CN104119404A - 硫酸化寡聚糖衍生物 - Google Patents
硫酸化寡聚糖衍生物 Download PDFInfo
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- CN104119404A CN104119404A CN201410353750.7A CN201410353750A CN104119404A CN 104119404 A CN104119404 A CN 104119404A CN 201410353750 A CN201410353750 A CN 201410353750A CN 104119404 A CN104119404 A CN 104119404A
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Classifications
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005219456B2 (en) * | 2004-03-04 | 2011-04-07 | Progen Pharmaceuticals Limited | Sulfated oligosaccharide derivatives |
| CN101203230A (zh) * | 2005-04-01 | 2008-06-18 | 克里斯托弗·理查德·帕里什 | 用nod因子例如葡糖胺寡糖调节血管发生 |
| AU2008314505C1 (en) * | 2007-10-16 | 2020-11-05 | Progen Pg500 Series Pty Ltd | Novel sulfated oligosaccharide derivatives |
| EP2307440A4 (en) * | 2008-07-01 | 2012-12-19 | Zacharon Pharmaceuticals Inc | HEPARAN SULFATE INHIBITORS |
| EP2149580A1 (en) | 2008-07-15 | 2010-02-03 | Istituto Scientifico di Chimica E Biochimica "G Ronzoni | Mimetics of sulfated oligosaccharides |
| CN101591401A (zh) * | 2009-02-27 | 2009-12-02 | 江南大学 | 一种制备高活性低分子量肝素的方法 |
| JP5701498B2 (ja) * | 2009-12-01 | 2015-04-15 | 公益財団法人微生物化学研究会 | 炎症性細胞からのヘパラナーゼの放出抑制剤、抗炎症剤、及び薬用組成物 |
| KR20140050605A (ko) * | 2011-06-09 | 2014-04-29 | 메디젠 바이오테크놀로지 코프 | 간암의 재발, 악화 또는 전이 억제용 의약조성물 |
| RU2760005C2 (ru) | 2014-03-13 | 2021-11-22 | Университет Базель | УГЛЕВОДНЫЕ ЛИГАНДЫ, КОТОРЫЕ СВЯЗЫВАЮТСЯ С IgM АНТИТЕЛАМИ ПРОТИВ МИЕЛИН-АССОЦИИРОВАННОГО ГЛИКОПРОТЕИНА |
| CN105017341B (zh) * | 2014-04-22 | 2018-05-15 | 华东师范大学 | 硫酸化岩藻-半乳四糖及其制备方法和应用 |
| CN105001278B (zh) * | 2015-06-19 | 2018-07-06 | 天津红日药业股份有限公司 | 一种磺达肝癸钠二糖中间体片段的合成方法 |
| 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 |
| AU2016323377B2 (en) | 2015-09-16 | 2021-04-15 | Universität Basel | Carbohydrate ligands that bind to antibodies against glycoepitopes of glycosphingolipids |
| JP2016199579A (ja) * | 2016-07-08 | 2016-12-01 | 基亜生物科技股▲ふん▼有限公司Ｍｅｄｉｇｅｎ Ｂｉｏｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐ． | 肝癌の再発、悪化または転移の抑制に用いる医薬組成物 |
| WO2018103680A1 (zh) * | 2016-12-10 | 2018-06-14 | 扬州蓝色生物医药科技有限公司 | 甘露寡聚糖类化合物及其作为抗rna病毒药物的应用 |
| JP2020503377A (ja) | 2016-12-13 | 2020-01-30 | ベータ セラピューティクス プロプライアタリー リミティド | ヘパラナーゼ阻害剤及びそれの使用 |
| US11787783B2 (en) | 2016-12-13 | 2023-10-17 | Beta Therapeutics Pty Ltd | Heparanase inhibitors and use thereof |
| KR20190134591A (ko) | 2016-12-15 | 2019-12-04 | 프로젠 피지500 시리즈 피티와이 리미티드 | 조성물 및 그의 용도 |
| US10842804B2 (en) * | 2017-03-01 | 2020-11-24 | Medigen Biotechnology Corporation | Muparfostat for use in treating patients with hepatitis virus-related hepatocellular carcinoma after surgical resection |
| KR102377358B1 (ko) | 2017-10-16 | 2022-03-23 | 삼성전자주식회사 | 반도체 메모리 소자 및 그 제조 방법 |
| KR102753401B1 (ko) | 2017-12-15 | 2025-01-10 | 오스트레일리언 내셔널 유니버시티 | 세포외 히스톤 매개된 병리를 치료 및 예방하기 위한 화합물 |
| JP6619830B2 (ja) * | 2018-02-22 | 2019-12-11 | 基亜生物科技股▲ふん▼有限公司Ｍｅｄｉｇｅｎ Ｂｉｏｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐ． | 肝癌の再発、悪化または転移の抑制に用いる医薬組成物 |
| CN109762032A (zh) * | 2019-01-16 | 2019-05-17 | 天津科技大学 | 一种磺酸化路易斯x三糖及其合成方法和应用 |
| EA202192345A1 (ru) | 2019-02-25 | 2021-12-06 | Дзе Острэйлиан Нэшнл Юниверсити | Соединения для лечения и предотвращения осложнений, ассоциированных с net |
| CN116813675B (zh) * | 2023-08-23 | 2023-11-24 | 北京远大九和药业有限公司 | 一种化合物晶型及其制备、组合物和用途 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996009828A1 (en) * | 1994-09-26 | 1996-04-04 | Glycomed Incorporated | Highly sulfated maltooligosaccharides with heparin-like properties |
| EP0771815A1 (en) * | 1995-10-31 | 1997-05-07 | Sanwa Kagaku Kenkyusho Co., Ltd. | Sulfated and phosphated saccharide derivatives, process for the preparation of the same and use thereof |
| CN1183043A (zh) * | 1995-04-28 | 1998-05-27 | 澳大利亚国立大学 | 硫酸化低聚糖的制备方法和用途 |
| CN1450075A (zh) * | 2002-04-11 | 2003-10-22 | 中国科学院生态环境研究中心 | 一类寡糖及其硫酸化产物和它们的制备方法及含该寡糖的药物组合物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0338092A1 (en) | 1987-10-30 | 1989-10-25 | Chugai Seiyaku Kabushiki Kaisha | Anti-hiv agent |
| FR2704226B1 (fr) * | 1993-04-22 | 1995-07-21 | Sanofi Elf | 3-desoxy oligosaccharides, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| AU700451B2 (en) * | 1993-10-07 | 1999-01-07 | Glycomed Incorporated | Highly sulfated maltooligosaccharides with heparin-like properties |
| ATE414094T1 (de) * | 1995-04-28 | 2008-11-15 | Takara Bio Inc | Zuckerverbindungen |
| IL120722A (en) * | 1996-05-08 | 1999-07-14 | Akzo Nobel Nv | Polysulfated tetrasaccharide derivatives and pharmaceutical compositions containing them |
| AUPO556297A0 (en) | 1997-03-11 | 1997-04-10 | Australian National University, The | Sulfated oligosaccharides having anticoagulant/ antithrombotic activity |
| IL126893A (en) * | 1997-11-19 | 2003-05-29 | Akzo Nobel Nv | Sulfated pentasaccharide derivatives and pharmaceutical compositions containing them |
| FR2773801B1 (fr) * | 1998-01-19 | 2000-05-12 | Sanofi Sa | Nouveaux pentasaccharides, procedes pour leurs preparations et compositions pharmaceutiques les contenant |
| AU2005219456B2 (en) * | 2004-03-04 | 2011-04-07 | Progen Pharmaceuticals Limited | Sulfated oligosaccharide derivatives |
-
2005
- 2005-03-04 AU AU2005219456A patent/AU2005219456B2/en not_active Ceased
- 2005-03-04 WO PCT/AU2005/000314 patent/WO2005085264A1/en not_active Ceased
- 2005-03-04 ES ES05706346.3T patent/ES2531880T3/es not_active Expired - Lifetime
- 2005-03-04 EP EP05706346.3A patent/EP1720889B1/en not_active Expired - Lifetime
- 2005-03-04 RU RU2006134972/04A patent/RU2392281C2/ru not_active IP Right Cessation
- 2005-03-04 CN CNA2005800068338A patent/CN1989146A/zh active Pending
- 2005-03-04 BR BRPI0508144-0A patent/BRPI0508144A/pt not_active Application Discontinuation
- 2005-03-04 CN CN201410353750.7A patent/CN104119404A/zh active Pending
- 2005-03-04 CN CN201410042932.2A patent/CN103788141B/zh not_active Expired - Fee Related
- 2005-03-04 TW TW094106609A patent/TWI426080B/zh not_active IP Right Cessation
- 2005-03-04 US US10/591,577 patent/US7875592B2/en not_active Expired - Fee Related
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- 2005-03-04 JP JP2007501068A patent/JP5139797B2/ja not_active Expired - Fee Related
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- 2005-03-04 KR KR1020067020704A patent/KR101156273B1/ko not_active Expired - Fee Related
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- 2006-08-23 ZA ZA2006/07057A patent/ZA200607057B/en unknown
- 2006-09-03 IL IL177870A patent/IL177870A/en active IP Right Grant
- 2006-10-03 NO NO20064489A patent/NO338461B1/no not_active IP Right Cessation
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996009828A1 (en) * | 1994-09-26 | 1996-04-04 | Glycomed Incorporated | Highly sulfated maltooligosaccharides with heparin-like properties |
| CN1183043A (zh) * | 1995-04-28 | 1998-05-27 | 澳大利亚国立大学 | 硫酸化低聚糖的制备方法和用途 |
| EP0771815A1 (en) * | 1995-10-31 | 1997-05-07 | Sanwa Kagaku Kenkyusho Co., Ltd. | Sulfated and phosphated saccharide derivatives, process for the preparation of the same and use thereof |
| CN1450075A (zh) * | 2002-04-11 | 2003-10-22 | 中国科学院生态环境研究中心 | 一类寡糖及其硫酸化产物和它们的制备方法及含该寡糖的药物组合物 |
Non-Patent Citations (2)
| Title |
|---|
| GUANGLI YU等: "Preparation and anticoagulant activity of the phosphosulfomannan PI-88", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
| KANAME KATSURAYA等: "Synthesis of sulfated oligosaccharide glycosides having high anti-HIV activity and the relationship between activity and chemical structure", 《CARBOHYDRATE RESEARCH》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2006134972A (ru) | 2008-04-10 |
| EP1720889B1 (en) | 2014-11-26 |
| MXPA06010049A (es) | 2007-04-10 |
| BRPI0508144A (pt) | 2007-07-24 |
| CN103788141B (zh) | 2016-08-17 |
| KR20070007815A (ko) | 2007-01-16 |
| EP1720889A4 (en) | 2008-03-19 |
| ZA200607057B (en) | 2008-04-30 |
| TW200602351A (en) | 2006-01-16 |
| NO338461B1 (no) | 2016-08-15 |
| CN103788141A (zh) | 2014-05-14 |
| US7875592B2 (en) | 2011-01-25 |
| TWI426080B (zh) | 2014-02-11 |
| US8173606B2 (en) | 2012-05-08 |
| EP1720889A1 (en) | 2006-11-15 |
| IL177870A0 (en) | 2006-12-31 |
| AU2005219456A1 (en) | 2005-09-15 |
| HK1199263A1 (en) | 2015-06-26 |
| JP2007526257A (ja) | 2007-09-13 |
| US20110130354A1 (en) | 2011-06-02 |
| WO2005085264A1 (en) | 2005-09-15 |
| NO20064489L (no) | 2006-11-27 |
| CA2557989A1 (en) | 2005-09-15 |
| JP5139797B2 (ja) | 2013-02-06 |
| US20070185037A1 (en) | 2007-08-09 |
| IL177870A (en) | 2011-08-31 |
| RU2392281C2 (ru) | 2010-06-20 |
| ES2531880T3 (es) | 2015-03-20 |
| KR101156273B1 (ko) | 2012-06-13 |
| CN1989146A (zh) | 2007-06-27 |
| CA2557989C (en) | 2013-04-23 |
| AU2005219456B2 (en) | 2011-04-07 |
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