WO2015074632A1 - Nanofibers containing photocurable ester derivative of hyaluronic acid or its salt, photocured nanofibers, method of synthesis thereof, preparation containing photocured nanofibers and use thereof - Google Patents
Nanofibers containing photocurable ester derivative of hyaluronic acid or its salt, photocured nanofibers, method of synthesis thereof, preparation containing photocured nanofibers and use thereof Download PDFInfo
- Publication number
- WO2015074632A1 WO2015074632A1 PCT/CZ2014/000138 CZ2014000138W WO2015074632A1 WO 2015074632 A1 WO2015074632 A1 WO 2015074632A1 CZ 2014000138 W CZ2014000138 W CZ 2014000138W WO 2015074632 A1 WO2015074632 A1 WO 2015074632A1
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- WO
- WIPO (PCT)
- Prior art keywords
- nanofibers
- salt
- hyaluronic acid
- reaction
- water
- Prior art date
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- 239000002121 nanofiber Substances 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 52
- 150000003839 salts Chemical class 0.000 title claims abstract description 45
- -1 ester derivative of hyaluronic acid Chemical class 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 title claims description 18
- 238000003786 synthesis reaction Methods 0.000 title claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 166
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 154
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 96
- 229910001868 water Inorganic materials 0.000 claims description 77
- 229920002674 hyaluronan Polymers 0.000 claims description 60
- 239000000539 dimer Substances 0.000 claims description 58
- 230000004913 activation Effects 0.000 claims description 52
- 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 claims description 37
- 229960003160 hyaluronic acid Drugs 0.000 claims description 36
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 238000001523 electrospinning Methods 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 19
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 14
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002798 polar solvent Substances 0.000 claims description 9
- ZCJLOOJRNPHKAV-ONEGZZNKSA-N (e)-3-(furan-2-yl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CO1 ZCJLOOJRNPHKAV-ONEGZZNKSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 8
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 8
- 238000009987 spinning Methods 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000012454 non-polar solvent Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000016 photochemical curing Methods 0.000 claims description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 108010010803 Gelatin Proteins 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 239000008273 gelatin Substances 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 235000011852 gelatine desserts Nutrition 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920001610 polycaprolactone Polymers 0.000 claims description 3
- 239000004632 polycaprolactone Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 230000001172 regenerating effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000002407 tissue scaffold Substances 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 229920001661 Chitosan Polymers 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 238000006352 cycloaddition reaction Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000004626 polylactic acid Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000004584 polyacrylic acid Substances 0.000 claims 2
- TVZDIFXOIOIPJG-UHFFFAOYSA-N 2,3,4-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1Cl TVZDIFXOIOIPJG-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 1
- 229920000747 poly(lactic acid) Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 117
- 238000006243 chemical reaction Methods 0.000 description 116
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 51
- 239000000047 product Substances 0.000 description 40
- 238000006467 substitution reaction Methods 0.000 description 30
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-MNSSHETKSA-N 0.000 description 25
- 239000000126 substance Substances 0.000 description 25
- 229940099552 hyaluronan Drugs 0.000 description 24
- 229920001282 polysaccharide Polymers 0.000 description 24
- 239000011780 sodium chloride Substances 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 150000004676 glycans Chemical group 0.000 description 22
- 239000005017 polysaccharide Substances 0.000 description 22
- 239000012153 distilled water Substances 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 20
- 238000000569 multi-angle light scattering Methods 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000004132 cross linking Methods 0.000 description 17
- LXZFMKLKTRIZDJ-UHFFFAOYSA-N 2-(furan-2-yl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CO1 LXZFMKLKTRIZDJ-UHFFFAOYSA-N 0.000 description 16
- 229920002385 Sodium hyaluronate Polymers 0.000 description 16
- 238000005100 correlation spectroscopy Methods 0.000 description 16
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- 238000001556 precipitation Methods 0.000 description 16
- 229940010747 sodium hyaluronate Drugs 0.000 description 16
- 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 16
- 239000011734 sodium Substances 0.000 description 15
- 239000000835 fiber Substances 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 13
- 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 11
- 230000008569 process Effects 0.000 description 11
- OZGSEIVTQLXWRO-UHFFFAOYSA-N 2,4,6-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=C(Cl)C=C1Cl OZGSEIVTQLXWRO-UHFFFAOYSA-N 0.000 description 9
- 206010052428 Wound Diseases 0.000 description 9
- 208000027418 Wounds and injury Diseases 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 229940014041 hyaluronate Drugs 0.000 description 6
- KIUKXJAPPMFGSW-YXBJCWEESA-N (2s,4s,5r,6s)-6-[(2s,3r,5s,6r)-3-acetamido-2-[(3s,4r,5r,6r)-6-[(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]1C(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(O[C@@H]3[C@@H]([C@@H](O)C(O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)C(C(O)=O)O1 KIUKXJAPPMFGSW-YXBJCWEESA-N 0.000 description 5
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical group CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 5
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- KKMZQOIASVGJQE-UHFFFAOYSA-N 3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CS1 KKMZQOIASVGJQE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 230000010933 acylation Effects 0.000 description 4
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- 238000001878 scanning electron micrograph Methods 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- LICUXCPUOTUYBC-UHFFFAOYSA-N 2-(furan-2-ylmethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)CC1=CC=CO1 LICUXCPUOTUYBC-UHFFFAOYSA-N 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
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- 230000008901 benefit Effects 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
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- 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 2
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- D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
- D01F6/50—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polyalcohols, polyacetals or polyketals
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- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
- D01F6/56—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polymers of cyclic compounds with one carbon-to-carbon double bond in the side chain
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
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- A—HUMAN NECESSITIES
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- 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
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/81—Preparation or application process involves irradiation
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- 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
- C08J2329/00—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 at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
- C08J2329/02—Homopolymers or copolymers of unsaturated alcohols
- C08J2329/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2339/00—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 at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08J2339/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J2371/02—Polyalkylene oxides
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- 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
- C08J2451/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2451/02—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to polysaccharides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
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- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2321/00—Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D10B2321/08—Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds polymers of unsaturated carboxylic acids or unsaturated organic esters, e.g. polyacrylic esters, polyvinyl acetate
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2331/00—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products
- D10B2331/06—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products polyethers
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- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
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- D—TEXTILES; PAPER
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- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2509/00—Medical; Hygiene
- D10B2509/02—Bandages, dressings or absorbent pads
- D10B2509/022—Wound dressings
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Abstract
Description
Claims
Priority Applications (5)
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BR112016011519A BR112016011519A8 (en) | 2013-11-21 | 2014-11-21 | NANOFIBERS BASED ON HYALURONIC ACID ESTER DERIVATIVES AND ITS SALT, METHOD FOR SYNTHESIS OF NANOFIBERS, METHOD FOR PHOTOCURING NANOFIBERS, PHOTOCURING NANOFIBERS BASED ON HYALURONIC ACID DERIVATIVES, PREPARATION INCLUDING PHOTOCURED NANOFIBERS |
US15/038,078 US20160312385A1 (en) | 2013-11-21 | 2014-11-21 | Nanofibers Containing Photocurable Ester Derivative of Hyaluronic Acid or Its Salt, Photocured Nanofibers, Method of Synthesis Thereof, Preparation Containing Photocured Nanofibers and Use Thereof |
KR1020167016462A KR102366202B1 (en) | 2013-11-21 | 2014-11-21 | Nanofibers containing photocurable ester derivative of hyaluronic acid or its salt, photocured nanofibers, method of synthesis thereof, preparation containing photocured nanofibers and use thereof |
ES14827154.7T ES2648311T3 (en) | 2013-11-21 | 2014-11-21 | Nanofibers containing a photocurable ester derivative of hyaluronic acid or its salt, photocured nanofibers, their synthesis method, preparation containing photocured nanofibers and their use |
EP14827154.7A EP3071602B1 (en) | 2013-11-21 | 2014-11-21 | Nanofibers containing photocurable ester derivative of hyaluronic acid or its salt, photocured nanofibers, method of synthesis thereof, preparation containing photocured nanofibers and use thereof |
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CZ2013-914A CZ304977B6 (en) | 2013-11-21 | 2013-11-21 | Nanofibers comprising photocurable ester derivative of hyaluronic acid or a salt thereof, photocured nanofibers, method of their synthesis, composition comprising photocured nanofibers and use thereof |
CZPV2013-914 | 2013-11-21 |
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EP (1) | EP3071602B1 (en) |
KR (1) | KR102366202B1 (en) |
BR (1) | BR112016011519A8 (en) |
CZ (1) | CZ304977B6 (en) |
ES (1) | ES2648311T3 (en) |
WO (1) | WO2015074632A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2022161557A1 (en) * | 2021-01-26 | 2022-08-04 | Contipro A.S. | Wound healing means, method of manufacture thereof and use thereof |
Families Citing this family (6)
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JP2017071873A (en) * | 2015-10-07 | 2017-04-13 | キヤノン株式会社 | Polymer nano fiber accumulation body and manufacturing method thereof |
CZ2016827A3 (en) * | 2016-12-23 | 2018-02-07 | Contipro A.S. | An ophthalmic preparation |
KR101884873B1 (en) | 2017-10-12 | 2018-08-02 | 충남대학교산학협력단 | Fibers having a functional group and methods for their preparation |
KR102203403B1 (en) * | 2019-04-10 | 2021-01-15 | 주식회사 아이코어바이오 | Novel polymer, a fabricating method of the polymer, nanofibers from the polymer and a fabricating method of the nanofibers |
WO2022063312A1 (en) * | 2020-09-28 | 2022-03-31 | 吾奇生物医疗科技(江苏)有限公司 | Hyaluronic acid hydrogel and hyaluronic acid film, preparation method therefor, and applications thereof |
CN115558040B (en) * | 2022-09-30 | 2024-01-23 | 华熙生物科技股份有限公司 | Production method of hyaluronic acid or salt thereof without preservative addition |
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2013
- 2013-11-21 CZ CZ2013-914A patent/CZ304977B6/en unknown
-
2014
- 2014-11-21 EP EP14827154.7A patent/EP3071602B1/en active Active
- 2014-11-21 US US15/038,078 patent/US20160312385A1/en not_active Abandoned
- 2014-11-21 ES ES14827154.7T patent/ES2648311T3/en active Active
- 2014-11-21 KR KR1020167016462A patent/KR102366202B1/en active IP Right Grant
- 2014-11-21 WO PCT/CZ2014/000138 patent/WO2015074632A1/en active Application Filing
- 2014-11-21 BR BR112016011519A patent/BR112016011519A8/en not_active Application Discontinuation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022161557A1 (en) * | 2021-01-26 | 2022-08-04 | Contipro A.S. | Wound healing means, method of manufacture thereof and use thereof |
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US20160312385A1 (en) | 2016-10-27 |
CZ2013914A3 (en) | 2015-02-25 |
EP3071602A1 (en) | 2016-09-28 |
BR112016011519A8 (en) | 2018-04-03 |
KR20160089431A (en) | 2016-07-27 |
ES2648311T3 (en) | 2017-12-29 |
BR112016011519A2 (en) | 2017-08-08 |
EP3071602B1 (en) | 2017-08-23 |
KR102366202B1 (en) | 2022-02-21 |
CZ304977B6 (en) | 2015-02-25 |
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