AU2011262606B2 - Trisaccharide derivates, and their use as adjuvants - Google Patents
Trisaccharide derivates, and their use as adjuvants Download PDFInfo
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- AU2011262606B2 AU2011262606B2 AU2011262606A AU2011262606A AU2011262606B2 AU 2011262606 B2 AU2011262606 B2 AU 2011262606B2 AU 2011262606 A AU2011262606 A AU 2011262606A AU 2011262606 A AU2011262606 A AU 2011262606A AU 2011262606 B2 AU2011262606 B2 AU 2011262606B2
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- AU
- Australia
- Prior art keywords
- trisaccharide
- fatty acid
- derivate
- acid
- raffinose
- 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.)
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- 150000004043 trisaccharides Chemical class 0.000 title claims abstract description 92
- 239000002671 adjuvant Substances 0.000 title claims abstract description 85
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- 229930195729 fatty acid Natural products 0.000 claims abstract description 58
- 239000000194 fatty acid Substances 0.000 claims abstract description 58
- 229960005486 vaccine Drugs 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 28
- 125000004185 ester group Chemical group 0.000 claims abstract description 11
- -1 sulphate ester Chemical class 0.000 claims description 33
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 30
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- 102000036639 antigens Human genes 0.000 claims description 29
- 108091007433 antigens Proteins 0.000 claims description 29
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- 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 description 25
- 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 description 25
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- 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 description 21
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Classifications
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- 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)
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- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
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- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
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- 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 |
|---|---|---|---|
| EP10165707.0 | 2010-06-11 | ||
| EP10165707A EP2397484A1 (en) | 2010-06-11 | 2010-06-11 | 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 |
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| AU2011262606A1 AU2011262606A1 (en) | 2013-01-10 |
| AU2011262606B2 true AU2011262606B2 (en) | 2016-10-27 |
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| EP (3) | EP2397484A1 (enExample) |
| JP (2) | JP6004586B2 (enExample) |
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| CN (1) | CN103154013B (enExample) |
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| 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 |
| KR20250052985A (ko) | 2023-10-11 | 2025-04-21 | 세종대학교산학협력단 | 삼당류의 제조방법 |
Citations (3)
| 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 |
| EP1792607A1 (en) * | 2005-12-01 | 2007-06-06 | Wella Aktiengesellschaft | Use of di- or oligosaccharide polyester in hair styling products |
| US20090042816A1 (en) * | 2007-04-16 | 2009-02-12 | Suri Saranathan Iyer | Synthetic Ligands For The Differentiation Of Closely Related Toxins And Pathogens |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| FI970867A7 (fi) * | 1994-08-04 | 1997-04-08 | Quadrant Drug Delivery Ltd | Kiinteät, annostelusysteemit hallittua vapautumista varten, joihin sys teemeihin molekyylit on sisällytetty ja menetelmät niiden valmistamise ksi |
| BE1008978A5 (fr) | 1994-12-27 | 1996-10-01 | Solvay | Adjuvants pour vaccins. |
| US6517860B1 (en) * | 1996-12-31 | 2003-02-11 | Quadrant Holdings Cambridge, Ltd. | Methods and compositions for improved 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 |
| US9242010B2 (en) * | 2008-05-16 | 2016-01-26 | Research Foundation Of The City University Of New York | Living copolymer-protein/peptide hybrids for biomedical applications |
| WO2010087207A1 (ja) * | 2009-02-02 | 2010-08-05 | 大塚化学株式会社 | 低分子量多硫酸化ヒアルロン酸誘導体及びこれを含有する医薬 |
| 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
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2011
- 2011-06-03 HU HUE11725217A patent/HUE035187T2/hu unknown
- 2011-06-03 HR HRP20171947TT patent/HRP20171947T1/hr unknown
- 2011-06-03 LT LTEP11725217.1T patent/LT2580226T/lt 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 PT PT117252171T patent/PT2580226T/pt unknown
- 2011-06-03 SM SM20170603T patent/SMT201700603T1/it unknown
- 2011-06-03 RU RU2013100945/04A patent/RU2595717C2/ru active
- 2011-06-03 WO PCT/NL2011/050393 patent/WO2011155822A1/en not_active Ceased
- 2011-06-03 RS RS20171307A patent/RS56690B1/sr unknown
- 2011-06-03 PL PL11725217T patent/PL2580226T3/pl unknown
- 2011-06-03 EP EP17204140.2A patent/EP3312188A1/en not_active Withdrawn
- 2011-06-03 DK DK11725217.1T patent/DK2580226T3/en active
- 2011-06-03 BR BR112012031440A patent/BR112012031440A2/pt not_active Application Discontinuation
- 2011-06-03 CN CN201180034937.5A patent/CN103154013B/zh not_active Expired - Fee Related
- 2011-06-03 US US13/703,329 patent/US9327020B2/en not_active Expired - Fee Related
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2016
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- 2016-06-15 JP JP2016119032A patent/JP2016216471A/ja active Pending
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2017
- 2017-12-21 CY CY20171101340T patent/CY1119704T1/el unknown
Patent Citations (3)
| 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 |
| EP1792607A1 (en) * | 2005-12-01 | 2007-06-06 | Wella Aktiengesellschaft | Use of di- or oligosaccharide polyester in hair styling products |
| US20090042816A1 (en) * | 2007-04-16 | 2009-02-12 | Suri Saranathan Iyer | Synthetic Ligands For The Differentiation Of Closely Related Toxins And Pathogens |
Non-Patent Citations (4)
| Title |
|---|
| : YAO, Q. ET AL.: "Chemoenzymatic synthesis of iGb3 and Gb3", ORGANIC LETTERS, vol. 8, no. 6, 2006, pages 911-914, * |
| AKOH, C.C. AND SWANSON, B.G.: "One stage synthesis of raffinose fatty acid polyesters", JOURNAL OF FOOD SCIENCE, vol. 52, no. 6, 1987, pages 1570-1576 * |
| ARNDT PET AL: "Preparation of Cellulose Oligomers from Cellulose Triacetate (Standard Procedure)", CELLULOSE, KLUWER ACADEMIC PUBLISHERS, DO, vol. 12, no. 3, 1 June 2005, pages 317-326, * |
| MOGEMARK, M. ET AL.: ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 1, 2003, pages 2063-2069, * |
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