JPS61138601A - 架橋ヒアルロン酸ゲル組成物 - Google Patents
架橋ヒアルロン酸ゲル組成物Info
- Publication number
- JPS61138601A JPS61138601A JP60147612A JP14761285A JPS61138601A JP S61138601 A JPS61138601 A JP S61138601A JP 60147612 A JP60147612 A JP 60147612A JP 14761285 A JP14761285 A JP 14761285A JP S61138601 A JPS61138601 A JP S61138601A
- Authority
- JP
- Japan
- Prior art keywords
- hyaluronic acid
- salt
- gel
- weight
- acid
- 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
Links
- 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 description 152
- 229920002674 hyaluronan Polymers 0.000 title claims description 152
- 229960003160 hyaluronic acid Drugs 0.000 title claims description 152
- 239000000203 mixture Substances 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 54
- 229920000642 polymer Polymers 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 29
- 239000011541 reaction mixture Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 25
- 238000004132 cross linking Methods 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkali metal salt Chemical class 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 12
- 229920000669 heparin Polymers 0.000 claims description 11
- 229960002897 heparin Drugs 0.000 claims description 11
- 235000019271 petrolatum Nutrition 0.000 claims description 11
- 239000004264 Petrolatum Substances 0.000 claims description 10
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 10
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 10
- 229940066842 petrolatum Drugs 0.000 claims description 10
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 9
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 9
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 9
- 102000008186 Collagen Human genes 0.000 claims description 8
- 108010035532 Collagen Proteins 0.000 claims description 8
- 239000012670 alkaline solution Substances 0.000 claims description 8
- 229920001436 collagen Polymers 0.000 claims description 8
- 150000004676 glycans Chemical class 0.000 claims description 8
- 229920001282 polysaccharide Polymers 0.000 claims description 8
- 239000005017 polysaccharide Substances 0.000 claims description 8
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 6
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 6
- 239000004106 carminic acid Substances 0.000 claims description 6
- DGQLVPJVXFOQEV-NGOCYOHBSA-N carminic acid Chemical group OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-NGOCYOHBSA-N 0.000 claims description 6
- 229940114118 carminic acid Drugs 0.000 claims description 6
- 235000012730 carminic acid Nutrition 0.000 claims description 6
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 5
- 239000005995 Aluminium silicate Substances 0.000 claims description 5
- 235000012211 aluminium silicate Nutrition 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 235000019197 fats Nutrition 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical group O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 235000019198 oils Nutrition 0.000 claims description 5
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 3
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 3
- 102000016942 Elastin Human genes 0.000 claims description 3
- 108010014258 Elastin Proteins 0.000 claims description 3
- 102000006395 Globulins Human genes 0.000 claims description 3
- 108010044091 Globulins Proteins 0.000 claims description 3
- 102000011782 Keratins Human genes 0.000 claims description 3
- 108010076876 Keratins Proteins 0.000 claims description 3
- 239000004166 Lanolin Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 235000013871 bee wax Nutrition 0.000 claims description 3
- 239000012166 beeswax Substances 0.000 claims description 3
- 229940059329 chondroitin sulfate Drugs 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 229920002549 elastin Polymers 0.000 claims description 3
- 239000003925 fat Substances 0.000 claims description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 3
- 235000019388 lanolin Nutrition 0.000 claims description 3
- 229940039717 lanolin Drugs 0.000 claims description 3
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 229920003169 water-soluble polymer Polymers 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000002091 nanocage Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 8
- 125000000524 functional group Chemical group 0.000 claims 8
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 4
- 102000009027 Albumins Human genes 0.000 claims 2
- 108010088751 Albumins Proteins 0.000 claims 2
- 229960005188 collagen Drugs 0.000 claims 2
- 229920000591 gum Polymers 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 description 151
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 239000000243 solution Substances 0.000 description 53
- 230000008961 swelling Effects 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 229920002385 Sodium hyaluronate Polymers 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 229940010747 sodium hyaluronate Drugs 0.000 description 13
- 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 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000008187 granular material Substances 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 5
- 229940099259 vaseline Drugs 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000007863 gel particle Substances 0.000 description 3
- 229940097043 glucuronic acid Drugs 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N 2-Amino-2-Deoxy-Hexose Chemical compound NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KGULFLCOPRYBEV-KTKRTIGZSA-N 2-[2-[2-[(z)-octadec-9-enoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCOCCOCCO KGULFLCOPRYBEV-KTKRTIGZSA-N 0.000 description 1
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 1
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 102000009123 Fibrin Human genes 0.000 description 1
- 108010073385 Fibrin Proteins 0.000 description 1
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- SNIXRMIHFOIVBB-UHFFFAOYSA-N N-Hydroxyl-tryptamine Chemical compound C1=CC=C2C(CCNO)=CNC2=C1 SNIXRMIHFOIVBB-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 239000000512 collagen gel Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229950003499 fibrin Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 238000004442 gravimetric analysis Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 229940075643 oleth-3 Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MBHCWRKFAXKMRT-UHFFFAOYSA-N propanoic acid;1-tetradecoxytetradecane Chemical compound CCC(O)=O.CCCCCCCCCCCCCCOCCCCCCCCCCCCCC MBHCWRKFAXKMRT-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 108091005994 sulfated proteins Proteins 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000004454 trace mineral analysis Methods 0.000 description 1
- 150000004043 trisaccharides Chemical group 0.000 description 1
- 210000003954 umbilical cord Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- 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
-
- 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
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- 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
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
-
- 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
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/678,895 US4582865A (en) | 1984-12-06 | 1984-12-06 | Cross-linked gels of hyaluronic acid and products containing such gels |
| US678895 | 1984-12-06 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1232667A Division JPH0637575B2 (ja) | 1984-12-06 | 1989-09-06 | 架橋ヒアルロン酸ゲル組成物及び製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61138601A true JPS61138601A (ja) | 1986-06-26 |
| JPH0430961B2 JPH0430961B2 (enExample) | 1992-05-25 |
Family
ID=24724742
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60147612A Granted JPS61138601A (ja) | 1984-12-06 | 1985-07-04 | 架橋ヒアルロン酸ゲル組成物 |
| JP1232667A Expired - Lifetime JPH0637575B2 (ja) | 1984-12-06 | 1989-09-06 | 架橋ヒアルロン酸ゲル組成物及び製造法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1232667A Expired - Lifetime JPH0637575B2 (ja) | 1984-12-06 | 1989-09-06 | 架橋ヒアルロン酸ゲル組成物及び製造法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4582865A (enExample) |
| JP (2) | JPS61138601A (enExample) |
| AU (2) | AU569157B2 (enExample) |
| CA (1) | CA1230186A (enExample) |
| DE (2) | DE3520008A1 (enExample) |
| FR (1) | FR2574414B1 (enExample) |
| GB (4) | GB2168067B (enExample) |
| IT (1) | IT1187737B (enExample) |
| SE (2) | SE460792B (enExample) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61172808A (ja) * | 1985-01-29 | 1986-08-04 | Seikagaku Kogyo Co Ltd | 皮膚化粧料 |
| JPH02145600A (ja) * | 1988-11-28 | 1990-06-05 | Denki Kagaku Kogyo Kk | ヒアルロン酸固定化蛋白質及びその製造方法 |
| JPH0539480U (ja) * | 1991-10-31 | 1993-05-28 | ジユーキ株式会社 | ミシンの針棒 |
| WO1998054224A1 (en) * | 1997-05-28 | 1998-12-03 | Tapic International Co., Ltd. | Collagen gel |
| WO2006051950A1 (ja) * | 2004-11-15 | 2006-05-18 | Shiseido Co., Ltd. | 架橋ヒアルロン酸ゲルの製造方法 |
| JP2006522851A (ja) * | 2003-04-10 | 2006-10-05 | コルネアル アンデュストリー | 低分子量及び高分子量の多糖の架橋；注射用単相ヒドロゲルの調製；多糖及び得られたヒドロゲル |
| JP2007500027A (ja) * | 2003-07-30 | 2007-01-11 | アンタイス エス．エイ． | 生物医学的な使用のための複合マトリックス |
| JP2007519779A (ja) * | 2003-12-30 | 2007-07-19 | ジェンザイム コーポレイション | 架橋したヒアルロナンおよび／またはハイランに由来する粘着性ゲル、その調製および使用法 |
| JP2007526239A (ja) * | 2003-05-15 | 2007-09-13 | ユニヴァーシティー オヴ ユタ リサーチ ファウンデーション | 抗癒着複合体、および、その方法および用法 |
| WO2008136536A1 (ja) | 2007-05-01 | 2008-11-13 | National University Corporation Tokyo Medical And Dental University | 化学架橋ヒアルロン酸誘導体を含むハイブリッドゲルおよびそれを用いた医薬組成物 |
| US8143391B2 (en) | 2004-09-07 | 2012-03-27 | Chugai Seiyaku Kabushiki Kaisha | Process for producing water-soluble hyaluronic acid modification |
| JP2019529645A (ja) * | 2016-09-16 | 2019-10-17 | グリコロジクス、エルエルシー | プロテオグリカン模倣物としての硫酸化グリコサミノグリカン生体材料 |
| JP2023525155A (ja) * | 2020-05-14 | 2023-06-14 | アラーガン ファーマシューティカルズ インターナショナル リミテッド | ヒアルロン酸に架橋したトロポエラスチンを含む組成物及びその使用方法 |
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| US5099013A (en) * | 1985-03-12 | 1992-03-24 | Biomatrix, Inc, | Hylan preparation and method of recovery thereof from animal tissues |
| US4713448A (en) * | 1985-03-12 | 1987-12-15 | Biomatrix, Inc. | Chemically modified hyaluronic acid preparation and method of recovery thereof from animal tissues |
| US5202431A (en) * | 1985-07-08 | 1993-04-13 | Fidia, S.P.A. | Partial esters of hyaluronic acid |
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| DE3684887D1 (de) * | 1985-11-29 | 1992-05-21 | Biomatrix Inc | Arzneistoffabgabesysteme auf basis von hyaluronan, dessen derivaten und salzen sowie verfahren zu deren herstellung. |
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Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61172808A (ja) * | 1985-01-29 | 1986-08-04 | Seikagaku Kogyo Co Ltd | 皮膚化粧料 |
| JPH02145600A (ja) * | 1988-11-28 | 1990-06-05 | Denki Kagaku Kogyo Kk | ヒアルロン酸固定化蛋白質及びその製造方法 |
| JPH0539480U (ja) * | 1991-10-31 | 1993-05-28 | ジユーキ株式会社 | ミシンの針棒 |
| WO1998054224A1 (en) * | 1997-05-28 | 1998-12-03 | Tapic International Co., Ltd. | Collagen gel |
| JP2006522851A (ja) * | 2003-04-10 | 2006-10-05 | コルネアル アンデュストリー | 低分子量及び高分子量の多糖の架橋；注射用単相ヒドロゲルの調製；多糖及び得られたヒドロゲル |
| JP2007526239A (ja) * | 2003-05-15 | 2007-09-13 | ユニヴァーシティー オヴ ユタ リサーチ ファウンデーション | 抗癒着複合体、および、その方法および用法 |
| JP2007500027A (ja) * | 2003-07-30 | 2007-01-11 | アンタイス エス．エイ． | 生物医学的な使用のための複合マトリックス |
| JP2007519779A (ja) * | 2003-12-30 | 2007-07-19 | ジェンザイム コーポレイション | 架橋したヒアルロナンおよび／またはハイランに由来する粘着性ゲル、その調製および使用法 |
| US8143391B2 (en) | 2004-09-07 | 2012-03-27 | Chugai Seiyaku Kabushiki Kaisha | Process for producing water-soluble hyaluronic acid modification |
| US9394379B2 (en) | 2004-09-07 | 2016-07-19 | Chugai Seiyaku Kabushiki Kaisha | Process for producing water-soluble hyaluronic acid modification |
| JPWO2006051950A1 (ja) * | 2004-11-15 | 2008-05-29 | 株式会社資生堂 | 架橋ヒアルロン酸ゲルの製造方法 |
| JP4875988B2 (ja) * | 2004-11-15 | 2012-02-15 | 株式会社 資生堂 | 架橋ヒアルロン酸ゲルの製造方法 |
| WO2006051950A1 (ja) * | 2004-11-15 | 2006-05-18 | Shiseido Co., Ltd. | 架橋ヒアルロン酸ゲルの製造方法 |
| WO2008136536A1 (ja) | 2007-05-01 | 2008-11-13 | National University Corporation Tokyo Medical And Dental University | 化学架橋ヒアルロン酸誘導体を含むハイブリッドゲルおよびそれを用いた医薬組成物 |
| US8987230B2 (en) | 2007-05-01 | 2015-03-24 | National University Corporation Tokyo Medical And Dental University | Hybrid gel comprising chemically crosslinked hyaluronic acid derivative and pharmaceutical composition comprising the same |
| JP2019529645A (ja) * | 2016-09-16 | 2019-10-17 | グリコロジクス、エルエルシー | プロテオグリカン模倣物としての硫酸化グリコサミノグリカン生体材料 |
| US11975019B2 (en) | 2016-09-16 | 2024-05-07 | Glycologix, Inc. | Sulfated glycosaminoglycan biomaterials as proteoglycan mimics |
| JP2023525155A (ja) * | 2020-05-14 | 2023-06-14 | アラーガン ファーマシューティカルズ インターナショナル リミテッド | ヒアルロン酸に架橋したトロポエラスチンを含む組成物及びその使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8503486L (sv) | 1986-06-07 |
| US4582865A (en) | 1986-04-15 |
| AU572419B2 (en) | 1988-05-05 |
| JPH0430961B2 (enExample) | 1992-05-25 |
| AU569157B2 (en) | 1988-01-21 |
| SE8901672L (sv) | 1989-05-10 |
| SE8901672D0 (sv) | 1989-05-10 |
| GB2181148B (en) | 1989-06-07 |
| GB2205848B (en) | 1989-05-24 |
| GB8817772D0 (en) | 1988-09-01 |
| GB8512072D0 (en) | 1985-06-19 |
| DE3520008C2 (enExample) | 1991-10-10 |
| SE8503486D0 (sv) | 1985-07-15 |
| GB8618720D0 (en) | 1986-09-10 |
| CA1230186A (en) | 1987-12-08 |
| IT8522089A0 (it) | 1985-09-09 |
| DE3546811C2 (enExample) | 1993-09-02 |
| JPH0637575B2 (ja) | 1994-05-18 |
| DE3520008A1 (de) | 1986-06-19 |
| SE460792B (sv) | 1989-11-20 |
| FR2574414B1 (fr) | 1987-07-03 |
| JPH02138346A (ja) | 1990-05-28 |
| GB8618719D0 (en) | 1986-09-10 |
| IT1187737B (it) | 1987-12-23 |
| GB2181147A (en) | 1987-04-15 |
| GB2168067B (en) | 1989-06-07 |
| AU4304585A (en) | 1986-06-12 |
| FR2574414A1 (fr) | 1986-06-13 |
| AU7217387A (en) | 1987-08-27 |
| SE501828C2 (sv) | 1995-05-22 |
| GB2168067A (en) | 1986-06-11 |
| GB2205848A (en) | 1988-12-21 |
| GB2181148A (en) | 1987-04-15 |
| GB2181147B (en) | 1989-06-07 |
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