JP5602734B2 - 側鎖としてシクロデキストリンを有するアクリル系ハイドロゲル、その製造方法ならびに放出系およびコンタクトレンズ成分としてのその使用 - Google Patents
側鎖としてシクロデキストリンを有するアクリル系ハイドロゲル、その製造方法ならびに放出系およびコンタクトレンズ成分としてのその使用 Download PDFInfo
- Publication number
- JP5602734B2 JP5602734B2 JP2011521606A JP2011521606A JP5602734B2 JP 5602734 B2 JP5602734 B2 JP 5602734B2 JP 2011521606 A JP2011521606 A JP 2011521606A JP 2011521606 A JP2011521606 A JP 2011521606A JP 5602734 B2 JP5602734 B2 JP 5602734B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclodextrin
- acrylic
- hydrogel
- methacrylic
- dimethacrylate
- 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.)
- Expired - Fee Related
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims description 108
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 98
- 239000000017 hydrogel Substances 0.000 title claims description 98
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 31
- 230000008569 process Effects 0.000 title claims description 10
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 56
- 229940079593 drug Drugs 0.000 claims description 41
- 239000003814 drug Substances 0.000 claims description 36
- 239000000178 monomer Substances 0.000 claims description 35
- -1 acryl Chemical group 0.000 claims description 31
- 239000003223 protective agent Substances 0.000 claims description 28
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 25
- 229960004853 betadex Drugs 0.000 claims description 25
- 239000013543 active substance Substances 0.000 claims description 24
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 6
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 6
- 125000005011 alkyl ether group Chemical group 0.000 claims description 6
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 6
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 6
- 125000004386 diacrylate group Chemical group 0.000 claims description 6
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 6
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 6
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 5
- 230000001588 bifunctional effect Effects 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 238000007654 immersion Methods 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 3
- ICCCRCJXHNMZPJ-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) 2,2-dimethyl-3-prop-2-enoyloxypropanoate Chemical compound C=CC(=O)OCC(C)(C)COC(=O)C(C)(C)COC(=O)C=C ICCCRCJXHNMZPJ-UHFFFAOYSA-N 0.000 claims description 2
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 2
- SNCMCDMEYCLVBO-UHFFFAOYSA-N 3-aminopropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCN SNCMCDMEYCLVBO-UHFFFAOYSA-N 0.000 claims description 2
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 claims description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- XWUNIDGEMNBBAQ-UHFFFAOYSA-N Bisphenol A ethoxylate diacrylate Chemical compound C=1C=C(OCCOC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCCOC(=O)C=C)C=C1 XWUNIDGEMNBBAQ-UHFFFAOYSA-N 0.000 claims description 2
- UUEYEUDSRFNIQJ-UHFFFAOYSA-N CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O Chemical compound CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O UUEYEUDSRFNIQJ-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 claims description 2
- UXRNWUYCCQFHIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C UXRNWUYCCQFHIH-UHFFFAOYSA-N 0.000 claims description 2
- PSSYEWWHQGPWGA-UHFFFAOYSA-N [2-hydroxy-3-[2-hydroxy-3-(2-hydroxy-3-prop-2-enoyloxypropoxy)propoxy]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(O)COCC(O)COCC(O)COC(=O)C=C PSSYEWWHQGPWGA-UHFFFAOYSA-N 0.000 claims description 2
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 claims description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 2
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 claims description 2
- 125000005641 methacryl group Chemical group 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 25
- 239000001116 FEMA 4028 Substances 0.000 description 22
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 22
- 229940097362 cyclodextrins Drugs 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 8
- YZOUYRAONFXZSI-SBHWVFSVSA-N (1S,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-37,39,40,41,42,43,44,45,46,47,48,49-dodecamethoxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38-diol Chemical compound O([C@@H]([C@H]([C@@H]1OC)OC)O[C@H]2[C@@H](O)[C@@H]([C@@H](O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3O)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O3)O[C@@H]2CO)OC)[C@H](CO)[C@H]1O[C@@H]1[C@@H](OC)[C@H](OC)[C@H]3[C@@H](CO)O1 YZOUYRAONFXZSI-SBHWVFSVSA-N 0.000 description 7
- 229960001259 diclofenac Drugs 0.000 description 6
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 6
- 238000010348 incorporation Methods 0.000 description 6
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 229960001193 diclofenac sodium Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- WZFRVPNOSKXDDQ-UHFFFAOYSA-N C(C(=C)C)(=O)O.C(C=C)(=O)N(CC)CC Chemical compound C(C(=C)C)(=O)O.C(C=C)(=O)N(CC)CC WZFRVPNOSKXDDQ-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 206010013774 Dry eye Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000607 artificial tear Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6903—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being semi-solid, e.g. an ointment, a gel, a hydrogel or a solidifying gel
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
- A61K8/738—Cyclodextrins
-
- 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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- 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
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/16—Cyclodextrin; Derivatives thereof
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
-
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/16—Cyclodextrin; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Nanotechnology (AREA)
- Birds (AREA)
- Ophthalmology & Optometry (AREA)
- Physics & Mathematics (AREA)
- Biophysics (AREA)
- Dermatology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medical Informatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Optics & Photonics (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- General Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Medicinal Preparation (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Cosmetics (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Eyeglasses (AREA)
Description
本発明は、ポリマー格子によって形成された、側鎖として(pendant)シクロデキストリンを有するアクリル系ハイドロゲル、単官能性および二官能性アクリルまたはメタクリルモノマーの重合によってそのハイドロゲルの製造方法(一度形成されるとそのモノマーにはシクロデキストリン単位が共有結合している)、ならびに病理学的または生理学的状態の治療に有用な薬物、活性物質または保護剤を組み込む能力を有するコンタクトレンズの製造における、医薬品または活性物質の局所、経皮、または経粘膜放出系の製造における、および化粧品の製造におけるその組成物の使用および応用に関する。
近年、眼のバイオアベイラビリティを最適化し、簡単な薬量学的計画を用いることによって急性および慢性病理の治療を可能にするという目的で、前角膜領域に薬物を長期放出することができる貯蔵器としてソフトコンタクトレンズを使用することへの関心が高まってきている(Alvarez-Lorenzo et al. Am. J. Drug Del. 4: 131-151, 2006)。
0.0714mlのエチレングリコールジメタクリレート(EGDMA、8mM)、0.074gのアゾイソブチロニトリル(AIBN、10mM)および0.245mlのグリシジルメタクリレート(GMA、300mM)を6mlのHEMAに溶解し、その混合物を、ポリプロピレンシートで内面を被覆し、0.4mm厚のシリコンフレームにより仕切られているガラス板によって形成された鋳型に射出し、50℃で12時間そして70℃でさらに24時間加熱することによって、ヒドロキシエチルメタクリレート(HEMA)ハイドロゲルを製造した。そのハイドロゲルシートを沸騰水に15分間浸漬し、反応していないモノマーを除去し、かつディスクを直径10mmに切りやすくした。そのディスクを水に24時間、その後0.9%NaClにさらに24時間、最後に水にさらに24時間浸漬した。
実施例1において得られたβ−シクロデキストリン、ヒドロキシプロピル−β−シクロデキストリン、または側鎖としてメチル−β−シクロデキストリンを有するアクリル系ハイドロゲル組成物におけるβ−シクロデキストリン、ヒドロキシプロピル−β−シクロデキストリン、またはメチル−β−シクロデキストリンの含量を測定するために、次の方法を用いた。各ハイドロゲルの乾燥ディスクを3−メチル安息香酸の水溶液(0.5mg/ml、1ディスク当たり10ml)に浸漬し暗所で48時間維持した。一度この期間が経過したら、3−メチル安息香酸の濃度を分光光度法により281nmで測定しハイドロゲルによって捕捉された3−メチル安息香酸の総量を初期濃度との差を用いて推定した。
0.0714mlのエチレングリコールジメタクリレート(EGDMA、8mM)、0.074gのアゾイソブチロニトリル(AIBN、10mM)、および0.041〜0.327mlの量のグリシジルメタクリレート(GMA)(50〜400mM)を6mlのHEMAに溶解し、その混合物を、ポリプロピレンシートで内面をコーティングし、0.4mm厚のシリコンフレームにより仕切られているガラス板によって形成された鋳型に射出し、50℃で12時間そして70℃でさらに24時間加熱することによって、ヒドロキシエチルメタクリレート(HEMA)のハイドロゲルを製造した。そのハイドロゲルシートを沸騰水に15分間浸漬し、反応していないモノマーを除去し、かつディスクを直径10mmに切りやすくした。そのディスクを水に24時間、その後0.9%NaClにさらに24時間、最後に水にさらに24時間浸漬した。
異なる側鎖β−シクロデキストリン含量を有するヒドロキシエチルメタクリレートのハイドロゲル(表1)を直径8mmのディスクに切り、10mlのジクロフェナクナトリウム(80mg/L)溶液が入ったバイアルに入れ、それを25℃に維持した。一度4日が経過したら、アッセイ開始時と終了時との間での溶液に存在するジクロフェナクの量の差を用いて、組み込まれたジクロフェナクを定量した(276nmでの分光光度滴定、Agilent 8453, Germany)。例として、表2は、異なる組成を有するハイドロゲルディスクのジクロフェナク含量を示す。側鎖β−シクロデキストリン含量が最も高いハイドロゲルは、側鎖β−シクロデキストリンを含まない同じ組成のアクリル系ハイドロゲルによって捕捉されるよりも28倍多いジクロフェナク量を捕捉した。
Claims (22)
- アルキル基を有する架橋アクリルまたはメタクリル鎖によって形成され、該アルキル基に、側鎖としてシクロデキストリンがエーテル結合により結合する、三次元網目構造のハイドロゲルであって、
該アクリルまたはメタクリル鎖が、アルキルエーテル基を有するアクリルまたはメタクリル単位、二官能化アクリルまたはメタクリル単位、および単官能化アクリルまたはメタクリル単位によって形成され、かつ
アルカリ性pHのシクロデキストリン溶液へ、グリシジル基を有する架橋アクリルまたはメタクリル鎖によって形成された三次元網目構造のハイドロゲルを浸漬することにより、ハイドロゲルと、シクロデキストリンとの間にエーテル結合が形成されて得られうる、ハイドロゲル。 - アルキルエーテル基を含むアクリルまたはメタクリル単位の割合が、ハイドロゲルの0.1重量%〜10重量%である、請求項1に記載のハイドロゲル。
- 前記二官能化アクリルまたはメタクリル単位の割合が、ハイドロゲルの0.1重量%〜10重量%である、請求項1または2に記載のハイドロゲル。
- 前記シクロデキストリンが、α−、β−、もしくはγ−シクロデキストリン、9単位以上のα−1,4−グルコピラノースによって形成されたシクロデキストリン、または直鎖状もしくは分岐状のアルキル、直鎖状もしくは分岐状のヒドロキシアルキル、アセチル−、プロピオニル−、ブチリル−、スクシニル−、ベンゾイル−、パルミチル−、トルエンスルホニル−、アセチルアルキル、グルコシル−、マルトシル−、カルボキシメチルエーテル−、カルボキシメチルアルキル−、リン酸エステル−、3−トリメチルアンモニウム−、スルホブチルエーテル−シクロデキストリン誘導体、またはシクロデキストリンポリマーから選択されるものである、請求項1〜3のいずれか一項に記載のハイドロゲル。
- 前記シクロデキストリンの割合が、各アルキルエーテル基に対して、シクロデキストリン1〜0.2単位である、請求項1〜4のいずれか一項に記載のハイドロゲル。
- 前記シクロデキストリンが、薬物または活性物質と包接錯体を形成しているまたは形成していない、請求項1〜5のいずれか一項に記載のハイドロゲル。
- アルカリ性pHのシクロデキストリン溶液への、グリシジル基を有するアクリルまたはメタクリル単位、二官能化アクリルまたはメタクリル単位、および単官能化アクリルまたはメタクリル単位によって形成されるハイドロゲルの浸漬を含む、請求項1に記載の三次元網目構造のハイドロゲルの製造方法。
- 前記シクロデキストリン溶液が1重量%〜5重量%の濃度を含む、請求項7に記載の方法。
- 前記シクロデキストリンが、α−、β−もしくはγ−シクロデキストリン、9単位以上のα−1,4−グルコピラノースによって形成されたシクロデキストリン、または直鎖状もしくは分岐状のアルキル、直鎖状もしくは分岐状のヒドロキシアルキル、アセチル−、プロピオニル−、ブチリル−、スクシニル−、ベンゾイル−、パルミチル−、トルエンスルホニル−、アセチルアルキル、グルコシル−、マルトシル−、カルボキシメチルエーテル−、カルボキシメチルアルキル−、リン酸エステル−、3−トリメチルアンモニウム−、スルホブチルエーテル−シクロデキストリン誘導体、またはシクロデキストリンポリマーから選択されるものである、請求項7に記載の方法。
- 前記シクロデキストリンが薬物または活性物質と包接錯体を形成しているまたは形成していない、請求項7〜9のいずれか一項に記載の方法。
- シクロデキストリン溶液への前記ハイドロゲルの前記浸漬が、60〜90℃で選択される温度に維持される、請求項7に記載の方法。
- 重合プライマーの存在下でのグリシジル基を有するアクリルまたはメタクリルモノマー、単官能化アクリルまたはメタクリルモノマー、および二官能化アクリルまたはメタクリルモノマーの重合を含む、グリシジル基を有するアクリルまたはメタクリル単位、二官能化アクリルまたはメタクリル単位、および単官能化アクリルまたはメタクリル単位によって形成されるハイドロゲルの請求項7に記載の製造方法。
- グリシジル基を有する前記アクリルまたはメタクリルモノマーが、グリシジルアクリレートまたはグリシジルメタクリレートである、請求項12に記載の方法。
- 前記二官能化アクリルまたはメタクリルモノマーが、エチレングリコールジメタクリレート、1,3−ブタンジオールジアクリレート、1,4−ブタンジオールジアクリレート、1,6−ヘキサンジオールジアクリレート、エチレングリコールジアクリレート、フルオレセイン 0,0’−ジアクリレート、グリセロール 1,3−ジグリセロレートジアクリレート、ペンタエリトリトールジアクリレートモノステアレート、1,6−ヘキサンジオールエトキシレートジアクリレート、3−ヒドロキシ−2,2−ジメチルプロピル 3−ヒドロキシ−2,2−ジメチルプロピオネートジアクリレート、ビスフェノールA エトキシレートジアクリレート、ジ(エチレングリコール)ジアクリレート、ネオペンチルグリコールジアクリレート、ポリ(エチレングリコール)ジアクリレート、ポリ(プロピレングリコール)ジアクリレート、プロピレングリコールグリセロレートジアクリレート、テトラ(エチレングリコール)ジアクリレート、1,3−ブタンジオールジメタクリレート、1,4−ブタンジオールジメタクリレート、1,6−ヘキサンジオールジメタクリレート、ビスフェノールA ジメタクリレート、ジウレタンジメタクリレート、エチレングリコールジメタクリレート、フルオレセイン 0,0’−ジメタクリレート、グリセロールジメタクリレート、ビスフェノールA エトキシレートジメタクリレート、ビスフェノールA グリセロレートジメタクリレート、ジ(エチレングリコール)ジメタクリレート、ポリ(エチレングリコール)ジメタクリレート、ポリ(プロピレングリコール)ジメタクリレート、テトラエチレングリコールジメタクリレート、トリ(エチレングリコール)ジメタクリレート、トリエチレングリコールジメタクリレート、ポリ(ラウリルメタクリレート−コ−エチレングリコールジメタクリレート)、ポリ(メチルメタクリレート−コ−エチレングリコールジメタクリレート)から選択されるものである、請求項12または13に記載の方法。
- 前記単官能化アクリルまたはメタクリルモノマーが、ヒドロキシエチルメタクリレート、1−(トリストリメチルシロキシシリルプロピル)−メタクリレート、メチルメタクリレート、N,N−ジメチルアクリルアミド、N,N−ジエチルアクリルアミド、メタクリル酸、アクリル酸、アミノプロピルメタクリレート、シクロヘキシルメタクリレート、またはフルオロ−シロキサンアクリレートから選択されるものである、請求項12〜14のいずれか一項に記載の方法。
- グリシジル基を有するアクリルまたはメタクリルモノマーの割合が0.1〜10%である、請求項12に記載の方法。
- 二官能化アクリルまたはメタクリルモノマーの割合が0.1〜10%である、請求項12〜16のいずれか一項に記載の方法。
- 前記重合が鋳型内で行われる、請求項12〜17のいずれか一項に記載の方法。
- 薬物、活性物質、または保護剤の投与用の薬学上の担体としての、請求項1〜6のいずれか一項に記載のハイドロゲルの使用。
- 薬物、活性物質、または保護剤を所望により組み込むことができるコンタクトレンズを製造するための、請求項1〜6のいずれか一項に記載のハイドロゲルの使用。
- 薬物、活性物質、または保護剤の局所、経皮、または経粘膜放出系を製造するための、請求項1〜6のいずれか一項に記載のハイドロゲルの使用。
- 化粧品を製造するための、請求項1〜6のいずれか一項に記載のハイドロゲルの使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ESP200802364 | 2008-08-06 | ||
ES200802364A ES2335958B2 (es) | 2008-08-06 | 2008-08-06 | Hidrogeles acrilicos con ciclodextrinas colgantes, su preparacion y su aplicacion como sistemas de liberacion y componentes de lentes de contacto. |
PCT/ES2009/070333 WO2010018293A1 (es) | 2008-08-06 | 2009-08-04 | Hidrogeles acrílicos con ciclodextrinas colgantes, su preparación y su aplicación como sistemas de liberación y componentes de lentes de contacto |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011529998A JP2011529998A (ja) | 2011-12-15 |
JP5602734B2 true JP5602734B2 (ja) | 2014-10-08 |
Family
ID=41668745
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011521606A Expired - Fee Related JP5602734B2 (ja) | 2008-08-06 | 2009-08-04 | 側鎖としてシクロデキストリンを有するアクリル系ハイドロゲル、その製造方法ならびに放出系およびコンタクトレンズ成分としてのその使用 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8951548B2 (ja) |
EP (1) | EP2314640B1 (ja) |
JP (1) | JP5602734B2 (ja) |
DK (1) | DK2314640T3 (ja) |
ES (1) | ES2335958B2 (ja) |
WO (1) | WO2010018293A1 (ja) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013162019A1 (ja) * | 2012-04-27 | 2013-10-31 | 国立大学法人大阪大学 | 自己修復性及び形状記憶性を有するゲル、及びその製造方法 |
US9395468B2 (en) | 2012-08-27 | 2016-07-19 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
JP2017505922A (ja) | 2013-11-15 | 2017-02-23 | タンジブル サイエンス リミテッド ライアビリティ カンパニー | 親水性層を有するコンタクトレンズ |
JP6774947B2 (ja) | 2014-12-09 | 2020-10-28 | タンジブル サイエンス インコーポレイテッド | 生体適合性層を有する医療デバイスコーティング |
CN106589241B (zh) * | 2016-12-06 | 2018-08-17 | 兰州大学 | 一种三元共聚物水凝胶及其制备方法和用途 |
US20200166671A1 (en) * | 2017-05-05 | 2020-05-28 | Universidade De Santiago De Compostela | Lipoic acid hydrogels |
TW202009013A (zh) * | 2018-08-14 | 2020-03-01 | 優你康光學股份有限公司 | 具有功能性成分的隱形眼鏡及其產品 |
CN113527581B (zh) * | 2020-04-13 | 2024-08-02 | 晶硕光学股份有限公司 | 水胶组成物及水胶镜片 |
CN112708024A (zh) * | 2020-12-21 | 2021-04-27 | 湖南中岩建材科技有限公司 | 一种聚羧酸减水剂及其制备方法 |
CN113292675B (zh) * | 2021-05-31 | 2022-09-16 | 大连医科大学 | GMA-羧甲基-β-环糊精单体、整体柱及手性药物分离方法 |
JP2022187798A (ja) | 2021-06-08 | 2022-12-20 | 信越化学工業株式会社 | オルガノポリシロキサン変性シクロデキストリン化合物及びこれを含有する化粧料 |
JP2023000461A (ja) | 2021-06-18 | 2023-01-04 | 信越化学工業株式会社 | オルガノポリシロキサン変性シクロデキストリン化合物及びその製造方法、ならびにこれを含有する化粧料 |
JPWO2023012947A1 (ja) * | 2021-08-04 | 2023-02-09 | ||
CN117752867A (zh) * | 2023-12-21 | 2024-03-26 | 大连医科大学附属第一医院 | 一种眼科注射用的载细胞微凝胶及其制备方法与应用 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3647736A (en) * | 1970-05-25 | 1972-03-07 | Kontur Kontact Lens Co Inc | Hydrophilic contact lens material |
JPS5575402A (en) * | 1978-11-30 | 1980-06-06 | Mitsubishi Chem Ind Ltd | Fixing of cyclodextrin |
JPS60202115A (ja) * | 1984-03-27 | 1985-10-12 | Ichiro Shibauchi | エポキシ樹脂用硬化剤 |
DE4009825A1 (de) * | 1990-03-27 | 1991-10-02 | Consortium Elektrochem Ind | Wasserunloesliche cyclodextrin-polymerisate und verfahren zu deren herstellung |
DK0586332T3 (da) | 1992-08-05 | 1997-04-14 | Max Planck Gesellschaft | Kontaktlinser af lipofiliserede cyclodextriner |
US6407145B1 (en) | 1994-08-04 | 2002-06-18 | Novartis Ag | Photocrosslinkable materials and applications |
US6229062B1 (en) * | 1999-04-29 | 2001-05-08 | Basf Aktiengesellschaft Corporation | Superabsorbent polymer containing odor controlling compounds and methods of making the same |
JP3475252B2 (ja) | 2000-04-28 | 2003-12-08 | 株式会社先端科学技術インキュベーションセンター | 架橋ポリロタキサンを有する化合物 |
US7351430B2 (en) * | 2002-11-06 | 2008-04-01 | Uluru Inc. | Shape-retentive hydrogel particle aggregates and their uses |
JP4093557B2 (ja) * | 2002-11-14 | 2008-06-04 | 東洋合成工業株式会社 | 感光性樹脂組成物および含水ゲルの形成方法並びに含水ゲル |
JP4596774B2 (ja) * | 2003-12-26 | 2010-12-15 | 独立行政法人 日本原子力研究開発機構 | 化粧料 |
JP4482633B2 (ja) | 2004-03-31 | 2010-06-16 | 国立大学法人 東京大学 | ポリロタキサンを有するポリマー材料、並びにその製造方法 |
ES2310948B2 (es) | 2005-02-25 | 2009-09-16 | Universidade De Santiago De Compostela | Procedimiento de obtencion de hidrogeles de ciclodextrinas con glicidileteres, las composiciones obtenidas y sus aplicaciones. |
CN101163745A (zh) | 2005-04-25 | 2008-04-16 | 国立大学法人东京大学 | 凝胶状组合物及其制造方法 |
JP2007130386A (ja) | 2005-11-14 | 2007-05-31 | Univ Of Tokyo | 眼用装置 |
-
2008
- 2008-08-06 ES ES200802364A patent/ES2335958B2/es active Active
-
2009
- 2009-08-04 US US13/057,621 patent/US8951548B2/en not_active Expired - Fee Related
- 2009-08-04 DK DK09806481.9T patent/DK2314640T3/en active
- 2009-08-04 EP EP09806481.9A patent/EP2314640B1/en not_active Not-in-force
- 2009-08-04 JP JP2011521606A patent/JP5602734B2/ja not_active Expired - Fee Related
- 2009-08-04 WO PCT/ES2009/070333 patent/WO2010018293A1/es active Application Filing
Also Published As
Publication number | Publication date |
---|---|
US20110200661A1 (en) | 2011-08-18 |
ES2335958A1 (es) | 2010-04-06 |
US8951548B2 (en) | 2015-02-10 |
DK2314640T3 (en) | 2015-10-12 |
EP2314640B1 (en) | 2015-07-01 |
JP2011529998A (ja) | 2011-12-15 |
WO2010018293A1 (es) | 2010-02-18 |
EP2314640A4 (en) | 2011-12-14 |
EP2314640A1 (en) | 2011-04-27 |
ES2335958B2 (es) | 2010-11-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5602734B2 (ja) | 側鎖としてシクロデキストリンを有するアクリル系ハイドロゲル、その製造方法ならびに放出系およびコンタクトレンズ成分としてのその使用 | |
dos Santos et al. | Poly (hydroxyethyl methacrylate-co-methacrylated-β-cyclodextrin) hydrogels: synthesis, cytocompatibility, mechanical properties and drug loading/release properties | |
Sokker et al. | Synthesis and characterization of hydrogels based on grafted chitosan for the controlled drug release | |
Khutoryanskiy | Hydrogen-bonded interpolymer complexes as materials for pharmaceutical applications | |
KR101180169B1 (ko) | 폴리로탁산을 갖는 중합체 재료, 및 그의 제조 방법 | |
KR101231292B1 (ko) | 폴리로탁산 및 중합체를 갖는 재료, 및 그의 제조 방법 | |
Verestiuc et al. | Dual-stimuli-responsive hydrogels based on poly (N-isopropylacrylamide)/chitosan semi-interpenetrating networks | |
Don et al. | Synthesis and characterization of AB-crosslinked graft copolymers based on maleilated chitosan and N-isopropylacrylamide | |
KR20060136474A (ko) | 폴리로탁산을 갖는 중합체 재료, 및 그의 제조 방법 | |
US7049351B2 (en) | Moldings and preparation and uses thereof | |
TW201125915A (en) | Wettable hydrogel materials for use in ophthalmic applications and methods | |
WO2006115255A1 (ja) | ゲル状組成物及びその製造方法 | |
JP2006513286A (ja) | 感光性高分子網目 | |
Ejaz et al. | Evaluation of redox-responsive disulfide cross-linked poly (hydroxyethyl methacrylate) hydrogels | |
Swain et al. | Biomedical applications of acrylic-based nanohydrogels | |
Shukla et al. | Applications of tamarind seeds polysaccharide-based copolymers in controlled drug delivery: An overview | |
Rasool et al. | Chitosan‐based smart polymeric hydrogels and their prospective applications in biomedicine | |
PT104879A (pt) | Hidrogel de dextrino para aplicações biomédicas | |
Havanur et al. | Synthesis and optimization of poly (N, N-diethylacrylamide) hydrogel and evaluation of its anticancer drug doxorubicin’s release behavior | |
Zhang et al. | Perspectives on: strategies to fabricate starch-based hydrogels with potential biomedical applications | |
TW201902460A (zh) | 類脂酸水凝膠 | |
Gawel et al. | Impregnation of weakly charged anionic microhydrogels with cationic polyelectrolytes and their swelling properties monitored by a high resolution interferometric technique. Transformation from a polyelectrolyte to polyampholyte hydrogel | |
Ramteke et al. | Stimuli sensitive hydrogels in drug delivery systems | |
Giri et al. | Prospect of plant and algal polysaccharides-based hydrogels | |
Arslan et al. | Cyclodextrin-containing hydrogel networks |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120214 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130604 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130614 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130912 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130920 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131015 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131022 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131112 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131119 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131216 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140725 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140820 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5602734 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |