CA2652968C - Polymer mixtures of anionic and cationic polysaccharides and use thereof - Google Patents
Polymer mixtures of anionic and cationic polysaccharides and use thereof Download PDFInfo
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- CA2652968C CA2652968C CA2652968A CA2652968A CA2652968C CA 2652968 C CA2652968 C CA 2652968C CA 2652968 A CA2652968 A CA 2652968A CA 2652968 A CA2652968 A CA 2652968A CA 2652968 C CA2652968 C CA 2652968C
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- chitosan
- polysaccharide
- polysaccharide compositions
- polysaccharides
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- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 131
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 131
- -1 cationic polysaccharides Chemical class 0.000 title description 8
- 125000000129 anionic group Chemical group 0.000 title description 6
- 229920002959 polymer blend Polymers 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 127
- 229920001661 Chitosan Polymers 0.000 claims abstract description 85
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 33
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 32
- 230000007170 pathology Effects 0.000 claims abstract description 10
- 238000001356 surgical procedure Methods 0.000 claims abstract description 6
- 150000004804 polysaccharides Chemical class 0.000 claims description 122
- 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 101
- 229920002674 hyaluronan Polymers 0.000 claims description 96
- 229960003160 hyaluronic acid Drugs 0.000 claims description 95
- 229920000642 polymer Polymers 0.000 claims description 62
- 235000010443 alginic acid Nutrition 0.000 claims description 29
- 229920000615 alginic acid Polymers 0.000 claims description 29
- 229920001586 anionic polysaccharide Polymers 0.000 claims description 27
- 150000004836 anionic polysaccharides Chemical class 0.000 claims description 27
- 239000007864 aqueous solution Substances 0.000 claims description 20
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 13
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 9
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 9
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 9
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 9
- 239000008101 lactose Substances 0.000 claims description 9
- 229920000936 Agarose Polymers 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
- 229920001525 carrageenan Polymers 0.000 claims description 8
- 238000001212 derivatisation Methods 0.000 claims description 6
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 claims description 6
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 claims description 5
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 claims description 5
- 235000010418 carrageenan Nutrition 0.000 claims description 5
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 claims description 5
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- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229920002971 Heparan sulfate Polymers 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 239000001814 pectin Substances 0.000 claims description 3
- 235000010987 pectin Nutrition 0.000 claims description 3
- 229920001277 pectin Polymers 0.000 claims description 3
- 230000000472 traumatic effect Effects 0.000 claims description 3
- 229920001285 xanthan gum Polymers 0.000 claims description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- 229920000045 Dermatan sulfate Polymers 0.000 claims description 2
- 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 2
- 229920000288 Keratan sulfate Polymers 0.000 claims description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- LUEWUZLMQUOBSB-UHFFFAOYSA-N UNPD55895 Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(OC3C(OC(O)C(O)C3O)CO)C(O)C2O)CO)C(O)C1O LUEWUZLMQUOBSB-UHFFFAOYSA-N 0.000 claims description 2
- QLTSDROPCWIKKY-PMCTYKHCSA-N beta-D-glucosaminyl-(1->4)-beta-D-glucosamine Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O)[C@@H](CO)O1 QLTSDROPCWIKKY-PMCTYKHCSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 2
- DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 claims description 2
- FYGDTMLNYKFZSV-ZWSAEMDYSA-N cellotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-ZWSAEMDYSA-N 0.000 claims description 2
- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 claims description 2
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 claims description 2
- 229940051593 dermatan sulfate Drugs 0.000 claims description 2
- 229960002897 heparin Drugs 0.000 claims description 2
- KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 claims description 2
- 210000003041 ligament Anatomy 0.000 claims description 2
- UYQJCPNSAVWAFU-UHFFFAOYSA-N malto-tetraose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)O1 UYQJCPNSAVWAFU-UHFFFAOYSA-N 0.000 claims description 2
- LUEWUZLMQUOBSB-OUBHKODOSA-N maltotetraose Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O[C@@H]3[C@@H](O[C@@H](O)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-OUBHKODOSA-N 0.000 claims description 2
- 230000005499 meniscus Effects 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 143
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 48
- 229920000447 polyanionic polymer Polymers 0.000 description 30
- 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 description 25
- 229940072056 alginate Drugs 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000003993 interaction Effects 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 10
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- 239000000872 buffer Substances 0.000 description 8
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
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- 238000006268 reductive amination reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 4
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- 238000000295 emission spectrum Methods 0.000 description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 4
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
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- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 3
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- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
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- 239000000568 immunological adjuvant Substances 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000002597 lactoses Chemical class 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
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- RDZTWEVXRGYCFV-UHFFFAOYSA-M sodium 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonate Chemical compound [Na+].OCCN1CCN(CCS([O-])(=O)=O)CC1 RDZTWEVXRGYCFV-UHFFFAOYSA-M 0.000 description 1
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/20—Polysaccharides
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- A—HUMAN NECESSITIES
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- C08L1/08—Cellulose derivatives
- C08L1/26—Cellulose ethers
- C08L1/28—Alkyl ethers
- C08L1/286—Alkyl ethers substituted with acid radicals, e.g. carboxymethyl cellulose [CMC]
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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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- 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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- C08L5/04—Alginic acid; Derivatives thereof
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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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- C08L5/06—Pectin; Derivatives thereof
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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
- 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
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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
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/10—Heparin; Derivatives thereof
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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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- C08L5/12—Agar or agar-agar, i.e. mixture of agarose and agaropectin; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
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- Biomedical Technology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Medical Uses (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITPD2006A000202 | 2006-05-22 | ||
| IT000202A ITPD20060202A1 (it) | 2006-05-22 | 2006-05-22 | Miscele polimeriche di polisaccaridi anionici e cationici e loro impiego |
| PCT/EP2007/054860 WO2007135116A1 (en) | 2006-05-22 | 2007-05-21 | Polymer mixtures of anionic and cationic polysaccharides and use thereof |
Publications (2)
| Publication Number | Publication Date |
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| CA2652968A1 CA2652968A1 (en) | 2007-11-29 |
| CA2652968C true CA2652968C (en) | 2014-08-05 |
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| CA2652968A Active CA2652968C (en) | 2006-05-22 | 2007-05-21 | Polymer mixtures of anionic and cationic polysaccharides and use thereof |
Country Status (10)
| Country | Link |
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| US (1) | US8951991B2 (enExample) |
| EP (1) | EP2021408B1 (enExample) |
| JP (1) | JP2009537597A (enExample) |
| CN (1) | CN101454392A (enExample) |
| AT (1) | ATE479453T1 (enExample) |
| BR (1) | BRPI0711620A2 (enExample) |
| CA (1) | CA2652968C (enExample) |
| DE (1) | DE602007008879D1 (enExample) |
| IT (1) | ITPD20060202A1 (enExample) |
| WO (1) | WO2007135116A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IT1391668B1 (it) * | 2008-07-23 | 2012-01-17 | Universita' Degli Studi Di Trieste | Materiali nanocompositi basati su nanoparticelle metalliche stabilizzate con polisaccaridi a struttura ramificata. |
| IT1391669B1 (it) * | 2008-07-23 | 2012-01-17 | Universita' Degli Studi Di Trieste | Materiali nanocompositi formati da una matrice polisaccaridica e nanoparticelle metalliche, loro preparazione ed uso |
| IT1404145B1 (it) * | 2010-12-27 | 2013-11-15 | Altergon Sa | Composizioni di acido ialuronico stabilizzate verso l'azione di degradazione del calore o degli enzimi |
| CN103084079B (zh) * | 2013-02-04 | 2015-08-05 | 浙江大学 | 可原位水分散聚电解质络合物渗透汽化膜的制备方法 |
| CN105903087A (zh) * | 2015-12-14 | 2016-08-31 | 上海其胜生物制剂有限公司 | 一种兼具内聚性和弥散性的粘弹剂的制备方法 |
| ITUA20164153A1 (it) * | 2016-06-07 | 2017-12-07 | Jointherapeutics S R L | Composizioni polisaccaridiche impiegabili nella riparazione tissutale |
| IT201600075246A1 (it) * | 2016-07-19 | 2018-01-19 | Jointherapeutics S R L | Composizioni comprendenti una matrice polisaccaridica per il rilascio controllato di principi attivi. |
| IT201600130342A1 (it) | 2016-12-22 | 2018-06-22 | Biopolife S R L | Addotti solubili di acido borico o suoi derivati e precursori con derivati oligosaccaridici del chitosano |
| IT201700060530A1 (it) * | 2017-06-01 | 2018-12-01 | Jointherapeutics S R L | Derivati polisaccaridici idrosolubili, loro procedimento di preparazione e loro usi |
| HRP20230566T1 (hr) | 2017-08-22 | 2023-08-18 | Moebius Medical Ltd. | Liposomalna formulacija za podmazivanje zglobova |
| IT201700111939A1 (it) * | 2017-10-05 | 2019-04-05 | Jointherapeutics S R L | Composizione farmaceutica per l’uso nel trattamento di stati infiammatori |
| IT201900006250A1 (it) | 2019-04-23 | 2020-10-23 | Fidia Farm Spa | Medicazione per il trattamento della cute lesa |
| CN108918495B (zh) * | 2018-08-21 | 2020-10-09 | 辽宁大学 | 基于2-醛基罗丹明类衍生物的分光光度法定量检测氰根离子的方法 |
| EP3733755A1 (en) | 2019-04-30 | 2020-11-04 | Universita Degli Studi di Trieste | Homogeneous hydrogels from chitosan oligosaccharide derivatives and applications thereof |
| CN110075360B (zh) * | 2019-05-21 | 2021-12-07 | 福建吉特瑞生物科技有限公司 | 一种壳聚糖/ha基个性化颅、颌面、脊椎骨修复材料及其制备方法 |
| IT201900010740A1 (it) | 2019-07-02 | 2021-01-02 | Medacta Int Sa | Biocompatible compositions comprising a biocompatible thickening polymer and a chitosan derivative |
| CN112920369B (zh) * | 2021-01-28 | 2022-07-26 | 孝感市易生新材料有限公司 | 自抗菌性乳酸基水性聚氨酯、其制备方法及其乳液 |
| WO2022240264A1 (ko) * | 2021-05-14 | 2022-11-17 | (주)유레 | 폴리머 조성물 및 이의 제조방법 |
| CN114306725B (zh) * | 2021-11-30 | 2022-10-04 | 南方科技大学 | 一种单面粘合水凝胶粘合剂及其制备方法、应用 |
| CN114632445B (zh) * | 2022-02-25 | 2023-04-28 | 湖南益安生物科技有限公司 | 一种复合医用生物高分子材料及其制备方法 |
| CN114793769A (zh) * | 2022-05-06 | 2022-07-29 | 四川省通惠田源集团有限公司 | 一种牧草种植方法 |
| CN115212349B (zh) * | 2022-07-05 | 2023-11-21 | 浦易(上海)生物技术股份有限公司 | 可凝胶化的组合物及其制备方法和应用 |
| CN117126306A (zh) * | 2023-09-25 | 2023-11-28 | 江苏恒辉安防股份有限公司 | 一种生物质防老剂以及浅色导电手套及其制备方法 |
| CN118078854A (zh) * | 2024-03-14 | 2024-05-28 | 华南理工大学 | 一种聚电解质仿生滑液复合物及其制备方法与应用 |
Family Cites Families (7)
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|---|---|---|---|---|
| US5409904A (en) * | 1984-11-13 | 1995-04-25 | Alcon Laboratories, Inc. | Hyaluronic acid compositions and methods |
| US5318780A (en) * | 1991-10-30 | 1994-06-07 | Mediventures Inc. | Medical uses of in situ formed gels |
| CN1090022C (zh) * | 1995-04-04 | 2002-09-04 | 俄克拉荷马创伤治疗所 | 通过光动力疗法与免疫佐剂联合应用治疗癌症 |
| US5972326A (en) * | 1995-04-18 | 1999-10-26 | Galin; Miles A. | Controlled release of pharmaceuticals in the anterior chamber of the eye |
| US6277792B1 (en) * | 1998-12-28 | 2001-08-21 | Venture Innovations, Inc. | Viscosified aqueous fluids and viscosifier therefor |
| KR20020014189A (ko) * | 2000-08-16 | 2002-02-25 | 윤광심 | 키토산-알긴산를 이용한 화상상처 치료제 개발 |
| US6756363B1 (en) | 2000-11-17 | 2004-06-29 | Wound Healing Of Oklahoma, Inc. | Solutions and films of glycated chitosan |
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2006
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- 2007-05-21 WO PCT/EP2007/054860 patent/WO2007135116A1/en not_active Ceased
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- 2007-05-21 AT AT07729304T patent/ATE479453T1/de not_active IP Right Cessation
- 2007-05-21 EP EP07729304A patent/EP2021408B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8951991B2 (en) | 2015-02-10 |
| BRPI0711620A2 (pt) | 2017-05-09 |
| JP2009537597A (ja) | 2009-10-29 |
| CA2652968A1 (en) | 2007-11-29 |
| ITPD20060202A1 (it) | 2007-11-23 |
| EP2021408B1 (en) | 2010-09-01 |
| CN101454392A (zh) | 2009-06-10 |
| ATE479453T1 (de) | 2010-09-15 |
| US20090197832A1 (en) | 2009-08-06 |
| EP2021408A1 (en) | 2009-02-11 |
| WO2007135116A1 (en) | 2007-11-29 |
| DE602007008879D1 (de) | 2010-10-14 |
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