JP2013528211A5 - - Google Patents
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- Publication number
- JP2013528211A5 JP2013528211A5 JP2013514126A JP2013514126A JP2013528211A5 JP 2013528211 A5 JP2013528211 A5 JP 2013528211A5 JP 2013514126 A JP2013514126 A JP 2013514126A JP 2013514126 A JP2013514126 A JP 2013514126A JP 2013528211 A5 JP2013528211 A5 JP 2013528211A5
- Authority
- JP
- Japan
- Prior art keywords
- trisaccharide
- fatty acid
- ester
- substituted
- groups
- 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
Links
- 150000004043 trisaccharides Chemical class 0.000 claims 59
- 235000014113 dietary fatty acids Nutrition 0.000 claims 39
- 229930195729 fatty acid Natural products 0.000 claims 39
- 239000000194 fatty acid Substances 0.000 claims 39
- 238000000034 method Methods 0.000 claims 17
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 claims 16
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 15
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 claims 15
- 229920006395 saturated elastomer Polymers 0.000 claims 15
- 150000004671 saturated fatty acids Chemical class 0.000 claims 15
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 15
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 15
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 claims 15
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 claims 13
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 claims 13
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 claims 13
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 12
- 150000002148 esters Chemical class 0.000 claims 12
- QWIZNVHXZXRPDR-UHFFFAOYSA-N D-melezitose Natural products O1C(CO)C(O)C(O)C(O)C1OC1C(O)C(CO)OC1(CO)OC1OC(CO)C(O)C(O)C1O QWIZNVHXZXRPDR-UHFFFAOYSA-N 0.000 claims 11
- 150000004665 fatty acids Chemical class 0.000 claims 11
- QWIZNVHXZXRPDR-WSCXOGSTSA-N melezitose Chemical compound O([C@@]1(O[C@@H]([C@H]([C@@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)CO)CO)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWIZNVHXZXRPDR-WSCXOGSTSA-N 0.000 claims 11
- 125000000129 anionic group Chemical group 0.000 claims 10
- 239000002671 adjuvant Substances 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 7
- -1 fatty acid ester Chemical class 0.000 claims 7
- 239000005639 Lauric acid Substances 0.000 claims 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 6
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims 6
- 229910019142 PO4 Inorganic materials 0.000 claims 5
- 239000010452 phosphate Substances 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 235000021314 Palmitic acid Nutrition 0.000 claims 3
- 235000021355 Stearic acid Nutrition 0.000 claims 3
- 125000004185 ester group Chemical group 0.000 claims 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 3
- 239000008117 stearic acid Substances 0.000 claims 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims 2
- ODEHMIGXGLNAKK-OESPXIITSA-N 6-kestotriose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 ODEHMIGXGLNAKK-OESPXIITSA-N 0.000 claims 1
- DBTMGCOVALSLOR-VXXRBQRTSA-N alpha-D-Glcp-(1->3)-alpha-D-Glcp-(1->3)-D-Glcp Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](CO)OC(O)[C@@H]2O)O)O[C@H](CO)[C@H]1O DBTMGCOVALSLOR-VXXRBQRTSA-N 0.000 claims 1
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims 1
- 239000007764 o/w emulsion Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000865 phosphorylative effect Effects 0.000 claims 1
- 229950008882 polysorbate Drugs 0.000 claims 1
- 229920000136 polysorbate Polymers 0.000 claims 1
- 235000003441 saturated fatty acids Nutrition 0.000 claims 1
- 229940032094 squalane Drugs 0.000 claims 1
- 230000001180 sulfating effect Effects 0.000 claims 1
- 230000019635 sulfation Effects 0.000 claims 1
- 238000005670 sulfation reaction Methods 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10165707A EP2397484A1 (en) | 2010-06-11 | 2010-06-11 | Trisaccharide derivates, and their use as adjuvants |
| EP10165707.0 | 2010-06-11 | ||
| PCT/NL2011/050393 WO2011155822A1 (en) | 2010-06-11 | 2011-06-03 | Trisaccharide derivates, and their use as adjuvants |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016119032A Division JP2016216471A (ja) | 2010-06-11 | 2016-06-15 | 三糖誘導体及びアジュバントとしてのその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013528211A JP2013528211A (ja) | 2013-07-08 |
| JP2013528211A5 true JP2013528211A5 (enExample) | 2014-06-05 |
| JP6004586B2 JP6004586B2 (ja) | 2016-10-12 |
Family
ID=43734127
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013514126A Expired - Fee Related JP6004586B2 (ja) | 2010-06-11 | 2011-06-03 | 三糖誘導体及びアジュバントとしてのその使用 |
| JP2016119032A Pending JP2016216471A (ja) | 2010-06-11 | 2016-06-15 | 三糖誘導体及びアジュバントとしてのその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016119032A Pending JP2016216471A (ja) | 2010-06-11 | 2016-06-15 | 三糖誘導体及びアジュバントとしてのその使用 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US9327020B2 (enExample) |
| EP (3) | EP2397484A1 (enExample) |
| JP (2) | JP6004586B2 (enExample) |
| KR (1) | KR101929973B1 (enExample) |
| CN (1) | CN103154013B (enExample) |
| AU (1) | AU2011262606B2 (enExample) |
| BR (1) | BR112012031440A2 (enExample) |
| CA (1) | CA2802023C (enExample) |
| CY (1) | CY1119704T1 (enExample) |
| DK (1) | DK2580226T3 (enExample) |
| ES (1) | ES2654156T3 (enExample) |
| HR (1) | HRP20171947T1 (enExample) |
| HU (1) | HUE035187T2 (enExample) |
| IL (1) | IL223570A (enExample) |
| LT (1) | LT2580226T (enExample) |
| MX (1) | MX342946B (enExample) |
| NO (1) | NO2580226T3 (enExample) |
| PL (1) | PL2580226T3 (enExample) |
| PT (1) | PT2580226T (enExample) |
| RS (1) | RS56690B1 (enExample) |
| RU (1) | RU2595717C2 (enExample) |
| SI (1) | SI2580226T1 (enExample) |
| SM (1) | SMT201700603T1 (enExample) |
| WO (1) | WO2011155822A1 (enExample) |
| ZA (1) | ZA201209395B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2397484A1 (en) * | 2010-06-11 | 2011-12-21 | Immunovo B.V. | Trisaccharide derivates, and their use as adjuvants |
| NZ728551A (en) * | 2014-07-24 | 2023-02-24 | Litevax B V | Sulphated carbohydrate fatty acid esters as vaccine adjuvants |
| KR102922337B1 (ko) | 2023-10-11 | 2026-02-05 | 세종대학교산학협력단 | 삼당류의 제조방법 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4232150A (en) * | 1979-07-09 | 1980-11-04 | American Cyanamid Company | Oligosaccharide precursors to substituted O-α-D and O-β-D-multigalactopyranosyl and glucopyranosyl 1→4 and 1→6 galactopyranosyl 1→6α-D-glucopyranoses |
| GB8703128D0 (en) * | 1987-02-11 | 1987-03-18 | Donmarn Ltd | Anti-scaling compounds |
| US5543505A (en) * | 1993-03-15 | 1996-08-06 | Sloan-Kettering Institute For Cancer Research | Synthetic compounds which bind to H. pylori, and uses thereof |
| US5708163A (en) * | 1994-03-15 | 1998-01-13 | Sloan-Kettering Institute Of Cancer Research | Synthesis of the breast tumor-associated antigen defined by monoclonalantibody MBRL and uses thereof |
| US6303120B1 (en) * | 1994-03-15 | 2001-10-16 | Memorial Sloan-Kettering Institute For Cancer Research | Synthesis of glycoconjugates of the lewis y epitope and uses thereof |
| ATE252373T1 (de) * | 1994-08-04 | 2003-11-15 | Elan Drug Delivery Ltd | Feste verabreichungssysteme zur gesteuerten freisetzung von darin eingebauten molekülen sowie verfahren zu deren herstellung |
| BE1008978A5 (fr) | 1994-12-27 | 1996-10-01 | Solvay | Adjuvants pour vaccins. |
| ZA9711732B (en) * | 1996-12-31 | 1998-12-28 | Quadrant Holdings Cambridge | Methods and compositions for improvement bioavailability of bioactive agents for mucosal delivery |
| US6352722B1 (en) * | 1997-12-23 | 2002-03-05 | Quadrant Holdings Cambridge Limited | Derivatized carbohydrates, compositions comprised thereof and methods of use thereof |
| JP3041799B1 (ja) * | 1998-09-29 | 2000-05-15 | 株式会社微生物化学研究所 | 新規なアジュバント及びそれを用いたワクチン |
| EP1104767A1 (en) * | 1999-11-30 | 2001-06-06 | Stichting Dienst Landbouwkundig Onderzoek | Mono- and disaccharide derivatives containing both fatty acid ester and sulfate ester groups |
| GB0124710D0 (en) * | 2001-10-15 | 2001-12-05 | Quadrant Healthcare Uk Ltd | Therapeutic composition |
| DE602005010101D1 (de) * | 2005-12-01 | 2008-11-13 | Wella Ag | Verwendung von Di- oder Oligosaccharidepolyestern in Haarstylingprodukten |
| US9045516B2 (en) * | 2007-04-16 | 2015-06-02 | Suri Saranathan Iyer | Synthetic ligands for the differentiation of closely related toxins and pathogens |
| WO2009140683A1 (en) * | 2008-05-16 | 2009-11-19 | Research Foundation Of The City University Of New York | Living copolymer protein/peptide hybrids for biomedical applications |
| US8993536B2 (en) * | 2009-02-02 | 2015-03-31 | Otsuka Chemical Co., Ltd. | Low-molecular polysulfated hyaluronic acid derivative and medicine containing same |
| EP2397484A1 (en) * | 2010-06-11 | 2011-12-21 | Immunovo B.V. | Trisaccharide derivates, and their use as adjuvants |
-
2010
- 2010-06-11 EP EP10165707A patent/EP2397484A1/en not_active Withdrawn
-
2011
- 2011-06-03 EP EP17204140.2A patent/EP3312188A1/en not_active Withdrawn
- 2011-06-03 BR BR112012031440A patent/BR112012031440A2/pt not_active Application Discontinuation
- 2011-06-03 LT LTEP11725217.1T patent/LT2580226T/lt unknown
- 2011-06-03 CN CN201180034937.5A patent/CN103154013B/zh not_active Expired - Fee Related
- 2011-06-03 PT PT117252171T patent/PT2580226T/pt unknown
- 2011-06-03 RS RS20171307A patent/RS56690B1/sr unknown
- 2011-06-03 PL PL11725217T patent/PL2580226T3/pl unknown
- 2011-06-03 SM SM20170603T patent/SMT201700603T1/it unknown
- 2011-06-03 HU HUE11725217A patent/HUE035187T2/hu unknown
- 2011-06-03 SI SI201131368T patent/SI2580226T1/en unknown
- 2011-06-03 ES ES11725217.1T patent/ES2654156T3/es active Active
- 2011-06-03 CA CA2802023A patent/CA2802023C/en not_active Expired - Fee Related
- 2011-06-03 MX MX2012014422A patent/MX342946B/es active IP Right Grant
- 2011-06-03 EP EP11725217.1A patent/EP2580226B1/en active Active
- 2011-06-03 WO PCT/NL2011/050393 patent/WO2011155822A1/en not_active Ceased
- 2011-06-03 DK DK11725217.1T patent/DK2580226T3/en active
- 2011-06-03 NO NO11725217A patent/NO2580226T3/no unknown
- 2011-06-03 RU RU2013100945/04A patent/RU2595717C2/ru active
- 2011-06-03 US US13/703,329 patent/US9327020B2/en not_active Expired - Fee Related
- 2011-06-03 AU AU2011262606A patent/AU2011262606B2/en not_active Ceased
- 2011-06-03 JP JP2013514126A patent/JP6004586B2/ja not_active Expired - Fee Related
- 2011-06-03 KR KR1020137000623A patent/KR101929973B1/ko not_active Expired - Fee Related
- 2011-06-03 HR HRP20171947TT patent/HRP20171947T1/hr unknown
-
2012
- 2012-12-11 IL IL223570A patent/IL223570A/en active IP Right Grant
- 2012-12-11 ZA ZA2012/09395A patent/ZA201209395B/en unknown
-
2016
- 2016-04-05 US US15/090,853 patent/US20170057987A1/en not_active Abandoned
- 2016-06-15 JP JP2016119032A patent/JP2016216471A/ja active Pending
-
2017
- 2017-12-21 CY CY20171101340T patent/CY1119704T1/el unknown
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