NO309460B1 - Ikke-vevd stoff omfattende hyaluronsyre-estere, fremgangsmåte for fremstilling av disse stoffene og farmasöytisk blanding - Google Patents

Info

Publication number

NO309460B1

NO309460B1 NO942330A NO942330A NO309460B1 NO 309460 B1 NO309460 B1 NO 309460B1 NO 942330 A NO942330 A NO 942330A NO 942330 A NO942330 A NO 942330A NO 309460 B1 NO309460 B1 NO 309460B1

Authority

NO

Norway

Prior art keywords

woven fabric

hyaluronic acid

ester

derivative

fabric according

Prior art date

1991-12-18

Links

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• Global Dossier
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• 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 class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims abstract description 110
• 239000004745 nonwoven fabric Substances 0.000 title claims abstract description 56
• 238000000034 method Methods 0.000 title claims description 60
• 238000002360 preparation method Methods 0.000 title description 30
• 239000000126 substance Substances 0.000 title description 10
• 230000008569 process Effects 0.000 title description 6
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 229920002674 hyaluronan Polymers 0.000 claims abstract description 120
• 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 117
• 239000000463 material Substances 0.000 claims abstract description 42
• 150000002148 esters Chemical class 0.000 claims abstract description 32
• 229920000642 polymer Polymers 0.000 claims abstract description 24
• 235000010443 alginic acid Nutrition 0.000 claims abstract description 7
• 229920000615 alginic acid Polymers 0.000 claims abstract description 7
• 239000000783 alginic acid Substances 0.000 claims abstract description 5
• 229960001126 alginic acid Drugs 0.000 claims abstract description 5
• 150000004781 alginic acids Chemical class 0.000 claims abstract description 5
• -1 hyaluronic acid ester Chemical class 0.000 claims description 93
• 239000000203 mixture Substances 0.000 claims description 40
• 239000000835 fiber Substances 0.000 claims description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
• 238000004519 manufacturing process Methods 0.000 claims description 15
• 125000001931 aliphatic group Chemical group 0.000 claims description 8
• 125000004494 ethyl ester group Chemical group 0.000 claims description 7
• 102000008186 Collagen Human genes 0.000 claims description 6
• 108010035532 Collagen Proteins 0.000 claims description 6
• 229920001436 collagen Polymers 0.000 claims description 6
• 239000000499 gel Substances 0.000 claims description 6
• 239000003242 anti bacterial agent Substances 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 5
• 229920001817 Agar Polymers 0.000 claims description 4
• 229920000936 Agarose Polymers 0.000 claims description 4
• 229920002101 Chitin Polymers 0.000 claims description 4
• 229920001661 Chitosan Polymers 0.000 claims description 4
• 229920002148 Gellan gum Polymers 0.000 claims description 4
• 229920002683 Glycosaminoglycan Polymers 0.000 claims description 4
• 229920000954 Polyglycolide Polymers 0.000 claims description 4
• 229920002472 Starch Polymers 0.000 claims description 4
• 239000008272 agar Substances 0.000 claims description 4
• 239000001913 cellulose Substances 0.000 claims description 4
• 229920002678 cellulose Polymers 0.000 claims description 4
• 235000010980 cellulose Nutrition 0.000 claims description 4
• LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 claims description 4
• 239000001814 pectin Substances 0.000 claims description 4
• 235000010987 pectin Nutrition 0.000 claims description 4
• 229920000747 poly(lactic acid) Polymers 0.000 claims description 4
• 239000004633 polyglycolic acid Substances 0.000 claims description 4
• 239000004626 polylactic acid Substances 0.000 claims description 4
• 238000004080 punching Methods 0.000 claims description 4
• 239000008107 starch Substances 0.000 claims description 4
• 235000019698 starch Nutrition 0.000 claims description 4
• 229920001059 synthetic polymer Polymers 0.000 claims description 4
• 229920002230 Pectic acid Polymers 0.000 claims description 3
• 230000003115 biocidal effect Effects 0.000 claims description 3
• 229920001577 copolymer Polymers 0.000 claims description 3
• 239000010318 polygalacturonic acid Substances 0.000 claims description 3
• 229920001282 polysaccharide Polymers 0.000 claims description 3
• 239000005017 polysaccharide Substances 0.000 claims description 3
• 150000004804 polysaccharides Chemical class 0.000 claims description 3
• 229920005989 resin Polymers 0.000 claims description 3
• 239000011347 resin Substances 0.000 claims description 3
• 229920001285 xanthan gum Polymers 0.000 claims description 3
• GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical class C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 2
• 238000000975 co-precipitation Methods 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 229920002627 poly(phosphazenes) Polymers 0.000 claims description 2
• 229920002492 poly(sulfone) Polymers 0.000 claims description 2
• 229920005749 polyurethane resin Polymers 0.000 claims description 2
• 239000000230 xanthan gum Substances 0.000 claims description 2
• 235000010493 xanthan gum Nutrition 0.000 claims description 2
• 229940082509 xanthan gum Drugs 0.000 claims description 2
• 244000043261 Hevea brasiliensis Species 0.000 claims 2
• 239000013543 active substance Substances 0.000 claims 2
• 229920001277 pectin Polymers 0.000 claims 2
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
• 229940072056 alginate Drugs 0.000 claims 1
• MYPYJXKWCTUITO-KIIOPKALSA-N chembl3301825 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)C(O)[C@H](C)O1 MYPYJXKWCTUITO-KIIOPKALSA-N 0.000 claims 1
• 239000011159 matrix material Substances 0.000 abstract description 3
• 239000012620 biological material Substances 0.000 abstract 1
• 230000008929 regeneration Effects 0.000 abstract 1
• 238000011069 regeneration method Methods 0.000 abstract 1
• 238000001356 surgical procedure Methods 0.000 abstract 1
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 129
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 77
• 239000000243 solution Substances 0.000 description 54
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 38
• 238000003756 stirring Methods 0.000 description 34
• 239000002244 precipitate Substances 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
• 125000004185 ester group Chemical group 0.000 description 29
• 239000000047 product Substances 0.000 description 29
• 150000001298 alcohols Chemical class 0.000 description 26
• 239000000178 monomer Substances 0.000 description 25
• 150000003839 salts Chemical class 0.000 description 20
• 125000002843 carboxylic acid group Chemical group 0.000 description 18
• 125000000524 functional group Chemical group 0.000 description 16
• 238000004458 analytical method Methods 0.000 description 15
• 239000011780 sodium chloride Substances 0.000 description 15
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 238000005345 coagulation Methods 0.000 description 10
• 230000015271 coagulation Effects 0.000 description 10
• 238000011282 treatment Methods 0.000 description 10
• 239000002585 base Substances 0.000 description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
• 229910052751 metal Inorganic materials 0.000 description 9
• 239000002184 metal Substances 0.000 description 9
• 239000011734 sodium Substances 0.000 description 8
• 125000000217 alkyl group Chemical group 0.000 description 7
• 238000009960 carding Methods 0.000 description 7
• 230000032050 esterification Effects 0.000 description 7
• 238000005886 esterification reaction Methods 0.000 description 7
• 239000004744 fabric Substances 0.000 description 7
• DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 7
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 150000002739 metals Chemical class 0.000 description 6
• 125000001183 hydrocarbyl group Chemical group 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 238000005303 weighing Methods 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 4
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
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• 150000007530 organic bases Chemical class 0.000 description 4
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• WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 3
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• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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