DE69832616T2 - Verwendung von hyaluonsäurederivaten zur herstellung von biomaterial - Google Patents
Verwendung von hyaluonsäurederivaten zur herstellung von biomaterial Download PDFInfo
- Publication number
- DE69832616T2 DE69832616T2 DE69832616T DE69832616T DE69832616T2 DE 69832616 T2 DE69832616 T2 DE 69832616T2 DE 69832616 T DE69832616 T DE 69832616T DE 69832616 T DE69832616 T DE 69832616T DE 69832616 T2 DE69832616 T2 DE 69832616T2
- Authority
- DE
- Germany
- Prior art keywords
- hyaluronic acid
- biomaterials according
- succinic
- acid
- biomaterials
- 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.)
- Expired - Lifetime
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Classifications
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- 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
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- 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
- A61L31/04—Macromolecular materials
- A61L31/041—Mixtures of macromolecular compounds
-
- 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
- A61L31/04—Macromolecular materials
- A61L31/042—Polysaccharides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/418—Agents promoting blood coagulation, blood-clotting agents, embolising agents
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- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/04—Materials for stopping bleeding
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Surgery (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
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- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITPD970170 | 1997-07-28 | ||
| IT97PD000170A IT1294797B1 (it) | 1997-07-28 | 1997-07-28 | Uso dei derivati dell'acido ialuronico nella preparazione di biomateriali aventi attivita' emostatica fisica e tamponante |
| PCT/EP1998/004716 WO1999004828A2 (en) | 1997-07-28 | 1998-07-28 | Use of hyaluronic acid derivatives in the preparation of biomaterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69832616D1 DE69832616D1 (de) | 2006-01-05 |
| DE69832616T2 true DE69832616T2 (de) | 2006-08-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69832616T Expired - Lifetime DE69832616T2 (de) | 1997-07-28 | 1998-07-28 | Verwendung von hyaluonsäurederivaten zur herstellung von biomaterial |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7202230B2 (enExample) |
| EP (1) | EP0999859B1 (enExample) |
| JP (1) | JP4417547B2 (enExample) |
| AT (1) | ATE311208T1 (enExample) |
| AU (1) | AU749627B2 (enExample) |
| CA (1) | CA2298733C (enExample) |
| DE (1) | DE69832616T2 (enExample) |
| DK (1) | DK0999859T3 (enExample) |
| ES (1) | ES2253827T3 (enExample) |
| IL (2) | IL134140A0 (enExample) |
| IT (1) | IT1294797B1 (enExample) |
| WO (1) | WO1999004828A2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1306679B1 (it) * | 1999-06-29 | 2001-10-02 | Fidia Advanced Biopolymers Srl | Uso dei derivati dell'acido ialuronico per la preparazione dicomposizoni farmaceutiche e biomateriali per la prevenzione della |
| WO2001097826A2 (en) * | 2000-06-16 | 2001-12-27 | University Of Medicine And Dentistry Of New Jersey | Hemostatic compositions, devices and methods |
| US7094428B2 (en) | 2000-06-16 | 2006-08-22 | The University Of Medicine And Dentistry Of New Jersey | Hemostatic compositions, devices and methods |
| US6235796B1 (en) * | 2000-06-26 | 2001-05-22 | Sarfaraz K. Niazi | Use of fluorocarbons for the prevention of surgical adhesions |
| EP1659143A4 (en) * | 2003-07-28 | 2008-10-08 | Teijin Ltd | HYDROGEL SENSITIVE AT TEMPERATURE |
| DE10349722A1 (de) * | 2003-10-23 | 2005-06-16 | Beschorner, Katharina, Dr. | Zusammensetzung zur Arthrose-/Arthritisbehandlung, insbesondere von Gelenken |
| RU2369408C2 (ru) * | 2004-07-09 | 2009-10-10 | Ферросан А/С | Гемостатическая композиция, включающая гиалуроновую кислоту |
| ITPD20040245A1 (it) * | 2004-10-08 | 2005-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali costituiti da acido ialuronico solfatato e gellano utilizzabili nella prevenzione delle adesioni spinali |
| DE602005009978D1 (de) * | 2004-12-14 | 2008-11-06 | Fidia Advanced Biopolymers Srl | Verfahren zur herstellung von zwei- und dreidimensionalen polymergerüsten |
| ITPD20040312A1 (it) * | 2004-12-15 | 2005-03-15 | Fidia Advanced Biopolymers Srl | Protesi e o supporto per la sostituzione, riparazione, rigenerazione del menisco |
| ITPD20050206A1 (it) | 2005-07-07 | 2007-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali in forma di fibra da impiegarsi come dispositivi medici nel trattamento delle ferite e loro processi di produzione |
| ITMI20051415A1 (it) * | 2005-07-22 | 2007-01-23 | Fidia Advanced Biopolymers Srl | Biomateriali a base di corbossimetilcellulosa salificata con zinco associata a derivati dell'acido ialuronico da impiegarsi come dispositivi medici con attivita' antimicrobica ed antifungina e loro processo di produzione |
| WO2007103993A2 (en) * | 2006-03-07 | 2007-09-13 | Axle International | Bioactive scaffold for therapeutic and adhesion prevention applications |
| ITPD20060219A1 (it) | 2006-05-31 | 2007-12-01 | Fidia Farmaceutici | Composizioni farmaceutiche contenenti acido ialuronico solfatato nel trattamento dell'osteoartrosi |
| CA2716872C (en) | 2008-02-29 | 2015-02-10 | Ferrosan Medical Devices A/S | Device for promotion of hemostasis and/or wound healing |
| US8343942B2 (en) | 2008-04-04 | 2013-01-01 | University Of Utah Research Foundation | Methods for treating interstitial cystitis |
| JP5758797B2 (ja) | 2008-04-04 | 2015-08-05 | ユニバーシティ・オブ・ユタ・リサーチ・ファウンデイション | アルキル化半合成グリコサミノグリカンエーテルならびにその製造および使用方法 |
| EP2324064B1 (en) * | 2008-09-02 | 2017-11-08 | Tautona Group LP | Threads of hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
| TWI458833B (zh) | 2010-05-11 | 2014-11-01 | Univ China Medical | 奈米金屬分散液及其製法 |
| JP6062917B2 (ja) | 2011-03-23 | 2017-01-18 | ザ ユニバーシティ オブ ユタ リサーチ ファウンデイション | 泌尿器科の炎症の治療及び予防の方法 |
| CA2865349C (en) | 2012-03-06 | 2021-07-06 | Ferrosan Medical Devices A/S | Pressurized container containing haemostatic paste |
| RU2636240C2 (ru) | 2012-06-12 | 2017-11-21 | Ферросан Медикал Дивайсиз А/С | Сухая гемостатическая композиция |
| EP3010419B1 (en) | 2013-06-21 | 2020-05-20 | Ferrosan Medical Devices A/S | Vacuum expanded dry composition and syringe for retaining same |
| BR112016013322B1 (pt) | 2013-12-11 | 2020-07-21 | Ferrosan Medical Devices A/S | métodos para preparação de uma composição seca e para reconstituir uma composição seca, composição seca, uso de uma composição seca, e, kit |
| SMT202200083T1 (it) | 2014-02-27 | 2022-03-21 | Synartro Ab | Coniugati di ialuronano con sostanze farmaceuticamente attive, metodi e composizioni |
| RU2715235C2 (ru) | 2014-10-13 | 2020-02-26 | Ферросан Медикал Дивайсиз А/С | Сухая композиция для использования при гемостазе и заживлении ран |
| CA2970710A1 (en) | 2014-12-24 | 2016-06-30 | Ferrosan Medical Devices A/S | Syringe for retaining and mixing first and second substances |
| CN107771093B (zh) | 2015-07-03 | 2021-06-15 | 弗罗桑医疗设备公司 | 用于混合两种组分和用于在存储条件下保持真空的注射器 |
| KR20180027126A (ko) * | 2016-09-06 | 2018-03-14 | (주)한국비엠아이 | 가교화 히알루론산 유도체 매트릭스가 포함된 지혈 조성물 |
| WO2018053111A1 (en) | 2016-09-15 | 2018-03-22 | University Of Utah Research Foundation | In situ gelling compositions for the treatment or prevention of inflammation and tissue damage |
| CN112368028A (zh) | 2018-05-09 | 2021-02-12 | 弗罗桑医疗设备公司 | 用于制备止血组合物的方法 |
| CN111228653A (zh) | 2018-11-13 | 2020-06-05 | 格莱科米拉治疗公司 | 用电离辐射加强癌症治疗的方法 |
| KR101980063B1 (ko) * | 2019-01-25 | 2019-05-17 | 주식회사 휴메딕스 | 히알루론산을 포함하는 스펀지형 생분해성 지혈제 조성물 |
| CN113754795B (zh) * | 2021-10-19 | 2023-03-10 | 澳门大学 | 磺酸化透明质酸类化合物、其制备方法及其应用 |
| CN116688216A (zh) * | 2023-05-26 | 2023-09-05 | 北京福爱乐科技发展有限公司 | 一种生物可降解医用凝胶及其制备方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| US5202431A (en) | 1985-07-08 | 1993-04-13 | Fidia, S.P.A. | Partial esters of hyaluronic acid |
| 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 |
| US6174999B1 (en) * | 1987-09-18 | 2001-01-16 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| IT1219587B (it) * | 1988-05-13 | 1990-05-18 | Fidia Farmaceutici | Polisaccaridi carbossiilici autoreticolati |
| GB8911177D0 (en) * | 1989-05-16 | 1989-07-05 | Vilain Jean | Alginate gel pharmaceutical product |
| IT1247157B (it) | 1991-02-11 | 1994-12-12 | Fidia Spa | Canali di guida biodegradabili e bioassorbibili da impiegare per la rigenerazione nervosa. |
| US5332809A (en) | 1991-02-11 | 1994-07-26 | Fidia S.P.A. | Partial esters of gellan |
| GB9109367D0 (en) * | 1991-05-01 | 1991-06-26 | Merck Sharp & Dohme | Surgical dressing |
| IT1247472B (it) | 1991-05-31 | 1994-12-17 | Fidia Spa | Processo per la preparazione di microsfere contenenti componenti biologicamente attivi. |
| IT1254704B (it) | 1991-12-18 | 1995-10-09 | Mini Ricerca Scient Tecnolog | Tessuto non tessuto essenzialmente costituito da derivati dell'acido ialuronico |
| IT1264322B (it) | 1992-07-30 | 1996-09-23 | Lanfranco Callegaro | Esteri di gellano autoreticolato, procedimento di preparazione e loro applicazioni farmaceutiche e biomedico-sanitarie |
| IT1259141B (it) | 1992-08-03 | 1996-03-11 | Fidia Spa | Canali di guida biodegradabili e bioriassorbibili da impiegare per la riparazione tissutale come adiuvante in interventi chirurgici |
| ITPD940054A1 (it) * | 1994-03-23 | 1995-09-23 | Fidia Advanced Biopolymers Srl | Polisaccaridi solfatati |
| FR2723847A1 (fr) * | 1994-08-29 | 1996-03-01 | Debiopharm Sa | Compositions antithrombotiques et non hemorragiques a base d'heparine, procede pour leur preparation et applications therapeutiques. |
| IT1281877B1 (it) * | 1995-05-10 | 1998-03-03 | Fidia Advanced Biopolymers Srl | Sali di metalli pesanti di succinil derivati dell'acido ialuronico e loro impiego come potenziali agenti terapeutici |
| GB9514361D0 (en) * | 1995-07-13 | 1995-09-13 | Bristol Myers Squibb Co | A film for topical use in the treatment of wounds |
| CN1301139C (zh) * | 1995-08-29 | 2007-02-21 | 菲迪亚高级生物聚合物公司 | 包括透明质酸衍生物的用于预防手术后粘连的生物材料 |
| IT1282994B1 (it) * | 1996-05-10 | 1998-04-03 | Inalco Spa | Derivati del polisaccaride k5 aventi elevata attivita' anticoagulante |
| IT1287698B1 (it) | 1996-08-29 | 1998-08-18 | Fidia Advanced Biopolymers Srl | Fili da sutura essenzialmente costituiti da derivati esterei dello acido ialuronico |
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1997
- 1997-07-28 IT IT97PD000170A patent/IT1294797B1/it active IP Right Grant
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1998
- 1998-07-28 EP EP98945104A patent/EP0999859B1/en not_active Expired - Lifetime
- 1998-07-28 ES ES98945104T patent/ES2253827T3/es not_active Expired - Lifetime
- 1998-07-28 WO PCT/EP1998/004716 patent/WO1999004828A2/en not_active Ceased
- 1998-07-28 AT AT98945104T patent/ATE311208T1/de active
- 1998-07-28 CA CA002298733A patent/CA2298733C/en not_active Expired - Lifetime
- 1998-07-28 IL IL13414098A patent/IL134140A0/xx active IP Right Grant
- 1998-07-28 JP JP2000503879A patent/JP4417547B2/ja not_active Expired - Fee Related
- 1998-07-28 AU AU92555/98A patent/AU749627B2/en not_active Ceased
- 1998-07-28 DE DE69832616T patent/DE69832616T2/de not_active Expired - Lifetime
- 1998-07-28 DK DK98945104T patent/DK0999859T3/da active
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Also Published As
| Publication number | Publication date |
|---|---|
| IT1294797B1 (it) | 1999-04-15 |
| ES2253827T3 (es) | 2006-06-01 |
| WO1999004828A3 (en) | 1999-06-10 |
| AU9255598A (en) | 1999-02-16 |
| US20030060448A1 (en) | 2003-03-27 |
| CA2298733A1 (en) | 1999-02-04 |
| ITPD970170A1 (it) | 1999-01-28 |
| JP4417547B2 (ja) | 2010-02-17 |
| IL134140A (en) | 2006-08-20 |
| CA2298733C (en) | 2009-09-01 |
| EP0999859B1 (en) | 2005-11-30 |
| EP0999859A2 (en) | 2000-05-17 |
| HK1028210A1 (en) | 2001-02-09 |
| IL134140A0 (en) | 2001-04-30 |
| JP2001510713A (ja) | 2001-08-07 |
| WO1999004828A2 (en) | 1999-02-04 |
| AU749627B2 (en) | 2002-06-27 |
| ATE311208T1 (de) | 2005-12-15 |
| DK0999859T3 (da) | 2006-03-27 |
| US7202230B2 (en) | 2007-04-10 |
| DE69832616D1 (de) | 2006-01-05 |
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