CA2866682C - Process for the preparation of polysaccharide nanoparticles - Google Patents
Process for the preparation of polysaccharide nanoparticles Download PDFInfo
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- CA2866682C CA2866682C CA2866682A CA2866682A CA2866682C CA 2866682 C CA2866682 C CA 2866682C CA 2866682 A CA2866682 A CA 2866682A CA 2866682 A CA2866682 A CA 2866682A CA 2866682 C CA2866682 C CA 2866682C
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- Prior art keywords
- process according
- aldehyde groups
- nanoparticles
- polysaccharide
- group
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- 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
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/26—Cellulose ethers
- C08L1/28—Alkyl ethers
- C08L1/286—Alkyl ethers substituted with acid radicals, e.g. carboxymethyl cellulose [CMC]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/02—Dextran; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B1/00—Nanostructures formed by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
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- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL398450A PL221351B1 (pl) | 2012-03-14 | 2012-03-14 | Sposób otrzymywania nanocząstek polisacharydowych |
| PLPL398450 | 2012-03-14 | ||
| PCT/PL2013/000030 WO2013137755A1 (en) | 2012-03-14 | 2013-03-12 | Process for the preparation of polysaccharide nanoparticles |
Publications (2)
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| CA2866682A1 CA2866682A1 (en) | 2013-09-19 |
| CA2866682C true CA2866682C (en) | 2016-05-17 |
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| WO2016093352A1 (ja) * | 2014-12-12 | 2016-06-16 | 日本化薬株式会社 | 核酸代謝拮抗剤が結合した多分岐化合物 |
| DK3491092T3 (da) * | 2016-08-01 | 2023-11-13 | Integrity Bio Chemicals Llc | Biopolymerer til styring af flygtigt støv |
| US10736964B2 (en) * | 2017-05-01 | 2020-08-11 | China Medical University | Immunomagnetic nanocapsule and kit for treating cancer |
| CN107446054B (zh) * | 2017-08-11 | 2021-05-18 | 武汉理工大学 | 一种生物质基纳米粒子及其制备方法和应用 |
| PL424773A1 (pl) * | 2018-03-06 | 2019-09-09 | Nanovelos Spółka Akcyjna | Enkapsulowana polisacharydem antracyklina do zastosowania w leczeniu nowotworów |
| CN108553448A (zh) * | 2018-05-30 | 2018-09-21 | 江西师范大学 | 一种pH响应的药物缓释纤维素纳米颗粒的制备方法 |
| CN108676181B (zh) * | 2018-05-30 | 2022-05-17 | 江西师范大学 | 通过二醛基纤维素制备纤维素纳米颗粒的方法 |
| PL240772B1 (pl) | 2018-06-11 | 2022-06-06 | Nanothea Spolka Akcyjna | Sposób wytwarzania nanocząstek polimerowych chelatujących izotopy promieniotwórcze do zastosowania w diagnostyce i terapii |
| CN112353781B (zh) * | 2020-11-12 | 2022-08-19 | 云南开放大学 | 一种药物载体空心纳米球的制备方法 |
| CN112516310B (zh) * | 2020-12-11 | 2022-11-29 | 武汉理工大学 | 一种肿瘤酸环境响应的纳米前药的制备方法及其应用 |
| CN112830979A (zh) * | 2021-01-15 | 2021-05-25 | 江南大学 | 一种改性黄原胶及其制备方法与应用 |
| CN113800501B (zh) * | 2021-10-08 | 2023-04-18 | 山西大学 | 一种用于检测pH和精氨酸的橙红色荧光碳点的制备方法及其应用 |
| WO2023092208A1 (pt) * | 2021-11-25 | 2023-06-01 | Universidade Estadual De Campinas | Processo de obtenção de solução polimérica injetável fotoreticulável, solução polimérica injetável fotoreticulável e seus usos |
| CN115463262B (zh) * | 2022-08-11 | 2024-06-04 | 南方医科大学第五附属医院 | 一种水凝胶复合修复补片及其制备方法与应用 |
Family Cites Families (26)
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| SU825542A1 (ru) * | 1979-04-04 | 1981-04-30 | Inst Orch Chimii Aka | Способ получения n-производных полисахаридов 1 |
| US4452773A (en) * | 1982-04-05 | 1984-06-05 | Canadian Patents And Development Limited | Magnetic iron-dextran microspheres |
| US4693912A (en) * | 1985-02-28 | 1987-09-15 | Technicon Instruments Corporation | Lyophilization of reagent-coated particles |
| US4699784A (en) * | 1986-02-25 | 1987-10-13 | Center For Molecular Medicine & Immunology | Tumoricidal methotrexate-antibody conjugate |
| JPS62221637A (ja) * | 1986-03-24 | 1987-09-29 | Green Cross Corp:The | 制癌剤−抗体複合体の製造方法 |
| JPS62283101A (ja) * | 1986-05-30 | 1987-12-09 | Green Cross Corp:The | 制癌作用物質複合体の製造方法 |
| JPS63264427A (ja) * | 1986-12-17 | 1988-11-01 | Green Cross Corp:The | 制癌作用物質複合体 |
| JPH01190636A (ja) * | 1988-01-22 | 1989-07-31 | Green Cross Corp:The | 制癌作用物質複合体 |
| EP0999222A1 (en) | 1998-11-02 | 2000-05-10 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Carbohydrate oxidation products |
| NZ511792A (en) * | 1998-11-20 | 2003-08-29 | Skyepharma Canada Inc | Dispersible phospholipid stabilized microparticles |
| IL131074A0 (en) * | 1999-07-23 | 2001-03-19 | Polygene Ltd | A biodegradable polycation composition for delivery of an anionic macromolecule |
| US20030166513A1 (en) | 2000-06-29 | 2003-09-04 | Akihiro Imura | Dds compound and process for the preparation thereof |
| DE10129369C1 (de) * | 2001-06-21 | 2003-03-06 | Fresenius Kabi De Gmbh | Wasserlösliches, einen Aminozucker aufweisendes Antibiotikum in Form eines Pol ysaccharid-Konjugats |
| TWI313609B (en) | 2001-08-21 | 2009-08-21 | Mitsubishi Tanabe Pharma Corp | Pharmaceutical composition for inhibiting the metastasis or preventing the recurrence of malignant tumor |
| DE10209821A1 (de) | 2002-03-06 | 2003-09-25 | Biotechnologie Ges Mittelhesse | Kopplung von Proteinen an ein modifiziertes Polysaccharid |
| CA2487720A1 (en) * | 2002-06-03 | 2003-12-11 | Alnis Biosciences, Inc. | Therapeutic agent-containing polymeric nanoarticles |
| KR100578382B1 (ko) * | 2004-07-16 | 2006-05-11 | 나재운 | 항암제의 전달체용 수용성 키토산 나노입자 및 그 제조방법 |
| GB0502095D0 (en) | 2005-02-01 | 2005-03-09 | Chiron Srl | Conjugation of streptococcal capsular saccharides |
| BRPI0610469A2 (pt) * | 2005-05-27 | 2012-10-23 | Royer Biomedical Inc | composição bioerodìvel para a administração de um agente bioativo, kit para a formação de uma composição bioerodìvel, métodos de produção de uma composição bioerodìvel solidificada para a administração de um agente bioativo, de produção de uma fibra bioerodìvel para a administração de um agente bioativo e de formação de um filme bioerodìvel para a administração de um agente bioativo, dispositivo médico implantável, e, método de administração de um agente bioativo para um local do corpo necessitando do mesmo |
| CA2620416A1 (en) | 2005-08-24 | 2007-03-01 | Novartis Vaccines And Diagnostics S.R.L. | Zwitterionization of capsular saccharides |
| GB2436745B8 (en) * | 2005-09-09 | 2019-03-13 | Jae Woon Nah | Method for enhancing the solubility of paclitaxel |
| AU2006293426A1 (en) * | 2005-09-22 | 2007-03-29 | Hadasit Medical Research Services & Development Limited | Dextran and arabinogalactan conjugates of therapeutically active compounds |
| US8563066B2 (en) * | 2007-12-17 | 2013-10-22 | New World Pharmaceuticals, Llc | Sustained release of nutrients in vivo |
| CN105833337B (zh) * | 2008-11-19 | 2020-01-21 | 阿克塔马克斯手术器材有限责任公司 | 纤维组织封合剂及其使用方法 |
| CZ302503B6 (cs) * | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
| EP2590680A1 (en) | 2010-07-09 | 2013-05-15 | Fresenius Kabi Deutschland GmbH | Conjugates comprising hydroxyalkyl starch and a cytotoxic agent and process for their preparation |
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2012
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2013
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- 2013-03-12 IN IN1651MUN2014 patent/IN2014MN01651A/en unknown
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| CN104169305B (zh) | 2016-07-27 |
| IL234572A (en) | 2017-01-31 |
| PL221351B1 (pl) | 2016-03-31 |
| RU2632019C2 (ru) | 2017-10-02 |
| JP2015514059A (ja) | 2015-05-18 |
| CN104169305A (zh) | 2014-11-26 |
| WO2013137755A1 (en) | 2013-09-19 |
| MX2014010979A (es) | 2015-02-24 |
| EP2825563A1 (en) | 2015-01-21 |
| JP6470169B2 (ja) | 2019-02-13 |
| MX369114B (es) | 2019-10-29 |
| EP2825563B1 (en) | 2020-02-05 |
| IN2014MN01651A (US07794700-20100914-C00152.png) | 2015-05-29 |
| CA2866682A1 (en) | 2013-09-19 |
| ES2780387T3 (es) | 2020-08-25 |
| AU2013232850B2 (en) | 2016-01-07 |
| US10258579B2 (en) | 2019-04-16 |
| BR112014022767B1 (pt) | 2021-08-31 |
| PL398450A1 (pl) | 2013-09-16 |
| US20150072946A1 (en) | 2015-03-12 |
| RU2014133962A (ru) | 2016-03-20 |
| AU2013232850A1 (en) | 2014-09-11 |
| BR112014022767A2 (US07794700-20100914-C00152.png) | 2017-10-03 |
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