CN110446511B - 短效的基于肝素的抗凝血剂化合物和方法 - Google Patents

短效的基于肝素的抗凝血剂化合物和方法 Download PDF

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CN110446511B
CN110446511B CN201880020095.XA CN201880020095A CN110446511B CN 110446511 B CN110446511 B CN 110446511B CN 201880020095 A CN201880020095 A CN 201880020095A CN 110446511 B CN110446511 B CN 110446511B
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heparin
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CN110446511A (zh
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刘健
王章杰
谢柏宏
徐咏梅
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University of North Carolina at Chapel Hill
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726Glycosaminoglycans, i.e. mucopolysaccharides
    • A61K31/727Heparin; Heparan
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006Heteroglycans, 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
    • C08B37/0063Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
    • C08B37/0075Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/16Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/43Enzymes; Proenzymes; Derivatives thereof
    • A61K38/46Hydrolases (3)
    • A61K38/48Hydrolases (3) acting on peptide bonds (3.4)
    • A61K38/482Serine endopeptidases (3.4.21)
    • A61K38/4846Factor VII (3.4.21.21); Factor IX (3.4.21.22); Factor Xa (3.4.21.6); Factor XI (3.4.21.27); Factor XII (3.4.21.38)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00Preparation of compounds containing saccharide radicals
    • C12P19/04Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00Preparation of compounds containing saccharide radicals
    • C12P19/18Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D15/00Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08Selective adsorption, e.g. chromatography
    • B01D15/26Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/38Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 and B01D15/30 - B01D15/36, e.g. affinity, ligand exchange or chiral chromatography
    • B01D15/3804Affinity chromatography
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
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  • Wood Science & Technology (AREA)
  • Epidemiology (AREA)
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  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Dermatology (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
CN201880020095.XA 2017-03-10 2018-03-12 短效的基于肝素的抗凝血剂化合物和方法 Active CN110446511B (zh)

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PCT/US2018/021986 WO2018165656A1 (en) 2017-03-10 2018-03-12 Short-acting heparin-based anticoagulant compounds and methods

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Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
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
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
JPWO2023157899A1 (https=) * 2022-02-17 2023-08-24
CN115417937B (zh) * 2022-08-12 2023-06-06 山东大学 一种含双抗凝血酶结合序列的肝素十二糖及其制备方法与应用
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

Family Cites Families (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
IT1232939B (it) 1987-11-06 1992-03-10 Opocrin Spa Eparan solfato caratterizzato da elevata attivita' antitrombotica, elevata biodisponibilita', assenza di attivita' anticoagulante; suo processo di estrazione da organi e da tessuti e relative composizioni farmaceutiche
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
AU2561792A (en) 1991-09-06 1993-04-05 Children's Medical Center Corporation Cell-type specific heparan sulfate proteoglycans and their uses
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
US5527785A (en) 1993-05-14 1996-06-18 The Regents Of The University Of California Selectin receptor modulating compositions
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
JP3713276B2 (ja) 1995-09-29 2005-11-09 バイオマリン ファーマシューティカル インコーポレイテッド 炎症反応の軽減のためのヘパリナーゼの使用
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
IL127851A0 (en) 1998-12-30 1999-10-28 Applied Research Systems Inhibition of TNF activity
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
US6977248B1 (en) * 1999-08-25 2005-12-20 Massachusetts Institute Of Technology Pharmaceutical preparations for the inhibition of herpes simplex virus 1 entry
US7101859B2 (en) 2000-01-10 2006-09-05 Yissum Research Development Company Of The Hebrew University Of Jerusalem Use of lipid conjugates in the treatment of diseases
EP2845596A3 (en) 2000-01-10 2015-07-15 Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. Use of lipid conjugates in the treatment of disease
WO2002004471A1 (fr) 2000-07-07 2002-01-17 Seikagaku Corporation Fractions oligosaccharidiques d'acide hyaluronique et medicament les contenant
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
US20040259142A1 (en) 2003-06-04 2004-12-23 Imperial College Innovations Limited Products and methods
ATE502062T1 (de) 2003-10-24 2011-04-15 3M Innovative Properties Co Wässrige dispersionen von polytetrafluorethylenteilchen
US7655445B2 (en) 2003-11-12 2010-02-02 Massachusetts Institute Of Technology Methods for synthesis of sulfated saccharides
US7619637B2 (en) 2004-04-09 2009-11-17 Samsung Electronics Co., Ltd. Systems and methods for improved gamut mapping from one image data set to another
WO2005118609A2 (en) 2004-05-26 2005-12-15 California Institute Of Technology Small molecule stimulators of neuronal growth
US20050282775A1 (en) 2004-06-16 2005-12-22 Paringenix, Inc. Method and medicament for sulfated polysaccharide treatment of inflammation without inducing platelet activation and heparin-induced thrombocytopenia syndrome
WO2006015171A2 (en) 2004-07-28 2006-02-09 The Texas A & M University System Use of glycosoaminoglycans for the prevention and treatment of sepsis
WO2006124801A2 (en) 2005-05-12 2006-11-23 The University Of North Carolina At Chapel Hill Enzymatic synthesis of sulfated polysaccharides
WO2007023867A1 (ja) 2005-08-24 2007-03-01 Seikagaku Corporation 新規コンドロイチン画分製造方法
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
ES2567079T3 (es) 2007-11-02 2016-04-19 Momenta Pharmaceuticals, Inc. Composiciones de polisacáridos que no son anticoagulantes
WO2009079693A1 (en) 2007-12-21 2009-07-02 Glycan Biosciences Design and selection of medicaments that modulate the function and activity of interleukin 13
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
CA2750188C (en) 2009-02-02 2016-11-29 Otsuka Chemical Co., Ltd. Low-molecular polysulfated hyaluronic acid derivative and compositions containing same
BRPI1010516A2 (pt) 2009-04-09 2015-08-25 Univ North Carolina Métodos de tratamento de edema relacionados à isquemia-reperfusão
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
DK2646037T3 (en) 2010-12-01 2019-03-04 Univ Australian National use of polyanions to inhibit the cytotoxic activity of histones in the treatment of sepsis
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
CA2901225C (en) 2013-03-08 2023-09-19 Csl Behring Gmbh Treatment and prevention of remote ischemia-reperfusion injury
ES2924830T3 (es) 2013-06-17 2022-10-11 Univ North Carolina Chapel Hill Moléculas de heparina reversibles
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
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
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
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
JP7670561B2 (ja) 2021-06-28 2025-04-30 日本航空電子工業株式会社 コネクタ

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Chemoenzymatic synthesis of Homogeneous Ultralow Molecular Weight Heparins";Y. Xu等;《SCIENCE》;20111027;498-501 *
"Using a 3-O-Sulfated Heparin Octasaccharide To Inhibit the Entry of Herpes Simplex Virus Type 1";Ronald Copeland等;《Biochemistry》;20080506;5774–5783 *

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CN116622006A (zh) 2023-08-22
US20210137967A1 (en) 2021-05-13
JP7330893B2 (ja) 2023-08-22
US20240066048A1 (en) 2024-02-29
JP2020510119A (ja) 2020-04-02
WO2018165656A1 (en) 2018-09-13
CN116622006B (zh) 2025-05-30
US11903963B2 (en) 2024-02-20
EP3579897A1 (en) 2019-12-18
EP3579897A4 (en) 2020-12-30
JP7702454B2 (ja) 2025-07-03
US12539311B2 (en) 2026-02-03
JP2023166387A (ja) 2023-11-21
CN110446511A (zh) 2019-11-12

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