JP2005505565A5 - - Google Patents
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- Publication number
- JP2005505565A5 JP2005505565A5 JP2003526933A JP2003526933A JP2005505565A5 JP 2005505565 A5 JP2005505565 A5 JP 2005505565A5 JP 2003526933 A JP2003526933 A JP 2003526933A JP 2003526933 A JP2003526933 A JP 2003526933A JP 2005505565 A5 JP2005505565 A5 JP 2005505565A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- acyl
- benzyl
- protecting
- 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
Links
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 125000005251 aryl acyl group Chemical group 0.000 claims 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 32
- -1 trichloroacetimidoyl Chemical group 0.000 claims 32
- 125000005258 alkyl aryl acyl group Chemical group 0.000 claims 29
- 125000006239 protecting group Chemical group 0.000 claims 28
- 125000005257 alkyl acyl group Chemical group 0.000 claims 25
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 17
- 125000005587 carbonate group Chemical group 0.000 claims 16
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 10
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims 9
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 7
- 229910019142 PO4 Inorganic materials 0.000 claims 6
- 235000021317 phosphate Nutrition 0.000 claims 6
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 5
- 239000010452 phosphate Substances 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 4
- 150000002016 disaccharides Chemical class 0.000 claims 4
- 125000004001 thioalkyl group Chemical group 0.000 claims 4
- 125000005000 thioaryl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000011987 methylation Effects 0.000 claims 2
- 238000007069 methylation reaction Methods 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 150000004043 trisaccharides Chemical class 0.000 claims 2
- 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 2
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000021615 conjugation Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPR758701 | 2001-09-07 | ||
| AUPR7587 | 2001-09-07 | ||
| PCT/AU2002/001228 WO2003022860A1 (en) | 2001-09-07 | 2002-09-06 | Synthetic heparin pentasaccharides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005505565A JP2005505565A (ja) | 2005-02-24 |
| JP2005505565A5 true JP2005505565A5 (enExample) | 2006-03-16 |
| JP4688414B2 JP4688414B2 (ja) | 2011-05-25 |
Family
ID=34437858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003526933A Expired - Fee Related JP4688414B2 (ja) | 2001-09-07 | 2002-09-06 | 合成ヘパリン五糖 |
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) | CA2806561C (enExample) |
| DK (1) | DK1440077T3 (enExample) |
| ES (1) | ES2423888T3 (enExample) |
| PT (1) | PT1440077E (enExample) |
| WO (1) | WO2003022860A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7541445B2 (en) | 2001-09-07 | 2009-06-02 | Alchemia Limited | 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. |
| CA2757091A1 (en) | 2009-03-30 | 2010-10-14 | University Of Georgia Research Foundation, Inc. | Heparan sulfate synthesis |
| 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 |
| EP2683746A4 (en) * | 2011-03-10 | 2014-09-03 | Callaghan Innovation Res Ltd | oligosaccharide |
| 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 |
| JP6138241B2 (ja) * | 2012-05-25 | 2017-05-31 | ツェジャン ハイサン ファーマシューティカル カンパニー リミテッド | 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 |
| 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 |
| CN104619712B (zh) * | 2012-06-05 | 2017-09-12 | 中央研究院 | 制备磺达肝素的方法和中间体 |
| 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 |
| EP3024840B1 (en) * | 2013-07-25 | 2019-10-02 | ScinoPharm Taiwan, Ltd. | Process for the production of fondaparinux sodium |
| WO2015011517A1 (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 |
| US9909534B2 (en) | 2014-09-22 | 2018-03-06 | Ini Power Systems, Inc. | Carbureted engine having an adjustable fuel to air ratio |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| US11306157B2 (en) | 2018-12-21 | 2022-04-19 | California Institute Of Technology | Expedient synthesis of core disaccharide building 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 |
| EP4247826A1 (en) * | 2020-11-19 | 2023-09-27 | 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 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US187381A (en) * | 1877-02-13 | Improvement in air and steasvj blowers for furnaces | ||
| US13862A (en) * | 1855-12-04 | Cutting pile fabrics | ||
| US684691A (en) | 1901-03-23 | 1901-10-15 | Donald E Webster | Micrometer-gage. |
| IL61201A (en) | 1979-10-05 | 1984-09-30 | Choay Sa | Oligosaccharides having no more than 8 saccharide moieties,their obtention from heparin and pharmaceutical compositions containing them |
| CA1171375A (en) * | 1980-09-15 | 1984-07-24 | Ulf P.F. Lindahl | Oligosaccharides having selective anticoagulation activity |
| US4818816A (en) * | 1981-04-28 | 1989-04-04 | Choay, S.A. | Process for the organic synthesis of oligosaccharides and derivatives thereof |
| FR2504535B1 (fr) * | 1981-04-28 | 1987-08-14 | Choay Sa | Disaccharides derives d'un acide uronique et d'une glucosamine et compositions pharmaceutiques les contenant pour le controle de la coagulation sanguine |
| FR2519987A1 (fr) * | 1982-01-15 | 1983-07-22 | Choay Sa | Trisaccharides a structures d-glucosamine, acide d-glucuronique, d-glucosamine et leur preparation |
| FR2531436A1 (fr) * | 1982-08-06 | 1984-02-10 | Choay Sa | Pentasaccharides substitues possedant des proprietes biologiques, leur preparation et leurs applications en tant que medicaments |
| CA1247608A (fr) * | 1981-12-23 | 1988-12-28 | Jean Choay | Derives a structure acide uronique, leur preparation et leurs applications biologiques |
| FR2518550A1 (fr) * | 1981-12-23 | 1983-06-24 | Choay Sa | Procede de preparation de monosaccharides a structure acide l-iduronique |
| US4801583A (en) * | 1982-01-15 | 1989-01-31 | Choay S.A. | Oligosaccharides and their biological applications |
| AU563351C (en) | 1982-01-15 | 2003-06-19 | Glaxo Group Limited | Synthesis of oligosaccharides |
| FR2564468B1 (fr) * | 1984-05-16 | 1994-12-23 | Choay Sa | Nouveaux oligosaccharides, leur preparation par voie de synthese et leurs applications biologiques |
| JPS63218691A (ja) * | 1987-03-09 | 1988-09-12 | Rikagaku Kenkyusho | 新規な５糖類化合物及びその製造法並びに抗凝血及び抗血栓剤 |
| EP0333243A3 (en) * | 1988-03-10 | 1989-09-27 | Akzo N.V. | Sulphated k5 antigen and sulphated k5 antigen fragments |
| JPH03237101A (ja) * | 1989-12-18 | 1991-10-23 | Rikagaku Kenkyusho | グリコシルフォスファチジルイノシトールアンカー合成中間体及びグリコシルフォスファチジルイノシトールアンカー類縁体の合成中間体 |
| JPH0616692A (ja) * | 1992-07-03 | 1994-01-25 | Nisshin Oil Mills Ltd:The | 新規糖誘導体 |
| CA2100821C (en) * | 1993-07-19 | 2001-01-16 | Stephen Hanessian | Stereocontrolled glycosidation |
| JP3837876B2 (ja) * | 1996-11-05 | 2006-10-25 | 和光純薬工業株式会社 | アジドハロゲノベンジル誘導体及び水酸基の保護方法 |
| JP3005669B2 (ja) | 1996-12-19 | 2000-01-31 | 工業技術院長 | 不斉な含フッ素一級アミンの製造法 |
| US6538117B1 (en) * | 1999-08-10 | 2003-03-25 | The Scripps Research Institute | Programmable one-pot oligosaccharide synthesis |
| TWI289566B (en) * | 1999-12-07 | 2007-11-11 | N.V.Organon | Antithrombotic compound |
| CA2435637A1 (en) * | 2001-01-23 | 2002-08-01 | Massachusetts Institute Of Technology | Solid- and solution -phase synthesis of heparin and other glycosaminoglycans |
| US7541445B2 (en) | 2001-09-07 | 2009-06-02 | Alchemia Limited | Synthetic heparin pentasaccharides |
-
2002
- 2002-09-06 US US10/488,677 patent/US7541445B2/en not_active Expired - Fee Related
- 2002-09-06 AU AU2002331426A patent/AU2002331426B2/en not_active Ceased
- 2002-09-06 JP JP2003526933A patent/JP4688414B2/ja not_active Expired - Fee Related
- 2002-09-06 CA CA2806561A patent/CA2806561C/en not_active Expired - Fee Related
- 2002-09-06 DK DK02766941.5T patent/DK1440077T3/da active
- 2002-09-06 PT PT2766941T patent/PT1440077E/pt unknown
- 2002-09-06 CA CA2459562A patent/CA2459562C/en not_active Expired - Fee Related
- 2002-09-06 EP EP12188642.8A patent/EP2557086A3/en not_active Withdrawn
- 2002-09-06 CN CN028218558A patent/CN1558911B/zh not_active Expired - Fee Related
- 2002-09-06 ES ES02766941T patent/ES2423888T3/es not_active Expired - Lifetime
- 2002-09-06 WO PCT/AU2002/001228 patent/WO2003022860A1/en not_active Ceased
- 2002-09-06 EP EP02766941.5A patent/EP1440077B1/en not_active Expired - Lifetime
- 2002-09-06 CA CA2806604A patent/CA2806604C/en not_active Expired - Fee Related
- 2002-09-06 CA CA2806723A patent/CA2806723C/en not_active Expired - Fee Related
-
2009
- 2009-01-15 US US12/354,643 patent/US8114970B2/en not_active Expired - Fee Related
-
2011
- 2011-12-14 US US13/326,060 patent/US8686131B2/en not_active Expired - Fee Related
- 2011-12-14 US US13/326,147 patent/US8404833B2/en not_active Expired - Fee Related
-
2014
- 2014-01-29 US US14/167,822 patent/US9243018B2/en not_active Expired - Fee Related
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