CN103360439B - 制备肝素五糖的新中间体及其制备方法 - Google Patents

制备肝素五糖的新中间体及其制备方法 Download PDF

Info

Publication number
CN103360439B
CN103360439B CN201210102415.0A CN201210102415A CN103360439B CN 103360439 B CN103360439 B CN 103360439B CN 201210102415 A CN201210102415 A CN 201210102415A CN 103360439 B CN103360439 B CN 103360439B
Authority
CN
China
Prior art keywords
compound
formula
alkyl group
benzyl
group
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.)
Expired - Fee Related
Application number
CN201210102415.0A
Other languages
English (en)
Chinese (zh)
Other versions
CN103360439A (zh
Inventor
丁毅力
郭阳辉
白骅
吴迎秋
白灵卫
杨仕保
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang Hisun Pharmaceutical Co Ltd
Original Assignee
Zhejiang Hisun Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Zhejiang Hisun Pharmaceutical Co Ltd filed Critical Zhejiang Hisun Pharmaceutical Co Ltd
Priority to CN201210102415.0A priority Critical patent/CN103360439B/zh
Priority to US14/389,806 priority patent/US9624315B2/en
Priority to JP2015503738A priority patent/JP2015514098A/ja
Priority to PCT/CN2013/073601 priority patent/WO2013149576A1/zh
Priority to EP13772346.6A priority patent/EP2837635B1/en
Priority to IN9026DEN2014 priority patent/IN2014DN09026A/en
Publication of CN103360439A publication Critical patent/CN103360439A/zh
Application granted granted Critical
Publication of CN103360439B publication Critical patent/CN103360439B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02Acyclic radicals, not substituted by cyclic structures
    • C07H15/04Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18Acyclic radicals, substituted by carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06Aminosugars
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CN201210102415.0A 2012-04-02 2012-04-02 制备肝素五糖的新中间体及其制备方法 Expired - Fee Related CN103360439B (zh)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CN201210102415.0A CN103360439B (zh) 2012-04-02 2012-04-02 制备肝素五糖的新中间体及其制备方法
US14/389,806 US9624315B2 (en) 2012-04-02 2013-04-02 Preparation of new intermediate of heparin pentasaccharide and preparation method thereof
JP2015503738A JP2015514098A (ja) 2012-04-02 2013-04-02 ヘパリン五糖の新規中間体の調製およびその調製方法
PCT/CN2013/073601 WO2013149576A1 (zh) 2012-04-02 2013-04-02 制备肝素五糖的新中间体及其制备方法
EP13772346.6A EP2837635B1 (en) 2012-04-02 2013-04-02 New intermediates for the preparation of heparin pentasaccharide and preparation methods thereof
IN9026DEN2014 IN2014DN09026A (https=) 2012-04-02 2013-04-02

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201210102415.0A CN103360439B (zh) 2012-04-02 2012-04-02 制备肝素五糖的新中间体及其制备方法

Publications (2)

Publication Number Publication Date
CN103360439A CN103360439A (zh) 2013-10-23
CN103360439B true CN103360439B (zh) 2017-12-15

Family

ID=49299997

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201210102415.0A Expired - Fee Related CN103360439B (zh) 2012-04-02 2012-04-02 制备肝素五糖的新中间体及其制备方法

Country Status (6)

Country Link
US (1) US9624315B2 (https=)
EP (1) EP2837635B1 (https=)
JP (1) JP2015514098A (https=)
CN (1) CN103360439B (https=)
IN (1) IN2014DN09026A (https=)
WO (1) WO2013149576A1 (https=)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102718808A (zh) * 2012-06-04 2012-10-10 浙江星月药物科技股份有限公司 一类多糖衍生物及其中间体的制备方法
CN103570774B (zh) * 2012-08-07 2017-08-25 博瑞生物医药(苏州)股份有限公司 一种戊糖化合物的纯化方法
CN103992364B (zh) * 2014-03-25 2016-08-10 南京天翔医药科技有限公司 一种磺达肝癸钠的分离提取方法
CN103965269B (zh) * 2014-04-16 2018-05-04 杭州华东医药集团新药研究院有限公司 低水分高纯度的磺达肝癸钠及其制备方法
CN104098618A (zh) * 2014-07-25 2014-10-15 河北常山生化药业股份有限公司 磺达肝癸钠中间体及其中间体和磺达肝癸钠的制备方法
CN105037452B (zh) * 2015-06-19 2018-10-09 天津红日药业股份有限公司 一种快速制备高纯度磺达肝癸钠的精制方法
EP3398971A4 (en) * 2015-12-30 2019-09-25 Shenzhen Hepalink Pharmaceutical Group Co., Ltd. SULFATED HEPARINOLIGOSACCHARIDE AND MANUFACTURING METHOD AND APPLICATION THEREOF
CN108148101B (zh) * 2016-12-03 2021-12-24 烟台东诚药业集团股份有限公司 一种制备磺达肝癸钠的新工艺方法
CN115057896A (zh) * 2022-07-28 2022-09-16 苏州柯默拓医药科技有限公司 一种磺达肝癸钠的合成方法
CN117567665A (zh) * 2023-11-10 2024-02-20 山东大学 一种肝素六糖及其制备方法与应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4818816A (en) * 1981-04-28 1989-04-04 Choay, S.A. Process for the organic synthesis of oligosaccharides and derivatives thereof
CN1558911A (zh) * 2001-09-07 2004-12-29 合成肝素五糖
US20110003980A1 (en) * 2009-03-10 2011-01-06 The University Of Tokyo Oligo-Aminosaccharide compound
WO2011014793A2 (en) * 2009-07-31 2011-02-03 Reliable Biopharmaceutical Corporation Process for preparing fondaparinux sodium and intermediates useful in the synthesis thereof
US20110306757A1 (en) * 2008-10-08 2011-12-15 Laboratorios Farmaceuticos Rovi, S.A. Process for the synthesis of unprotected pentasaccharides from a protected pentasaccharide precursor

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0300099A1 (en) * 1987-07-20 1989-01-25 Akzo N.V. New pentasaccharides
AU2009299118B2 (en) * 2008-10-03 2015-12-17 Glycan Biosciences Llc Anionic conjugates of glycosylated bacterial metabolite
CN102718808A (zh) * 2012-06-04 2012-10-10 浙江星月药物科技股份有限公司 一类多糖衍生物及其中间体的制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4818816A (en) * 1981-04-28 1989-04-04 Choay, S.A. Process for the organic synthesis of oligosaccharides and derivatives thereof
CN1558911A (zh) * 2001-09-07 2004-12-29 合成肝素五糖
US20110306757A1 (en) * 2008-10-08 2011-12-15 Laboratorios Farmaceuticos Rovi, S.A. Process for the synthesis of unprotected pentasaccharides from a protected pentasaccharide precursor
US20110003980A1 (en) * 2009-03-10 2011-01-06 The University Of Tokyo Oligo-Aminosaccharide compound
WO2011014793A2 (en) * 2009-07-31 2011-02-03 Reliable Biopharmaceutical Corporation Process for preparing fondaparinux sodium and intermediates useful in the synthesis thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Synthesis of a tetrasaccharide substrate of heparanase;Jianfang Chen,等;《Carbohydrate Research》;20080618;第343卷;Fig1、Scheme4 *

Also Published As

Publication number Publication date
US20150299340A1 (en) 2015-10-22
EP2837635A4 (en) 2015-05-27
WO2013149576A1 (zh) 2013-10-10
EP2837635B1 (en) 2017-10-18
JP2015514098A (ja) 2015-05-18
US9624315B2 (en) 2017-04-18
EP2837635A1 (en) 2015-02-18
IN2014DN09026A (https=) 2015-05-22
CN103360439A (zh) 2013-10-23

Similar Documents

Publication Publication Date Title
CN103360439B (zh) 制备肝素五糖的新中间体及其制备方法
DK175970B1 (da) Fremgangsmåde til organisk syntese af oligosaccharider indeholdende galactosamin-uronsyre-mönstre, ved fremgangsmåden opnåede oligosaccharider og biologisk anvendelse af sådanne oligosaccharider
CN1241932C (zh) 新的低聚糖、其制备方法及其药物组合物
EP0084999B1 (fr) Procédé de synthèse organique d'oligosaccharides, correspondant à des fragments de muco-polysaccharides naturels, nouveaux oligosaccharides obtenus et leurs applications biologiques
HU188657B (en) Process for the preparation of anticoagulant mycopolysaccharides
US20130005954A1 (en) Process for preparing heparinoids and intermediates useful in the synthesis thereof
CN103601765B (zh) 磺达肝癸钠及其中间体、以及制备方法
US10870711B2 (en) Process for the preparation of polysaccharides
CA1265792A (fr) Oligosaccharides, leur preparation par voie de synthese et leurs applications biologiques
JP2005536577A (ja) N−アシル−(エピ)k5−アミン−o−硫酸塩誘導体の製造方法およびn−アシル−(エピ)k5−アミン−o−硫酸塩誘導体
CN104098618A (zh) 磺达肝癸钠中间体及其中间体和磺达肝癸钠的制备方法
CN103476782A (zh) N-取代的甘露糖胺衍生物及其制备方法和用途
CN118496286A (zh) 创伤弧菌生物2型a血清型o-抗原二糖片段的化学合成方法
WO2024046048A1 (zh) 一种抗凝血肝素寡糖苯联二聚体及其制备方法与应用
JP6138241B2 (ja) 完全に保護されたヘパリン五糖類およびその中間体を調製するための方法
DK174348B1 (da) Pentasaccharider, tetrasaccharider og mellemprodukter i form af pentasaccharider, tetrasaccharider og disaccharider til fremstilling af pentasaccharider, samt fremgangsmåde til fremstilling af pentasaccharider
CN110790845A (zh) 一种含硫苷键糖胺聚糖的制备方法及应用
CN116874626B (zh) 灵芝孢子glswa-1多糖十四糖及其子结构的制备方法与增强胰岛素蛋白活力的应用
US20240287214A1 (en) Chlorella mannogalactan or sulfated chlorella mannogalactan compound and application of sulfated chlorella mannogalactan compound
RU2333222C2 (ru) Эпимеризованные производные полисахарида к5 с высокой степенью сульфатирования
CN108148101B (zh) 一种制备磺达肝癸钠的新工艺方法
CN108265094B (zh) 一种α-2,3脱氨基唾液酸乳果糖制备方法
Haslett Synthesis of N-glycans implicated in asthma and allergy
JP2003301002A (ja) キトサンを基材とした複合型糖鎖多価結合体
FR2531436A1 (fr) Pentasaccharides substitues possedant des proprietes biologiques, leur preparation et leurs applications en tant que medicaments

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20171215

Termination date: 20190402