SI2580226T1 - Trisaccharide derivates, and their use as adjuvants - Google Patents
Trisaccharide derivates, and their use as adjuvants Download PDFInfo
- Publication number
- SI2580226T1 SI2580226T1 SI201131368T SI201131368T SI2580226T1 SI 2580226 T1 SI2580226 T1 SI 2580226T1 SI 201131368 T SI201131368 T SI 201131368T SI 201131368 T SI201131368 T SI 201131368T SI 2580226 T1 SI2580226 T1 SI 2580226T1
- Authority
- SI
- Slovenia
- Prior art keywords
- trisaccharide
- fatty acid
- groups
- esters
- substituted
- Prior art date
Links
- 150000004043 trisaccharides Chemical class 0.000 title claims abstract 40
- 239000002671 adjuvant Substances 0.000 title claims abstract 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract 18
- 229930195729 fatty acid Natural products 0.000 claims abstract 18
- 239000000194 fatty acid Substances 0.000 claims abstract 18
- 239000000203 mixture Substances 0.000 claims abstract 12
- 125000000129 anionic group Chemical group 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims abstract 3
- 229960005486 vaccine Drugs 0.000 claims abstract 3
- -1 fatty acid esters Chemical class 0.000 claims 10
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 8
- 150000003014 phosphoric acid esters Chemical class 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 6
- 239000005639 Lauric acid Substances 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 150000004671 saturated fatty acids Chemical class 0.000 claims 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 3
- 235000021314 Palmitic acid Nutrition 0.000 claims 2
- 235000021355 Stearic acid Nutrition 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000000839 emulsion Substances 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 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
- 239000008117 stearic acid Substances 0.000 claims 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 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 1
- 239000002253 acid Substances 0.000 claims 1
- 230000000890 antigenic effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 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 1
- 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 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims 1
- 229950008882 polysorbate Drugs 0.000 claims 1
- 229920000136 polysorbate Polymers 0.000 claims 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical group 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 1
- 239000002904 solvent Substances 0.000 claims 1
- 229940032094 squalane Drugs 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 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 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000005313 fatty acid group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dispersion Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
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 |
| EP11725217.1A EP2580226B1 (en) | 2010-06-11 | 2011-06-03 | Trisaccharide derivates, and their use as adjuvants |
| PCT/NL2011/050393 WO2011155822A1 (en) | 2010-06-11 | 2011-06-03 | Trisaccharide derivates, and their use as adjuvants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI2580226T1 true SI2580226T1 (en) | 2018-04-30 |
Family
ID=43734127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI201131368T SI2580226T1 (en) | 2010-06-11 | 2011-06-03 | Trisaccharide derivates, and their use as adjuvants |
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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