DK2236523T3 - Process for the preparation of crosslinked hyaluronic acid - Google Patents
Process for the preparation of crosslinked hyaluronic acid Download PDFInfo
- Publication number
- DK2236523T3 DK2236523T3 DK09004561.8T DK09004561T DK2236523T3 DK 2236523 T3 DK2236523 T3 DK 2236523T3 DK 09004561 T DK09004561 T DK 09004561T DK 2236523 T3 DK2236523 T3 DK 2236523T3
- Authority
- DK
- Denmark
- Prior art keywords
- cross
- hyaluronic acid
- linked hyaluronic
- acid according
- linking agent
- Prior art date
Links
- 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 163
- 229920002674 hyaluronan Polymers 0.000 title claims description 162
- 229960003160 hyaluronic acid Drugs 0.000 title claims description 161
- 238000000034 method Methods 0.000 title claims description 44
- 238000002360 preparation method Methods 0.000 title description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 99
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 238000004132 cross linking Methods 0.000 claims description 42
- 230000035484 reaction time Effects 0.000 claims description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 229920002385 Sodium hyaluronate Polymers 0.000 claims description 31
- 229940010747 sodium hyaluronate Drugs 0.000 claims description 31
- 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 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 20
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 claims description 16
- 229940014041 hyaluronate Drugs 0.000 claims description 16
- 230000007935 neutral effect Effects 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 238000007865 diluting Methods 0.000 claims description 4
- -1 polytetramethylene Polymers 0.000 claims description 4
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- VJVOFLWZDWLHNR-MRCUWXFGSA-N icosan-9-yl (z)-docos-13-enoate Chemical compound CCCCCCCCCCCC(CCCCCCCC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC VJVOFLWZDWLHNR-MRCUWXFGSA-N 0.000 claims description 2
- 229920000223 polyglycerol Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000499 gel Substances 0.000 description 21
- 239000000017 hydrogel Substances 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 15
- 230000003204 osmotic effect Effects 0.000 description 13
- 229910004354 OF 20 W Inorganic materials 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 12
- 229910021641 deionized water Inorganic materials 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 150000004676 glycans Chemical class 0.000 description 11
- 229920001282 polysaccharide Polymers 0.000 description 11
- 239000005017 polysaccharide Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 238000003760 magnetic stirring Methods 0.000 description 10
- 239000008055 phosphate buffer solution Substances 0.000 description 10
- 230000035479 physiological effects, processes and functions Effects 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000000502 dialysis Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 150000002016 disaccharides Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 3
- 108010003272 Hyaluronate lyase Proteins 0.000 description 3
- 102000001974 Hyaluronidases Human genes 0.000 description 3
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 229960002773 hyaluronidase Drugs 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920003123 carboxymethyl cellulose sodium Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229940097043 glucuronic acid Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 241000561734 Celosia cristata Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000037037 animal physiology Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 210000004127 vitreous body Anatomy 0.000 description 1
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cosmetics (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09004561.8A EP2236523B1 (en) | 2009-03-30 | 2009-03-30 | Method for producing cross-linked hyaluronic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2236523T3 true DK2236523T3 (en) | 2018-05-07 |
Family
ID=40908969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK09004561.8T DK2236523T3 (en) | 2009-03-30 | 2009-03-30 | Process for the preparation of crosslinked hyaluronic acid |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2236523B1 (enExample) |
| DK (1) | DK2236523T3 (enExample) |
| ES (1) | ES2662064T3 (enExample) |
| NO (1) | NO2236523T3 (enExample) |
| PL (1) | PL2236523T3 (enExample) |
| PT (1) | PT2236523T (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2861734B1 (fr) | 2003-04-10 | 2006-04-14 | Corneal Ind | Reticulation de polysaccharides de faible et forte masse moleculaire; preparation d'hydrogels monophasiques injectables; polysaccharides et hydrogels obtenus |
| US20120071437A1 (en) * | 2007-07-30 | 2012-03-22 | Allergan, Inc. | Tunable crosslinked polysaccharide compositions |
| US8318695B2 (en) | 2007-07-30 | 2012-11-27 | Allergan, Inc. | Tunably crosslinked polysaccharide compositions |
| US8697044B2 (en) | 2007-10-09 | 2014-04-15 | Allergan, Inc. | Crossed-linked hyaluronic acid and collagen and uses thereof |
| SI2818184T1 (sl) | 2007-11-16 | 2019-03-29 | Aclaris Therapeutics, Inc. | Sestava in postopki za zdravljenje purpure |
| US8394782B2 (en) | 2007-11-30 | 2013-03-12 | Allergan, Inc. | Polysaccharide gel formulation having increased longevity |
| US8394784B2 (en) | 2007-11-30 | 2013-03-12 | Allergan, Inc. | Polysaccharide gel formulation having multi-stage bioactive agent delivery |
| US8357795B2 (en) | 2008-08-04 | 2013-01-22 | Allergan, Inc. | Hyaluronic acid-based gels including lidocaine |
| CA2735173C (en) | 2008-09-02 | 2017-01-10 | Tautona Group Lp | Threads of hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
| US9371402B2 (en) | 2009-04-09 | 2016-06-21 | Scivision Biotech Inc. | Method for producing cross-linked hyaluronic acid |
| US9114188B2 (en) | 2010-01-13 | 2015-08-25 | Allergan, Industrie, S.A.S. | Stable hydrogel compositions including additives |
| US20110172180A1 (en) | 2010-01-13 | 2011-07-14 | Allergan Industrie. Sas | Heat stable hyaluronic acid compositions for dermatological use |
| EP2544652A2 (en) | 2010-03-12 | 2013-01-16 | Allergan Industrie SAS | A fluid composition comprising a hyaluronan polymer and mannitol for improving skin condition. |
| ES2729994T3 (es) | 2010-03-22 | 2019-11-07 | Allergan Inc | Hidrogeles reticulados de polisacárido y proteína-polisacárido para aumento de tejido blando |
| US8697057B2 (en) | 2010-08-19 | 2014-04-15 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US8889123B2 (en) | 2010-08-19 | 2014-11-18 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US9005605B2 (en) | 2010-08-19 | 2015-04-14 | Allergan, Inc. | Compositions and soft tissue replacement methods |
| US8883139B2 (en) | 2010-08-19 | 2014-11-11 | Allergan Inc. | Compositions and soft tissue replacement methods |
| FR2968305B1 (fr) | 2010-12-06 | 2014-02-28 | Teoxane | Procede de preparation d'un gel reticule |
| CN103501828A (zh) * | 2011-04-27 | 2014-01-08 | 株式会社美你康 | 人造玻璃体材料 |
| US9408797B2 (en) | 2011-06-03 | 2016-08-09 | Allergan, Inc. | Dermal filler compositions for fine line treatment |
| US9393263B2 (en) | 2011-06-03 | 2016-07-19 | Allergan, Inc. | Dermal filler compositions including antioxidants |
| US20130096081A1 (en) | 2011-06-03 | 2013-04-18 | Allergan, Inc. | Dermal filler compositions |
| RU2740454C2 (ru) | 2011-06-03 | 2021-01-14 | Аллерган Эндюстри, Сас | Составы кожного наполнителя, включая антиоксиданты |
| US20130244943A1 (en) | 2011-09-06 | 2013-09-19 | Allergan, Inc. | Hyaluronic acid-collagen matrices for dermal filling and volumizing applications |
| US9662422B2 (en) | 2011-09-06 | 2017-05-30 | Allergan, Inc. | Crosslinked hyaluronic acid-collagen gels for improving tissue graft viability and soft tissue augmentation |
| CN103554528B (zh) * | 2013-11-05 | 2016-05-11 | 北京化工大学 | 一种交联剂改性的透明质酸-聚天冬氨酸原位交联型水凝胶的制备方法 |
| ES2761558T3 (es) | 2014-09-30 | 2020-05-20 | Allergan Ind Sas | Composiciones de hidrogel estables que incluyen aditivos |
| TWI716365B (zh) | 2014-11-13 | 2021-01-21 | 德商梅茲製藥有限兩合公司 | 注射型真皮填充劑組合物及其套組、製備方法、與使用 |
| WO2016128783A1 (en) | 2015-02-09 | 2016-08-18 | Allergan Industrie Sas | Compositions and methods for improving skin appearance |
| ES2774051T3 (es) | 2015-02-13 | 2020-07-16 | Allergan Ind Sas | Implantes para esculpir, aumentar o corregir características faciales, tales como la barbilla |
| US11021580B2 (en) | 2015-07-27 | 2021-06-01 | Galderma Holding SA | Process for efficient cross-linking of hyaluronic acid |
| EP3165233B1 (en) | 2015-08-28 | 2021-08-18 | Latvijas Universitate | Biomaterial for treatment of acute and chronic skin wounds |
| US11020421B2 (en) | 2017-04-05 | 2021-06-01 | Gelesis Llc | Superabsorbent materials and methods of production thereof |
| RU2659175C1 (ru) * | 2017-04-12 | 2018-06-28 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Национальный исследовательский Мордовский государственный университет им. Н.П. Огарёва" | Композиция на основе бактериальной целлюлозы и гиалуроновой кислоты |
| FR3095206B1 (fr) * | 2019-04-17 | 2021-11-05 | Lab Vivacy | Procede de reticulation d’un polymere |
| CN111234271B (zh) * | 2019-08-29 | 2021-10-01 | 上海其胜生物制剂有限公司 | 一种引导交联透明质酸钠凝胶结构重排的方法 |
| EP4482581A4 (en) * | 2022-02-23 | 2025-07-30 | Vsy Biyoteknoloji Ve Ilac Sanayi Anonim Sirketi | Hyaluronic acid hydrogel formulation with phytoestrogen for the treatment of vaginal atrophy and vaginal rejuvenation and manufacturing process therefor |
| KR102868943B1 (ko) * | 2024-09-05 | 2025-10-13 | 주식회사 차메디텍 | 저온 용매 분산법을 포함하는 신규한 히알루론산 필러의 제조방법 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716224A (en) | 1984-05-04 | 1987-12-29 | Seikagaku Kogyo Co. Ltd. | Crosslinked hyaluronic acid and its use |
| SE442820B (sv) | 1984-06-08 | 1986-02-03 | Pharmacia Ab | Gel av tverbunden hyaluronsyra for anvendning som glaskroppssubstitut |
| DE69822285T2 (de) * | 1998-02-27 | 2005-01-27 | Stichting Hyppomedics | Verfahren zur Herstellung von vernetzter Hyaluronsäure |
| GB9902652D0 (en) * | 1999-02-05 | 1999-03-31 | Fermentech Med Ltd | Process |
| FR2861734B1 (fr) | 2003-04-10 | 2006-04-14 | Corneal Ind | Reticulation de polysaccharides de faible et forte masse moleculaire; preparation d'hydrogels monophasiques injectables; polysaccharides et hydrogels obtenus |
| AU2003901834A0 (en) | 2003-04-17 | 2003-05-01 | Clearcoll Pty Ltd | Cross-linked polysaccharide compositions |
| CN1829743B (zh) * | 2003-07-30 | 2010-06-30 | 安特易斯有限公司 | 生物医用的复合基质 |
| WO2005112888A2 (en) | 2004-05-20 | 2005-12-01 | Mentor Corporation | Methods for making injectable polymer hydrogels |
| EP1818344A4 (en) * | 2004-11-15 | 2012-04-18 | Shiseido Co Ltd | METHOD FOR SYNTHESIZING RETICULATED HYALURONIC ACID GEL |
-
2009
- 2009-03-30 NO NO09004561A patent/NO2236523T3/no unknown
- 2009-03-30 PT PT90045618T patent/PT2236523T/pt unknown
- 2009-03-30 PL PL09004561T patent/PL2236523T3/pl unknown
- 2009-03-30 ES ES09004561.8T patent/ES2662064T3/es active Active
- 2009-03-30 EP EP09004561.8A patent/EP2236523B1/en active Active
- 2009-03-30 DK DK09004561.8T patent/DK2236523T3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NO2236523T3 (enExample) | 2018-07-21 |
| EP2236523B1 (en) | 2018-02-21 |
| PL2236523T3 (pl) | 2018-07-31 |
| PT2236523T (pt) | 2018-03-21 |
| ES2662064T3 (es) | 2018-04-05 |
| EP2236523A1 (en) | 2010-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK2236523T3 (en) | Process for the preparation of crosslinked hyaluronic acid | |
| US9371402B2 (en) | Method for producing cross-linked hyaluronic acid | |
| US20100261893A1 (en) | Method for producing cross-linked hyaluronic acid | |
| JP5340093B2 (ja) | 架橋ヒアルロン酸の製造方法 | |
| CN101724164B (zh) | 交联透明质酸的制造方法 | |
| JP5789271B2 (ja) | 無菌ヒアルロン酸溶液 | |
| JP7621625B2 (ja) | 全分子量分布のヒアルロン酸ナトリウム及びその調製方法と応用 | |
| CA1263647A (en) | Method of preventing adhesion between body tissues, means for preventing such adhesion, and process for producing said means | |
| EP2820051B1 (en) | Derivates based on hyaluronic acid, capable of forming hydrogels, method of preparation thereof, hydrogels based on said derivatives, method of preparation thereof and use | |
| US20030027883A1 (en) | Biopolymers obtained by solid state irradiation in an unsaturated gaseous atmosphere | |
| US20100210587A1 (en) | Swellable Crosslinked Hyaluronan Powder And Method For Producing The Same | |
| TW200410987A (en) | Method for producing a double-crosslinked hyaluronate material | |
| CN101502677A (zh) | 一种注射用交联透明质酸钠凝胶及其制备方法 | |
| CN108478875B (zh) | 一种交联透明质酸凝胶微球的制备方法及其应用 | |
| EP2742070A1 (en) | Degradation-resistant cross-linked, low-molecular-weight hyaluronate | |
| La Gatta et al. | Hyaluronan dermal fillers via crosslinking with 1, 4‐butandiol diglycidyl ether: E xploitation of heterogeneous reaction conditions | |
| CN104774337A (zh) | 注射用含琼脂糖微球交联透明质酸钠凝胶及制备方法 | |
| Zhao et al. | Synthesis and characterization of a novel double crosslinked hyaluronan hydrogel | |
| KR102425496B1 (ko) | 고탄성, 고점도 및 고유효 가교율을 갖는 히알루론산 가교체, 및 이의 제조방법 | |
| CN112480440A (zh) | 一种单相交联透明质酸钠凝胶的制备方法 | |
| CN107349476A (zh) | 仿生关节滑液及其制备方法 | |
| CN104231285A (zh) | 透明质酸衍生物凝胶及其制备方法 | |
| Xu et al. | An engineered platform based on chitin-affinity immobilization for producing low molecular weight heparin | |
| EP2844310B1 (en) | Shape-memory cross-linked polysaccharides | |
| JP2002155103A (ja) | エンドトキシンフリーのβ１，３−グルカン及びその製造法並びに医療用ゲル素材 |