CA2916119A1 - Method for manufacturing a shaped cross-linked hyaluronic acid product - Google Patents
Method for manufacturing a shaped cross-linked hyaluronic acid product Download PDFInfo
- Publication number
- CA2916119A1 CA2916119A1 CA2916119A CA2916119A CA2916119A1 CA 2916119 A1 CA2916119 A1 CA 2916119A1 CA 2916119 A CA2916119 A CA 2916119A CA 2916119 A CA2916119 A CA 2916119A CA 2916119 A1 CA2916119 A1 CA 2916119A1
- Authority
- CA
- Canada
- Prior art keywords
- cross
- hyaluronic acid
- linked
- gel
- acid product
- 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.)
- Abandoned
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 abstract description 456
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 451
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 447
- 238000000034 method Methods 0.000 title claims abstract description 136
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 43
- 230000004048 modification Effects 0.000 claims abstract description 114
- 238000012986 modification Methods 0.000 claims abstract description 114
- 238000004132 cross linking Methods 0.000 claims abstract description 110
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 99
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 125000000600 disaccharide group Chemical group 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 75
- 239000000243 solution Substances 0.000 claims description 65
- 230000008961 swelling Effects 0.000 claims description 58
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000000835 fiber Substances 0.000 claims description 32
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 30
- 238000001556 precipitation Methods 0.000 claims description 23
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- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229920000573 polyethylene Polymers 0.000 claims description 9
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 7
- HEGWNIMGIDYRAU-UHFFFAOYSA-N 3-hexyl-2,4-dioxabicyclo[1.1.0]butane Chemical compound O1C2OC21CCCCCC HEGWNIMGIDYRAU-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 6
- 238000002316 cosmetic surgery Methods 0.000 claims description 6
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 6
- 238000012377 drug delivery Methods 0.000 claims description 6
- 229920001155 polypropylene Polymers 0.000 claims description 6
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- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 3
- 229940071643 prefilled syringe Drugs 0.000 claims description 3
- 239000000047 product Substances 0.000 description 236
- 239000000499 gel Substances 0.000 description 216
- 239000002609 medium Substances 0.000 description 75
- 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 class 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 description 62
- 229940014041 hyaluronate Drugs 0.000 description 59
- 238000009472 formulation Methods 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000523 sample Substances 0.000 description 25
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
- 239000011780 sodium chloride Substances 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 238000001125 extrusion Methods 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 108010003272 Hyaluronate lyase Proteins 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 238000012937 correction Methods 0.000 description 8
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 8
- 239000012467 final product Substances 0.000 description 8
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- 239000007924 injection Substances 0.000 description 8
- 239000002953 phosphate buffered saline Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 102000001974 Hyaluronidases Human genes 0.000 description 7
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- 238000000518 rheometry Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920002385 Sodium hyaluronate Polymers 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229940010747 sodium hyaluronate Drugs 0.000 description 6
- 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 6
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(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-MNSSHETKSA-N 0.000 description 4
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- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 3
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- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical group O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 3
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- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 210000003460 periosteum Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
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- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
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- 230000007480 spreading Effects 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- 230000002522 swelling effect Effects 0.000 description 1
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- 238000004448 titration Methods 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
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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
-
- 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
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F9/00—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/91—Injection
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Dispersion Chemistry (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Textile Engineering (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Inorganic Chemistry (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2013/063716 WO2014206500A1 (en) | 2013-06-28 | 2013-06-28 | Method for manufacturing a shaped cross-linked hyaluronic acid product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2916119A1 true CA2916119A1 (en) | 2014-12-31 |
Family
ID=48703545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2916119A Abandoned CA2916119A1 (en) | 2013-06-28 | 2013-06-28 | Method for manufacturing a shaped cross-linked hyaluronic acid product |
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| Country | Link |
|---|---|
| US (4) | US10077321B2 (enExample) |
| EP (2) | EP3617236B1 (enExample) |
| JP (1) | JP6434003B2 (enExample) |
| KR (1) | KR102048395B1 (enExample) |
| CN (2) | CN105473622B (enExample) |
| AU (1) | AU2013396752B2 (enExample) |
| BR (1) | BR112015031589A2 (enExample) |
| CA (1) | CA2916119A1 (enExample) |
| MX (1) | MX369409B (enExample) |
| RU (1) | RU2640865C2 (enExample) |
| WO (1) | WO2014206500A1 (enExample) |
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| US20210402050A1 (en) * | 2020-06-24 | 2021-12-30 | Anika Therapeutics, Inc. | Composite medical textile with non-resorbable fibers and bioresorbable hyaluronan-based fibers |
| BR112017016655B1 (pt) | 2015-02-13 | 2022-05-03 | Endo Derma Co., Ltd | Micro-agulha biodegradável contendo hidrogel de ácido hialurônico reticulado e método para sua preparação |
| EP3328351A1 (en) | 2015-07-27 | 2018-06-06 | Galderma S.A. | A process for efficient cross-linking of hyaluronic acid |
| KR101709608B1 (ko) * | 2015-09-03 | 2017-03-09 | (주)진우바이오 | 용융 방사에 의한 히알루론산염 파이버의 제조방법 및 이로부터 제조된 히알루론산염 파이버 |
| EP3350240B1 (en) * | 2015-09-18 | 2023-08-09 | Arkema, Inc. | Polyol pre-mixes having improved shelf life |
| KR20170090965A (ko) * | 2016-01-29 | 2017-08-08 | 한미약품 주식회사 | 복합 히알루론산 가교물 및 그 제조방법 |
| CN109996566A (zh) * | 2016-10-18 | 2019-07-09 | 奥尔胡斯大学 | 打印的透明质酸支架 |
| WO2018122344A1 (en) | 2016-12-29 | 2018-07-05 | Nestlé Skin Health Sa | Composition comprising a crosslinked hyaluronic acid (ha) in combination with a low-molecular ha and/or an agent stimulating endogenous ha synthesis |
| WO2018122342A1 (en) * | 2016-12-29 | 2018-07-05 | Nestlé Skin Health Sa | Micro- or nanoparticular multilamellar vesicles, compositions comprising the same and method for their use in skin care |
| EP3562469A1 (en) | 2016-12-29 | 2019-11-06 | Nestlé Skin Health SA | Micro- or nanoparticular vesicles comprising crosslinked hyaluronic acid, compositions comprising the same and method for their use in skin care |
| JP7216006B2 (ja) | 2017-03-22 | 2023-01-31 | ジェネンテック， インコーポレイテッド | ヒドロゲル架橋ヒアルロン酸プロドラッグ組成物及び方法 |
| EP3675922A1 (en) | 2017-10-12 | 2020-07-08 | Solyplus Berlin GmbH | Crosslinking of biopolymers in a semi-solid state |
| CN112334167A (zh) * | 2018-06-15 | 2021-02-05 | 克罗马药品有限责任公司 | 包含交联聚合物的水凝胶组合物 |
| BR112021018691A2 (pt) * | 2019-03-24 | 2021-11-23 | Allergan Pharmaceuticals Int Ltd | Géis homogêneos injetáveis compreendendo formas múltiplas de ácido hialurônico e métodos para sua fabricação |
| EP3956367A1 (en) * | 2019-04-19 | 2022-02-23 | Jointherapeutics S.r.l. | Crosslinked polymer of functionalized hyaluronic acid and its use in the treatment of inflammatory states |
| EP3797800A1 (en) * | 2019-05-02 | 2021-03-31 | Institut National De La Sante Et De La Recherche Medicale - Inserm | Hyaluronic acid hydrogels with prolonged antimicrobial activity |
| WO2020234167A1 (en) * | 2019-05-17 | 2020-11-26 | ETH Zürich | Printable hydrogel, method for generating a printable hydrogel, lyophilizate, printed product and 3d printing method |
| CN112147029A (zh) * | 2019-06-28 | 2020-12-29 | 杭州协合医疗用品有限公司 | 一种交联透明质酸钠凝胶溶胀度的测定方法 |
| EP3995530B1 (en) * | 2019-09-27 | 2025-05-28 | LG Chem, Ltd. | A method of preparing polymer microparticles, polymer microparticles, medical composition, cosmetic composition, medical articles, and cosmetic articles using the same |
| KR102173790B1 (ko) * | 2020-02-26 | 2020-11-03 | (주) 제이피케어즈 | 가교 히알루론산을 이용한 약물 전달 조성물 및 이의 제조방법 |
| KR102426699B1 (ko) * | 2020-11-26 | 2022-07-29 | (주)진우바이오 | 히알루론산염 파이버 및 이의 제조방법 |
| KR102527095B1 (ko) | 2020-12-18 | 2023-04-28 | 충남대학교산학협력단 | 가교 처리된 히알루론산 조성물의 가교율 측정방법 |
| CN113045779B (zh) * | 2021-03-22 | 2022-09-02 | 华熙生物科技股份有限公司 | 一种交联透明质酸凝胶粗品及其制备方法 |
| US20240352158A1 (en) * | 2021-10-15 | 2024-10-24 | Prohibix Llc | Crosslinked hyaluronic acid precipitates |
| CN114404355B (zh) * | 2021-12-28 | 2024-05-24 | 常州药物研究所有限公司 | 透明质酸钠凝胶及其制备方法、应用 |
| WO2023148619A1 (en) | 2022-02-01 | 2023-08-10 | Galderma Holding SA | Methods of producing crosslinked hyaluronic acid hydrogels |
| CN114894789B (zh) * | 2022-06-28 | 2025-08-15 | 华熙生物科技股份有限公司 | 一种透明质酸类物质指示剂组合物及其在快速检测透明质酸类物质中的应用 |
| TWI840941B (zh) * | 2022-09-06 | 2024-05-01 | 科妍生物科技股份有限公司 | 製造自體交聯透明質酸凝膠之方法及其產物 |
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| US4582865A (en) * | 1984-12-06 | 1986-04-15 | Biomatrix, Inc. | Cross-linked gels of hyaluronic acid and products containing such gels |
| US4605691A (en) * | 1984-12-06 | 1986-08-12 | Biomatrix, Inc. | Cross-linked gels of hyaluronic acid and products containing such gels |
| AU619760B2 (en) | 1987-12-10 | 1992-02-06 | Genzyme Biosurgery Corporation | Hylan preparation and method of recovery thereof from animal tissues |
| JPH01197501A (ja) | 1988-02-02 | 1989-08-09 | Mitsubishi Acetate Co Ltd | 精製サイリウムガムの製造方法 |
| US5827937A (en) * | 1995-07-17 | 1998-10-27 | Q Med Ab | Polysaccharide gel composition |
| GB9902412D0 (en) * | 1999-02-03 | 1999-03-24 | Fermentech Med Ltd | Process |
| TW574301B (en) * | 2001-05-02 | 2004-02-01 | Ind Tech Res Inst | Manufacturing method of epoxide crosslinked polysaccharides matrix |
| DE10223310A1 (de) * | 2002-05-24 | 2003-12-11 | Biotronik Mess & Therapieg | Verfahren zum Beschichten von Implantaten mit einer Polysaccharid-Lage |
| TWI251596B (en) * | 2002-12-31 | 2006-03-21 | Ind Tech Res Inst | Method for producing a double-crosslinked hyaluronate material |
| US7323425B2 (en) * | 2004-08-27 | 2008-01-29 | Stony Brook Technology And Applied Research | Crosslinking of hyaluronan solutions and nanofiberous membranes made therefrom |
| US20060105022A1 (en) | 2004-11-15 | 2006-05-18 | Shiseido Co., Ltd. | Process for preparing crosslinked hyaluronic acid gel |
| JP4875988B2 (ja) | 2004-11-15 | 2012-02-15 | 株式会社 資生堂 | 架橋ヒアルロン酸ゲルの製造方法 |
| KR101250846B1 (ko) * | 2005-07-04 | 2013-04-05 | 주식회사 엘지생명과학 | 히알루론산 가교물의 제조방법 |
| FR2908415B1 (fr) * | 2006-11-10 | 2009-01-23 | Abr Dev Sarl | Acide hyaluronique reticule et son procede de preparation |
| KR20080062092A (ko) * | 2006-12-29 | 2008-07-03 | 주식회사 핸슨바이오텍 | 세포전달체로서의 히알루론산 유도체 및 이의 제조 방법 |
| CN101313915B (zh) * | 2007-05-30 | 2011-04-20 | 北京泰克美科技有限公司 | 透明质酸及其盐、交联透明质酸及其盐在制备治疗或预防海泡伤药物中的应用 |
| US8318695B2 (en) * | 2007-07-30 | 2012-11-27 | Allergan, Inc. | Tunably crosslinked polysaccharide compositions |
| FR2920786B1 (fr) * | 2007-09-07 | 2010-09-10 | Univ Claude Bernard Lyon | Fibres creuses, notamment multi membranaires, leur procede de preparation par filage et dispositif pour la mise en oeuvre dudit procede |
| CN101821294B (zh) * | 2007-09-28 | 2012-10-31 | 株式会社资生堂 | 溶胀性交联透明质酸粉末及其制造方法 |
| ITMI20072416A1 (it) | 2007-12-21 | 2009-06-22 | Sigea Srl | Derivati polisaccaridici dell'acido lipoico, loro preparazione ed uso come dermocosmetici e presidi medicali |
| DK2413894T3 (en) | 2009-04-02 | 2017-04-03 | Allergan Inc | HIGHLY FORMED HYDROGLES FOR SOFTWARE STRENGTH |
| BR112012002117A2 (pt) * | 2009-07-30 | 2019-09-24 | Carbylan Biosurgery Inc | composições poliméricas modificadas de ácido hialurônico e métodos relacionados. |
| US20130274222A1 (en) * | 2010-10-20 | 2013-10-17 | Tautona Group Lp | Threads of cross-linked hyaluronic acid and methods of preparation and use thereof |
| CZ302994B6 (cs) * | 2010-12-31 | 2012-02-08 | Cpn S.R.O. | Hyaluronová vlákna, zpusob jejich prípravy a použití |
| CN102552974A (zh) * | 2012-02-17 | 2012-07-11 | 上海白衣缘生物工程有限公司 | 皮肤注射填充用凝胶组合物及其制备 |
| CN102660040B (zh) * | 2012-05-03 | 2014-03-12 | 杭州协合医疗用品有限公司 | 一种透明质酸钠凝胶的制备方法 |
| CN102731801B (zh) * | 2012-07-13 | 2013-12-25 | 常州药物研究所有限公司 | 外科整形用交联透明质酸钠凝胶及其制备方法 |
| CN102863631B (zh) * | 2012-09-29 | 2013-11-13 | 杭州嘉伟生物制品有限公司 | 外科整形用组织填充剂交联透明质酸钠凝胶及其制备方法 |
-
2013
- 2013-06-28 RU RU2016101734A patent/RU2640865C2/ru not_active IP Right Cessation
- 2013-06-28 CN CN201380079033.3A patent/CN105473622B/zh not_active Expired - Fee Related
- 2013-06-28 US US14/901,546 patent/US10077321B2/en active Active
- 2013-06-28 JP JP2016522286A patent/JP6434003B2/ja not_active Expired - Fee Related
- 2013-06-28 CA CA2916119A patent/CA2916119A1/en not_active Abandoned
- 2013-06-28 BR BR112015031589A patent/BR112015031589A2/pt not_active Application Discontinuation
- 2013-06-28 EP EP19202714.2A patent/EP3617236B1/en active Active
- 2013-06-28 WO PCT/EP2013/063716 patent/WO2014206500A1/en not_active Ceased
- 2013-06-28 KR KR1020167002526A patent/KR102048395B1/ko active Active
- 2013-06-28 EP EP13732529.6A patent/EP3013865B1/en active Active
- 2013-06-28 CN CN201910026542.9A patent/CN109734825B/zh not_active Expired - Fee Related
- 2013-06-28 AU AU2013396752A patent/AU2013396752B2/en not_active Ceased
- 2013-06-28 MX MX2015017526A patent/MX369409B/es active IP Right Grant
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2018
- 2018-08-24 US US16/111,561 patent/US20180362670A1/en not_active Abandoned
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2020
- 2020-02-04 US US16/781,264 patent/US10982016B2/en active Active
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2021
- 2021-03-29 US US17/216,084 patent/US11702484B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BR112015031589A2 (pt) | 2017-07-25 |
| AU2013396752A1 (en) | 2016-02-18 |
| US10077321B2 (en) | 2018-09-18 |
| EP3617236B1 (en) | 2024-07-31 |
| US20200247913A1 (en) | 2020-08-06 |
| US11702484B2 (en) | 2023-07-18 |
| RU2016101734A (ru) | 2017-08-02 |
| US10982016B2 (en) | 2021-04-20 |
| RU2640865C2 (ru) | 2018-01-12 |
| US20160145357A1 (en) | 2016-05-26 |
| JP2016524016A (ja) | 2016-08-12 |
| KR20160027095A (ko) | 2016-03-09 |
| CN105473622B (zh) | 2019-01-29 |
| WO2014206500A1 (en) | 2014-12-31 |
| MX369409B (es) | 2019-11-07 |
| EP3013865A1 (en) | 2016-05-04 |
| US20180362670A1 (en) | 2018-12-20 |
| CN109734825A (zh) | 2019-05-10 |
| JP6434003B2 (ja) | 2018-12-05 |
| EP3617236A1 (en) | 2020-03-04 |
| CN105473622A (zh) | 2016-04-06 |
| CN109734825B (zh) | 2022-01-28 |
| US20210214468A1 (en) | 2021-07-15 |
| AU2013396752B2 (en) | 2018-11-08 |
| HK1224314A1 (en) | 2017-08-18 |
| KR102048395B1 (ko) | 2019-11-25 |
| MX2015017526A (es) | 2016-08-05 |
| EP3013865B1 (en) | 2019-10-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180614 |
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| FZDE | Discontinued |
Effective date: 20210831 |