JP2016523535A5 - - Google Patents
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- JP2016523535A5 JP2016523535A5 JP2016521505A JP2016521505A JP2016523535A5 JP 2016523535 A5 JP2016523535 A5 JP 2016523535A5 JP 2016521505 A JP2016521505 A JP 2016521505A JP 2016521505 A JP2016521505 A JP 2016521505A JP 2016523535 A5 JP2016523535 A5 JP 2016523535A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfotransferase
- paps
- phosphosulfate
- phosphoadenosine
- substrate
- 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.)
- Granted
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- GACDQMDRPRGCTN-KQYNXXCUSA-N 3'-phospho-5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O GACDQMDRPRGCTN-KQYNXXCUSA-N 0.000 claims description 189
- 239000000758 substrate Substances 0.000 claims description 110
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims description 75
- 102100029001 Heparan sulfate 2-O-sulfotransferase 1 Human genes 0.000 claims description 67
- 101710096984 Heparan sulfate 2-O-sulfotransferase 1 Proteins 0.000 claims description 67
- ZXNYUXIMAXVSFN-IVMDWMLBSA-N 2,2,2-trifluoro-n-[(3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide Chemical compound OC[C@H]1OC(O)[C@H](NC(=O)C(F)(F)F)[C@@H](O)[C@@H]1O ZXNYUXIMAXVSFN-IVMDWMLBSA-N 0.000 claims description 64
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 37
- 102100023315 N-acetyllactosaminide beta-1,6-N-acetylglucosaminyl-transferase Human genes 0.000 claims description 37
- 108010056664 N-acetyllactosaminide beta-1,6-N-acetylglucosaminyltransferase Proteins 0.000 claims description 37
- PRDZVHCOEWJPOB-IVMDWMLBSA-N N-sulfo-D-glucosamine Chemical group OC[C@H]1OC(O)[C@H](NS(O)(=O)=O)[C@@H](O)[C@@H]1O PRDZVHCOEWJPOB-IVMDWMLBSA-N 0.000 claims description 37
- KZWHEHSUEBTKJM-SLPGGIOYSA-N [(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]sulfamic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NS(O)(=O)=O KZWHEHSUEBTKJM-SLPGGIOYSA-N 0.000 claims description 37
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 claims description 37
- 229940097043 glucuronic acid Drugs 0.000 claims description 37
- 230000001180 sulfating effect Effects 0.000 claims description 35
- 229960002897 heparin Drugs 0.000 claims description 31
- 229920000669 heparin Polymers 0.000 claims description 31
- 238000006345 epimerization reaction Methods 0.000 claims description 29
- -1 heparin compound Chemical class 0.000 claims description 29
- 150000002772 monosaccharides Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- PZUPAGRIHCRVKN-UHFFFAOYSA-N 5-[5-[3,4-dihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]-5-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-[(3,4,5-trihydroxyoxan-2-yl)oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound OCC1OC(O)C(O)C(O)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(COC4C(C(O)C(O)CO4)O)O3)O)C(COC3C(C(O)C(O)CO3)O)O2)O)C(COC2C(C(O)C(O)CO2)O)O1 PZUPAGRIHCRVKN-UHFFFAOYSA-N 0.000 claims description 21
- 102000004190 Enzymes Human genes 0.000 claims description 11
- 108090000790 Enzymes Proteins 0.000 claims description 11
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 11
- 230000002194 synthesizing effect Effects 0.000 claims description 11
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 9
- 238000005670 sulfation reaction Methods 0.000 claims description 9
- 108700023372 Glycosyltransferases Proteins 0.000 claims description 6
- 102000051366 Glycosyltransferases Human genes 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
- 230000014508 negative regulation of coagulation Effects 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 241000588724 Escherichia coli Species 0.000 claims description 3
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 claims description 3
- 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 description 3
- 241000606856 Pasteurella multocida Species 0.000 claims description 3
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 3
- 229940051027 pasteurella multocida Drugs 0.000 claims description 3
- 229930182480 glucuronide Natural products 0.000 claims description 2
- 150000008134 glucuronides Chemical class 0.000 claims description 2
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 6
- 102000007327 Protamines Human genes 0.000 claims 3
- 108010007568 Protamines Proteins 0.000 claims 3
- 229940048914 protamine Drugs 0.000 claims 3
- 230000002441 reversible effect Effects 0.000 claims 3
- 206010062237 Renal impairment Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 239000003055 low molecular weight heparin Substances 0.000 claims 1
- 229940127215 low-molecular weight heparin Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 36
- 229920002971 Heparan sulfate Polymers 0.000 description 16
- 102000001708 Protein Isoforms Human genes 0.000 description 6
- 108010029485 Protein Isoforms Proteins 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 239000004019 antithrombin Substances 0.000 description 5
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 4
- LNQVTSROQXJCDD-KQYNXXCUSA-N 3'-AMP Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]1O LNQVTSROQXJCDD-KQYNXXCUSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 102000004896 Sulfotransferases Human genes 0.000 description 4
- 108090001033 Sulfotransferases Proteins 0.000 description 4
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 102100022717 Atypical chemokine receptor 1 Human genes 0.000 description 2
- 101100478237 Caenorhabditis elegans ost-1 gene Proteins 0.000 description 2
- 101000678879 Homo sapiens Atypical chemokine receptor 1 Proteins 0.000 description 2
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 229960002442 glucosamine Drugs 0.000 description 2
- IAJILQKETJEXLJ-LECHCGJUSA-N iduronic acid Chemical group O=C[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-LECHCGJUSA-N 0.000 description 2
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 1
- 108010074860 Factor Xa Proteins 0.000 description 1
- 102100023929 Heparan sulfate glucosamine 3-O-sulfotransferase 3A1 Human genes 0.000 description 1
- 102100023926 Heparan sulfate glucosamine 3-O-sulfotransferase 3B1 Human genes 0.000 description 1
- 101710158396 Heparan sulfate glucosamine 3-O-sulfotransferase 3B1 Proteins 0.000 description 1
- 101001048118 Homo sapiens Heparan sulfate glucosamine 3-O-sulfotransferase 3A1 Proteins 0.000 description 1
- 229940122055 Serine protease inhibitor Drugs 0.000 description 1
- 101710102218 Serine protease inhibitor Proteins 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- GXYKBDAKQXPXFV-SLPGGIOYSA-N [(2r,3r,4r,5r)-2-amino-4,5,6-trihydroxy-1-oxohexan-3-yl] hydrogen sulfate Chemical group O=C[C@H](N)[C@@H](OS(O)(=O)=O)[C@H](O)[C@H](O)CO GXYKBDAKQXPXFV-SLPGGIOYSA-N 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004676 glycans Polymers 0.000 description 1
- 108010048322 heparin-glucosamine 3-O-sulfotransferase Proteins 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 230000007502 viral entry Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361835875P | 2013-06-17 | 2013-06-17 | |
| US61/835,875 | 2013-06-17 | ||
| PCT/US2014/042683 WO2014204929A2 (en) | 2013-06-17 | 2014-06-17 | Reversible heparin molecules and methods of making and using the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016523535A JP2016523535A (ja) | 2016-08-12 |
| JP2016523535A5 true JP2016523535A5 (https=) | 2017-08-03 |
| JP6670235B2 JP6670235B2 (ja) | 2020-03-18 |
Family
ID=52105487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016521505A Active JP6670235B2 (ja) | 2013-06-17 | 2014-06-17 | 可逆的ヘパリン分子、その製法及びその使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9951149B2 (https=) |
| EP (1) | EP3011043B1 (https=) |
| JP (1) | JP6670235B2 (https=) |
| CN (1) | CN105452479B (https=) |
| ES (1) | ES2924830T3 (https=) |
| WO (1) | WO2014204929A2 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11203772B2 (en) | 2010-12-23 | 2021-12-21 | The University Of North Carolina At Chapel Hill | Chemoenzymatic synthesis of structurally homogeneous ultra-low molecular weight heparins |
| ES2924830T3 (es) | 2013-06-17 | 2022-10-11 | Univ North Carolina Chapel Hill | Moléculas de heparina reversibles |
| EP3273239A1 (en) * | 2016-07-19 | 2018-01-24 | Laboratorios Farmacéuticos Rovi, S.A. | Procedure of analysis of glycosaminoglycans, heparins and their derivatives by nuclear magnetic resonance |
| TWI769176B (zh) | 2016-09-07 | 2022-07-01 | 瑞瑟勒綜合技術協會 | 生合成肝素 |
| CN110446511B (zh) * | 2017-03-10 | 2024-04-02 | 北卡罗来纳大学查珀尔希尔分校 | 短效的基于肝素的抗凝血剂化合物和方法 |
| US10864227B2 (en) | 2017-03-20 | 2020-12-15 | Rensselaer Polytechnic Institute | Enzymatic preparation of increased anticoagulant bovine sourced heparin |
| WO2019010216A1 (en) | 2017-07-03 | 2019-01-10 | The University Of North Carolina At Chapel Hill | ENZYMATIC SYNTHESIS OF HOMOGENEOUS CHONDROITIN SULFATE OLIGOSACCHARIDES |
| JP7495061B2 (ja) | 2017-11-03 | 2024-06-04 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | 抗炎症作用を有する硫酸化オリゴ糖 |
| US11141428B2 (en) * | 2017-12-12 | 2021-10-12 | Academia Sinica | Octasaccharides and uses thereof |
| CN111867603A (zh) * | 2018-03-01 | 2020-10-30 | 中央研究院 | 检测癌细胞的装置与方法 |
| CN112437667B (zh) | 2018-06-20 | 2024-05-28 | 北卡罗来纳大学查珀尔希尔分校 | 细胞保护方法和组合物 |
| CN109321508B (zh) * | 2018-10-12 | 2022-12-27 | 北京化工大学 | 产heparosan的基因工程菌及其应用 |
| WO2022015794A1 (en) | 2020-07-14 | 2022-01-20 | Optimvia, Llc | Methods for synthesizing non-anticoagulant heparan sulfate |
| CN113646427A (zh) | 2019-01-15 | 2021-11-12 | 奥普蒂姆维亚有限公司 | 工程化芳基硫酸酯依赖性酶 |
| CA3144968A1 (en) | 2019-07-09 | 2021-01-14 | Optimvia Llc | Methods for synthesizing anticoagulant polysaccharides |
| WO2021097345A1 (en) | 2019-11-13 | 2021-05-20 | The University Of North Carolina At Chapel Hill | Heparan sulfate (hs) oligosaccharides effect in liver ischemia reperfusion injury |
| CN111154819B (zh) * | 2020-01-15 | 2022-08-30 | 山东大学 | 一种非动物源低分子量肝素及其制备方法与应用 |
| CN113583151B (zh) * | 2021-07-07 | 2023-06-20 | 山东大学 | 含at结合序列和连续2-o-葡糖醛酸残基的肝素分子及其制备方法与应用 |
| CN113564139B (zh) * | 2021-08-02 | 2023-03-10 | 山东大学 | 巴氏杆菌肝素骨架合酶BtHS1及其突变体与应用 |
| CN116120484B (zh) * | 2022-09-01 | 2024-11-08 | 山东大学 | 一种抗凝血肝素寡糖苯联二聚体及其制备方法与应用 |
| CN116297984A (zh) * | 2023-04-12 | 2023-06-23 | 重庆望业药物研究有限公司 | 一种采用lc-ms检测低分子肝素中寡糖含量的方法及应用 |
| WO2026057759A1 (en) * | 2024-09-13 | 2026-03-19 | Sanofi | Novel bioengineered heparins, low molecular weight heparins derived thereof, and their method of production |
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|---|---|---|---|---|
| US4554101A (en) | 1981-01-09 | 1985-11-19 | New York Blood Center, Inc. | Identification and preparation of epitopes on antigens and allergens on the basis of hydrophilicity |
| US4865870A (en) | 1988-07-07 | 1989-09-12 | Becton, Dickinson And Company | Method for rendering a substrate surface antithrombogenic |
| PT93847A (pt) | 1989-04-24 | 1990-11-20 | Harvard College | Processo para a preparacao de oligossacaridos de baixo peso molecular derivados de heparina ou de sulfato de heparano despolimerizados e de composicoes farmaceuticas que os contem |
| US5378829A (en) | 1990-04-23 | 1995-01-03 | Akzo N.V. | Sulfated glycosaminoglycanoid derivatives of the heparin and heparan sulfate type |
| IT1260137B (it) | 1992-04-17 | 1996-03-28 | Alfa Wassermann Spa | Glicosaminoglicani semisintetici a struttura eparinica od eparanica modificati nella posizione 2 dell'acido alfa-l-iduronico-2-0-solfato |
| JP3818676B2 (ja) | 1994-07-22 | 2006-09-06 | 生化学工業株式会社 | ヘパラン硫酸６−ｏ−硫酸基転移酵素 |
| IT1271057B (it) | 1994-11-04 | 1997-05-26 | Inalco Spa | Polisaccaridi aventi un elevato contenuto di acido iduronico |
| JP3672359B2 (ja) | 1995-07-24 | 2005-07-20 | 生化学工業株式会社 | ヘパラン硫酸 ２−ｏ−硫酸基転移酵素 |
| US5935824A (en) | 1996-01-31 | 1999-08-10 | Technologene, Inc. | Protein expression system |
| US6861254B1 (en) | 1997-10-24 | 2005-03-01 | Massachusetts Institute Of Technology | Heparan sulfate D-glucosaminyl 3-O-sulfotransferases, and uses therefor |
| US8088604B2 (en) | 1998-04-02 | 2012-01-03 | The Board Of Regents Of The University Of Oklahoma | Production of defined monodisperse heparosan polymers and unnatural polymers with polysaccharide synthases |
| US7307159B2 (en) | 2001-05-08 | 2007-12-11 | The Board Of Regents Of The University Of Oklahoma | Heparin/heparosan synthase from P. multocida and methods of making and using same |
| US6624141B1 (en) * | 1999-03-17 | 2003-09-23 | The Regents Of The University Of Michigan | Protamine fragment compositions and methods of use |
| US6255088B1 (en) | 1999-05-11 | 2001-07-03 | The Scripps Research Institute | Enzymatic sulfation of biomolecules |
| US8067196B2 (en) | 2001-03-28 | 2011-11-29 | Massachusetts Institute Of Technology | 6-O sulfated polysaccharides and methods of preparation thereof |
| US7300922B2 (en) | 2001-05-25 | 2007-11-27 | Duke University | Modulators of pharmacological agents |
| WO2003018598A2 (en) * | 2001-08-30 | 2003-03-06 | University College Dublin | Monosaccharide derivatives |
| WO2004005475A2 (en) | 2002-07-05 | 2004-01-15 | University Of North Carolina At Chapel Hill | Purified and isolated heparan sulfate 3-o-sulfotransferase isoform 5 nucleic acids and polypeptides and therapeutic and screening methods using same |
| GB0216861D0 (en) | 2002-07-19 | 2002-08-28 | Univ Birmingham | Saccharide libraries |
| AU2003262794A1 (en) * | 2002-08-23 | 2004-03-11 | Neose Technologies, Inc. | Total synthesis of heparin |
| WO2005014619A2 (en) * | 2003-03-28 | 2005-02-17 | Thomas Jefferson University | Heparin-binding peptides and uses thereof |
| US7655445B2 (en) | 2003-11-12 | 2010-02-02 | Massachusetts Institute Of Technology | Methods for synthesis of sulfated saccharides |
| WO2006124801A2 (en) | 2005-05-12 | 2006-11-23 | The University Of North Carolina At Chapel Hill | Enzymatic synthesis of sulfated polysaccharides |
| CN101495517B (zh) * | 2006-05-25 | 2012-10-10 | 莫曼塔医药品有限公司 | 低分子量肝素及其用途 |
| WO2009014715A2 (en) * | 2007-07-23 | 2009-01-29 | The University Of North Carolina At Chapel Hill | Enzymatic synthesis of sulfated polysaccharides without iduronic acid residues |
| EP2364165B1 (en) | 2008-11-14 | 2018-01-03 | Portola Pharmaceuticals, Inc. | Antidotes for factor xa inhibitors and methods of using the same in combination with blood coagulating agents |
| US20110054236A1 (en) | 2009-08-25 | 2011-03-03 | The Regents Of The University Of Michigan | Compositions and methods for targeting tumors |
| EP2480237A1 (en) | 2009-09-23 | 2012-08-01 | Momenta Pharmaceuticals, Inc. | Methods of treatment with a low molecular weight heparin composition |
| US11203772B2 (en) * | 2010-12-23 | 2021-12-21 | The University Of North Carolina At Chapel Hill | Chemoenzymatic synthesis of structurally homogeneous ultra-low molecular weight heparins |
| TW201309305A (zh) * | 2011-02-22 | 2013-03-01 | Rensselaer Polytech Inst | 用於製造生物工程肝素之單一步驟肝素前體之ｎ－去乙醯化作用及解聚合作用 |
| US8519189B2 (en) | 2011-06-01 | 2013-08-27 | University Of British Columbia | Polymers for reversing heparin-based anticoagulation |
| ES2924830T3 (es) | 2013-06-17 | 2022-10-11 | Univ North Carolina Chapel Hill | Moléculas de heparina reversibles |
-
2014
- 2014-06-17 ES ES14812890T patent/ES2924830T3/es active Active
- 2014-06-17 WO PCT/US2014/042683 patent/WO2014204929A2/en not_active Ceased
- 2014-06-17 JP JP2016521505A patent/JP6670235B2/ja active Active
- 2014-06-17 US US14/898,865 patent/US9951149B2/en active Active
- 2014-06-17 CN CN201480044429.9A patent/CN105452479B/zh active Active
- 2014-06-17 EP EP14812890.3A patent/EP3011043B1/en active Active
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