JP2007529559A5 - - Google Patents
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- Publication number
- JP2007529559A5 JP2007529559A5 JP2007504258A JP2007504258A JP2007529559A5 JP 2007529559 A5 JP2007529559 A5 JP 2007529559A5 JP 2007504258 A JP2007504258 A JP 2007504258A JP 2007504258 A JP2007504258 A JP 2007504258A JP 2007529559 A5 JP2007529559 A5 JP 2007529559A5
- Authority
- JP
- Japan
- Prior art keywords
- chitosan
- hydrogel
- deacetylation
- solution
- degree
- 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.)
- Granted
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- 229920001661 Chitosan Polymers 0.000 claims description 263
- 239000000017 hydrogel Substances 0.000 claims description 109
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 63
- 239000000243 solution Substances 0.000 claims description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 53
- 238000003381 deacetylation reaction Methods 0.000 claims description 49
- 230000006196 deacetylation Effects 0.000 claims description 48
- 229920001187 thermosetting polymer Polymers 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 29
- 229910019142 PO4 Inorganic materials 0.000 claims description 20
- 235000021317 phosphate Nutrition 0.000 claims description 20
- 239000002245 particle Substances 0.000 claims description 18
- 150000002009 diols Chemical class 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 16
- 239000010452 phosphate Substances 0.000 claims description 16
- 239000003929 acidic solution Substances 0.000 claims description 13
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 7
- 238000001879 gelation Methods 0.000 claims description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 7
- 230000001376 precipitating effect Effects 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 230000007928 solubilization Effects 0.000 claims description 7
- 238000005063 solubilization Methods 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000012377 drug delivery Methods 0.000 claims description 5
- 239000002609 medium Substances 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 230000003381 solubilizing effect Effects 0.000 claims description 5
- 230000001954 sterilising effect Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 32
- 230000008569 process Effects 0.000 description 32
- 238000003756 stirring Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000499 gel Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 238000006386 neutralization reaction Methods 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 9
- 229920002101 Chitin Polymers 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 3
- 230000000975 bioactive effect Effects 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229950006780 n-acetylglucosamine Drugs 0.000 description 3
- 238000001542 size-exclusion chromatography Methods 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 238000001248 thermal gelation Methods 0.000 description 3
- 241000238557 Decapoda Species 0.000 description 2
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical group N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 239000012493 hydrazine sulfate Substances 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- -1 sugars monophosphate Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007838 tissue remodeling Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2004/002988 WO2005097871A1 (en) | 2004-03-22 | 2004-03-22 | Pseudo-thermosetting neutralized chitosan composition forming a hydrogel and a process for producing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007529559A JP2007529559A (ja) | 2007-10-25 |
| JP2007529559A5 true JP2007529559A5 (enExample) | 2011-01-13 |
| JP5083967B2 JP5083967B2 (ja) | 2012-11-28 |
Family
ID=34957126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007504258A Expired - Fee Related JP5083967B2 (ja) | 2004-03-22 | 2004-03-22 | ヒドロゲルを形成する、偽熱硬化性の中和されたキトサン組成物、および、この組成物を製造するためのプロセス |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8835514B2 (enExample) |
| EP (1) | EP1730216A1 (enExample) |
| JP (1) | JP5083967B2 (enExample) |
| CA (1) | CA2560432C (enExample) |
| WO (1) | WO2005097871A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1730216A1 (en) * | 2004-03-22 | 2006-12-13 | Universite De Geneve | Pseudo-thermosetting neutralized chitosan composition forming a hydrogel and a process for producing the same |
| CN100431624C (zh) * | 2005-12-07 | 2008-11-12 | 浙江大学 | 可注射聚乳酸微载体/壳聚糖水凝胶复合支架的制备方法 |
| CN1330386C (zh) * | 2005-12-07 | 2007-08-08 | 浙江大学 | 用于组织工程的可注射性壳聚糖水凝胶的制备方法 |
| DK1978925T3 (da) * | 2005-12-23 | 2009-12-14 | Medidom Lab | Termohærdende neutraliseret chitosansammensætning, der danner en hydrogel, lyofilisat og fremgangsmåder til fremstilling deraf |
| US9034348B2 (en) | 2006-12-11 | 2015-05-19 | Chi2Gel Ltd. | Injectable chitosan mixtures forming hydrogels |
| JP2011511123A (ja) * | 2008-01-31 | 2011-04-07 | ザ プロクター アンド ギャンブル カンパニー | キトサンのアセチル化 |
| JP5746617B2 (ja) * | 2008-06-11 | 2015-07-08 | チ２ジェル リミテッドＣｈｉ２Ｇｅｌ Ｌｔｄ． | キトサン混合物を形成する注入可能なヒドロゲル |
| CN105142399B (zh) * | 2013-03-14 | 2018-06-12 | 金珂生物医疗公司 | 生物相容的和生物可吸收的衍生的壳聚糖组合物 |
| FR3016882A1 (fr) | 2014-01-30 | 2015-07-31 | Sofradim Production | Procede de preparation de chitosane a haut degre d’acetylation |
| CN114805859B (zh) * | 2022-06-16 | 2023-08-29 | 安阳师范学院 | 一种热定型壳聚糖水凝胶的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4659700A (en) * | 1984-03-02 | 1987-04-21 | Johnson & Johnson Products, Inc. | Chitosan-glycerol-water gel |
| JPS624702A (ja) * | 1985-06-28 | 1987-01-10 | Lion Corp | 水溶性アシル化キトサンの製造方法 |
| JPH0790005A (ja) * | 1993-09-24 | 1995-04-04 | Daiichi Seimo Kk | 水溶性キトサンの製造法 |
| JP3118423B2 (ja) * | 1996-08-30 | 2000-12-18 | ツヤック株式会社 | 水溶性の部分アセチル化キトサン液の製造方法 |
| CA2212300A1 (en) | 1997-08-04 | 1999-02-04 | Abdellatif Chenite | In vitro or in vivo gelfying chitosan and therapeutic uses thereof |
| FR2822842B1 (fr) * | 2001-03-30 | 2004-11-19 | Genevrier Lab | Procede de preparation d'un neo-tissu cartilagineux |
| NO20015986D0 (no) * | 2001-08-02 | 2001-12-06 | Einar J Mustaparta | Produktet chitosan, samt fremstillingsmetode og anvendelse av chitosan |
| FR2836044A1 (fr) * | 2002-02-15 | 2003-08-22 | Octaris | Composition pour la reparation et la cicatrisation cutanee comprenant exclusivement un vrai hydrogel physique de chitosane |
| EP1730216A1 (en) * | 2004-03-22 | 2006-12-13 | Universite De Geneve | Pseudo-thermosetting neutralized chitosan composition forming a hydrogel and a process for producing the same |
| JP2007090005A (ja) | 2005-09-27 | 2007-04-12 | Oputisu Engineering Company:Kk | 腹筋等鍛練器具 |
| JP2010072502A (ja) | 2008-09-22 | 2010-04-02 | Hitachi Displays Ltd | 液晶表示装置 |
-
2004
- 2004-03-22 EP EP04722250A patent/EP1730216A1/en not_active Withdrawn
- 2004-03-22 US US10/593,678 patent/US8835514B2/en not_active Expired - Fee Related
- 2004-03-22 WO PCT/EP2004/002988 patent/WO2005097871A1/en not_active Ceased
- 2004-03-22 JP JP2007504258A patent/JP5083967B2/ja not_active Expired - Fee Related
- 2004-03-22 CA CA2560432A patent/CA2560432C/en not_active Expired - Fee Related
-
2009
- 2009-12-29 US US12/654,700 patent/US8507563B2/en not_active Expired - Fee Related
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