CA2459562C - Synthetic heparin pentasaccharides - Google Patents

Synthetic heparin pentasaccharides Download PDF

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Publication number
CA2459562C
CA2459562C CA2459562A CA2459562A CA2459562C CA 2459562 C CA2459562 C CA 2459562C CA 2459562 A CA2459562 A CA 2459562A CA 2459562 A CA2459562 A CA 2459562A CA 2459562 C CA2459562 C CA 2459562C
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CA
Canada
Prior art keywords
group
mpm
sop
groups
substituted
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
CA2459562A
Other languages
English (en)
French (fr)
Other versions
CA2459562A1 (en
Inventor
Joachim Seifert
Latika Singh
Tracie Elizabeth Ramsdale
Michael Leo West
Nicholas Barry Drinnan
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.)
Dr Reddys Laboratories SA
Original Assignee
Alchemia Pty 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 Alchemia Pty Ltd filed Critical Alchemia Pty Ltd
Priority to CA2806723A priority Critical patent/CA2806723C/en
Priority to CA2806604A priority patent/CA2806604C/en
Priority to CA2806561A priority patent/CA2806561C/en
Publication of CA2459562A1 publication Critical patent/CA2459562A1/en
Application granted granted Critical
Publication of CA2459562C publication Critical patent/CA2459562C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • 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
    • C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
    • 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
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds 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
    • C07H5/04—Compounds 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/02—Acyclic radicals
    • C07H7/033—Uronic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
CA2459562A 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides Expired - Fee Related CA2459562C (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA2806723A CA2806723C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806604A CA2806604C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806561A CA2806561C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AUPR7587 2001-09-07
AUPR758701 2001-09-07
PCT/AU2002/001228 WO2003022860A1 (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides

Related Child Applications (3)

Application Number Title Priority Date Filing Date
CA2806723A Division CA2806723C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806561A Division CA2806561C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806604A Division CA2806604C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides

Publications (2)

Publication Number Publication Date
CA2459562A1 CA2459562A1 (en) 2003-03-20
CA2459562C true CA2459562C (en) 2013-05-07

Family

ID=34437858

Family Applications (4)

Application Number Title Priority Date Filing Date
CA2459562A Expired - Fee Related CA2459562C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806561A Expired - Fee Related CA2806561C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806604A Expired - Fee Related CA2806604C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806723A Expired - Fee Related CA2806723C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides

Family Applications After (3)

Application Number Title Priority Date Filing Date
CA2806561A Expired - Fee Related CA2806561C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806604A Expired - Fee Related CA2806604C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides
CA2806723A Expired - Fee Related CA2806723C (en) 2001-09-07 2002-09-06 Synthetic heparin pentasaccharides

Country Status (10)

Country Link
US (5) US7541445B2 (enExample)
EP (2) EP2557086A3 (enExample)
JP (1) JP4688414B2 (enExample)
CN (1) CN1558911B (enExample)
AU (1) AU2002331426B2 (enExample)
CA (4) CA2459562C (enExample)
DK (1) DK1440077T3 (enExample)
ES (1) ES2423888T3 (enExample)
PT (1) PT1440077E (enExample)
WO (1) WO2003022860A1 (enExample)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003022860A1 (en) 2001-09-07 2003-03-20 Alchemia Pty Ltd Synthetic heparin pentasaccharides
AU2002950657A0 (en) * 2002-08-08 2002-09-12 Alchemia Limited Derivatives of monosaccharides for drug discovery
JP2006143694A (ja) * 2004-11-16 2006-06-08 Tokyo Kasei Kogyo Kk 新規ｐ−メトキシフェニル糖誘導体
ES2336297B1 (es) 2008-10-08 2011-01-24 Laboratorios Farmaceuticos Rovi, S.A. Procedimiento de sintesis de pentasacaridos desprotegidos a partir deun pentasacarido precursos protegido.
EP2414371A4 (en) * 2009-03-30 2014-06-25 Univ Georgia HEPARANSULFATSYNTHESE
EP3666786A1 (en) 2009-07-31 2020-06-17 Reliable Biopharmaceutical Corporation Process for preparing fondaparinux sodium and intermediates useful in the synthesis thereof
US8420790B2 (en) 2009-10-30 2013-04-16 Reliable Biopharmaceutical Corporation Efficient and scalable process for the manufacture of Fondaparinux sodium
EP2512448B1 (en) * 2009-12-18 2016-07-06 Endotis Pharma Pharmaceutical oral dosage form containing a synthetic oligosaccharide
WO2012121617A1 (en) * 2011-03-10 2012-09-13 Industrial Research Limited Oligosaccharide compounds
US20130005954A1 (en) * 2011-06-28 2013-01-03 Apicore, Llc Process for preparing heparinoids and intermediates useful in the synthesis thereof
CN103360439B (zh) 2012-04-02 2017-12-15 浙江海正药业股份有限公司 制备肝素五糖的新中间体及其制备方法
US20150284419A1 (en) * 2012-05-25 2015-10-08 Zhejiang Hisun Pharmaceutical Co., Ltd. Method for preparing fully protection heparin pentasaccharide and intermediate thereof
CN102690302B (zh) * 2012-05-30 2015-07-01 济南圣泉唐和唐生物科技有限公司 1,2-O-异亚丙基-3-O-苄基-α-D-呋喃葡萄糖苷的制备方法
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
WO2013184564A1 (en) * 2012-06-05 2013-12-12 Academia Sinica Methods and intermediates for the preparation of fondaparinux
CN102775450B (zh) * 2012-07-03 2015-04-08 华东师范大学 一种1,6-脱水-2-叠氮-2-脱氧-β-D-吡喃葡萄糖的制备方法
CN102898487B (zh) * 2012-11-13 2016-03-09 麦科罗夫（南通）生物制药有限公司 一种磺达肝葵钠二糖中间体片段ba及其合成方法
CN102942601B (zh) * 2012-11-30 2015-09-30 江苏华泰晨光药业有限公司 一种磺达肝癸钠的中间体的制备方法
WO2014205115A2 (en) 2013-06-19 2014-12-24 The Regents Of The University Of California Regioselective silyl exchange of per-silylated oligosaccharides
JP6339673B2 (ja) * 2013-07-25 2018-06-06 サイノファーム タイワン，リミティド フォンダパリヌクスナトリウムを製造するための方法
WO2015011519A1 (en) * 2013-07-25 2015-01-29 Scinopharm Taiwan, Ltd. Process for the production of fondaparinux sodium
US10072039B2 (en) * 2013-07-25 2018-09-11 Scinopharm Taiwan, Ltd. Process for the production of Fondaparinux sodium
US9346844B2 (en) 2013-07-25 2016-05-24 Scinopharm Taiwan, Ltd. Process for the production of fondaparinux sodium
CN103601765B (zh) * 2013-09-02 2017-01-04 上海艾康睿医药科技有限公司 磺达肝癸钠及其中间体、以及制备方法
JP2016537349A (ja) 2013-11-14 2016-12-01 浙江海正薬業股▲ふん▼有限公司Ｚｈｅｊｉａｎｇ Ｈｉｓｕｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌ ＣＯ．，ＬＴＤ． 二糖中間体及びその合成方法
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
WO2016040779A1 (en) * 2014-09-12 2016-03-17 The Board Of Trustees Of The University Of Illinois Urea derivatives of polyene macrolide antibiotics
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CN105985387A (zh) * 2015-02-04 2016-10-05 苏州朗科生物技术有限公司 一种磺达肝癸钠杂质化合物及其制备方法和用途
CN105985388A (zh) * 2015-02-04 2016-10-05 苏州朗科生物技术有限公司 磺达肝癸钠杂质化合物及其制备方法和应用
CN104876979B (zh) * 2015-06-19 2018-10-09 天津红日药业股份有限公司 一种具有抗Xa因子活性的磺酸化五糖化合物
CN104910217B (zh) * 2015-06-19 2018-04-17 天津红日药业股份有限公司 用于磺达肝癸钠质量控制的参比化合物
US10023603B2 (en) * 2015-07-16 2018-07-17 Formosa Laboratories, Inc. Preparation of monosaccharides, disaccharides, trisaccharides, and pentasaccharides of heparinoids
CN106518935B (zh) * 2016-10-26 2019-05-21 陕西国防工业职业技术学院 一种3,6-二去氧-3-氨基-l-艾杜糖及其衍生物的合成方法
CN107501359B (zh) * 2017-08-24 2020-07-31 深圳市海滨制药有限公司 一种磺达肝癸钠杂质化合物及其制备方法与应用
WO2020132625A1 (en) * 2018-12-21 2020-06-25 California Institute Of Technology Synthesis of disaccharide blocks from natural polysaccharides for heparan sulfate oligosaccharide assembly
CN109734757B (zh) * 2019-03-11 2020-09-11 淮北师范大学 一种磺达肝癸钠注射液有关物质b的制备方法
WO2021043631A1 (en) 2019-09-02 2021-03-11 Hepoligo Solutions Aps Intermediates useful for preparing iduronic acid containing di- and polysaccharides
WO2021083735A1 (en) 2019-10-29 2021-05-06 Hepoligo Solutions Aps Process for the production of 1,6-anhydro sugars
CN110746471B (zh) * 2019-11-04 2021-06-25 江苏美迪克化学品有限公司 一种磺达肝癸钠双糖中间体的制备方法
WO2022107013A1 (en) * 2020-11-19 2022-05-27 Indian Institute Of Science Education And Research Silver assisted gold catalysis for the preparation of fondaparinux pentasaccharide and intermediates
CN112552359B (zh) * 2020-12-21 2022-11-25 北京大学 一种磺达肝葵钠五糖中间体自动化制备方法

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Also Published As

Publication number Publication date
CA2806604C (en) 2014-04-08
US8404833B2 (en) 2013-03-26
CN1558911A (zh) 2004-12-29
PT1440077E (pt) 2013-06-04
US8114970B2 (en) 2012-02-14
CA2806561A1 (en) 2003-03-20
US20090187013A1 (en) 2009-07-23
US8686131B2 (en) 2014-04-01
CA2806604A1 (en) 2003-03-20
AU2002331426A1 (en) 2003-03-24
JP4688414B2 (ja) 2011-05-25
CA2806561C (en) 2015-12-22
US7541445B2 (en) 2009-06-02
US20120220759A1 (en) 2012-08-30
CA2806723C (en) 2015-12-29
JP2005505565A (ja) 2005-02-24
US20120208993A1 (en) 2012-08-16
WO2003022860A1 (en) 2003-03-20
AU2002331426B2 (en) 2008-01-10
DK1440077T3 (da) 2013-07-08
CN1558911B (zh) 2010-05-12
EP1440077A4 (en) 2010-06-02
EP1440077A1 (en) 2004-07-28
EP1440077B1 (en) 2013-05-01
US20150005485A1 (en) 2015-01-01
ES2423888T3 (es) 2013-09-25
CA2459562A1 (en) 2003-03-20
EP2557086A2 (en) 2013-02-13
EP2557086A3 (en) 2014-11-05
CA2806723A1 (en) 2003-03-20
US20050080042A1 (en) 2005-04-14
US9243018B2 (en) 2016-01-26

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