JP4558213B2 - 疎水性および親水性の成分を有する水性ゲル形成システム - Google Patents
疎水性および親水性の成分を有する水性ゲル形成システム Download PDFInfo
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- JP4558213B2 JP4558213B2 JP2000610306A JP2000610306A JP4558213B2 JP 4558213 B2 JP4558213 B2 JP 4558213B2 JP 2000610306 A JP2000610306 A JP 2000610306A JP 2000610306 A JP2000610306 A JP 2000610306A JP 4558213 B2 JP4558213 B2 JP 4558213B2
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| BR0314266A (pt) * | 2002-09-13 | 2005-07-26 | Ocular Sciences Inc | Dispositivos e métodos para a melhora de visão |
| WO2004064816A1 (en) * | 2003-01-16 | 2004-08-05 | Cornell Research Foundation, Inc. | PARTIALLY BIODEGRADABLE TEMPERATURE AND pH SENSITIVE HYDROGEL |
| US8545830B2 (en) * | 2003-03-24 | 2013-10-01 | University Of Tennessee Research Foundation | Multi-functional polymeric materials and their uses |
| WO2005041987A1 (en) * | 2003-10-29 | 2005-05-12 | Gentis, Inc. | Polymerizable emulsions for tissue engineering |
| ATE524203T1 (de) * | 2003-11-03 | 2011-09-15 | Medtronic Inc | Hydrogel für zellspezifisches einwachsen |
| MY144221A (en) * | 2004-03-03 | 2011-08-15 | Polynovo Biomaterials Pty Ltd | Biocompatible polymer compositions for dual or multistaged curing. |
| EP1735378A1 (en) * | 2004-03-17 | 2006-12-27 | Ciphergen Biosystems, Inc. | Photocrosslinked hydrogel blend surface coatings |
| JP2007530169A (ja) | 2004-03-26 | 2007-11-01 | サーモディクス,インコーポレイティド | 生物適合性表面を調製するための組成物及び方法 |
| GB0407661D0 (en) * | 2004-04-03 | 2004-05-05 | Univ Hull | Liquid crystalline interpenetrating polymer networks |
| JP4599550B2 (ja) * | 2004-04-09 | 2010-12-15 | 国立大学法人 東京医科歯科大学 | ナノゲル工学によるハイブリッドゲルの調製とバイオマテリアル応用 |
| US8241655B2 (en) * | 2004-05-12 | 2012-08-14 | Surmodics, Inc. | Coatings for medical articles including natural biodegradable polysaccharides |
| CA2566961A1 (en) | 2004-05-20 | 2005-12-08 | Coopervision, Inc. | Corneal onlays and wavefront aberration correction to enhance vision |
| US7446131B1 (en) | 2004-06-10 | 2008-11-04 | The United States Of America As Represented By The Secretary Of Agriculture | Porous polymeric matrices made of natural polymers and synthetic polymers and optionally at least one cation and methods of making |
| US8246993B2 (en) | 2004-06-10 | 2012-08-21 | Cytogel Pharma, Llc | Advantageous hydrogel composition |
| US20060013886A1 (en) | 2004-06-28 | 2006-01-19 | Daqing Wu | Injectable microspheres |
| US7235592B2 (en) * | 2004-10-12 | 2007-06-26 | Zimmer Gmbh | PVA hydrogel |
| AU2006216655B2 (en) * | 2005-02-23 | 2012-05-31 | Zimmer Technology, Inc. | Blend hydrogels and methods of making |
| US20060222596A1 (en) | 2005-04-01 | 2006-10-05 | Trivascular, Inc. | Non-degradable, low swelling, water soluble radiopaque hydrogel polymer |
| WO2007033418A1 (en) | 2005-09-20 | 2007-03-29 | Polynovo Biomaterials Pty Limited | Chain extenders |
| WO2007040557A1 (en) * | 2005-09-21 | 2007-04-12 | Surmodics, Inc. | Coatings and articles including natural biodegradable polysaccharides |
| ATE454908T1 (de) * | 2005-09-21 | 2010-01-15 | Surmodics Inc | In situ okklusionszusammensetzungen mit natürlichen biologisch abbaubaren polysacchariden |
| US20070098799A1 (en) * | 2005-10-28 | 2007-05-03 | Zimmer, Inc. | Mineralized Hydrogels and Methods of Making and Using Hydrogels |
| CA2632120C (en) * | 2005-12-07 | 2014-07-08 | Zimmer, Inc. | Methods of bonding or modifying hydrogels using irradiation |
| US20070141108A1 (en) * | 2005-12-20 | 2007-06-21 | Zimmer, Inc. | Fiber-reinforced water-swellable articles |
| EP1801135B1 (en) * | 2005-12-22 | 2010-09-29 | Zimmer Inc. | Perfluorocyclobutane crosslinked hydrogels |
| WO2007092550A2 (en) * | 2006-02-08 | 2007-08-16 | Coopervision Inc. | Corneal onlays and related methods |
| EP1999160B1 (en) * | 2006-03-14 | 2009-12-30 | Novozymes Biopharma DK A/S | Acrylated hyaluronic acid |
| US8110242B2 (en) * | 2006-03-24 | 2012-02-07 | Zimmer, Inc. | Methods of preparing hydrogel coatings |
| US8795709B2 (en) | 2006-03-29 | 2014-08-05 | Incept Llc | Superabsorbent, freeze dried hydrogels for medical applications |
| US20070232762A1 (en) * | 2006-03-31 | 2007-10-04 | Depuy Products, Inc. | Bearing material of medical implant having reduced wear rate and method for reducing wear rate |
| US7812098B2 (en) * | 2006-03-31 | 2010-10-12 | Depuy Products, Inc. | Bearing material of medical implant having reduced wear rate and method for reducing wear rate |
| US7883520B2 (en) * | 2006-04-10 | 2011-02-08 | Forsight Labs, Llc | Corneal epithelial pocket formation systems, components and methods |
| US7872068B2 (en) * | 2006-05-30 | 2011-01-18 | Incept Llc | Materials formable in situ within a medical device |
| CN101522788B (zh) * | 2006-08-02 | 2013-04-10 | 宝利诺沃生物材料有限公司 | 生物相容性聚合物组合物 |
| US20080075785A1 (en) * | 2006-09-22 | 2008-03-27 | San-Laung Chow | Controlled release hydrogel formulation |
| US20110165236A1 (en) * | 2006-09-22 | 2011-07-07 | Biokey, Inc. | Controlled release hydrogel formulation |
| US20080154241A1 (en) * | 2006-12-07 | 2008-06-26 | Burkstrand Michael J | Latent stabilization of bioactive agents releasable from implantable medical articles |
| US9125807B2 (en) | 2007-07-09 | 2015-09-08 | Incept Llc | Adhesive hydrogels for ophthalmic drug delivery |
| US7731988B2 (en) * | 2007-08-03 | 2010-06-08 | Zimmer, Inc. | Multi-polymer hydrogels |
| US20090043398A1 (en) * | 2007-08-09 | 2009-02-12 | Zimmer, Inc. | Method of producing gradient articles by centrifugation molding or casting |
| US20110136935A1 (en) * | 2007-08-30 | 2011-06-09 | National University Of Singapore | Bone and/or dental cement composition and uses thereof |
| US8062739B2 (en) * | 2007-08-31 | 2011-11-22 | Zimmer, Inc. | Hydrogels with gradient |
| WO2009043099A1 (en) * | 2007-10-03 | 2009-04-09 | Polynovo Biomaterials Limited | High modulus polyurethane and polyurethane/urea compositions |
| US7947784B2 (en) | 2007-11-16 | 2011-05-24 | Zimmer, Inc. | Reactive compounding of hydrogels |
| US8034362B2 (en) * | 2008-01-04 | 2011-10-11 | Zimmer, Inc. | Chemical composition of hydrogels for use as articulating surfaces |
| EP2271379B1 (en) | 2008-03-28 | 2015-11-25 | SurModics, Inc. | Insertable medical devices having microparticulate-associated elastic substrates and methods for drug delivery |
| EP2296630A2 (en) | 2008-05-07 | 2011-03-23 | SurModics, Inc. | Delivery of nucleic acid complexes from particles |
| US20100087920A1 (en) * | 2008-10-07 | 2010-04-08 | Forsight Labs, Llc | Corneal Onlay Lenses and Related Methods for Improving Vision of Presbyopic Patients |
| US8409606B2 (en) | 2009-02-12 | 2013-04-02 | Incept, Llc | Drug delivery through hydrogel plugs |
| CA2977830C (en) | 2009-05-04 | 2019-09-17 | Incept, Llc | Biomaterials for track and puncture closure |
| JP2012235797A (ja) | 2009-09-18 | 2012-12-06 | Terumo Corp | ステント |
| NZ599524A (en) | 2009-11-09 | 2014-04-30 | Spotlight Technology Partners Llc | Polysaccharide based hydrogels |
| WO2011057133A1 (en) | 2009-11-09 | 2011-05-12 | Spotlight Technology Partners Llc | Fragmented hydrogels |
| EP3960215B1 (en) | 2009-12-15 | 2024-10-16 | Incept, LLC | Implants and biodegradable fiducial markers |
| EP2574172A4 (en) | 2010-05-21 | 2013-10-30 | Cytogel Pharma Llc | MATERIALS AND METHOD FOR TREATING INFLAMMATION |
| US8961501B2 (en) | 2010-09-17 | 2015-02-24 | Incept, Llc | Method for applying flowable hydrogels to a cornea |
| US8901092B2 (en) | 2010-12-29 | 2014-12-02 | Surmodics, Inc. | Functionalized polysaccharides for active agent delivery |
| EP3081937B1 (en) | 2011-07-18 | 2019-11-13 | President and Fellows of Harvard College | Engineered microbe-targeting molecules and uses thereof |
| US10226417B2 (en) | 2011-09-16 | 2019-03-12 | Peter Jarrett | Drug delivery systems and applications |
| RU2521194C2 (ru) * | 2011-11-16 | 2014-06-27 | Общество с ограниченной ответственностью предприятие "Репер" | Матрица для клеточной трансплантологии |
| CN109200013A (zh) | 2011-12-05 | 2019-01-15 | 因赛普特有限责任公司 | 医用有机凝胶方法和组合物 |
| BR112015024703A2 (pt) * | 2013-03-27 | 2017-07-18 | Centre Hospitalier Univ Vaudois C H U V | formulação farmacêutica, método de tratamento e/ou prevenção de restenose e kit para o tratamento e/ou prevenção de restenose |
| EP3848045A1 (en) | 2013-05-21 | 2021-07-14 | President and Fellows of Harvard College | Engineered heme-binding compositions and uses thereof |
| WO2015095604A2 (en) | 2013-12-18 | 2015-06-25 | President And Fellows Of Harvard College | Methods and assays relating to circulating tumor cells |
| US10519443B2 (en) | 2014-09-08 | 2019-12-31 | University Of Iowa Research Foundation | Microrna inhibitor system and methods of use thereof |
| CN108289928B (zh) | 2015-08-06 | 2024-09-17 | 哈佛大学校长及研究员协会 | 改进的微生物-结合分子和其用途 |
| US10273476B2 (en) | 2016-04-30 | 2019-04-30 | University Of Iowa Research Foundation | MicroRNA-200 based approaches for modulating bone formation inhibition and bone regeneration |
| MX2019006868A (es) * | 2016-12-16 | 2019-09-23 | Du Pont | Derivados de polisacáridos anfifílicos y composiciones que los comprenden. |
| CN106913915B (zh) * | 2017-04-21 | 2019-05-31 | 浙江大学 | 一种自愈合支架复合涂层及其制备方法和应用 |
| CN107216450B (zh) * | 2017-04-21 | 2019-06-11 | 浙江大学 | 一种自愈合抗菌涂层及其制备方法和应用 |
| US10975121B2 (en) | 2017-06-24 | 2021-04-13 | Cytogel Pharma, Llc | Analgesic mu-opioid receptor binding peptide pharmaceutical formulations and uses thereof |
| CN110108537B (zh) * | 2018-02-01 | 2020-08-25 | 中国科学技术大学 | 一种用于生物组织包埋的包埋剂和包埋方法 |
| CN108359054A (zh) * | 2018-02-10 | 2018-08-03 | 西北大学 | 一种葡萄糖敏感型全互穿网络水凝胶及其制备方法 |
| CN116496475B (zh) * | 2023-06-26 | 2023-09-22 | 海杰亚(北京)医疗器械有限公司 | 用于栓塞微球的可降解交联剂、可降解栓塞微球及其制备方法和药物组合物 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002173A (en) | 1974-07-23 | 1977-01-11 | International Paper Company | Diester crosslinked polyglucan hydrogels and reticulated sponges thereof |
| US4032488A (en) * | 1975-10-03 | 1977-06-28 | Meito Sangyo Kabushiki Kaisha | Dextran ester-olefin compound copolymer and process for preparing same |
| SU729197A1 (ru) * | 1977-07-05 | 1980-04-25 | Ордена Ленина Институт Элементоорганических Соединений Ан Ссср | Сшитые сополимеры хитозана |
| US4277582A (en) * | 1978-03-03 | 1981-07-07 | Ciba-Geigy Corporation | Water-insoluble hydrophilic copolymers |
| GB8418772D0 (en) | 1984-07-24 | 1984-08-30 | Geistlich Soehne Ag | Chemical substances |
| US4857602A (en) * | 1986-09-05 | 1989-08-15 | American Cyanamid Company | Bioabsorbable surgical suture coating |
| US4938763B1 (en) | 1988-10-03 | 1995-07-04 | Atrix Lab Inc | Biodegradable in-situ forming implants and method of producing the same |
| US5410016A (en) * | 1990-10-15 | 1995-04-25 | Board Of Regents, The University Of Texas System | Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers |
| US5529914A (en) * | 1990-10-15 | 1996-06-25 | The Board Of Regents The Univeristy Of Texas System | Gels for encapsulation of biological materials |
| US5626863A (en) | 1992-02-28 | 1997-05-06 | Board Of Regents, The University Of Texas System | Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers |
| US5210111A (en) * | 1991-08-22 | 1993-05-11 | Ciba-Geigy Corporation | Crosslinked hydrogels derived from hydrophilic polymer backbones |
| US5837747A (en) | 1991-10-29 | 1998-11-17 | Vivorx, Inc. | Crosslinkable polysaccharides, polycations and lipids useful for encapsulation and drug release |
| WO1993016176A1 (en) | 1992-02-13 | 1993-08-19 | Bio-Metric Systems, Inc. | Immobilization of chemical species in crosslinked matrices |
| BR9306038A (pt) | 1992-02-28 | 1998-01-13 | Univ Texas | Hidrogéis biodegradáveis fotopolimerizáveis como materiais de contato de tecidos e condutores de liberação controlada |
| US5573934A (en) * | 1992-04-20 | 1996-11-12 | Board Of Regents, The University Of Texas System | Gels for encapsulation of biological materials |
| IT1260154B (it) | 1992-07-03 | 1996-03-28 | Lanfranco Callegaro | Acido ialuronico e suoi derivati in polimeri interpenetranti (ipn) |
| US5514379A (en) | 1992-08-07 | 1996-05-07 | The General Hospital Corporation | Hydrogel compositions and methods of use |
| NZ258533A (en) | 1992-11-30 | 1996-08-27 | Ciba Geigy Ag | Vinyl ester and amide derivatives of a dicarboxylic acid cyclic-oligomeric carbohydrate half ester; use for forming contact lenses, as thickeners, surfactants and lens cleaning agents |
| KR0141431B1 (ko) | 1994-05-17 | 1998-07-01 | 김상웅 | 생분해성 하이드로겔 고분자 |
| TW291481B (en) * | 1994-10-27 | 1996-11-21 | Novartis Erfind Verwalt Gmbh | Poly-unsaturated carbohydrate derivatives, polymers thereof and their use |
| US5607686A (en) | 1994-11-22 | 1997-03-04 | United States Surgical Corporation | Polymeric composition |
| US5540929A (en) | 1995-03-08 | 1996-07-30 | Board Of Trustees Operating Michigan State University | Polysaccharides grafted with aliphatic polyesters derived from cyclic esters |
| US5900245A (en) | 1996-03-22 | 1999-05-04 | Focal, Inc. | Compliant tissue sealants |
| CA2228118A1 (en) * | 1995-07-28 | 1997-02-13 | Focal, Inc. | Multiblock biodegradable hydrogels for use as controlled release agents for drugs delivery and tissue treatments agents |
| JP3572144B2 (ja) * | 1996-05-31 | 2004-09-29 | 名糖産業株式会社 | デキストランエステル共重合体 |
| US5854382A (en) * | 1997-08-18 | 1998-12-29 | Meadox Medicals, Inc. | Bioresorbable compositions for implantable prostheses |
| WO1999011692A1 (en) * | 1997-09-03 | 1999-03-11 | The Regents Of The University Of California | Novel biomimetic hydrogel materials |
| ATE297440T1 (de) * | 1998-08-31 | 2005-06-15 | Cornell Res Foundation Inc | Dextran-maleinsäuremonoester und hydrogele daraus |
| DE60038010T2 (de) | 1999-04-12 | 2009-03-05 | Cornell Research Foundation, Inc. | Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten |
| US6716445B2 (en) | 1999-04-12 | 2004-04-06 | Cornell Research Foundation, Inc. | Hydrogel entrapping therapeutic agent and stent with coating comprising this |
| US6388035B1 (en) * | 1999-09-02 | 2002-05-14 | Alcon Universal Ltd. | Hydrophobically-bound, hydrophilic coating compositions for surgical implants |
| US6503538B1 (en) | 2000-08-30 | 2003-01-07 | Cornell Research Foundation, Inc. | Elastomeric functional biodegradable copolyester amides and copolyester urethanes |
| CA2450123C (en) | 2001-08-02 | 2013-01-29 | Cornell Research Foundation, Inc. | Biodegradable polyhydric alcohol esters |
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2000
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- 2000-03-20 EP EP00917865A patent/EP1168934B1/en not_active Expired - Lifetime
- 2000-03-20 DK DK00917865T patent/DK1168934T3/da active
- 2000-03-20 JP JP2000610306A patent/JP4558213B2/ja not_active Expired - Fee Related
- 2000-03-20 US US09/531,451 patent/US6388047B1/en not_active Expired - Lifetime
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| DE60038010D1 (de) | 2008-03-27 |
| CA2368617A1 (en) | 2000-10-19 |
| JP2002541308A (ja) | 2002-12-03 |
| US20040122165A1 (en) | 2004-06-24 |
| US20020161169A1 (en) | 2002-10-31 |
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| CA2368617C (en) | 2010-03-16 |
| US6709668B2 (en) | 2004-03-23 |
| US6583219B2 (en) | 2003-06-24 |
| EP1168934A4 (en) | 2004-12-08 |
| DK1168934T3 (da) | 2008-05-13 |
| ATE386075T1 (de) | 2008-03-15 |
| US6388047B1 (en) | 2002-05-14 |
| ES2298135T3 (es) | 2008-05-16 |
| DE60038010T2 (de) | 2009-03-05 |
| US20030125509A1 (en) | 2003-07-03 |
| EP1168934A1 (en) | 2002-01-09 |
| EP1168934B1 (en) | 2008-02-13 |
| WO2000060956A1 (en) | 2000-10-19 |
| US6916857B2 (en) | 2005-07-12 |
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