KR102191353B1 - 히알루론산의 c6-c18-아실화된 유도체, 이의 제조 방법, 이를 기재로 하는 나노미쉘형 조성물, 이의 제조 방법, 및 안정화된 나노미쉘형 조성물의 제조 방법, 및 이의 용도 - Google Patents
히알루론산의 c6-c18-아실화된 유도체, 이의 제조 방법, 이를 기재로 하는 나노미쉘형 조성물, 이의 제조 방법, 및 안정화된 나노미쉘형 조성물의 제조 방법, 및 이의 용도 Download PDFInfo
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- KR102191353B1 KR102191353B1 KR1020157016788A KR20157016788A KR102191353B1 KR 102191353 B1 KR102191353 B1 KR 102191353B1 KR 1020157016788 A KR1020157016788 A KR 1020157016788A KR 20157016788 A KR20157016788 A KR 20157016788A KR 102191353 B1 KR102191353 B1 KR 102191353B1
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- hyaluronan
- hyaluronic acid
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- 238000000034 method Methods 0.000 title claims abstract description 90
- 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 82
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
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- 229920002674 hyaluronan Polymers 0.000 claims abstract description 157
- 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 abstract description 146
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- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 19
- 125000000524 functional group Chemical group 0.000 claims abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 11
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
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- 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 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
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- 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 4
- KKMZQOIASVGJQE-UHFFFAOYSA-N 3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CS1 KKMZQOIASVGJQE-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-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
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing 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
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
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- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
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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 |
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| KR20150088848A KR20150088848A (ko) | 2015-08-03 |
| KR102191353B1 true KR102191353B1 (ko) | 2020-12-16 |
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| KR1020157016788A Active KR102191353B1 (ko) | 2012-11-27 | 2013-11-26 | 히알루론산의 c6-c18-아실화된 유도체, 이의 제조 방법, 이를 기재로 하는 나노미쉘형 조성물, 이의 제조 방법, 및 안정화된 나노미쉘형 조성물의 제조 방법, 및 이의 용도 |
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| EP (1) | EP2934592B1 (enExample) |
| JP (1) | JP2016500130A (enExample) |
| KR (1) | KR102191353B1 (enExample) |
| BR (1) | BR112015012191A8 (enExample) |
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| 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 |
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| 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 |
| CN116459213A (zh) * | 2023-02-20 | 2023-07-21 | 莫佳杰 | 一种具有过氧化氢响应性胶束及制备方法和应用 |
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Also Published As
| Publication number | Publication date |
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| CZ2012842A3 (cs) | 2014-08-20 |
| RU2640287C2 (ru) | 2017-12-27 |
| HUE038664T2 (hu) | 2018-11-28 |
| US20150320873A1 (en) | 2015-11-12 |
| WO2014082609A1 (en) | 2014-06-05 |
| CZ304654B6 (cs) | 2014-08-20 |
| BR112015012191A2 (pt) | 2017-07-11 |
| US9999678B2 (en) | 2018-06-19 |
| EP2934592B1 (en) | 2018-05-16 |
| KR20150088848A (ko) | 2015-08-03 |
| JP2016500130A (ja) | 2016-01-07 |
| EP2934592A1 (en) | 2015-10-28 |
| BR112015012191A8 (pt) | 2018-01-23 |
| DK2934592T3 (en) | 2018-07-02 |
| PL2934592T3 (pl) | 2018-12-31 |
| RU2015125076A (ru) | 2017-01-13 |
| ES2683993T3 (es) | 2018-10-01 |
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