NO313687B1 - Fremgangsmåte for belegning av gjenstander med hyaluronsyre, derivater derav, og semisyntetiske polymerer - Google Patents
Fremgangsmåte for belegning av gjenstander med hyaluronsyre, derivater derav, og semisyntetiske polymerer Download PDFInfo
- Publication number
- NO313687B1 NO313687B1 NO19973648A NO973648A NO313687B1 NO 313687 B1 NO313687 B1 NO 313687B1 NO 19973648 A NO19973648 A NO 19973648A NO 973648 A NO973648 A NO 973648A NO 313687 B1 NO313687 B1 NO 313687B1
- Authority
- NO
- Norway
- Prior art keywords
- hyaluronic acid
- plasma
- ester
- semi
- coupling agent
- Prior art date
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims description 109
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- 229940010747 sodium hyaluronate Drugs 0.000 description 1
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- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/085—Macromolecular materials
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Materials For Medical Uses (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Paints Or Removers (AREA)
- Media Introduction/Drainage Providing Device (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT95PD000030A IT1282187B1 (it) | 1995-02-07 | 1995-02-07 | Processo di rivestimento di oggetti con acido ialuronico e derivati |
| IT95PD000243 IT1282218B1 (it) | 1995-12-20 | 1995-12-20 | Processo di rivestimento di oggetti con acido ialuronico o suoi derivati. |
| PCT/EP1996/000509 WO1996024392A1 (en) | 1995-02-07 | 1996-02-07 | Process for the coating of objects with hyaluronic acid, derivatives thereof, and semisynthetic polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO973648D0 NO973648D0 (no) | 1997-08-07 |
| NO973648L NO973648L (no) | 1997-10-03 |
| NO313687B1 true NO313687B1 (no) | 2002-11-18 |
Family
ID=26331822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19973648A NO313687B1 (no) | 1995-02-07 | 1997-08-07 | Fremgangsmåte for belegning av gjenstander med hyaluronsyre, derivater derav, og semisyntetiske polymerer |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6129956A (ja) |
| EP (1) | EP0808181B1 (ja) |
| JP (2) | JPH10513378A (ja) |
| CN (1) | CN1141149C (ja) |
| AT (1) | ATE219381T1 (ja) |
| AU (1) | AU704047B2 (ja) |
| BR (1) | BR9607516A (ja) |
| CA (1) | CA2212519C (ja) |
| CZ (1) | CZ293637B6 (ja) |
| DE (1) | DE69621911T2 (ja) |
| ES (1) | ES2179930T3 (ja) |
| HU (1) | HU219815B (ja) |
| MX (1) | MX9706054A (ja) |
| NO (1) | NO313687B1 (ja) |
| NZ (1) | NZ302264A (ja) |
| PL (1) | PL182804B1 (ja) |
| TR (1) | TR199700760T1 (ja) |
| WO (1) | WO1996024392A1 (ja) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITPD940054A1 (it) * | 1994-03-23 | 1995-09-23 | Fidia Advanced Biopolymers Srl | Polisaccaridi solfatati |
| IT1291452B1 (it) * | 1997-04-14 | 1999-01-11 | Fidia Advanced Biopolymers Srl | Rivestimento a base di acido ialuronico e suoi derivati per la protezione di parti elettroniche da agenti esterni |
| DE19729279A1 (de) | 1997-07-09 | 1999-01-14 | Peter Hildebrandt | Urologisches Implantat, insbesondere Gefäßwandstütze für den Urinaltrakt |
| US8039026B1 (en) | 1997-07-28 | 2011-10-18 | Johnson & Johnson Consumer Companies, Inc | Methods for treating skin pigmentation |
| ITPD980037A1 (it) * | 1998-02-25 | 1999-08-25 | Fidia Advanced Biopolymers Srl | Acido ialuronico solfatato e i suoi derivati legati covalentemente a polimeri sintetici pe la preparazione di biomateriali e per il rivesti |
| BR9910574A (pt) * | 1998-04-30 | 2001-09-11 | Maruha Corp | Compostos tendo derivado de ácido glicurÈnico e derivado de glicosamina em sua estrutura, método para a produção dos compostos, e uso dos compostos |
| US6500481B1 (en) | 1998-06-11 | 2002-12-31 | Johnson & Johnson Vision Care, Inc. | Biomedical devices with amid-containing coatings |
| US8093293B2 (en) | 1998-07-06 | 2012-01-10 | Johnson & Johnson Consumer Companies, Inc. | Methods for treating skin conditions |
| US8106094B2 (en) | 1998-07-06 | 2012-01-31 | Johnson & Johnson Consumer Companies, Inc. | Compositions and methods for treating skin conditions |
| US6248127B1 (en) * | 1998-08-21 | 2001-06-19 | Medtronic Ave, Inc. | Thromboresistant coated medical device |
| US6099852A (en) * | 1998-09-23 | 2000-08-08 | Johnson & Johnson Vision Products, Inc. | Wettable silicone-based lenses |
| EP1048304A1 (en) * | 1999-04-30 | 2000-11-02 | Novartis AG | Neutral coatings |
| US7985404B1 (en) | 1999-07-27 | 2011-07-26 | Johnson & Johnson Consumer Companies, Inc. | Reducing hair growth, hair follicle and hair shaft size and hair pigmentation |
| WO2001009646A1 (en) * | 1999-08-03 | 2001-02-08 | Galin Miles A | Polysaccharide coating of contact lenses |
| US6478423B1 (en) | 1999-10-12 | 2002-11-12 | Johnson & Johnson Vison Care, Inc. | Contact lens coating selection and manufacturing process |
| JP3504548B2 (ja) * | 1999-11-08 | 2004-03-08 | 朝日インテック株式会社 | 潤滑性ガイディングカテーテル |
| US8431550B2 (en) | 2000-10-27 | 2013-04-30 | Johnson & Johnson Consumer Companies, Inc. | Topical anti-cancer compositions and methods of use thereof |
| US7192615B2 (en) | 2001-02-28 | 2007-03-20 | J&J Consumer Companies, Inc. | Compositions containing legume products |
| US6835410B2 (en) * | 2001-05-21 | 2004-12-28 | Novartis Ag | Bottle-brush type coatings with entangled hydrophilic polymer |
| US20030045942A1 (en) * | 2001-09-05 | 2003-03-06 | Lai Wen-Fu T. | Regenerative bone implants |
| US20030113812A1 (en) * | 2001-10-02 | 2003-06-19 | Hemperly John J. | Proliferation and differentiation of stem cells using extracellular matrix and other molecules |
| EP1444325A4 (en) * | 2001-11-15 | 2006-02-15 | Becton Dickinson Co | METHODS AND DEVICES FOR INTEGRATED DISCOVERY OF CELL CULTURE ENVIRONMENTS |
| US20030161938A1 (en) * | 2002-02-22 | 2003-08-28 | Bo Johnson | Composition and method for coating medical devices |
| ITPD20020064A1 (it) | 2002-03-12 | 2003-09-12 | Fidia Advanced Biopolymers Srl | Derivati esterei dell'acido ialuronico per la preparazione di idrogelda utilizzare in campo biomedico, sanitario e chirurgico e come sistem |
| US20040062882A1 (en) * | 2002-09-30 | 2004-04-01 | Andrea Liebmann-Vinson | Cell adhesion resisting surfaces |
| US20040126405A1 (en) * | 2002-12-30 | 2004-07-01 | Scimed Life Systems, Inc. | Engineered scaffolds for promoting growth of cells |
| ZA200507803B (en) * | 2003-04-04 | 2007-03-28 | Bayco Tech Ltd | Vascular stent |
| DE10328815A1 (de) * | 2003-06-21 | 2005-01-05 | Biotronik Meß- und Therapiegeräte GmbH & Co. Ingenieurbüro Berlin | Beschichtungssystem für Implantate zur Erhöhung der Gewebsverträglichkeit |
| US20050058687A1 (en) * | 2003-09-12 | 2005-03-17 | Becton, Dickinson And Company | Covalently attached collagen VI for cell attachment and proliferation |
| EP1744795A1 (en) * | 2004-05-14 | 2007-01-24 | Becton, Dickinson and Company | Articles having bioactive surfaces and solvent-free methods of preparation thereof |
| US20080248972A1 (en) * | 2004-05-14 | 2008-10-09 | Matsuhiko Nishizawa | Method of Immobilizing Protein, Protein Chip, Method of Immobilizing Cell and Cell Chip |
| JP2008515511A (ja) * | 2004-10-06 | 2008-05-15 | ベイコ テック リミテッド | ヒアルロン酸で被覆された骨インプラント素子 |
| US20070009568A1 (en) * | 2005-06-03 | 2007-01-11 | Bhatnagar Rajendra S | Methods for immobilizing molecules on surfaces |
| CA2615607A1 (en) * | 2005-07-21 | 2007-02-08 | Fmc Biopolymer As | Medical devices coated with a fast dissolving biocompatible coating |
| US8475886B2 (en) * | 2005-08-05 | 2013-07-02 | Corning Incorporated | Methods for producing surfaces that resist non-specific protein binding and cell attachment |
| BRPI0504797B1 (pt) * | 2005-10-27 | 2020-02-04 | Pele Nova Biotecnologia S A | formulação tópica, método de tratamento cosmético para rejuvenescimento da pele, método de tratamento cosmético e uso de uma formulação |
| GB2434368B (en) * | 2006-01-20 | 2010-08-25 | P2I Ltd | Plasma coated laboratory consumables |
| EP1847316A1 (en) * | 2006-04-19 | 2007-10-24 | Eppendorf Array Technologies SA (EAT) | Method for stabilizing functional groups on a surface of a polymer used as solid support for making microarrays |
| JP5231006B2 (ja) * | 2007-12-12 | 2013-07-10 | 株式会社 資生堂 | 表面処理粉体及びそれを配合した化粧料 |
| US8426196B2 (en) * | 2008-06-05 | 2013-04-23 | Lynn L. H. Huang | Method for regulating proliferation of cells |
| MC200122A1 (fr) * | 2008-10-03 | 2009-04-15 | M Exsymol Sa | Complexe associant un dérivé organique du siliciumavec des fragments calibrés d'acide hyaluronique, à action préventive et réparatrice des dégradatio ns cutanées |
| US11174299B2 (en) * | 2008-12-29 | 2021-11-16 | Dispersebio Ltd. | Peptides and compositions for prevention of cell adhesion and methods of using same |
| KR101383408B1 (ko) | 2008-12-29 | 2014-04-17 | 텔 하쇼머 메디컬 리서치 인프라스트럭쳐 앤드 서비시스 리미티드． | 세포 유착 방지를 위한 펩티드와 조성물 및 그것의 사용 방법 |
| CN101487841B (zh) * | 2009-02-13 | 2014-06-04 | 深圳市人民医院 | 一种包被载体及其在检测精子成熟度和无创分离成熟精子方法中的应用 |
| PL2251453T3 (pl) | 2009-05-13 | 2014-05-30 | Sio2 Medical Products Inc | Uchwyt na pojemnik |
| US9458536B2 (en) | 2009-07-02 | 2016-10-04 | Sio2 Medical Products, Inc. | PECVD coating methods for capped syringes, cartridges and other articles |
| IT1399508B1 (it) * | 2010-04-22 | 2013-04-19 | Nobil Bio Ricerche Srl | Dispositivo per impianto con proprieta' antibatteriche e superficie multifunzionale |
| MY154750A (en) | 2010-07-30 | 2015-07-15 | Novartis Ag | Silicone hydrogel lenses with water-rich surfaces |
| US9878101B2 (en) | 2010-11-12 | 2018-01-30 | Sio2 Medical Products, Inc. | Cyclic olefin polymer vessels and vessel coating methods |
| US9272095B2 (en) | 2011-04-01 | 2016-03-01 | Sio2 Medical Products, Inc. | Vessels, contact surfaces, and coating and inspection apparatus and methods |
| US8852693B2 (en) | 2011-05-19 | 2014-10-07 | Liquipel Ip Llc | Coated electronic devices and associated methods |
| MY164605A (en) | 2011-10-12 | 2018-01-30 | Novartis Ag | Method for making uv-absorbing ophthalmic lenses |
| US20130122583A1 (en) | 2011-11-10 | 2013-05-16 | Celxcel Pty Ltd | Sterilization process |
| FR2985908B1 (fr) | 2012-01-24 | 2014-02-07 | Univ Claude Bernard Lyon | Substrat sur lequel est greffe par liaison covalente du chitosane ou du collagene |
| US9180289B2 (en) | 2012-08-29 | 2015-11-10 | Cardiac Pacemakers, Inc. | Enhanced low friction coating for medical leads and methods of making |
| CN103785067B (zh) * | 2012-11-01 | 2016-03-23 | 中国科学院上海硅酸盐研究所 | 透明质酸改性的多孔钛涂层及其制备方法 |
| CN103785063B (zh) * | 2012-11-01 | 2015-08-19 | 中国科学院上海硅酸盐研究所 | I型胶原/透明质酸改性的钛涂层及其制备方法 |
| WO2014081893A2 (en) | 2012-11-21 | 2014-05-30 | Cardiac Pacemakers, Inc. | Medical electrodes with layered coatings |
| US9764093B2 (en) | 2012-11-30 | 2017-09-19 | Sio2 Medical Products, Inc. | Controlling the uniformity of PECVD deposition |
| WO2014095690A1 (en) | 2012-12-17 | 2014-06-26 | Novartis Ag | Method for making improved uv-absorbing ophthalmic lenses |
| US9662450B2 (en) | 2013-03-01 | 2017-05-30 | Sio2 Medical Products, Inc. | Plasma or CVD pre-treatment for lubricated pharmaceutical package, coating process and apparatus |
| JP6453841B2 (ja) | 2013-03-11 | 2019-01-16 | エスアイオーツー・メディカル・プロダクツ・インコーポレイテッド | 被覆包装 |
| WO2014144926A1 (en) | 2013-03-15 | 2014-09-18 | Sio2 Medical Products, Inc. | Coating method |
| CN103439491B (zh) * | 2013-09-17 | 2015-05-13 | 北京润诺思医疗科技有限公司 | 一种制备透明质酸化学发光定量测定试剂盒的方法 |
| HUE038809T2 (hu) | 2013-12-17 | 2018-11-28 | Novartis Ag | Térhálósított hidrofíl bevonattal ellátott szilikon hidrogél lencse |
| CN103990148A (zh) * | 2014-05-04 | 2014-08-20 | 韩金花 | 一种果味钡餐配方及其制备方法 |
| CA2947829C (en) * | 2014-05-09 | 2018-08-21 | Interojo Inc. | Hydrogel contact lens having wet surface, and manufacturing method therefor |
| HUE046948T2 (hu) | 2014-08-26 | 2020-03-30 | Novartis Ag | Eljárás stabil bevonat felvitelére szilikon hidrogél kontaktlencsékre |
| EP3115031B1 (en) * | 2015-07-06 | 2021-12-22 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Intraocular device and method for preparing the same |
| KR102604468B1 (ko) | 2015-12-15 | 2023-11-22 | 알콘 인코포레이티드 | 실리콘 하이드로겔 콘택트 렌즈 상에 안정한 코팅을 적용하기 위한 방법 |
| JP7299162B2 (ja) * | 2017-05-12 | 2023-06-27 | マイクロベンション インコーポレイテッド | 医療機器を作成するための方法及び医療機器をコーティングする方法 |
| WO2019116139A1 (en) | 2017-12-13 | 2019-06-20 | Novartis Ag | Weekly and monthly disposable water gradient contact lenses |
| CN110629228B (zh) * | 2019-10-18 | 2020-10-23 | 浙江广慈医疗器械有限公司 | 一种接骨用钛钉的表面处理工艺及钛钉 |
| CN111514433B (zh) * | 2020-02-21 | 2022-05-31 | 上海威高医疗技术发展有限公司 | 一种介入导管、其制备方法及应用 |
| CN112978987B (zh) * | 2021-02-19 | 2021-11-12 | 北京九泉科技有限公司 | 一种新型环保材料的净水设备 |
| CN115120785A (zh) * | 2022-08-09 | 2022-09-30 | 北京化工大学 | 一种具有多糖涂层的医用导管及其制备方法 |
| EP4389162A1 (en) | 2022-12-24 | 2024-06-26 | Jozef Stefan Institute | A method for preparation of chitosan-coated catheters and a catheter prepared with said method |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8200751L (sv) * | 1982-02-09 | 1983-08-10 | Olle Larm | Forfarande for kovalent koppling for framstellning av konjugat och hervid erhallna produkter |
| EP0094924A3 (en) * | 1982-05-14 | 1985-01-30 | Astra Meditec AB | Articles exhibiting a biocompatible surface layer and process for providing articles with such a surface layer |
| JPS59183762A (ja) * | 1983-03-31 | 1984-10-18 | 工業技術院長 | 新規な抗血栓性材料 |
| IE57931B1 (en) * | 1983-10-11 | 1993-05-19 | Fidia Spa | Hyaluronic acid fractions having pharmaceutical activity,methods for preparation thereof,and pharmaceutical compositions containing the same |
| US4959074A (en) * | 1984-08-23 | 1990-09-25 | Gergory Halpern | Method of hydrophilic coating of plastics |
| US5023114A (en) * | 1984-08-23 | 1991-06-11 | Gregory Halpern | Method of hydrophilic coating of plastics |
| US4801475A (en) * | 1984-08-23 | 1989-01-31 | Gregory Halpern | Method of hydrophilic coating of plastics |
| US5037677A (en) * | 1984-08-23 | 1991-08-06 | Gregory Halpern | Method of interlaminar grafting of coatings |
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| US4663233A (en) * | 1985-10-24 | 1987-05-05 | Universal High Technologies | Lens with hydrophilic coating |
| EP0233708A3 (en) * | 1986-02-18 | 1988-08-03 | Precision-Cosmet Co., Inc. | Coated substrates |
| US4722867A (en) * | 1986-04-16 | 1988-02-02 | Gregory Halpern | Albumin-enhanced polysaccharide solution |
| US4810586A (en) * | 1986-04-16 | 1989-03-07 | Gregory Halpern | Method enhanced polysaccharide coating of plastic objects |
| US4657820A (en) * | 1986-04-16 | 1987-04-14 | Gregory Halpern | Plastic article containing a top coat comprising an albumin and polysaccharide mixture |
| IT1203814B (it) * | 1986-06-30 | 1989-02-23 | Fidia Farmaceutici | Esteri dell'acido alginico |
| IT1198449B (it) * | 1986-10-13 | 1988-12-21 | F I D I Farmaceutici Italiani | Esteri di alcoli polivalenti di acido ialuronico |
| IT1219942B (it) * | 1988-05-13 | 1990-05-24 | Fidia Farmaceutici | Esteri polisaccaridici |
| IT1219587B (it) * | 1988-05-13 | 1990-05-18 | Fidia Farmaceutici | Polisaccaridi carbossiilici autoreticolati |
| US5080924A (en) * | 1989-04-24 | 1992-01-14 | Drexel University | Method of making biocompatible, surface modified materials |
| JP2609559B2 (ja) * | 1990-09-14 | 1997-05-14 | 株式会社バイオマテリアル研究所 | 組織系細胞の培養に用いる基質 |
| US5132108A (en) * | 1990-11-08 | 1992-07-21 | Cordis Corporation | Radiofrequency plasma treated polymeric surfaces having immobilized anti-thrombogenic agents |
| US5244654A (en) * | 1990-11-08 | 1993-09-14 | Cordis Corporation | Radiofrequency plasma biocompatibility treatment of inside surfaces of medical tubing and the like |
| DE69210879T2 (de) * | 1991-02-11 | 1996-10-17 | Fidia Spa | Gellanester |
| US5356433A (en) * | 1991-08-13 | 1994-10-18 | Cordis Corporation | Biocompatible metal surfaces |
| IT1254119B (it) * | 1991-09-13 | 1995-09-08 | Fidia | Esteri di derivati carbossilici di polisaccaridi |
| JP2984118B2 (ja) * | 1991-11-29 | 1999-11-29 | 京セラ株式会社 | 生体インプラント材とその製法 |
| IT1264321B (it) * | 1992-01-13 | 1996-09-23 | Mini Ricerca Scient Tecnolog | Esteri di acidi pectici e pectinici, procedimento di preparazione e loro applicazioni farmaceutiche e biosanitarie |
| JP2855307B2 (ja) * | 1992-02-05 | 1999-02-10 | 生化学工業株式会社 | 光反応性グリコサミノグリカン、架橋グリコサミノグリカン及びそれらの製造方法 |
| IT1264322B (it) * | 1992-07-30 | 1996-09-23 | Lanfranco Callegaro | Esteri di gellano autoreticolato, procedimento di preparazione e loro applicazioni farmaceutiche e biomedico-sanitarie |
| JP2974854B2 (ja) * | 1992-08-24 | 1999-11-10 | 株式会社クラレ | 生理活性材料およびその製造方法 |
| IL106922A (en) * | 1992-09-14 | 1998-08-16 | Novartis Ag | Complex materials with one or more wettable surfaces and a process for their preparation |
| US5308641A (en) * | 1993-01-19 | 1994-05-03 | Medtronic, Inc. | Biocompatibility of solid surfaces |
| SE500964C2 (sv) * | 1993-01-19 | 1994-10-10 | Medicarb Ab | Fast bärare med modifierad yta varvid modifikationen åstadkommes genom en primer innehållande en polysackarid och förfarande för framställning av en sådan bärare |
| DE19630879A1 (de) * | 1996-07-31 | 1998-02-05 | Hanno Lutz Prof Dr Baumann | Verfahren zur Herstellung blutverträglicher Werkstoffe durch Oberflächenbeschichtung von synthetischen Polymeren mit wasserlöslichen Substanzen aus natürlichen oder modifizierten Oligo- und Polysacchariden über kovalente Bindungen |
-
1996
- 1996-02-07 CN CNB961918098A patent/CN1141149C/zh not_active Expired - Fee Related
- 1996-02-07 EP EP96904009A patent/EP0808181B1/en not_active Expired - Lifetime
- 1996-02-07 US US08/930,858 patent/US6129956A/en not_active Expired - Lifetime
- 1996-02-07 PL PL96321781A patent/PL182804B1/pl not_active IP Right Cessation
- 1996-02-07 WO PCT/EP1996/000509 patent/WO1996024392A1/en active IP Right Grant
- 1996-02-07 AT AT96904009T patent/ATE219381T1/de not_active IP Right Cessation
- 1996-02-07 NZ NZ302264A patent/NZ302264A/en not_active IP Right Cessation
- 1996-02-07 ES ES96904009T patent/ES2179930T3/es not_active Expired - Lifetime
- 1996-02-07 HU HU9702114A patent/HU219815B/hu not_active IP Right Cessation
- 1996-02-07 TR TR97/00760T patent/TR199700760T1/xx unknown
- 1996-02-07 BR BR9607516A patent/BR9607516A/pt not_active Application Discontinuation
- 1996-02-07 JP JP8523988A patent/JPH10513378A/ja not_active Withdrawn
- 1996-02-07 CA CA002212519A patent/CA2212519C/en not_active Expired - Lifetime
- 1996-02-07 DE DE69621911T patent/DE69621911T2/de not_active Expired - Lifetime
- 1996-02-07 CZ CZ19972509A patent/CZ293637B6/cs not_active IP Right Cessation
- 1996-02-07 AU AU47884/96A patent/AU704047B2/en not_active Ceased
-
1997
- 1997-08-07 NO NO19973648A patent/NO313687B1/no not_active IP Right Cessation
- 1997-08-07 MX MX9706054A patent/MX9706054A/es not_active IP Right Cessation
-
2007
- 2007-12-04 JP JP2007313385A patent/JP2008080153A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10513378A (ja) | 1998-12-22 |
| CN1141149C (zh) | 2004-03-10 |
| WO1996024392A1 (en) | 1996-08-15 |
| EP0808181B1 (en) | 2002-06-19 |
| NO973648L (no) | 1997-10-03 |
| ATE219381T1 (de) | 2002-07-15 |
| PL182804B1 (pl) | 2002-03-29 |
| CA2212519A1 (en) | 1996-08-15 |
| DE69621911T2 (de) | 2003-01-30 |
| NO973648D0 (no) | 1997-08-07 |
| HUP9702114A2 (hu) | 1998-04-28 |
| AU704047B2 (en) | 1999-04-15 |
| CA2212519C (en) | 2005-08-23 |
| ES2179930T3 (es) | 2003-02-01 |
| HUP9702114A3 (en) | 1998-06-29 |
| US6129956A (en) | 2000-10-10 |
| NZ302264A (en) | 1998-02-26 |
| BR9607516A (pt) | 1997-12-30 |
| HU219815B (hu) | 2001-08-28 |
| AU4788496A (en) | 1996-08-27 |
| JP2008080153A (ja) | 2008-04-10 |
| CN1173824A (zh) | 1998-02-18 |
| CZ250997A3 (cs) | 1998-01-14 |
| DE69621911D1 (de) | 2002-07-25 |
| MX9706054A (es) | 1998-07-31 |
| CZ293637B6 (cs) | 2004-06-16 |
| TR199700760T1 (xx) | 1998-02-21 |
| EP0808181A1 (en) | 1997-11-26 |
| PL321781A1 (en) | 1997-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |