ZA200201667B - Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them. - Google Patents
Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them. Download PDFInfo
- Publication number
- ZA200201667B ZA200201667B ZA200201667A ZA200201667A ZA200201667B ZA 200201667 B ZA200201667 B ZA 200201667B ZA 200201667 A ZA200201667 A ZA 200201667A ZA 200201667 A ZA200201667 A ZA 200201667A ZA 200201667 B ZA200201667 B ZA 200201667B
- Authority
- ZA
- South Africa
- Prior art keywords
- disaccharide
- ribitol
- mixture
- benzyl
- new
- Prior art date
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- 150000002482 oligosaccharides Chemical class 0.000 title claims description 66
- 229920001542 oligosaccharide Polymers 0.000 title claims description 63
- 229960005486 vaccine Drugs 0.000 title claims description 45
- 239000000203 mixture Substances 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 67
- 150000002016 disaccharides Chemical class 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 238000003786 synthesis reaction Methods 0.000 claims description 46
- 230000015572 biosynthetic process Effects 0.000 claims description 37
- 125000006850 spacer group Chemical group 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 29
- 150000004676 glycans Chemical class 0.000 claims description 28
- 229920001282 polysaccharide Polymers 0.000 claims description 27
- 239000005017 polysaccharide Substances 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 16
- 102000004169 proteins and genes Human genes 0.000 claims description 15
- 108090000623 proteins and genes Proteins 0.000 claims description 15
- 241000606768 Haemophilus influenzae Species 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 12
- 230000021615 conjugation Effects 0.000 claims description 12
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- 238000005481 NMR spectroscopy Methods 0.000 description 9
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 9
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- VIWPPFXRYOIYFA-UHFFFAOYSA-N 3-(ethyliminomethylideneamino)propane-1,1-diamine Chemical compound CCN=C=NCCC(N)N VIWPPFXRYOIYFA-UHFFFAOYSA-N 0.000 description 1
- QXZGLTYKKZKGLN-UHFFFAOYSA-N 4-(2,5-dioxopyrrolidin-1-yl)oxy-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)ON1C(=O)CCC1=O QXZGLTYKKZKGLN-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108010071134 CRM197 (non-toxic variant of diphtheria toxin) Proteins 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VJDOAZKNBQCAGE-LMVFSUKVSA-N D-ribitol 5-phosphate Chemical compound OC[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O VJDOAZKNBQCAGE-LMVFSUKVSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- GHWQRAYJKZGQQA-UHFFFAOYSA-N O.CCO.CC(O)=O.CCOC(C)=O Chemical compound O.CCO.CC(O)=O.CCOC(C)=O GHWQRAYJKZGQQA-UHFFFAOYSA-N 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- OUWPRBIEBFOLJW-UHFFFAOYSA-N acetic acid;ethyl acetate;methanol;hydrate Chemical compound O.OC.CC(O)=O.CCOC(C)=O OUWPRBIEBFOLJW-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 238000005937 allylation reaction Methods 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001727 anti-capsular Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000011545 carbonate/bicarbonate buffer Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- TXWRERCHRDBNLG-UHFFFAOYSA-N cubane Chemical compound C12C3C4C1C1C4C3C12 TXWRERCHRDBNLG-UHFFFAOYSA-N 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- DAKIDYQCFJQMDF-UHFFFAOYSA-N dichloromethane;pyridine Chemical compound ClCCl.C1=CC=NC=C1 DAKIDYQCFJQMDF-UHFFFAOYSA-N 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000012869 ethanol precipitation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 229960004443 hemophilus influenzae b vaccines Drugs 0.000 description 1
- 108010037896 heparin-binding hemagglutinin Proteins 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000010324 immunological assay Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- VJMRKWPMFQGIPI-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-(hydroxymethyl)-3-methyl-1-[2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzothiophen-7-yl]pyrazole-4-carboxamide Chemical compound OCC1=C(C(=O)NCCO)C(C)=NN1C1=CC=CC2=C1SC(CC=1C=C(C=CC=1)C(F)(F)F)=C2 VJMRKWPMFQGIPI-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 150000004713 phosphodiesters Chemical class 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003290 ribose derivatives Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940031351 tetravalent vaccine Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
-
- 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
- A61K39/02—Bacterial antigens
- A61K39/102—Pasteurellales, e.g. Actinobacillus, Pasteurella; Haemophilus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CU1999121A CU22904A1 (es) | 1999-08-30 | 1999-08-30 | Oligosacáridos derivados de ribosa- ribitol-fosfato, métodos para prepararlos, inmunógenos que los comprenden y vacunas que comprenden dichos inmunógenos |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201667B true ZA200201667B (en) | 2003-08-27 |
Family
ID=5459405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201667A ZA200201667B (en) | 1999-08-30 | 2002-02-27 | Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6765091B1 (pt) |
| EP (1) | EP1212334B1 (pt) |
| JP (1) | JP4850377B2 (pt) |
| KR (1) | KR100818163B1 (pt) |
| CN (1) | CN1205217C (pt) |
| AR (1) | AR025435A1 (pt) |
| AT (1) | ATE308551T1 (pt) |
| AU (1) | AU780816B2 (pt) |
| BR (1) | BRPI0013686B8 (pt) |
| CA (1) | CA2382602C (pt) |
| CO (1) | CO5180646A1 (pt) |
| CU (1) | CU22904A1 (pt) |
| CZ (1) | CZ2002721A3 (pt) |
| DE (1) | DE60023722T2 (pt) |
| DK (1) | DK1212334T3 (pt) |
| EA (1) | EA005381B1 (pt) |
| ES (1) | ES2252045T3 (pt) |
| HK (1) | HK1050693A1 (pt) |
| MX (1) | MXPA02002066A (pt) |
| NZ (1) | NZ517464A (pt) |
| SI (1) | SI1212334T1 (pt) |
| UA (1) | UA75579C2 (pt) |
| WO (1) | WO2001016146A1 (pt) |
| ZA (1) | ZA200201667B (pt) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005072778A2 (en) * | 2004-01-29 | 2005-08-11 | Biosynexus, Inc. | Use of amino-oxy functional groups in the preparation of vaccines conjugates |
| US8647621B2 (en) | 2009-07-27 | 2014-02-11 | Fina Biosolutions, Llc | Method of producing protein-carbohydrate vaccines reduced in free carbohydrate |
| CA2762366C (en) | 2009-07-31 | 2017-09-19 | National Research Council Of Canada | H. pylori lipopolysaccharide outer core epitope |
| BR112012014882B1 (pt) | 2009-12-17 | 2022-05-31 | Fina Biosolutions, Llc | Processo de conjugação de carboidratos na preparação de vacinas conjugadas e suas respectivas vacinas ou agentes diagnósticos |
| AU2010351576B2 (en) | 2010-04-23 | 2014-08-14 | FinaBioSolutions, LLC | Simple method for simultaneous removal of multiple impurities from culture supernatants to ultralow levels |
| CN109843899B (zh) | 2016-07-28 | 2022-04-19 | 马克斯·普朗克科学促进学会 | 用作对流感嗜血杆菌b型的疫苗的稳定耐水解的合成的聚核糖基核糖醇磷酸衍生物 |
| CA3094406C (en) * | 2018-03-23 | 2024-05-14 | Koranex Capital | Precision glycoconjugates as therapeutic tools |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ223009A (en) * | 1986-12-31 | 1990-06-26 | Nl Rivm Of Thoven | Oligosaccharides containing d-ribose d-ribitol and phosphate units mimicing haemophilus influenzae type b antigens |
| EP0320942A3 (en) * | 1987-12-18 | 1989-10-04 | American Cyanamid Company | Novel polysaccharides novel macromolecular conjugates of the polysaccharides |
| US5843463A (en) * | 1990-12-21 | 1998-12-01 | Antexbiologics, Inc. | Adhesin-oligosaccharide conjugate vaccine for Haemophilus influenzae |
-
1999
- 1999-08-30 CU CU1999121A patent/CU22904A1/es unknown
-
2000
- 2000-08-15 BR BRPI0013686A patent/BRPI0013686B8/pt not_active IP Right Cessation
- 2000-08-15 CA CA2382602A patent/CA2382602C/en not_active Expired - Fee Related
- 2000-08-15 NZ NZ517464A patent/NZ517464A/en not_active IP Right Cessation
- 2000-08-15 ES ES00956040T patent/ES2252045T3/es not_active Expired - Lifetime
- 2000-08-15 CZ CZ2002721A patent/CZ2002721A3/cs unknown
- 2000-08-15 US US10/070,101 patent/US6765091B1/en not_active Expired - Lifetime
- 2000-08-15 EP EP00956040A patent/EP1212334B1/en not_active Expired - Lifetime
- 2000-08-15 MX MXPA02002066A patent/MXPA02002066A/es active IP Right Grant
- 2000-08-15 DE DE60023722T patent/DE60023722T2/de not_active Expired - Lifetime
- 2000-08-15 DK DK00956040T patent/DK1212334T3/da active
- 2000-08-15 KR KR1020027002706A patent/KR100818163B1/ko not_active IP Right Cessation
- 2000-08-15 SI SI200030780T patent/SI1212334T1/sl unknown
- 2000-08-15 AU AU68173/00A patent/AU780816B2/en not_active Ceased
- 2000-08-15 AT AT00956040T patent/ATE308551T1/de active
- 2000-08-15 EA EA200200314A patent/EA005381B1/ru not_active IP Right Cessation
- 2000-08-15 UA UA2002021613A patent/UA75579C2/uk unknown
- 2000-08-15 CN CNB008134731A patent/CN1205217C/zh not_active Expired - Lifetime
- 2000-08-15 WO PCT/CU2000/000003 patent/WO2001016146A1/es active IP Right Grant
- 2000-08-15 JP JP2001519710A patent/JP4850377B2/ja not_active Expired - Fee Related
- 2000-08-28 CO CO00064095A patent/CO5180646A1/es active IP Right Grant
- 2000-08-29 AR ARP000104496A patent/AR025435A1/es not_active Application Discontinuation
-
2002
- 2002-02-27 ZA ZA200201667A patent/ZA200201667B/en unknown
-
2003
- 2003-04-23 HK HK03102864A patent/HK1050693A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6765091B1 (en) | 2004-07-20 |
| EA200200314A1 (ru) | 2002-10-31 |
| ES2252045T3 (es) | 2006-05-16 |
| HK1050693A1 (en) | 2003-07-04 |
| AU6817300A (en) | 2001-03-26 |
| UA75579C2 (en) | 2006-05-15 |
| AR025435A1 (es) | 2002-11-27 |
| KR20020068501A (ko) | 2002-08-27 |
| BR0013686A (pt) | 2002-08-13 |
| SI1212334T1 (sl) | 2006-04-30 |
| BRPI0013686B1 (pt) | 2016-07-26 |
| EP1212334B1 (en) | 2005-11-02 |
| EA005381B1 (ru) | 2005-02-24 |
| CZ2002721A3 (cs) | 2002-07-17 |
| BRPI0013686B8 (pt) | 2021-05-25 |
| DE60023722D1 (de) | 2005-12-08 |
| DK1212334T3 (da) | 2006-03-20 |
| DE60023722T2 (de) | 2006-07-20 |
| CU22904A1 (es) | 2004-01-23 |
| JP4850377B2 (ja) | 2012-01-11 |
| KR100818163B1 (ko) | 2008-03-31 |
| MXPA02002066A (es) | 2004-07-30 |
| EP1212334A1 (en) | 2002-06-12 |
| CN1205217C (zh) | 2005-06-08 |
| WO2001016146A1 (es) | 2001-03-08 |
| CA2382602A1 (en) | 2001-03-08 |
| CA2382602C (en) | 2010-02-16 |
| JP2003528032A (ja) | 2003-09-24 |
| ATE308551T1 (de) | 2005-11-15 |
| NZ517464A (en) | 2004-03-26 |
| AU780816B2 (en) | 2005-04-21 |
| CO5180646A1 (es) | 2002-07-30 |
| CN1376158A (zh) | 2002-10-23 |
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