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 PDFInfo
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- 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
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- benzyl
- alkyl
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- 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 title claims abstract description 28
- 229960002897 heparin Drugs 0.000 title claims abstract description 27
- 229920000669 heparin Polymers 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
- -1 methoxy-benzyl Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 14
- 229910001415 sodium ion Inorganic materials 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 9
- 238000006722 reduction reaction Methods 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical group CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 7
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
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- 229960003661 fondaparinux sodium Drugs 0.000 claims description 6
- 230000001180 sulfating effect Effects 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
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- YYHPEVZFVMVUNJ-UHFFFAOYSA-N n,n-diethylethanamine;sulfur trioxide Chemical compound O=S(=O)=O.CCN(CC)CC YYHPEVZFVMVUNJ-UHFFFAOYSA-N 0.000 claims description 2
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- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 4
- 241000219094 Vitaceae Species 0.000 claims 2
- 235000021021 grapes Nutrition 0.000 claims 2
- GVFLAEFIIMXUPC-UHFFFAOYSA-N [S].CN(C)C Chemical compound [S].CN(C)C GVFLAEFIIMXUPC-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 claims 1
- XEKSTYNIJLDDAZ-JASSWCPGSA-F fondaparinux sodium Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O[C@@H]1[C@@H](NS([O-])(=O)=O)[C@@H](OC)O[C@H](COS([O-])(=O)=O)[C@H]1O[C@H]1[C@H](OS([O-])(=O)=O)[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](OS([O-])(=O)=O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](COS([O-])(=O)=O)O4)NS([O-])(=O)=O)[C@H](O3)C(O)=O)O)[C@@H](COS([O-])(=O)=O)O2)NS([O-])(=O)=O)[C@H](C(O)=O)O1 XEKSTYNIJLDDAZ-JASSWCPGSA-F 0.000 claims 1
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 239000002904 solvent Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 6
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 6
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- XEKSTYNIJLDDAZ-JASSWCPGSA-D decasodium;(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5r,6r)-6-[(2r,3s,4s,5r,6r)-2-carboxylato-4-hydroxy-6-[(2r,3s,4r,5r,6s)-4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-5-sulfonatooxyoxan-3-yl]oxy-5-(sulfonatoamino)-4-sulfonatooxy-2-(sul Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O[C@@H]1[C@@H](NS([O-])(=O)=O)[C@@H](OC)O[C@H](COS([O-])(=O)=O)[C@H]1O[C@H]1[C@H](OS([O-])(=O)=O)[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](OS([O-])(=O)=O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](COS([O-])(=O)=O)O4)NS([O-])(=O)=O)[C@H](O3)C([O-])=O)O)[C@@H](COS([O-])(=O)=O)O2)NS([O-])(=O)=O)[C@H](C([O-])=O)O1 XEKSTYNIJLDDAZ-JASSWCPGSA-D 0.000 description 5
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- 239000006104 solid solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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
- 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
-
- 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
- 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
- C07H5/06—Aminosugars
-
- 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
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)
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 |
| IN9026DEN2014 IN2014DN09026A (enExample) | 2012-04-02 | 2013-04-02 | |
| EP13772346.6A EP2837635B1 (en) | 2012-04-02 | 2013-04-02 | New intermediates for the preparation of heparin pentasaccharide and preparation methods 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 |
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 (enExample) |
| EP (1) | EP2837635B1 (enExample) |
| JP (1) | JP2015514098A (enExample) |
| CN (1) | CN103360439B (enExample) |
| IN (1) | IN2014DN09026A (enExample) |
| WO (1) | WO2013149576A1 (enExample) |
Families Citing this family (9)
| 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 |
| US20190002596A1 (en) * | 2015-12-30 | 2019-01-03 | Shenzhen Hepalink Pharmaceutical Group Co., Ltd. | Sulfated heparin oligosaccharide and preparation 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 |
Citations (5)
| 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)
| 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 |
-
2012
- 2012-04-02 CN CN201210102415.0A patent/CN103360439B/zh not_active Expired - Fee Related
-
2013
- 2013-04-02 JP JP2015503738A patent/JP2015514098A/ja active Pending
- 2013-04-02 IN IN9026DEN2014 patent/IN2014DN09026A/en unknown
- 2013-04-02 WO PCT/CN2013/073601 patent/WO2013149576A1/zh not_active Ceased
- 2013-04-02 EP EP13772346.6A patent/EP2837635B1/en not_active Not-in-force
- 2013-04-02 US US14/389,806 patent/US9624315B2/en not_active Expired - Fee Related
Patent Citations (5)
| 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)
| 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 |
|---|---|
| EP2837635A1 (en) | 2015-02-18 |
| JP2015514098A (ja) | 2015-05-18 |
| EP2837635B1 (en) | 2017-10-18 |
| EP2837635A4 (en) | 2015-05-27 |
| WO2013149576A1 (zh) | 2013-10-10 |
| US20150299340A1 (en) | 2015-10-22 |
| CN103360439A (zh) | 2013-10-23 |
| IN2014DN09026A (enExample) | 2015-05-22 |
| US9624315B2 (en) | 2017-04-18 |
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