WO2011069475A2 - Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification - Google Patents
Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification Download PDFInfo
- Publication number
- WO2011069475A2 WO2011069475A2 PCT/CZ2010/000129 CZ2010000129W WO2011069475A2 WO 2011069475 A2 WO2011069475 A2 WO 2011069475A2 CZ 2010000129 W CZ2010000129 W CZ 2010000129W WO 2011069475 A2 WO2011069475 A2 WO 2011069475A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hyaluronic acid
- water
- hyaluronan
- oxidized
- tempo
- Prior art date
Links
- 0 C[*+]N(CC(C(C)C)C1OC(CO)C2O)C1C2OC(C(C1OC*(C)*C11)O)OC1C(O)=O Chemical compound C[*+]N(CC(C(C)C)C1OC(CO)C2O)C1C2OC(C(C1OC*(C)*C11)O)OC1C(O)=O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/728—Hyaluronic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
-
- 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
Definitions
- R is hydrogen or any substitute and the co-oxidant is sodium hypochlorite (NaClO) or trichloroisocyanuric acid (TCC).
- NaClO sodium hypochlorite
- TCC trichloroisocyanuric acid
- the hyaluronic acid is an important polysaccharide, composed of two repeating units of P-(l,3)-D-glucuronic acid and -(l,4)-N-acetyl-D-glucosamine.
- the molecular weight depending on the method of isolation and on the source material, is within the range from 5.10 4 to 5.10 6 g.mol '1 .
- the hyaluronic acid or its sodium salt hyaluronan is an essential component of connective tissues, synovial fluid of joints, and plays an important role in biological processes, such as hydratation, organization of proteoglycans, cell differentiation, proliferation and angiogenesis.
- the hyaluronic acid is a considerably hydrophilic polysaccharide and is soluble in water in the form of a salt in the whole range of pH.
- TEMPO is a relatively stable radical which can exist in reaction in three redox forms. Only the oxidized form of TEMPO is effective for alcohols or geminal diols oxidation.
- a catalytic amount of TEMPO is added to the reaction and therefore, it is necessary to use a co-oxidant which restores the presence of the TEMPO oxidized form.
- Oxidation of hyaluronan by use of TEMPO/NaClO system was described in the patent application WO 02/18448 A2. The authors also dealt with interactions of percarboxylated polysaccharides, while forming biological complexes.
- the physico-chemical properties of the resulting hydrogels have been elucidated by instrumental analyses FT-IR, SEM (scanning electron microscopy) and rheometry. Increasing the oxidation degree of the hyaluronan lead to a corresponding increase of hydrogels compatibility and decrease of water absorption capacity. Dermal fibroblasts were used to study the cell-hydrogel interactions. Both the hydrogels and their degradation products are biocompatible, as proved by the long-term cell viability assay. When cultured with cells, the hydrogel underwent a degradation within 4 weeks, with an obvious loss of cohesiveness. The good biocompatibility and biodegradability was further demonstrated in mice subdermal implantations. Lastly, in vitro and in vivo depositions of extracellular matrix in hydrogels were demonstrated by SEM analysis.
- the present invention relates to an improvement of a method of selective oxidation of the primary hydroxyl group of the hyaluronic acid in the position 6 of the polysaccharide glucosamine part to aldehyde.
- the new reaction is performed using a system of 2,2,6,6- -tetramethyl-l-piperidinyloxyl radical TEMPO / co-oxidant.
- Approaches published up to date have introduced either an aldehydic group to the position 2 and 3 of the hyaluronan glucuronic part, while opening the saccharide ring (scheme 6, structure 2), or a carboxyl group to the position 6 of the hyaluronan glucosamine part (scheme 6, structure 1).
- the method according to the invention is more advantageous in that the respective oxidation product (structure 3, scheme 6) maintains the structure of conjugated saccharide rings. Ring opening in the product oxidized to dialdehyde (structure 2, scheme 6) gives rise to the chain linearity subreakage" and, therefore, a significant change of the polysaccharide 3- dimensional structure compared to the non-modified hyaluronan. Although in the product oxidized to a carboxylic acid (structure 1, scheme 6) the chain linearity impartbreakage" does not occur, the carboxyl group does not enable such various modification (binding) possibilities like the aldehydic group.
- the prepared oxidized hyaluronan can be used for binding compounds containing for example an amino group.
- the binding can be realized either in an imine form or after the reduction in an amine form (reductive amination) (scheme 7):
- the modification of the hyaluronic acid derivative can be performed by a reaction of the oxidized derivative with an amine of the general formula H 2 N-R or with a hyaluronan substituted by an -R-NH 2 group, wherein R is an alkyl, linear or branched chain CI- C30, optionally containing aromatic or heteroaromatic groups.
- This amine can be an alkylamine, e.g. butylamine or hexanediamine, amino acid, peptide or polysaccharide containing a free amino group.
- cross-linked hyaluronan derivatives can be prepared.
- the cross-linked derivatives can be prepared also by the reaction of an aldehyde with a hyaluronan substituted by an aminoalkyl group HA-alkyl-NH 2 .
- Example 8 Oxidation of the hyaluronic acid by the TEMPO/TCC system
- TEMPO (0.01 eq) and TCC (0.2 eq) were added to a hyaluronic acid solution (1%) (O.lg, 20 kDa) in the mixture of DMF/water 70/30. The mixture was stirred for 100 hours at the temperature of -5°C. The solution was then diluted to 0.1 % and dialyzed against the mixture (0.1% NaCl, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was evaporated and analyzed.
- the solution was then mixed with NaBH 3 CN (3 eq) in 0.5 ml of water. The mixture was stirred for 24 hours at the temperature of 20°C. The solution was then diluted to 0.1% and dialyzed against the mixture (0.1% NaCl, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was evaporated and analyzed.
- the resulting solution was diluted to 0.1% and dialyzed against the mixture (0.1% NaCI, 0.1% NaHC0 3 ) 3 x 5 liters (once per day) and against distilled water 7 x 5 liters (twice per day). The resulting solution was then evaporated and analyzed.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK10812840.6T DK2510016T3 (en) | 2009-12-11 | 2010-12-10 | A process for preparing an oxidized derivative of hyaluronic acid and a process for modifying it |
JP2012542356A JP5886754B2 (ja) | 2009-12-11 | 2010-12-10 | ヒアルロン酸の酸化誘導体の調製方法及びその修飾方法 |
EP10812840.6A EP2510016B1 (fr) | 2009-12-11 | 2010-12-10 | Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification |
US13/512,484 US9434791B2 (en) | 2009-12-11 | 2010-12-10 | Method of preparation of an oxidized derivative of hyaluronic acid and a method of modification thereof |
KR1020127017887A KR101766693B1 (ko) | 2009-12-11 | 2010-12-10 | 히알루론산의 산화된 유도체의 제조 방법 및 이의 변형 방법 |
BR112012013955A BR112012013955B1 (pt) | 2009-12-11 | 2010-12-10 | método de preparação do derivado de ácido hialurônico seletivamente oxidado na posição (6) da parte glucosamina do polissacarídeo ao aldeído e método de modificação do derivado de ácido hialurônico |
RU2012125154/05A RU2559447C2 (ru) | 2009-12-11 | 2010-12-10 | Способ получения окисленного производного гиалуроновой кислоты и способ его модификации |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CZPV2009-835 | 2009-12-11 | ||
CZ20090835A CZ302503B6 (cs) | 2009-12-11 | 2009-12-11 | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2011069475A2 true WO2011069475A2 (fr) | 2011-06-16 |
WO2011069475A3 WO2011069475A3 (fr) | 2011-08-11 |
Family
ID=43978081
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CZ2010/000129 WO2011069475A2 (fr) | 2009-12-11 | 2010-12-10 | Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification |
Country Status (11)
Country | Link |
---|---|
US (1) | US9434791B2 (fr) |
EP (1) | EP2510016B1 (fr) |
JP (1) | JP5886754B2 (fr) |
KR (1) | KR101766693B1 (fr) |
BR (1) | BR112012013955B1 (fr) |
CZ (1) | CZ302503B6 (fr) |
DK (1) | DK2510016T3 (fr) |
HU (1) | HUE031497T2 (fr) |
PL (1) | PL2510016T3 (fr) |
RU (1) | RU2559447C2 (fr) |
WO (1) | WO2011069475A2 (fr) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013137755A1 (fr) | 2012-03-14 | 2013-09-19 | Nanovelos Sp. Z O.O. | Procédé pour la préparation de nanoparticules de polysaccharide |
WO2014023272A1 (fr) | 2012-08-08 | 2014-02-13 | Contipro Biotech S.R.O. | Dérivé d'acide hyaluronique, procédé de préparation de celui-ci, procédé de modification de celui-ci et d'utilisation de celui-ci |
WO2014082610A1 (fr) | 2012-11-27 | 2014-06-05 | Contipro Biotech S.R.O. | Fibres sans fin à base d'hyaluronane sélectivement oxydé en position 6 du groupe n-acétyl-d-glucosamine, leur préparation et utilisation, filés, fibres courtes, fils et tissus constitués de celles-ci et procédé pour la modification de celles-ci |
WO2015135511A1 (fr) * | 2014-03-11 | 2015-09-17 | Contipro Biotech S.R.O. | Conjugués d'oligomère d'acide hyaluronique ou d'un sel de celui-ci, procédé de préparation de celui-ci et utilisation de celui-ci |
US20150328328A1 (en) * | 2012-12-20 | 2015-11-19 | Pfizer Inc. | Glycoconjugation process |
US9403918B2 (en) | 2009-12-11 | 2016-08-02 | Contipro Pharma A.S. | Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof |
US9434791B2 (en) | 2009-12-11 | 2016-09-06 | Contipro Pharma A.S. | Method of preparation of an oxidized derivative of hyaluronic acid and a method of modification thereof |
US9492586B2 (en) | 2012-02-28 | 2016-11-15 | Contipro Biotech S.R.O. | Derivatives of hyaluronic acid capable of forming hydrogels |
WO2016202314A1 (fr) | 2015-06-15 | 2016-12-22 | Contipro A.S. | Procédé de réticulation de polysaccharides à l'aide de groupes protecteurs photoamovibles |
WO2016206661A1 (fr) | 2015-06-26 | 2016-12-29 | Contipro A.S. | Dérivés de polysaccharides sulfatés, procédé de préparation, modification et utilisation correspondants |
EP3156044A1 (fr) | 2015-10-16 | 2017-04-19 | Merz Pharma GmbH & Co. KGaA | Compositions de polysaccharide réticulable in situ et ses utilisations |
US9999678B2 (en) | 2012-11-27 | 2018-06-19 | Contipro A.S. | C6-C18-acylated derivative of hyaluronic acid and method of preparation thereof |
WO2020038500A1 (fr) * | 2018-08-23 | 2020-02-27 | Contipro A.S. | Dérivé chloré d'acide hyaluronique, son procédé de préparation, composition contenant le dérivé et son utilisation |
US10618984B2 (en) | 2016-06-27 | 2020-04-14 | Contipro A.S. | Unsaturated derivatives of polysaccharides, method of preparation thereof and use thereof |
US10617711B2 (en) | 2014-06-30 | 2020-04-14 | Contipro A.S. | Antitumor composition based on hyaluronic acid and inorganic nanoparticles, method of preparation thereof and use thereof |
US10689464B2 (en) | 2015-03-09 | 2020-06-23 | Contipro A.S. | Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of preparation and use thereof |
WO2020127407A1 (fr) | 2018-12-19 | 2020-06-25 | Merz Pharma Gmbh & Co. Kgaa | Acide hyaluronique modifié par un aldéhyde, son procédé de préparation et applications associées |
US11425907B2 (en) | 2018-08-23 | 2022-08-30 | Contipro A.S. | Composition comprising an iodide and a derivative of hyaluronic acid with an oxidative effect, method of preparation thereof and use thereof |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ304072B6 (cs) * | 2011-04-26 | 2013-09-25 | Contipro Biotech S.R.O. | Amfoterní materiál na bázi sítované kyseliny hyaluronové, zpusob jeho prípravy, materiály obsahující aktivní cinidla uzavrené v síti hyaluronanu, zpusob jejich prípravy a jejich pouzití |
CZ303722B6 (cs) * | 2012-01-16 | 2013-04-03 | Contipro Biotech S.R.O. | Kyselina hyaluronová znacená tritiem, zpusob znacení kyseliny hyaluronové tritiem a její pouzití |
CZ2012844A3 (cs) * | 2012-11-27 | 2014-02-05 | Contipro Biotech S.R.O. | Fotoreaktivní derivát kyseliny hyaluronové, způsob jeho přípravy, 3D síťovaný derivát kyseliny hyaluronové, způsob jeho přípravy a použití |
US9751849B1 (en) | 2016-12-06 | 2017-09-05 | King Fahd University Of Petroleum And Minerals | Method of producing a furanone compound |
WO2019175036A1 (fr) | 2018-03-12 | 2019-09-19 | Merz Pharma Gmbh & Co. Kgaa | Biomatériaux poreux pour régénération tissulaire |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002018448A2 (fr) | 2000-08-31 | 2002-03-07 | Fidia Farmaceutici S.P.A. | Polysaccharides percaboxyles, et procede d'elaboration |
US6683064B2 (en) | 1997-07-03 | 2004-01-27 | Depuy Acromed, Inc. | Cross-linked polysaccharide drug carrier |
Family Cites Families (120)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3720662A (en) | 1971-09-13 | 1973-03-13 | Nat Starch Chem Corp | Preparation of starch esters |
US3728223A (en) | 1971-10-08 | 1973-04-17 | Amano Pharma Co Ltd | Production of hyaluronidase from a strain of streptomyces |
CH628088A5 (en) | 1975-09-17 | 1982-02-15 | Dresden Arzneimittel | Process for obtaining streptococcal metabolic products |
US4205025A (en) | 1975-12-22 | 1980-05-27 | Champion International Corporation | Synthetic polymeric fibrids, fibrid products and process for their production |
JPS6033474B2 (ja) | 1978-05-11 | 1985-08-02 | 藤沢薬品工業株式会社 | 新規なヒアルロニダ−ゼbmp−8231およびその製造法 |
US4716224A (en) | 1984-05-04 | 1987-12-29 | Seikagaku Kogyo Co. Ltd. | Crosslinked hyaluronic acid and its use |
US4713448A (en) | 1985-03-12 | 1987-12-15 | Biomatrix, Inc. | Chemically modified hyaluronic acid preparation and method of recovery thereof from animal tissues |
US4851521A (en) | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
GB8519416D0 (en) | 1985-08-01 | 1985-09-04 | Unilever Plc | Oligosaccharides |
JPS62104579A (ja) | 1985-10-30 | 1987-05-15 | Kyowa Hakko Kogyo Co Ltd | ヒアルロニダ−ゼの製造法 |
JPH0751064B2 (ja) | 1986-08-13 | 1995-06-05 | 生化学工業株式会社 | 新規なヒアルロニダ−ゼsd−678およびその製造法 |
IT1219587B (it) | 1988-05-13 | 1990-05-18 | Fidia Farmaceutici | Polisaccaridi carbossiilici autoreticolati |
JPH0214019A (ja) | 1988-06-30 | 1990-01-18 | Tonen Corp | 繊維状成形物及びその製造方法 |
IT1254704B (it) | 1991-12-18 | 1995-10-09 | Mini Ricerca Scient Tecnolog | Tessuto non tessuto essenzialmente costituito da derivati dell'acido ialuronico |
US5824335A (en) | 1991-12-18 | 1998-10-20 | Dorigatti; Franco | Non-woven fabric material comprising auto-crosslinked hyaluronic acid derivatives |
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 |
FR2689131B1 (fr) | 1992-03-30 | 1994-05-20 | Oreal | Procede de preparation de monoesters majoritairement en position 6' du d-maltose et leur utilisation dans les domaines cosmetique, bucco-dentaire, pharmaceutique et alimentaire. |
JPH0625306A (ja) | 1992-04-21 | 1994-02-01 | Shiseido Co Ltd | 溶媒不溶化ヒアルロン酸及びその製造方法 |
IT1263316B (it) | 1993-02-12 | 1996-08-05 | Fidia Advanced Biopolymers Srl | Tessuto non tessuto multistrato in cui uno degli strati e' costituito essenzialmente da esteri dell'acido ialuronico |
NL9700003A (nl) | 1993-09-28 | 1997-07-01 | House Foods Corp | Werkwijze voor het inoculeren van Fistulina hepatica. |
US5616568A (en) | 1993-11-30 | 1997-04-01 | The Research Foundation Of State University Of New York | Functionalized derivatives of hyaluronic acid |
DE69513912T2 (de) | 1994-03-14 | 2000-05-18 | Seikagaku Kogyo Co Ltd | Material zum tragen auf dem augapfel |
US5455349A (en) | 1994-05-13 | 1995-10-03 | Polaroid Corporation | Vinylbenzyl thymine monomers |
US6025444A (en) | 1994-11-17 | 2000-02-15 | Seikagaku Kogyo Kabushiki Kaisha (Seikagaku Corporation) | Cinnamic acid derivative |
US5690961A (en) | 1994-12-22 | 1997-11-25 | Hercules Incorporated | Acidic polysaccharides crosslinked with polycarboxylic acids and their uses |
DK0813546T3 (da) | 1995-03-07 | 2002-11-04 | Novartis Ag | Fotokemisk tværbundne polysaccharidderivater som bærere til den chromatografiske separation af enantiomerer |
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 |
EP0763754B1 (fr) | 1995-09-13 | 2003-01-08 | Seikagaku Kogyo Kabushiki Kaisha (Seikagaku Corporation) | Lentille de contact à base d'acide hyaluronique photoréticulé |
DE19604706A1 (de) | 1996-02-09 | 1997-08-14 | Merck Patent Gmbh | Vernetzungsprodukte von Aminogruppen-haltigen Biopolymeren |
DE19616010C2 (de) | 1996-04-23 | 1998-07-09 | Seitz Filter Werke | Verfahren und Vorrichtung zur Herstellung von Fibrets (Fibriden) aus Zellulosederivaten |
IT1287698B1 (it) | 1996-08-29 | 1998-08-18 | Fidia Advanced Biopolymers Srl | Fili da sutura essenzialmente costituiti da derivati esterei dello acido ialuronico |
US6632802B2 (en) | 1996-08-29 | 2003-10-14 | Fidia Advanced Biopolymers S.R.L. | Hyaluronic acid esters, threads and biomaterials containing them, and their use in surgery |
RU2218922C2 (ru) | 1998-04-30 | 2003-12-20 | Маруха Корпорейшн | Соединения, имеющие в своей структуре фрагмент производного глюкуроновой кислоты и фрагмент производного глюкозамина, способы получения этих соединений и применение этих соединений |
KR20010071212A (ko) * | 1998-05-07 | 2001-07-28 | 추후보정 | 일차 알콜의 선택적 산화 반응 |
US6630457B1 (en) | 1998-09-18 | 2003-10-07 | Orthogene Llc | Functionalized derivatives of hyaluronic acid, formation of hydrogels in situ using same, and methods for making and using same |
IT1302534B1 (it) | 1998-12-21 | 2000-09-05 | Fidia Advanced Biopolymers Srl | Composizioni iniettabili, biocompatibili e biodegradabili comprendentialmeno un derivato dell'acido ialuronico, cellule condrogeniche, per |
JP2002533417A (ja) | 1998-12-23 | 2002-10-08 | エスパルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 局所施用薬剤の浸透性促進に使用されるヒアルロネートリアーゼ |
DE19917614C2 (de) | 1999-04-19 | 2001-07-05 | Thueringisches Inst Textil | Verfahren zur Herstellung von cellulosischen Formkörpern mit hohem Adsorptionsvermögen |
US6288043B1 (en) | 1999-06-18 | 2001-09-11 | Orquest, Inc. | Injectable hyaluronate-sulfated polysaccharide conjugates |
US6592794B1 (en) | 1999-09-28 | 2003-07-15 | Organogenesis Inc. | Process of making bioengineered collagen fibrils |
EP1237933A1 (fr) | 1999-11-08 | 2002-09-11 | SCA Hygiene Products Zeist B.V. | Procede d'oxydation d'alcools primaires |
DE10003397A1 (de) | 2000-01-27 | 2001-08-09 | Hartmann Paul Ag | Polyelektrolyt-Feststoffsystem, Verfahren zur Herstellung desselben sowie Wundverband |
IT1317358B1 (it) | 2000-08-31 | 2003-06-16 | Fidia Advanced Biopolymers Srl | Derivati cross-linkati dell'acido ialuronico. |
US6498269B1 (en) * | 2000-10-17 | 2002-12-24 | The University Of Connecticut | Method for the oxidation of aldehydes, hemiacetals and primary alcohols |
AU2002219718A1 (en) | 2000-12-13 | 2002-06-24 | Sca Hygiene Products Zeist B.V. | Process for oxidising primary alcohols |
EP1217008B1 (fr) | 2000-12-19 | 2006-03-01 | Seikagaku Corporation | Dérivé photodurcissable d'acide hyaluronique, procédé de préparation, dérivé réticulé et photodurci d'acide hyaluronique et matériel médical le contenant |
FR2819808B1 (fr) | 2001-01-19 | 2003-04-18 | Simafex | Compositions stabilisees d'acide o-iodoxybenzoique et leur procede de preparation |
US7893225B2 (en) | 2001-01-31 | 2011-02-22 | Seikagaku Corporation | Crosslinked polysaccharide sponge |
US6902548B1 (en) | 2001-03-19 | 2005-06-07 | Ed Schuler | Use of Streptomyces hyalurolyticus enzyme in ophthalmic treatments |
US6673919B2 (en) | 2001-03-30 | 2004-01-06 | Chisso Cororation | Chemically modified hyaluronic acid or salts thereof, and a process for producing thereof |
US6946284B2 (en) | 2001-11-16 | 2005-09-20 | University Of Massachusetts | Solubilizing cross-linked polymers with photolyase |
US20060189516A1 (en) | 2002-02-19 | 2006-08-24 | Industrial Technology Research Institute | Method for producing cross-linked hyaluronic acid-protein bio-composites |
JP3975267B2 (ja) | 2002-06-03 | 2007-09-12 | 独立行政法人産業技術総合研究所 | 多糖物質のアシル化方法 |
US20040101546A1 (en) | 2002-11-26 | 2004-05-27 | Gorman Anne Jessica | Hemostatic wound dressing containing aldehyde-modified polysaccharide and hemostatic agents |
US7550136B2 (en) | 2002-12-20 | 2009-06-23 | University Of Massachusetts | Photo-reactive polymers and devices for use in hair treatments |
US7465766B2 (en) | 2004-01-08 | 2008-12-16 | The Cleveland Clinic Foundation | Hydroxyphenyl cross-linked macromolecular network and applications thereof |
US6982298B2 (en) | 2003-01-10 | 2006-01-03 | The Cleveland Clinic Foundation | Hydroxyphenyl cross-linked macromolecular network and applications thereof |
FR2852012B1 (fr) | 2003-03-04 | 2006-06-23 | Oreal | Procede de preparation de derives o-acyles du glucose |
DE602004032525D1 (de) | 2003-03-11 | 2011-06-16 | Seikagaku Kogyo Co Ltd | Rstellungsverfahren dafür |
DE10331342B4 (de) | 2003-07-11 | 2009-03-12 | Thüringisches Institut für Textil- und Kunststoff-Forschung e.V. | Thermostabile Form- oder Spinnmasse |
WO2005028632A2 (fr) | 2003-09-19 | 2005-03-31 | Colorado State University Research Foundation (Csurf) | Esterification du hyaluronan par acylation pour des dispositifs moulables |
GB2408741B (en) | 2003-12-04 | 2008-06-18 | Ind Tech Res Inst | Hyaluronic acid derivative with urethane linkage |
US20100330143A1 (en) | 2003-12-04 | 2010-12-30 | University Of Utah Research Foundation | Modified macromolecules and methods of making and using thereof |
US8313765B2 (en) | 2003-12-04 | 2012-11-20 | Industrial Technology Research Institute | Biodegradable hyaluronic acid derivative, biodegradable polymeric micelle composition and pharmaceutical or bioactive composition |
WO2005082825A1 (fr) * | 2004-02-26 | 2005-09-09 | The Nutrasweet Company | Systeme catalyseur pour oxydation aerobie d'alcools primaires et secondaires |
JP2008505716A (ja) | 2004-07-09 | 2008-02-28 | ザ クリーヴランド クリニック ファウンデーション | ヒドロキシフェニル架橋高分子ネットワーク及びその用途 |
US7323425B2 (en) | 2004-08-27 | 2008-01-29 | Stony Brook Technology And Applied Research | Crosslinking of hyaluronan solutions and nanofiberous membranes made therefrom |
PL1817347T3 (pl) | 2004-11-24 | 2017-10-31 | Albumedix As | Sposób sieciowania kwasu hialuronowego za pomocą diwinylosulfonu |
US7214759B2 (en) | 2004-11-24 | 2007-05-08 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on polyesters and methods for fabricating the same |
US7680038B1 (en) * | 2005-04-25 | 2010-03-16 | Electronic Arts, Inc. | Dynamic bandwidth detection and response for online games |
GB0513552D0 (en) | 2005-07-01 | 2005-08-10 | Bristol Myers Squibb Co | Bandage |
RU2429018C2 (ru) | 2005-07-06 | 2011-09-20 | Сейкагаку Корпорейшн | Гель, полученный из фотосшитой гиалуроновой кислоты с введенным лекарственным средством |
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 |
US7993678B2 (en) | 2005-09-26 | 2011-08-09 | Novozymes Biopolymer A/S | Hyaluronic acid derivatives |
WO2007070617A1 (fr) | 2005-12-14 | 2007-06-21 | Anika Therapeutics, Inc. | Implant bioabsorbable de derive d'acide hyaluronique destine au traitement de defauts chondraux et osteochondraux |
US20070202570A1 (en) | 2006-02-24 | 2007-08-30 | Kikkoman Corporation | Enzyme composition, low molecular weight hyaluronan and process for preparing the same |
JP4892679B2 (ja) | 2006-03-27 | 2012-03-07 | 国立大学法人弘前大学 | ゲル紡糸によるヒアルロン酸繊維およびその製造方法 |
KR20070118730A (ko) | 2006-06-13 | 2007-12-18 | 주식회사 코오롱 | 보습성이 우수한 창상피복재 및 그의 제조방법 |
US20080124395A1 (en) | 2006-06-22 | 2008-05-29 | Weiliam Chen | Formulations and devices for treatment or prevention of neural ischemic damage |
US20080063617A1 (en) | 2006-09-07 | 2008-03-13 | Abrahams John M | Cosmetics formulations |
ITMI20061726A1 (it) | 2006-09-11 | 2008-03-12 | Fidia Farmaceutici | Derivati crosslinkati a base di acido ialuronico reticolato via click chemistry |
CZ302856B6 (cs) | 2006-09-27 | 2011-12-14 | Cpn Spol. S R. O. | Zpusob prípravy derivátu polysacharidu |
EP2107913B1 (fr) | 2006-12-22 | 2012-02-15 | Croma-Pharma Gesellschaft m.b.H. | Utilisation de polysaccharides comprenant des fonctions thiol pour l'augmentation tissulaire |
KR20080062092A (ko) | 2006-12-29 | 2008-07-03 | 주식회사 핸슨바이오텍 | 세포전달체로서의 히알루론산 유도체 및 이의 제조 방법 |
JP5329767B2 (ja) | 2007-02-26 | 2013-10-30 | 帝人株式会社 | 芳香族コポリアミド繊維の製造装置 |
RU2350625C2 (ru) * | 2007-04-04 | 2009-03-27 | Институт нефтехимии и катализа РАН | Производные гиалуроновой кислоты с пониженной биодеградируемостью |
CZ2007299A3 (cs) | 2007-04-24 | 2009-02-04 | Cpn Spol. S R. O. | Príprava nanovláken z polysacharidu a jejich smesí s polyvinylalkoholem |
JP5165281B2 (ja) | 2007-06-01 | 2013-03-21 | 株式会社バイオベルデ | 2反応剤型の医療用含水ゲル形成剤、及び、これより得られるヒアルロン酸ゲル |
WO2009037566A2 (fr) | 2007-06-19 | 2009-03-26 | Uvarkina Tamara P | Hyaluronidase et son procédé d'utilisation |
FR2921675B1 (fr) | 2007-09-28 | 2010-03-19 | Univ Claude Bernard Lyon | Filament a base d'acide hyaluronique et son procede d'obtention. |
WO2009101111A1 (fr) | 2008-02-11 | 2009-08-20 | Basf Se | Procédé de production de structures poreuses en polymères synthétiques |
EP3456749B1 (fr) | 2008-02-29 | 2021-07-14 | PVAC Medical Technologies Ltd. | Réactif d'alcool polyvinyl substitué |
JP5544107B2 (ja) * | 2008-03-31 | 2014-07-09 | 花王株式会社 | 高分子ビルダー |
WO2009148405A1 (fr) | 2008-06-05 | 2009-12-10 | Agency For Science, Technology And Research | Formation d'hydrogel en présence de peroxydase et d'une faible concentration de peroxyde d'hydrogène |
FR2934999B1 (fr) | 2008-08-13 | 2011-07-29 | Adocia | Polysaccharides fonctionnalises par des derives du tryptophane |
ES2658609T3 (es) | 2008-09-02 | 2018-03-12 | Tautona Group Lp | Hilos de ácido hialurónico y/o derivados de los mismos, métodos para fabricar los mismos, y usos de los mismos |
CZ2008705A3 (cs) | 2008-11-06 | 2010-04-14 | Cpn S. R. O. | Zpusob prípravy DTPA sítovaných derivátu kyseliny hyaluronové a jejich modifikace |
ITRM20080636A1 (it) | 2008-11-28 | 2010-05-29 | Univ Palermo | Procedimento per la produzione di derivati funzionalizzati dell acido ialuronico e relativi idrogeli. |
JP2010138276A (ja) | 2008-12-11 | 2010-06-24 | Nipro Corp | ヒアルロン酸単糸の製造方法 |
AU2010215203B2 (en) | 2009-02-21 | 2015-07-16 | Covidien Lp | Medical devices with an activated coating |
WO2010095049A1 (fr) | 2009-02-21 | 2010-08-26 | Sofradim Production | Fibres réticulées et leur procédé de production par extrusion |
WO2010095052A2 (fr) | 2009-02-21 | 2010-08-26 | Sofradim Production | Composés et dispositifs médicaux activés par des lieurs solvophobes |
CZ2009168A3 (cs) | 2009-03-17 | 2010-07-21 | Contipro C, A.S. | Zpusob prípravy derivátu kyseliny hyaluronové pomocí O-acyl-O´-alkylkarbonátu v prítomnosti substituovaného pyridinu |
US8551378B2 (en) | 2009-03-24 | 2013-10-08 | North Carolina State University | Nanospinning of polymer fibers from sheared solutions |
IT1396003B1 (it) | 2009-05-14 | 2012-11-09 | Fidia Farmaceutici | Ialuronidasi extracellulare da streptomyces koganeiensis |
WO2010138074A1 (fr) | 2009-05-29 | 2010-12-02 | Hilborn Joens | Systèmes d'administration à base d'acide hyaluronique |
KR101551681B1 (ko) | 2009-07-30 | 2015-09-09 | 카르빌란 테라퓨틱스, 인코포레이티드 | 변형된 히알루론산 폴리머 조성물 및 관련방법 |
KR101103423B1 (ko) | 2009-09-04 | 2012-01-06 | 아주대학교산학협력단 | 생체 주입형 조직 접착성 하이드로젤 및 이의 생의학적 용도 |
EP3067069B1 (fr) | 2009-11-11 | 2023-07-26 | Hy2Care B.V. | Hydrogels à base de polymères de dextrane-tyramine et conjugués tyramine de polymères naturels |
EP2498830B1 (fr) | 2009-11-11 | 2016-09-21 | University of Twente, Institute for Biomedical Technology and Technical Medicine (MIRA) | Hydrogels à base de dextrane-acide hyaluronique |
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 |
CZ2009836A3 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
US8197849B2 (en) | 2010-02-12 | 2012-06-12 | National Health Research Institutes | Cross-linked oxidated hyaluronic acid for use as a vitreous substitute |
CN101897976A (zh) | 2010-07-16 | 2010-12-01 | 沈阳药科大学 | 一种药物增溶载体及其制备方法和应用 |
CZ302994B6 (cs) | 2010-12-31 | 2012-02-08 | Cpn S.R.O. | Hyaluronová vlákna, zpusob jejich prípravy a použití |
CZ304072B6 (cs) | 2011-04-26 | 2013-09-25 | Contipro Biotech S.R.O. | Amfoterní materiál na bázi sítované kyseliny hyaluronové, zpusob jeho prípravy, materiály obsahující aktivní cinidla uzavrené v síti hyaluronanu, zpusob jejich prípravy a jejich pouzití |
CN102154738B (zh) | 2011-05-10 | 2012-08-01 | 青岛大学 | 一种红藻琼胶纤维的制备方法 |
CN104024494B (zh) | 2011-10-18 | 2017-11-10 | 海克私人有限公司 | 纤维成型方法和由此方法产生的纤维 |
CZ304512B6 (cs) | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
-
2009
- 2009-12-11 CZ CZ20090835A patent/CZ302503B6/cs unknown
-
2010
- 2010-12-10 KR KR1020127017887A patent/KR101766693B1/ko active IP Right Grant
- 2010-12-10 HU HUE10812840A patent/HUE031497T2/en unknown
- 2010-12-10 JP JP2012542356A patent/JP5886754B2/ja active Active
- 2010-12-10 US US13/512,484 patent/US9434791B2/en active Active
- 2010-12-10 RU RU2012125154/05A patent/RU2559447C2/ru active
- 2010-12-10 PL PL10812840T patent/PL2510016T3/pl unknown
- 2010-12-10 BR BR112012013955A patent/BR112012013955B1/pt active IP Right Grant
- 2010-12-10 WO PCT/CZ2010/000129 patent/WO2011069475A2/fr active Application Filing
- 2010-12-10 EP EP10812840.6A patent/EP2510016B1/fr active Active
- 2010-12-10 DK DK10812840.6T patent/DK2510016T3/en active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6683064B2 (en) | 1997-07-03 | 2004-01-27 | Depuy Acromed, Inc. | Cross-linked polysaccharide drug carrier |
US6953784B2 (en) | 1997-07-03 | 2005-10-11 | Depuy Spine, Inc. | Cross-linked polysaccharide drug carrier |
WO2002018448A2 (fr) | 2000-08-31 | 2002-03-07 | Fidia Farmaceutici S.P.A. | Polysaccharides percaboxyles, et procede d'elaboration |
Non-Patent Citations (7)
Title |
---|
ANGELINO, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 19, 2006, pages 4323 - 4326 |
CARBOHYDR RES, vol. 321, no. 3-4, 1999, pages 228 - 34 |
CARBOHYDR RES, vol. 327, no. 4, 2000, pages 455 - 61 |
SAHINER ET AL., J. BIOMATER. SCI. POLYM. ED, vol. 19, no. 2, 2008, pages 223 - 43 |
SCOTT ET AL., HISTOCHEMIE, vol. 19, no. 2, 1969, pages 155 - 61 |
WENG ET AL., BIOMATERIALS, vol. 29, no. 31, 2008, pages 4149 - 56 |
WENG ET AL., J BIOMED MATER RES A, vol. 85, no. 2, 2008, pages 352 - 65 |
Cited By (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9403918B2 (en) | 2009-12-11 | 2016-08-02 | Contipro Pharma A.S. | Oxidized derivative of hyaluronic acid, a method of preparation thereof and a method of modification thereof |
US9434791B2 (en) | 2009-12-11 | 2016-09-06 | Contipro Pharma A.S. | Method of preparation of an oxidized derivative of hyaluronic acid and a method of modification thereof |
US9492586B2 (en) | 2012-02-28 | 2016-11-15 | Contipro Biotech S.R.O. | Derivatives of hyaluronic acid capable of forming hydrogels |
CN104169305A (zh) * | 2012-03-14 | 2014-11-26 | 纳诺沃勒斯有限公司 | 制备多糖纳米粒的方法 |
US10258579B2 (en) | 2012-03-14 | 2019-04-16 | Nanovelos Sp. Z O.O. | Process for the preparation of polysaccharide nanoparticles |
WO2013137755A1 (fr) | 2012-03-14 | 2013-09-19 | Nanovelos Sp. Z O.O. | Procédé pour la préparation de nanoparticules de polysaccharide |
AU2013232850B2 (en) * | 2012-03-14 | 2016-01-07 | Nanovelos Sp. Z O.O. | Process for the preparation of polysaccharide nanoparticles |
RU2632019C2 (ru) * | 2012-03-14 | 2017-10-02 | Нановэлёс Сп. З О.О. | Способ получения наночастиц полисахаридов |
KR20150040966A (ko) * | 2012-08-08 | 2015-04-15 | 콘티프로 바이오테크 에스.알.오. | 히알루론산 유도체, 이의 제조 방법, 이의 변형 방법, 및 이의 용도 |
RU2647859C2 (ru) * | 2012-08-08 | 2018-03-21 | Контипро А.С. | Производное гиалуроновой кислоты, способ его получения, способ его модификации и его применение |
KR102060026B1 (ko) | 2012-08-08 | 2019-12-27 | 콘티프로 에이.에스. | 히알루론산 유도체, 이의 제조 방법, 이의 변형 방법, 및 이의 용도 |
WO2014023272A1 (fr) | 2012-08-08 | 2014-02-13 | Contipro Biotech S.R.O. | Dérivé d'acide hyaluronique, procédé de préparation de celui-ci, procédé de modification de celui-ci et d'utilisation de celui-ci |
US9522966B2 (en) | 2012-08-08 | 2016-12-20 | Contipro Biotech S.R.O. | Hyaluronic acid derivative, method of preparation thereof, method of modification thereof and use thereof |
US9999678B2 (en) | 2012-11-27 | 2018-06-19 | Contipro A.S. | C6-C18-acylated derivative of hyaluronic acid and method of preparation thereof |
WO2014082610A1 (fr) | 2012-11-27 | 2014-06-05 | Contipro Biotech S.R.O. | Fibres sans fin à base d'hyaluronane sélectivement oxydé en position 6 du groupe n-acétyl-d-glucosamine, leur préparation et utilisation, filés, fibres courtes, fils et tissus constitués de celles-ci et procédé pour la modification de celles-ci |
US20150328328A1 (en) * | 2012-12-20 | 2015-11-19 | Pfizer Inc. | Glycoconjugation process |
US11117928B2 (en) | 2012-12-20 | 2021-09-14 | Pfizer Inc. | Glycoconjugation process |
US10745438B2 (en) | 2012-12-20 | 2020-08-18 | Pfizer Inc. | Glycoconjugation process |
JP2016509081A (ja) * | 2012-12-20 | 2016-03-24 | ファイザー・インク | 糖複合化方法 |
AU2013365873B2 (en) * | 2012-12-20 | 2018-04-05 | Pfizer Inc. | Glycoconjugation process |
US10392420B2 (en) * | 2012-12-20 | 2019-08-27 | Pfizer Inc. | Glycoconjugation process |
AU2018204421B2 (en) * | 2012-12-20 | 2019-10-31 | Pfizer Inc. | Glycoconjugation process |
US11603384B2 (en) | 2012-12-20 | 2023-03-14 | Pfizer Inc. | Glycoconjugation process |
US10023658B2 (en) | 2014-03-11 | 2018-07-17 | Contipro A.S. | Conjugates of oligomer of hyaluronic acid or of a salt thereof, method of preparation thereof and use thereof |
RU2682509C2 (ru) * | 2014-03-11 | 2019-03-20 | Контипро А.С. | Конъюгаты олигомера гиалуроновой кислоты или ее соли, способ их получения и их применение |
WO2015135511A1 (fr) * | 2014-03-11 | 2015-09-17 | Contipro Biotech S.R.O. | Conjugués d'oligomère d'acide hyaluronique ou d'un sel de celui-ci, procédé de préparation de celui-ci et utilisation de celui-ci |
US10617711B2 (en) | 2014-06-30 | 2020-04-14 | Contipro A.S. | Antitumor composition based on hyaluronic acid and inorganic nanoparticles, method of preparation thereof and use thereof |
US10689464B2 (en) | 2015-03-09 | 2020-06-23 | Contipro A.S. | Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of preparation and use thereof |
RU2713295C2 (ru) * | 2015-06-15 | 2020-02-04 | Контипро А.С. | Способ сшивания полисахаридов при помощи фотоудаляемых защитных групп |
WO2016202314A1 (fr) | 2015-06-15 | 2016-12-22 | Contipro A.S. | Procédé de réticulation de polysaccharides à l'aide de groupes protecteurs photoamovibles |
US10759878B2 (en) | 2015-06-15 | 2020-09-01 | Contipro A.S. | Method of crosslinking of polysaccharides using photoremovable protecting groups |
US10414832B2 (en) | 2015-06-26 | 2019-09-17 | Contipro A.S | Derivatives of sulfated polysaccharides, method of preparation, modification and use thereof |
WO2016206661A1 (fr) | 2015-06-26 | 2016-12-29 | Contipro A.S. | Dérivés de polysaccharides sulfatés, procédé de préparation, modification et utilisation correspondants |
RU2734419C2 (ru) * | 2015-10-16 | 2020-10-16 | Мерц Фарма Гмбх Унд Ко. Кгаа | Сшиваемые in situ полисахаридные композиции и варианты их применения |
US11000467B2 (en) | 2015-10-16 | 2021-05-11 | Merz Pharma Gmbh & Co. Kgaa | In situ cross-linkable polysaccharide compositions and uses thereof |
WO2017063749A1 (fr) | 2015-10-16 | 2017-04-20 | Merz Pharma Gmbh & Co. Kgaa | Compositions de polysaccharide réticulable sur site et leurs utilisations |
EP3156044A1 (fr) | 2015-10-16 | 2017-04-19 | Merz Pharma GmbH & Co. KGaA | Compositions de polysaccharide réticulable in situ et ses utilisations |
US10618984B2 (en) | 2016-06-27 | 2020-04-14 | Contipro A.S. | Unsaturated derivatives of polysaccharides, method of preparation thereof and use thereof |
WO2020038500A1 (fr) * | 2018-08-23 | 2020-02-27 | Contipro A.S. | Dérivé chloré d'acide hyaluronique, son procédé de préparation, composition contenant le dérivé et son utilisation |
US11425907B2 (en) | 2018-08-23 | 2022-08-30 | Contipro A.S. | Composition comprising an iodide and a derivative of hyaluronic acid with an oxidative effect, method of preparation thereof and use thereof |
US11427652B2 (en) | 2018-08-23 | 2022-08-30 | Contipro A.S. | Chlorinated derivative of hyaluronic acid, method of preparation thereof, a composition containing the derivative, and use thereof |
WO2020127407A1 (fr) | 2018-12-19 | 2020-06-25 | Merz Pharma Gmbh & Co. Kgaa | Acide hyaluronique modifié par un aldéhyde, son procédé de préparation et applications associées |
CN113508143A (zh) * | 2018-12-19 | 2021-10-15 | 梅尔兹制药公司 | 醛改性的透明质酸,其制备方法以及其应用 |
Also Published As
Publication number | Publication date |
---|---|
BR112012013955A2 (pt) | 2016-06-07 |
HUE031497T2 (en) | 2017-07-28 |
WO2011069475A3 (fr) | 2011-08-11 |
KR101766693B1 (ko) | 2017-08-09 |
JP2013513672A (ja) | 2013-04-22 |
US9434791B2 (en) | 2016-09-06 |
DK2510016T3 (en) | 2016-10-10 |
JP5886754B2 (ja) | 2016-03-16 |
CZ2009835A3 (cs) | 2011-06-22 |
CZ302503B6 (cs) | 2011-06-22 |
RU2559447C2 (ru) | 2015-08-10 |
PL2510016T3 (pl) | 2017-02-28 |
RU2012125154A (ru) | 2014-01-20 |
US20120264913A1 (en) | 2012-10-18 |
KR20120095463A (ko) | 2012-08-28 |
BR112012013955B1 (pt) | 2020-01-14 |
EP2510016B1 (fr) | 2016-08-24 |
EP2510016A2 (fr) | 2012-10-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2011069475A2 (fr) | Procédé d'élaboration de dérivé oxydé d'acide hyaluronique et procédé de modification | |
EP2510017B1 (fr) | Dérivé oxydé d'acide hyaluronique, procédé d'élaboration et procédé de modification | |
US7683038B2 (en) | Percarboxylated polysaccharides, and a process for their preparation | |
US20160213787A1 (en) | Polymer-flavonoid conjugates and hydrogels for biomedical applications | |
JP6649892B2 (ja) | ヒアルロン酸オリゴマーの複合体又はその塩,その調製法及びその使用 | |
JP2015525820A (ja) | ヒアルロン酸誘導体,その調製方法,修飾方法及び使用 | |
CN112812201B (zh) | 巯基改性透明质酸及其制备方法和用途 | |
WO2012034544A2 (fr) | Procédé de préparation d'amides d'acide hyaluronique fortement substitués | |
RU2708327C2 (ru) | Производные сульфатированных полисахаридов, их способ получения, модификация и применение | |
CZ2004579A3 (cs) | Způsob přípravy derivátů hyaluronanu vázaných karbamátovou vazbou |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10812840 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13512484 Country of ref document: US |
|
REEP | Request for entry into the european phase |
Ref document number: 2010812840 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010812840 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012542356 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20127017887 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012125154 Country of ref document: RU |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112012013955 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112012013955 Country of ref document: BR Kind code of ref document: A2 Effective date: 20120611 |