CA2107124A1 - Anticoagulants and processes for preparing such - Google Patents
Anticoagulants and processes for preparing suchInfo
- Publication number
- CA2107124A1 CA2107124A1 CA002107124A CA2107124A CA2107124A1 CA 2107124 A1 CA2107124 A1 CA 2107124A1 CA 002107124 A CA002107124 A CA 002107124A CA 2107124 A CA2107124 A CA 2107124A CA 2107124 A1 CA2107124 A1 CA 2107124A1
- Authority
- CA
- Canada
- Prior art keywords
- groups
- saccharide
- sulphated
- ppm
- compound
- 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
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- 230000008569 process Effects 0.000 title claims description 17
- 239000003146 anticoagulant agent Substances 0.000 title abstract description 12
- 229940127219 anticoagulant drug Drugs 0.000 title abstract description 6
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 48
- 241000588724 Escherichia coli Species 0.000 claims abstract description 15
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- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical group N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
- AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical group O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 102000004411 Antithrombin III Human genes 0.000 claims description 6
- 108090000935 Antithrombin III Proteins 0.000 claims description 6
- 229960005348 antithrombin iii Drugs 0.000 claims description 6
- 238000003381 deacetylation reaction Methods 0.000 claims description 6
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- 230000000694 effects Effects 0.000 abstract description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 48
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
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- 239000006228 supernatant Substances 0.000 description 6
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- 239000013504 Triton X-100 Substances 0.000 description 4
- IAJILQKETJEXLJ-SKNVOMKLSA-N aldehydo-L-iduronic acid Chemical class O=C[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O IAJILQKETJEXLJ-SKNVOMKLSA-N 0.000 description 4
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- OVRNDRQMDRJTHS-BKJPEWSUSA-N N-acetyl-D-hexosamine Chemical group CC(=O)NC1C(O)O[C@H](CO)C(O)C1O OVRNDRQMDRJTHS-BKJPEWSUSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 241000429017 Pectis Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- CVBNMWXECPZOLM-UHFFFAOYSA-N Rhamnetin Natural products COc1cc(O)c2C(=O)C(=C(Oc2c1)c3ccc(O)c(O)c3O)O CVBNMWXECPZOLM-UHFFFAOYSA-N 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- 101150001411 STX2 gene Proteins 0.000 description 1
- 101100536893 Schizosaccharomyces pombe (strain 972 / ATCC 24843) thi9 gene Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose 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)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 108010046334 Urease Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 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
- OESFSXYRSCBAQJ-UHFFFAOYSA-M sodium;3-carboxy-3,5-dihydroxy-5-oxopentanoate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O OESFSXYRSCBAQJ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- FRGKKTITADJNOE-UHFFFAOYSA-N sulfanyloxyethane Chemical compound CCOS FRGKKTITADJNOE-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- 108010045269 tryptophyltryptophan Proteins 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Materials For Medical Uses (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9106757.9 | 1991-03-28 | ||
| GB9106757A GB2254083A (en) | 1991-03-28 | 1991-03-28 | Anticoagulants from e.coli saccharide |
| PCT/GB1992/000571 WO1992017507A1 (en) | 1991-03-28 | 1992-03-30 | Anticoagulants and processes for preparing such |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2107124A1 true CA2107124A1 (en) | 1992-09-29 |
Family
ID=10692438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002107124A Abandoned CA2107124A1 (en) | 1991-03-28 | 1992-03-30 | Anticoagulants and processes for preparing such |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPH07501684A (ja) |
| AU (1) | AU1430892A (ja) |
| CA (1) | CA2107124A1 (ja) |
| FI (1) | FI934141A (ja) |
| GB (2) | GB2254083A (ja) |
| HU (1) | HUT67208A (ja) |
| IE (1) | IE920982A1 (ja) |
| IT (1) | IT1254564B (ja) |
| PT (1) | PT100316A (ja) |
| TW (1) | TW209225B (ja) |
| WO (1) | WO1992017507A1 (ja) |
| ZA (1) | ZA922313B (ja) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2684385B1 (fr) * | 1991-11-28 | 1997-08-01 | Sanofi Elf | Heparosanes-n,o-sulfates de haute masse moleculaire, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| IT1270823B (it) * | 1993-06-04 | 1997-05-13 | Italfarmaco Spa | Polisaccaridi ad elevata attivita' antitrombotica e anticoagulante |
| US5700787A (en) * | 1994-09-02 | 1997-12-23 | Brigham & Women's Hospital, Inc. | Capsular polysaccharide immunomodulator |
| IT1271057B (it) * | 1994-11-04 | 1997-05-26 | Inalco Spa | Polisaccaridi aventi un elevato contenuto di acido iduronico |
| IT1282994B1 (it) * | 1996-05-10 | 1998-04-03 | Inalco Spa | Derivati del polisaccaride k5 aventi elevata attivita' anticoagulante |
| AUPO556297A0 (en) * | 1997-03-11 | 1997-04-10 | Australian National University, The | Sulfated oligosaccharides having anticoagulant/ antithrombotic activity |
| ITMI991465A1 (it) * | 1999-07-02 | 2001-01-02 | Inalco Spa | Processo per la preparazione dei polisaccaridi k4 e k5 da escherichiacoli |
| US20020062019A1 (en) | 2000-03-30 | 2002-05-23 | Pasqua Oreste | Glycosaminoglycans derived from K5 polysaccharide having high anticoagulant and antithrombotic activities and process for their preparation |
| SV2003000753A (es) | 2000-12-05 | 2003-06-16 | Brigham & Womens Hospital | Uso de polisacaridos zwitterionicos para la especifica modulacion del progreso inmunologico |
| ITMI20010397A1 (it) | 2001-02-27 | 2002-08-27 | Giorgio Zoppetti | Derivati altamente n,o-solfatati del polisaccaride k5 e loro preparazione |
| ITMI20010779A1 (it) * | 2001-04-12 | 2002-10-12 | Giorgio Zoppetti | Uso di polisaccaridi batterici solfati atti all'inibizione dell'angiogenesi |
| US20120253029A1 (en) | 2002-06-18 | 2012-10-04 | Pasqua Anna Oreste | Process for the preparation of highly o-sulfated epimerized derivatives of k5 polysaccharide and intermediates therein |
| CA2489870A1 (en) | 2002-06-18 | 2003-12-24 | Glycores 2000 S.R.L. | Low molecular weight oversulfated polysaccharide |
| EP1638581A2 (en) | 2003-03-31 | 2006-03-29 | The Brigham And Women's Hospital, Inc. | Zwitterionic immunomodulators for the treatment of asthma and allergy |
| WO2007092451A2 (en) | 2006-02-06 | 2007-08-16 | The Brigham And Women's Hospital, Inc. | Zwitterionic polysaccharides for promotion of immune system maturation and health |
| JP2011503104A (ja) | 2007-11-09 | 2011-01-27 | カリフォルニア インスティテュート オブ テクノロジー | 免疫調節化合物ならびに関連組成物および方法 |
| ITMI20091445A1 (it) * | 2009-08-07 | 2011-02-08 | Inalco S P A A Socio Unico | Derivati semi-sintetici del polisaccaride k5 per la prevenzione ed il trattamento del danno tissutale associato a ischemia e/o riperfusione |
| EP2555753B1 (en) | 2010-04-07 | 2018-08-01 | California Institute of Technology | Vehicle for delivering a compound to a mucous membrane and related compositions, methods and systems |
| WO2011146910A1 (en) | 2010-05-20 | 2011-11-24 | Round June L | Antigen specific tregs and related compositions, methods and systems |
| CN102199175A (zh) * | 2011-04-07 | 2011-09-28 | 福州大学 | 硫酸类肝素二糖的制备纯化方法及其纯化产品 |
| EP2731617A4 (en) | 2011-07-12 | 2015-07-01 | Brigham & Womens Hospital | LIPID-CONTAINING PSA COMPOSITIONS, METHODS OF ISOLATION AND METHODS OF USING SAME |
| EP2994161B1 (en) | 2013-05-10 | 2020-10-28 | California Institute of Technology | Probiotic prevention and treatment of colon cancer |
| US11331335B2 (en) | 2015-06-10 | 2022-05-17 | California Institute Of Technology | Sepsis treatment and related compositions methods and systems |
| JP6918365B2 (ja) | 2015-08-19 | 2021-08-11 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 脂質化ｐｓａ組成物および方法 |
| CA3030974A1 (en) | 2016-07-15 | 2018-01-18 | President And Fellows Of Harvard College | Glycolipid compositions and methods of use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2504535B1 (fr) * | 1981-04-28 | 1987-08-14 | Choay Sa | Disaccharides derives d'un acide uronique et d'une glucosamine et compositions pharmaceutiques les contenant pour le controle de la coagulation sanguine |
| FR2548189B1 (fr) * | 1983-07-01 | 1986-04-11 | Choay Sa | Nouveaux produits contenant des oligosaccharides, leur preparation et leurs applications biologiques et biochimiques |
| EP0333243A3 (en) * | 1988-03-10 | 1989-09-27 | Akzo N.V. | Sulphated k5 antigen and sulphated k5 antigen fragments |
| IT1217458B (it) * | 1988-05-02 | 1990-03-22 | Crinos Ind Farmacoriologica S | Sulfoamino derivati di condroitin solfati,del dermatan solfato e dell' acido ialuronico e loro proprieta' farmacologiche |
| FR2669932B1 (fr) * | 1990-12-03 | 1994-07-01 | Sanofi Sa | Nouvel heparosane-n,o-sulfate, son procede de preparation et les compositions pharmaceutiques qui le contiennent. |
-
1991
- 1991-03-28 GB GB9106757A patent/GB2254083A/en not_active Withdrawn
- 1991-03-28 GB GB9508157A patent/GB2286193A/en not_active Withdrawn
-
1992
- 1992-03-26 IT ITMI920722A patent/IT1254564B/it active
- 1992-03-27 IE IE098292A patent/IE920982A1/en unknown
- 1992-03-27 PT PT100316A patent/PT100316A/pt not_active Application Discontinuation
- 1992-03-30 ZA ZA922313A patent/ZA922313B/xx unknown
- 1992-03-30 JP JP4506945A patent/JPH07501684A/ja active Pending
- 1992-03-30 WO PCT/GB1992/000571 patent/WO1992017507A1/en not_active Application Discontinuation
- 1992-03-30 HU HU9302732A patent/HUT67208A/hu unknown
- 1992-03-30 AU AU14308/92A patent/AU1430892A/en not_active Abandoned
- 1992-03-30 CA CA002107124A patent/CA2107124A1/en not_active Abandoned
- 1992-05-11 TW TW081103646A patent/TW209225B/zh active
-
1993
- 1993-09-22 FI FI934141A patent/FI934141A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI920722A0 (it) | 1992-03-26 |
| ITMI920722A1 (it) | 1993-09-26 |
| WO1992017507A1 (en) | 1992-10-15 |
| GB2286193A (en) | 1995-08-09 |
| ZA922313B (en) | 1993-08-02 |
| FI934141A0 (fi) | 1993-09-22 |
| HU9302732D0 (en) | 1994-01-28 |
| AU1430892A (en) | 1992-11-02 |
| TW209225B (ja) | 1993-07-11 |
| PT100316A (pt) | 1993-07-30 |
| IE920982A1 (en) | 1992-10-07 |
| JPH07501684A (ja) | 1995-02-23 |
| GB9106757D0 (en) | 1991-05-15 |
| GB9508157D0 (en) | 1995-06-07 |
| GB2254083A (en) | 1992-09-30 |
| FI934141A (fi) | 1993-09-22 |
| HUT67208A (en) | 1995-02-28 |
| IT1254564B (it) | 1995-09-25 |
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