CN103834053A - Injectable crosslinked hyaluronic acid gel and preparation method thereof - Google Patents
Injectable crosslinked hyaluronic acid gel and preparation method thereof Download PDFInfo
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- CN103834053A CN103834053A CN201410074850.6A CN201410074850A CN103834053A CN 103834053 A CN103834053 A CN 103834053A CN 201410074850 A CN201410074850 A CN 201410074850A CN 103834053 A CN103834053 A CN 103834053A
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- hyaluronic acid
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims abstract description 229
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 157
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 154
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000001879 gelation Methods 0.000 title description 4
- 230000008961 swelling Effects 0.000 claims abstract description 48
- 238000004132 cross linking Methods 0.000 claims abstract description 37
- 238000001035 drying Methods 0.000 claims abstract description 24
- 238000011049 filling Methods 0.000 claims abstract description 21
- 238000002156 mixing Methods 0.000 claims abstract description 19
- 239000000839 emulsion Substances 0.000 claims abstract description 18
- 230000001954 sterilising effect Effects 0.000 claims abstract description 11
- 238000004659 sterilization and disinfection Methods 0.000 claims abstract description 9
- 239000007853 buffer solution Substances 0.000 claims abstract description 6
- 239000002245 particle Substances 0.000 claims description 87
- 239000000243 solution Substances 0.000 claims description 52
- 206010042674 Swelling Diseases 0.000 claims description 47
- 239000003795 chemical substances by application Substances 0.000 claims description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 238000009826 distribution Methods 0.000 claims description 25
- 238000010438 heat treatment Methods 0.000 claims description 23
- 239000012074 organic phase Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000004945 emulsification Methods 0.000 claims description 17
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- 230000015572 biosynthetic process Effects 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- YWGKLJXXVGSTCN-UHFFFAOYSA-N [Na].P(O)(O)(O)=O.[Cl] Chemical compound [Na].P(O)(O)(O)=O.[Cl] YWGKLJXXVGSTCN-UHFFFAOYSA-N 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 102000008186 Collagen Human genes 0.000 claims description 11
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
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- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 7
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- 239000003814 drug Substances 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 6
- 235000019198 oils Nutrition 0.000 claims description 6
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- 239000007864 aqueous solution Substances 0.000 claims description 5
- 230000001804 emulsifying effect Effects 0.000 claims description 5
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- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 claims description 4
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 claims description 4
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 claims description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 4
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 4
- 235000019800 disodium phosphate Nutrition 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
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- 239000001488 sodium phosphate Substances 0.000 claims description 4
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- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 3
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-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
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 claims description 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical group C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-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
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 239000008157 edible vegetable oil Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000007924 injection Substances 0.000 abstract description 33
- 238000002347 injection Methods 0.000 abstract description 33
- 230000000694 effects Effects 0.000 abstract description 20
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- 238000001727 in vivo Methods 0.000 abstract description 5
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- 230000009759 skin aging Effects 0.000 abstract description 2
- 239000008187 granular material Substances 0.000 abstract 4
- 210000004207 dermis Anatomy 0.000 abstract 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 abstract 1
- 239000000047 product Substances 0.000 description 39
- 239000000463 material Substances 0.000 description 8
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 7
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- 229920001436 collagen Polymers 0.000 description 6
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- 210000004027 cell Anatomy 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000001718 carbodiimides Chemical class 0.000 description 4
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- 230000003013 cytotoxicity Effects 0.000 description 4
- 231100000135 cytotoxicity Toxicity 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
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- 206010061218 Inflammation Diseases 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 229920001954 Restylane Polymers 0.000 description 2
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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 2
- 229940099552 hyaluronan Drugs 0.000 description 2
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- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
Abstract
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CN201410074850.6A CN103834053B (en) | 2014-02-28 | 2014-02-28 | A kind of injectable cross-linked hyaluronic acid gel and preparation method thereof |
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Cited By (31)
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CN104189952A (en) * | 2014-08-05 | 2014-12-10 | 北京爱美客生物科技有限公司 | Injection for correcting skin wrinkles and preparation method thereof |
CN105949478A (en) * | 2016-05-05 | 2016-09-21 | 广东东阳光药业有限公司 | Method for removing cross-linking agent in cross-linked hyaluronic acid |
CN106074213A (en) * | 2016-06-24 | 2016-11-09 | 上海建华精细生物制品有限公司 | Hyaluronic acid sodium gel for water optoinjection and its preparation method and application |
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