予防的処置のための方法及び薬学的組成物 |
| CA2925878A1 (en) | 2012-10-12 | 2014-04-17 | The Brigham And Women's Hospital, Inc. | Glycosphingolipids and methods of use thereof |
| EP3434684A4 (en) * | 2016-03-22 | 2019-11-27 | Keio University | COMPOUND OR SALT THEREOF, NATURAL KILLER T CELL ACTIVATOR AND PHARMACEUTICAL COMPOSITION |
| WO2017207040A1 (en) | 2016-06-01 | 2017-12-07 | Vib Vzw | ANTI-CANCER THERAPY USING A LEPTIN ANTAGONIST AND AN iNKT-CELL ACTIVATOR |
| EP4174074A1 (en) | 2021-10-29 | 2023-05-03 | Consejo Superior de Investigaciones Científicas (CSIC) | Multiantennary glycolipid mimetics |
| CN115286667B (zh) * | 2022-08-02 | 2024-03-26 | 华中农业大学 | 一种α-半乳糖基神经酰胺类似物及其制备方法和应用 |
| WO2025035125A1 (en) * | 2023-08-10 | 2025-02-13 | The Curators Of The University Of Missouri | Suppression of type 1 diabetes by intrathymic il-4 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0181351A4 (en) * | 1984-05-09 | 1989-06-21 | Univ Australian | METHOD FOR MODULATING IMMUNE REACTION. |
| US5936076A (en) * | 1991-08-29 | 1999-08-10 | Kirin Beer Kabushiki Kaisha | αgalactosylceramide derivatives |
| JPH0559081A (ja) * | 1991-08-29 | 1993-03-09 | Kirin Brewery Co Ltd | 新規スフインゴ糖脂質、その製造法および使用 |
| 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 |
| JP2005533057A (ja) * | 2002-06-13 | 2005-11-04 | ニューヨーク・ユニバーシティ | 合成ｃ−糖脂質、ならびに癌、感染性疾患および自己免疫疾患を処置するための合成ｃ−糖脂質の使用 |
| KR101377116B1 (ko) * | 2004-08-27 | 2014-03-24 | 알버트 아인슈타인 컬리지 오브 메디신 오브 예쉬바 유니버시티 | 면역 및 자가면역의 조절제로서의 세라마이드 유도체 |
-
2006
- 2006-12-30 KR KR1020060139200A patent/KR100868959B1/ko not_active Expired - Fee Related
-
2007
- 2007-12-27 JP JP2009543946A patent/JP5167273B2/ja active Active
- 2007-12-27 WO PCT/KR2007/006889 patent/WO2008082156A1/en not_active Ceased
- 2007-12-27 CN CNA2007800486889A patent/CN101573369A/zh active Pending
- 2007-12-27 EP EP07851806A patent/EP2102225A4/en not_active Withdrawn
- 2007-12-27 CN CN201210275308.8A patent/CN102816189B/zh active Active
- 2007-12-27 US US12/521,487 patent/US8883746B2/en active Active
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