CN103923229B - 一种交联透明质酸钠及其制备方法 - Google Patents
一种交联透明质酸钠及其制备方法 Download PDFInfo
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- CN103923229B CN103923229B CN201410180764.3A CN201410180764A CN103923229B CN 103923229 B CN103923229 B CN 103923229B CN 201410180764 A CN201410180764 A CN 201410180764A CN 103923229 B CN103923229 B CN 103923229B
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- Prior art keywords
- sodium
- hyaluronic acid
- cross
- preparation
- polyoxyethylene polyoxypropylene
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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 title claims abstract description 104
- 238000004132 cross linking Methods 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title claims abstract description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 66
- 229940059574 pentaerithrityl Drugs 0.000 claims abstract description 42
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000012065 filter cake Substances 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 28
- 239000011780 sodium chloride Substances 0.000 claims description 19
- 238000000108 ultra-filtration Methods 0.000 claims description 19
- 238000001556 precipitation Methods 0.000 claims description 18
- 238000012805 post-processing Methods 0.000 claims description 17
- 230000018044 dehydration Effects 0.000 claims description 10
- 238000006297 dehydration reaction Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 229920002674 hyaluronan Polymers 0.000 description 11
- 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 description 8
- 229960003160 hyaluronic acid Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 4
- 229920002385 Sodium hyaluronate Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 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 3
- 229940099552 hyaluronan Drugs 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 229940010747 sodium hyaluronate Drugs 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 241000561734 Celosia cristata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical group 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (5)
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CN201410180764.3A CN103923229B (zh) | 2014-04-30 | 2014-04-30 | 一种交联透明质酸钠及其制备方法 |
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CN103923229A CN103923229A (zh) | 2014-07-16 |
CN103923229B true CN103923229B (zh) | 2016-02-03 |
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CN107540763B (zh) * | 2016-06-24 | 2020-08-11 | 宁夏妙朗生物科技有限公司 | 一种利用生物交联剂制备注射型长效透明质酸凝胶的方法 |
CN106397846B (zh) * | 2016-08-31 | 2019-07-12 | 北京大清生物技术股份有限公司 | 一种交联透明质酸钠及其制备方法与应用 |
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JP4230135B2 (ja) * | 2001-08-21 | 2009-02-25 | 独立行政法人科学技術振興機構 | 多官能性架橋剤によって架橋したグリコサミノグリカン−コラーゲン複合体の製造法 |
US8318695B2 (en) * | 2007-07-30 | 2012-11-27 | Allergan, Inc. | Tunably crosslinked polysaccharide compositions |
CN103146003A (zh) * | 2013-03-06 | 2013-06-12 | 上海其胜生物制剂有限公司 | 一种低温二次交联透明质酸钠凝胶的制备方法 |
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Owner name: SUZHOU JINNUO BIOLOGICAL TECHNOLOGY CO., LTD. Free format text: FORMER OWNER: SUZHOU YOUNINGKANG INFORMATION TECHNOLOGY CO., LTD. Effective date: 20150331 |
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Effective date of registration: 20150331 Address after: 215400 Taicang Economic Development Zone, Jiangsu, Beijing West Road, No. 6, No. Applicant after: SUZHOU JINNUO BIOTECHNOLOGY Co.,Ltd. Address before: 706, room 1, building 225, Star Rainbow Building, No. 215000 middle Rainbow Road, Suzhou Industrial Park, Jiangsu, Suzhou Applicant before: SUZHOU YOUNINGKANG INFORMATION TECHNOLOGY Co.,Ltd. |
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Effective date of registration: 20190618 Address after: 215400 Room 103, Building 11, West Nanyuan Road, Chengxiang Town, Taicang City, Suzhou City, Jiangsu Province Patentee after: Guo Huijun Address before: 215400 6 Beijing West Road, Taicang Economic Development Zone, Suzhou, Jiangsu Patentee before: SUZHOU JINNUO BIOTECHNOLOGY Co.,Ltd. |
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