CN104194008A - 一种交联透明质酸凝胶微粒及其制备方法 - Google Patents
一种交联透明质酸凝胶微粒及其制备方法 Download PDFInfo
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- CN104194008A CN104194008A CN201410389983.2A CN201410389983A CN104194008A CN 104194008 A CN104194008 A CN 104194008A CN 201410389983 A CN201410389983 A CN 201410389983A CN 104194008 A CN104194008 A CN 104194008A
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- hyaluronic acid
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- gel
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Links
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 208
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 179
- 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 151
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 239000011859 microparticle Substances 0.000 title abstract 5
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- 230000007935 neutral effect Effects 0.000 claims description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 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 claims description 29
- 229940099552 hyaluronan Drugs 0.000 claims description 29
- 239000000017 hydrogel Substances 0.000 claims description 29
- 239000002245 particle Substances 0.000 claims description 28
- 239000002994 raw material Substances 0.000 claims description 24
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 20
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 20
- 235000019800 disodium phosphate Nutrition 0.000 claims description 20
- 230000003179 granulation Effects 0.000 claims description 20
- 238000005469 granulation Methods 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 16
- 239000003637 basic solution Substances 0.000 claims description 13
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 10
- 239000007853 buffer solution Substances 0.000 claims description 10
- 239000008363 phosphate buffer Substances 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 238000004090 dissolution Methods 0.000 claims description 8
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- 229940045641 monobasic sodium phosphate Drugs 0.000 claims description 6
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 6
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 5
- -1 glycidol ethers Chemical class 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 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 4
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 claims description 4
- 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
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 4
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 150000003016 phosphoric acids Chemical class 0.000 claims description 4
- 239000002585 base 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
- 239000008055 phosphate buffer solution Substances 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
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 108010025899 gelatin film Proteins 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 9
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- 239000004971 Cross linker Substances 0.000 description 7
- 238000007920 subcutaneous administration Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 3
- 238000005297 material degradation process Methods 0.000 description 3
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- 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 3
- 230000037303 wrinkles Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
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- 229920002334 Spandex Polymers 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019994 cava Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 201000010251 cutis laxa Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 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 1
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- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
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Abstract
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106589424A (zh) * | 2016-12-12 | 2017-04-26 | 华熙福瑞达生物医药有限公司 | 一种注射用交联透明质酸凝胶及其制备方法 |
WO2017162676A1 (en) * | 2016-03-24 | 2017-09-28 | Merz Pharma Gmbh & Co. Kgaa | Modified hyaluronic acid, method for making same and uses thereof |
CN109531857A (zh) * | 2019-01-02 | 2019-03-29 | 华熙福瑞达生物医药有限公司 | 一种透明质酸或其盐颗粒的制备方法及所得产品 |
CN109810264A (zh) * | 2018-12-03 | 2019-05-28 | 浙江景嘉医疗科技有限公司 | 一种低改性的高粘度透明质酸凝胶及其制备方法和应用 |
CN115721615A (zh) * | 2022-11-17 | 2023-03-03 | 华熙生物科技股份有限公司 | 一种透明质酸颗粒及其制备方法 |
Citations (3)
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CN101538377A (zh) * | 2008-03-20 | 2009-09-23 | 上海昊海生物科技有限公司 | 一种交联透明质酸凝胶及其制备方法 |
CN101721349A (zh) * | 2008-10-16 | 2010-06-09 | 常州百瑞吉生物医药有限公司 | 可注射原位交联水凝胶及其制备方法和用途 |
CN101759881A (zh) * | 2008-10-08 | 2010-06-30 | 上海建华精细生物制品有限公司 | 一种医用交联透明质酸钠凝胶衍生产品及其制备方法 |
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2014
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Patent Citations (3)
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CN101538377A (zh) * | 2008-03-20 | 2009-09-23 | 上海昊海生物科技有限公司 | 一种交联透明质酸凝胶及其制备方法 |
CN101759881A (zh) * | 2008-10-08 | 2010-06-30 | 上海建华精细生物制品有限公司 | 一种医用交联透明质酸钠凝胶衍生产品及其制备方法 |
CN101721349A (zh) * | 2008-10-16 | 2010-06-09 | 常州百瑞吉生物医药有限公司 | 可注射原位交联水凝胶及其制备方法和用途 |
Cited By (15)
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AU2017237457B2 (en) * | 2016-03-24 | 2021-04-08 | Merz Pharma Gmbh & Co. Kgaa | Modified hyaluronic acid, method for making same and uses thereof |
KR102316644B1 (ko) | 2016-03-24 | 2021-10-26 | 메르츠 파마 게엠베하 운트 코. 카가아 | 개질된 하이알루론산, 이의 제조 방법 및 이의 용도 |
CN108779185A (zh) * | 2016-03-24 | 2018-11-09 | 梅尔兹制药公司 | 修饰透明质酸、其制造方法以及其用途 |
KR20180127983A (ko) * | 2016-03-24 | 2018-11-30 | 메르츠 파마 게엠베하 운트 코. 카가아 | 개질된 하이알루론산, 이의 제조 방법 및 이의 용도 |
IL261574B2 (en) * | 2016-03-24 | 2024-03-01 | Merz Pharma Gmbh & Co Kgaa | Engineered hyaluronic acid, a method for its preparation and its uses |
JP2019509385A (ja) * | 2016-03-24 | 2019-04-04 | メルツ ファルマ ゲーエムベーハー ウント コンパニー カーゲーアーアー | 修飾ヒアルロン酸、その製造方法、およびそれらの使用 |
WO2017162676A1 (en) * | 2016-03-24 | 2017-09-28 | Merz Pharma Gmbh & Co. Kgaa | Modified hyaluronic acid, method for making same and uses thereof |
RU2733444C2 (ru) * | 2016-03-24 | 2020-10-01 | Мерц Фарма Гмбх Энд Ко. Кгаа | Модифицированная гиалуроновая кислота, способ ее получения и ее применения |
IL261574B1 (en) * | 2016-03-24 | 2023-11-01 | Merz Pharma Gmbh & Co Kgaa | Engineered hyaluronic acid, a method for its preparation and its uses |
US10640578B2 (en) | 2016-03-24 | 2020-05-05 | Merz Pharma Gmbh & Co. Kgaa | Modified hyaluronic acid, method for making same and uses thereof |
CN106589424A (zh) * | 2016-12-12 | 2017-04-26 | 华熙福瑞达生物医药有限公司 | 一种注射用交联透明质酸凝胶及其制备方法 |
CN109810264B (zh) * | 2018-12-03 | 2021-08-06 | 浙江景嘉医疗科技有限公司 | 一种低改性的高粘度透明质酸凝胶及其制备方法和应用 |
CN109810264A (zh) * | 2018-12-03 | 2019-05-28 | 浙江景嘉医疗科技有限公司 | 一种低改性的高粘度透明质酸凝胶及其制备方法和应用 |
CN109531857A (zh) * | 2019-01-02 | 2019-03-29 | 华熙福瑞达生物医药有限公司 | 一种透明质酸或其盐颗粒的制备方法及所得产品 |
CN115721615A (zh) * | 2022-11-17 | 2023-03-03 | 华熙生物科技股份有限公司 | 一种透明质酸颗粒及其制备方法 |
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