CA2110495A1 - Derives d'oligosaccharides immunosuppresseurs et tolerogenes - Google Patents
Derives d'oligosaccharides immunosuppresseurs et tolerogenesInfo
- Publication number
- CA2110495A1 CA2110495A1 CA002110495A CA2110495A CA2110495A1 CA 2110495 A1 CA2110495 A1 CA 2110495A1 CA 002110495 A CA002110495 A CA 002110495A CA 2110495 A CA2110495 A CA 2110495A CA 2110495 A1 CA2110495 A1 CA 2110495A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- oligosaccharide
- hydrogen
- saccharide
- methyl
- 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.)
- Abandoned
Links
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 102
- 150000002482 oligosaccharides Chemical class 0.000 title claims description 49
- 230000001506 immunosuppresive effect Effects 0.000 title description 11
- 230000003614 tolerogenic effect Effects 0.000 title 1
- 229930182470 glycoside Natural products 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 91
- -1 oligosaccharide glycosides Chemical class 0.000 claims abstract description 91
- 230000028709 inflammatory response Effects 0.000 claims abstract description 30
- 230000021633 leukocyte mediated immunity Effects 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 210000004369 blood Anatomy 0.000 claims description 75
- 239000008280 blood Substances 0.000 claims description 75
- 239000000427 antigen Substances 0.000 claims description 45
- 102000036639 antigens Human genes 0.000 claims description 45
- 108091007433 antigens Proteins 0.000 claims description 45
- 230000004044 response Effects 0.000 claims description 42
- 150000001720 carbohydrates Chemical group 0.000 claims description 39
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 35
- 230000028993 immune response Effects 0.000 claims description 35
- 241000124008 Mammalia Species 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 230000001629 suppression Effects 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 206010070834 Sensitisation Diseases 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 230000008313 sensitization Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 6
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 6
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 6
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical group N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 4
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229930182830 galactose Natural products 0.000 claims description 3
- 230000006698 induction Effects 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- SHZGCJCMOBCMKK-SXUWKVJYSA-N alpha-L-fucose Chemical compound C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-SXUWKVJYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 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 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- OVRNDRQMDRJTHS-CBQIKETKSA-N N-Acetyl-D-Galactosamine Chemical compound CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-CBQIKETKSA-N 0.000 claims 2
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 claims 2
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 229950006780 n-acetylglucosamine Drugs 0.000 claims 2
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims 1
- 210000004698 lymphocyte Anatomy 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 81
- 230000001404 mediated effect Effects 0.000 abstract description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 180
- 241000699670 Mus sp. Species 0.000 description 104
- 150000001875 compounds Chemical class 0.000 description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 52
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 44
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 description 43
- 230000005951 type IV hypersensitivity Effects 0.000 description 43
- 210000004027 cell Anatomy 0.000 description 41
- 239000000047 product Substances 0.000 description 41
- 238000003786 synthesis reaction Methods 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 39
- 102000003838 Sialyltransferases Human genes 0.000 description 38
- 108090000141 Sialyltransferases Proteins 0.000 description 38
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 38
- 239000002953 phosphate buffered saline Substances 0.000 description 38
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- 150000002338 glycosides Chemical class 0.000 description 27
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- 238000002649 immunization Methods 0.000 description 26
- SQVRNKJHWKZAKO-LUWBGTNYSA-N N-acetylneuraminic acid Chemical class CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-LUWBGTNYSA-N 0.000 description 25
- 238000012546 transfer Methods 0.000 description 25
- 239000000463 material Substances 0.000 description 22
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 230000008961 swelling Effects 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
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- 101710168515 Cell surface glycoprotein Proteins 0.000 description 19
- 101710099182 S-layer protein Proteins 0.000 description 19
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 19
- 101710125089 Bindin Proteins 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- NIGUVXFURDGQKZ-UQTBNESHSA-N alpha-Neup5Ac-(2->3)-beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O[C@]3(O[C@H]([C@H](NC(C)=O)[C@@H](O)C3)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O NIGUVXFURDGQKZ-UQTBNESHSA-N 0.000 description 18
- 230000002757 inflammatory effect Effects 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
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Classifications
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- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
-
- 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
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)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Epidemiology (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71416191A | 1991-06-10 | 1991-06-10 | |
| US07/714,161 | 1991-06-10 | ||
| US77125991A | 1991-10-02 | 1991-10-02 | |
| US07/771,259 | 1991-10-02 | ||
| US88901792A | 1992-05-26 | 1992-05-26 | |
| US07/889,017 | 1992-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2110495A1 true CA2110495A1 (fr) | 1992-12-23 |
Family
ID=27418920
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002110495A Abandoned CA2110495A1 (fr) | 1991-06-10 | 1992-06-09 | Derives d'oligosaccharides immunosuppresseurs et tolerogenes |
| CA002110997A Abandoned CA2110997A1 (fr) | 1991-06-10 | 1992-06-10 | Methodes utilisees pour la synthese d'oligosaccharides monofucosyles se terminant par des structures di-n-acetyllactosaminyles |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002110997A Abandoned CA2110997A1 (fr) | 1991-06-10 | 1992-06-10 | Methodes utilisees pour la synthese d'oligosaccharides monofucosyles se terminant par des structures di-n-acetyllactosaminyles |
Country Status (4)
| Country | Link |
|---|---|
| EP (2) | EP0588852A1 (fr) |
| JP (2) | JPH07502011A (fr) |
| CA (2) | CA2110495A1 (fr) |
| WO (2) | WO1992022301A1 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5559103A (en) * | 1993-07-21 | 1996-09-24 | Cytel Corporation | Bivalent sialyl X saccharides |
| US5631283A (en) * | 1994-02-02 | 1997-05-20 | The United States Of America As Represented By The Secretary Of The Army | Use of sialic acid or antibodies to sialidase as anti-infectious agents and anti-inflammatory agents |
| EP0727216B1 (fr) * | 1994-07-15 | 2003-05-28 | TAIYO KAGAKU Co., LTD. | Composition medicamenteuse contenant un derive d'acide sialique |
| EP0926154B1 (fr) * | 1996-07-23 | 2010-01-27 | Seikagaku Corporation | Nouveaux oligosaccharides a base de lactosamine et procede de preparation |
| CA2451051C (fr) * | 2001-06-19 | 2012-11-27 | Sorge Kelm | Inhibiteurs de siglec |
| DE10204000A1 (de) * | 2002-02-01 | 2003-08-14 | Nutricia Nv | Sialysierte Kohlenhydrate |
| EP1911850A1 (fr) * | 2006-10-09 | 2008-04-16 | Centre National De La Recherche Scientifique (Cnrs) | Procédé de production de glycoprotéines et glycoconjugates 6-thio-sialylées |
| WO2009155108A1 (fr) | 2008-05-30 | 2009-12-23 | Momenta Pharmaceuticals, Inc. | Structures saccharides et procédés destinés à fabriquer et à utiliser de telles structures |
| DK3116887T3 (da) | 2014-03-13 | 2021-04-26 | Univ Basel | Carbonhydratligander, der binder til igm-antistoffer mod myelin-associeret glykoprotein |
| CN108026134A (zh) | 2015-09-16 | 2018-05-11 | 巴塞尔大学 | 结合抗糖鞘脂糖蛋白表位抗体的碳水化合物配体 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0380084A3 (fr) * | 1989-01-27 | 1991-03-13 | The Biomembrane Institute | Méthode d'inhibition des interactions cellule-cellule et cellule-substrat par blocage des interactions entre hydrates de carbone |
| EP0395217A3 (fr) * | 1989-04-28 | 1991-01-23 | The Biomembrane Institute | Synthèse bio-organique de LeX (difucosyle y2; III3FucV3FucnLc6Cer) dimère et leurs analogues |
| US5109116A (en) * | 1989-07-24 | 1992-04-28 | Monsanto Company | Immunosuppressive glycoprotein |
| EP0496832B1 (fr) * | 1989-10-20 | 1996-12-11 | New England Medical Center | Inhibition de la liaison des cellules a mediation par padgem |
| AU8007791A (en) * | 1990-06-15 | 1992-01-07 | Cytel Corporation | Intercellular adhesion mediators |
| US5211937A (en) * | 1990-07-30 | 1993-05-18 | Glycomed Incorporated | Method of determining a site of inflammation utilizing elam-1 ligands |
| NZ240316A (en) * | 1990-10-25 | 1996-12-20 | Univ Michigan | Compound for treating disease mediated by the elaboration of elam-1 on endothelial cells |
-
1992
- 1992-06-09 JP JP4511195A patent/JPH07502011A/ja active Pending
- 1992-06-09 CA CA002110495A patent/CA2110495A1/fr not_active Abandoned
- 1992-06-09 WO PCT/CA1992/000244 patent/WO1992022301A1/fr not_active Application Discontinuation
- 1992-06-09 EP EP92911470A patent/EP0588852A1/fr not_active Withdrawn
- 1992-06-10 EP EP92911443A patent/EP0591256A1/fr not_active Ceased
- 1992-06-10 WO PCT/CA1992/000251 patent/WO1992022662A1/fr not_active Application Discontinuation
- 1992-06-10 CA CA002110997A patent/CA2110997A1/fr not_active Abandoned
- 1992-06-10 JP JP4511199A patent/JPH06510661A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2110997A1 (fr) | 1992-12-23 |
| EP0591256A1 (fr) | 1994-04-13 |
| JPH06510661A (ja) | 1994-12-01 |
| WO1992022662A1 (fr) | 1992-12-23 |
| WO1992022301A1 (fr) | 1992-12-23 |
| EP0588852A1 (fr) | 1994-03-30 |
| JPH07502011A (ja) | 1995-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |