JP2016500130A5 - - Google Patents
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- JP2016500130A5 JP2016500130A5 JP2015543316A JP2015543316A JP2016500130A5 JP 2016500130 A5 JP2016500130 A5 JP 2016500130A5 JP 2015543316 A JP2015543316 A JP 2015543316A JP 2015543316 A JP2015543316 A JP 2015543316A JP 2016500130 A5 JP2016500130 A5 JP 2016500130A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hyaluronic acid
- composition
- preparation
- water
- 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.)
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- 239000000203 mixture Substances 0.000 claims 29
- 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 claims 25
- 229920002674 hyaluronan Polymers 0.000 claims 21
- 229960003160 hyaluronic acid Drugs 0.000 claims 17
- 238000002360 preparation method Methods 0.000 claims 17
- 238000000034 method Methods 0.000 claims 14
- 229940088623 biologically active substance Drugs 0.000 claims 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 10
- 239000013543 active substance Substances 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 239000000693 micelle Substances 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 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 claims 7
- 239000003960 organic solvent Substances 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004434 sulfur atom Chemical group 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- 125000000524 functional group Chemical group 0.000 claims 4
- 229940099552 hyaluronan Drugs 0.000 claims 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 4
- 239000008158 vegetable oil Substances 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 239000000010 aprotic solvent Substances 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- -1 chloride activated C 6 Chemical class 0.000 claims 3
- 239000000539 dimer Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 239000002480 mineral oil Substances 0.000 claims 3
- 235000010446 mineral oil Nutrition 0.000 claims 3
- 239000011259 mixed solution Substances 0.000 claims 3
- 239000007908 nanoemulsion Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- 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 2
- RAFFVQBMVYYTQS-UHFFFAOYSA-N 2,4,6-trichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl RAFFVQBMVYYTQS-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims 2
- 150000001805 chlorine compounds Chemical class 0.000 claims 2
- 239000002537 cosmetic Substances 0.000 claims 2
- 238000004132 cross linking Methods 0.000 claims 2
- 239000003431 cross linking reagent Substances 0.000 claims 2
- 239000000824 cytostatic agent Substances 0.000 claims 2
- 230000001085 cytostatic effect Effects 0.000 claims 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000004530 micro-emulsion Substances 0.000 claims 2
- 239000012454 non-polar solvent Substances 0.000 claims 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
- 239000000419 plant extract Substances 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- 238000007348 radical reaction Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 238000000527 sonication Methods 0.000 claims 2
- 239000011782 vitamin Substances 0.000 claims 2
- 229940088594 vitamin Drugs 0.000 claims 2
- 229930003231 vitamin Natural products 0.000 claims 2
- 235000013343 vitamin Nutrition 0.000 claims 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- KKMZQOIASVGJQE-UHFFFAOYSA-N 3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CS1 KKMZQOIASVGJQE-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 1
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 238000004220 aggregation Methods 0.000 claims 1
- 230000002776 aggregation Effects 0.000 claims 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims 1
- 235000019395 ammonium persulphate Nutrition 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- 229940110767 coenzyme Q10 Drugs 0.000 claims 1
- 235000017471 coenzyme Q10 Nutrition 0.000 claims 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 1
- 238000000502 dialysis Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- 235000020778 linoleic acid Nutrition 0.000 claims 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 1
- 229960004488 linolenic acid Drugs 0.000 claims 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 229960002446 octanoic acid Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 235000021313 oleic acid Nutrition 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229960001295 tocopherol Drugs 0.000 claims 1
- 229930003799 tocopherol Natural products 0.000 claims 1
- 235000010384 tocopherol Nutrition 0.000 claims 1
- 239000011732 tocopherol Substances 0.000 claims 1
- 125000002640 tocopherol group Chemical group 0.000 claims 1
- 238000007738 vacuum evaporation Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2012-842A CZ304654B6 (cs) | 2012-11-27 | 2012-11-27 | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| CZPV2012-842 | 2012-11-27 | ||
| PCT/CZ2013/000156 WO2014082609A1 (en) | 2012-11-27 | 2013-11-26 | C6-c18-acylated derivative of hyaluronic acid, method of preparation thereof, nanomicellar composition on its basis, method of preparation thereof and method of preparation stabilized nanomicellar composition, and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016500130A JP2016500130A (ja) | 2016-01-07 |
| JP2016500130A5 true JP2016500130A5 (enExample) | 2018-02-08 |
Family
ID=50097520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015543316A Pending JP2016500130A (ja) | 2012-11-27 | 2013-11-26 | ヒアルロン酸のｃ６‐ｃ１８‐アシル化誘導体とその調製方法，それをベースとするナノミセル組成物及びその調製方法，並びに安定化されたナノミセル組成物の調製方法及びその使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9999678B2 (enExample) |
| EP (1) | EP2934592B1 (enExample) |
| JP (1) | JP2016500130A (enExample) |
| KR (1) | KR102191353B1 (enExample) |
| BR (1) | BR112015012191A8 (enExample) |
| CZ (1) | CZ304654B6 (enExample) |
| DK (1) | DK2934592T3 (enExample) |
| ES (1) | ES2683993T3 (enExample) |
| HU (1) | HUE038664T2 (enExample) |
| PL (1) | PL2934592T3 (enExample) |
| RU (1) | RU2640287C2 (enExample) |
| WO (1) | WO2014082609A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ304654B6 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| CZ305153B6 (cs) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
| CZ2014451A3 (cs) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití |
| CZ309295B6 (cs) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití |
| CN113786489A (zh) * | 2015-05-29 | 2021-12-14 | 生化学工业株式会社 | 包含糖胺聚糖衍生物和趋化因子受体活性调节材料的组合物 |
| CZ2015398A3 (cs) | 2015-06-15 | 2017-02-08 | Contipro A.S. | Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin |
| CZ306662B6 (cs) | 2015-06-26 | 2017-04-26 | Contipro A.S. | Deriváty sulfatovaných polysacharidů, způsob jejich přípravy, způsob jejich modifikace a použití |
| PL229276B1 (pl) * | 2015-07-17 | 2018-06-29 | Univ Jagiellonski | Nanokapsuła do przenoszenia związku lipofilowego i sposób jej wytwarzania |
| CZ307511B6 (cs) | 2015-12-23 | 2018-10-31 | Contipro A.S. | Fluorescenční konjugát kyseliny hyaluronové nebo jeho sůl, hydrofobizovaný konjugát, způsoby jejich přípravy a použití |
| CZ308106B6 (cs) | 2016-06-27 | 2020-01-08 | Contipro A.S. | Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití |
| CZ2016826A3 (cs) | 2016-12-22 | 2018-07-04 | Contipro A.S. | Léčivý prostředek s nosičem na bázi hyaluronanu a/nebo jeho derivátů, způsob výroby a použití |
| CZ2016827A3 (cs) * | 2016-12-23 | 2018-02-07 | Contipro A.S. | Oftalmologický prostředek |
| US12324789B2 (en) * | 2017-08-28 | 2025-06-10 | Apirx Pharmaceutical Usa, Llc | Method to treat psoriasis |
| WO2020002597A1 (en) | 2018-06-29 | 2020-01-02 | Merz Pharma Gmbh & Co. Kgaa | Fatty acid-grafted hyaluronic acid, dermal filler formulations comprising same, process for preparation and use thereof |
| FR3105922B1 (fr) | 2020-01-08 | 2022-12-02 | Le Rouge Francais | Composition cosmétique pour le traitement des lèvres sous forme de solide compact contenant au moins un agent probiotique et au moins un composé choisi parmi l'acide hyaluronique et ses dérivés. |
| TWI834948B (zh) * | 2020-02-05 | 2024-03-11 | 日商旭化成股份有限公司 | 玻尿酸衍生物組合物、醫藥組合物及玻尿酸衍生物－藥物結合體組合物 |
| EP4101860A4 (en) * | 2020-02-07 | 2023-07-19 | Asahi Kasei Kabushiki Kaisha | HYALURONIC ACID DERIVATIVE, PHARMACEUTICAL COMPOSITION AND MEDICINE CONJUGATE - HYALURONIC ACID DERIVATIVE - |
| KR102547183B1 (ko) * | 2020-10-19 | 2023-06-26 | 주식회사 메피온 | 필러 및 필러 제조 방법 |
| CN112159527B (zh) * | 2020-10-29 | 2023-06-06 | 绍兴文理学院 | 一种含有透明质酸基团的聚甘油脂肪酸酯ha-pg及其合成方法和其在制备药物制剂中的应用 |
| CN113476426B (zh) * | 2021-06-29 | 2023-11-24 | 大连工业大学 | 一种基于透明质酸的双靶向功能因子递送体系的制备及其在炎症性肠病中的应用 |
| CN114561827B (zh) * | 2022-02-25 | 2023-04-21 | 华南理工大学 | 一种全生物质基蜡乳液防水涂料及其制备方法与应用 |
| CN116444695B (zh) * | 2022-12-27 | 2024-09-06 | 山东丰金美业科技有限公司 | 一种低成本、低分子量乙酰化透明质酸钠的制备方法 |
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| KR101103423B1 (ko) | 2009-09-04 | 2012-01-06 | 아주대학교산학협력단 | 생체 주입형 조직 접착성 하이드로젤 및 이의 생의학적 용도 |
| WO2011059326A2 (en) | 2009-11-11 | 2011-05-19 | University Of Twente, Institute For Biomedical Technology And Technical Medicine (Mira) | Hydrogels based on polymers of dextran tyramine and tyramine conjugates of natural polymers |
| WO2011059325A2 (en) | 2009-11-11 | 2011-05-19 | University Of Twente, Institute For Biomedical Technology And Technical Medicine (Mira) | Dextran-hyaluronic acid based hydrogels |
| US20110111012A1 (en) | 2009-11-12 | 2011-05-12 | Hemcon Medical Technologies, Inc. | Nanomaterial wound dressing assembly |
| CZ302504B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
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| CN101897976A (zh) * | 2010-07-16 | 2010-12-01 | 沈阳药科大学 | 一种药物增溶载体及其制备方法和应用 |
| CZ20101001A3 (cs) | 2010-12-31 | 2012-02-08 | Cpn S.R.O. | Hyaluronová vlákna, zpusob jejich prípravy a použití |
| CZ304072B6 (cs) | 2011-04-26 | 2013-09-25 | Contipro Biotech S.R.O. | Amfoterní materiál na bázi sítované kyseliny hyaluronové, zpusob jeho prípravy, materiály obsahující aktivní cinidla uzavrené v síti hyaluronanu, zpusob jejich prípravy a jejich pouzití |
| CN102154738B (zh) | 2011-05-10 | 2012-08-01 | 青岛大学 | 一种红藻琼胶纤维的制备方法 |
| ITTO20110428A1 (it) | 2011-05-13 | 2012-11-14 | Rottapharm Spa | Esteri dell'acido ialuronico, loro preparazione ed uso in dermatologia |
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| CZ304512B6 (cs) | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
| CZ304654B6 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
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| CN103505736A (zh) | 2013-09-23 | 2014-01-15 | 天津大学 | 基于改性透明质酸的高分子脂质体及其制备方法 |
| CZ305153B6 (cs) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
-
2012
- 2012-11-27 CZ CZ2012-842A patent/CZ304654B6/cs unknown
-
2013
- 2013-11-26 KR KR1020157016788A patent/KR102191353B1/ko active Active
- 2013-11-26 HU HUE13829034A patent/HUE038664T2/hu unknown
- 2013-11-26 WO PCT/CZ2013/000156 patent/WO2014082609A1/en not_active Ceased
- 2013-11-26 US US14/647,626 patent/US9999678B2/en active Active
- 2013-11-26 PL PL13829034T patent/PL2934592T3/pl unknown
- 2013-11-26 BR BR112015012191A patent/BR112015012191A8/pt not_active Application Discontinuation
- 2013-11-26 DK DK13829034.1T patent/DK2934592T3/en active
- 2013-11-26 EP EP13829034.1A patent/EP2934592B1/en active Active
- 2013-11-26 ES ES13829034.1T patent/ES2683993T3/es active Active
- 2013-11-26 RU RU2015125076A patent/RU2640287C2/ru active
- 2013-11-26 JP JP2015543316A patent/JP2016500130A/ja active Pending
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