CA2992705A1 - Nanocapsule for delivery of lipophilic compound and process of preparation thereof - Google Patents
Nanocapsule for delivery of lipophilic compound and process of preparation thereof Download PDFInfo
- Publication number
- CA2992705A1 CA2992705A1 CA2992705A CA2992705A CA2992705A1 CA 2992705 A1 CA2992705 A1 CA 2992705A1 CA 2992705 A CA2992705 A CA 2992705A CA 2992705 A CA2992705 A CA 2992705A CA 2992705 A1 CA2992705 A1 CA 2992705A1
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- Prior art keywords
- capsules
- sulfate
- chitosan
- oil
- poly
- 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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- 239000002088 nanocapsule Substances 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 52
- 230000008569 process Effects 0.000 title claims description 18
- 150000002634 lipophilic molecules Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 26
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 36
- 239000005017 polysaccharide Substances 0.000 claims abstract description 36
- 150000004676 glycans Chemical class 0.000 claims abstract description 35
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000004094 surface-active agent Substances 0.000 claims abstract description 17
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 4
- 230000007774 longterm Effects 0.000 claims abstract description 3
- 239000002775 capsule Substances 0.000 claims description 122
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 38
- 229920001661 Chitosan Polymers 0.000 claims description 34
- 235000019198 oils Nutrition 0.000 claims description 31
- 239000003921 oil Substances 0.000 claims description 30
- -1 polyornityne Polymers 0.000 claims description 30
- 229920002674 hyaluronan Polymers 0.000 claims description 29
- 229960003160 hyaluronic acid Drugs 0.000 claims description 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 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 27
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 18
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000005642 Oleic acid Substances 0.000 claims description 18
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 18
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 18
- 229920000867 polyelectrolyte Polymers 0.000 claims description 17
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
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- 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 6
- 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 6
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- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 5
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 4
- 229920000856 Amylose Polymers 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229920002518 Polyallylamine hydrochloride Polymers 0.000 claims description 3
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- 238000001000 micrograph Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000002539 nanocarrier Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical group CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 108010011110 polyarginine Proteins 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5161—Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/5123—Organic compounds, e.g. fats, sugars
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/5176—Compounds of unknown constitution, e.g. material from plants or animals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Nanotechnology (AREA)
- Biomedical Technology (AREA)
- Dispersion Chemistry (AREA)
- Botany (AREA)
- Zoology (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Cosmetics (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PLP.413155 | 2015-07-17 | ||
| PL413155A PL229276B1 (pl) | 2015-07-17 | 2015-07-17 | Nanokapsuła do przenoszenia związku lipofilowego i sposób jej wytwarzania |
| PCT/PL2016/050032 WO2017014655A1 (en) | 2015-07-17 | 2016-07-12 | Nanocapsule for delivery of lipophilic compound and process of preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2992705A1 true CA2992705A1 (en) | 2017-01-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2992705A Pending CA2992705A1 (en) | 2015-07-17 | 2016-07-12 | Nanocapsule for delivery of lipophilic compound and process of preparation thereof |
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| Country | Link |
|---|---|
| US (2) | US10821083B2 (enExample) |
| EP (1) | EP3324939A1 (enExample) |
| JP (1) | JP6971217B2 (enExample) |
| KR (1) | KR20180025318A (enExample) |
| CN (1) | CN107847441B (enExample) |
| AU (3) | AU2016295949A1 (enExample) |
| CA (1) | CA2992705A1 (enExample) |
| MX (1) | MX387005B (enExample) |
| PL (1) | PL229276B1 (enExample) |
| RU (1) | RU2723374C1 (enExample) |
| WO (1) | WO2017014655A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2018176047A (ja) * | 2017-04-10 | 2018-11-15 | パナソニックＩｐマネジメント株式会社 | マイクロカプセル及びマイクロカプセルの製造方法、並びに、化粧料及び化粧料の製造方法 |
| CN109535430A (zh) * | 2017-09-22 | 2019-03-29 | 天津大学 | 一种油酰化壳寡糖胍接枝聚乙烯亚胺的两亲性衍生物及其制备方法 |
| ES2711669A1 (es) * | 2017-11-02 | 2019-05-06 | Univ Santiago Compostela | Sistemas de liberacion de farmacos de acido polisialico y metodos |
| CN108246215B (zh) * | 2017-12-21 | 2020-06-30 | 四川大学 | 一种超薄壁壳聚糖微囊及其制备方法 |
| PL240632B1 (pl) * | 2018-04-06 | 2022-05-09 | Univ Jagiellonski | Zastosowanie nanokapsuły z ciekłym rdzeniem olejowym w terapii przeciwnowotworowej |
| CN108739807B (zh) * | 2018-06-21 | 2021-07-13 | 中国热带农业科学院农产品加工研究所 | 植物油酸-壳聚糖基纳米微胶囊农药、其制备方法及其应用 |
| CN112888428A (zh) * | 2018-08-17 | 2021-06-01 | 克里兹托夫·斯梅拉 | 包封亲脂和亲水性化合物的纳米胶囊包纳米胶囊型的多隔室体系及相关生产方法 |
| CN109925983B (zh) * | 2019-03-08 | 2021-12-28 | 紫罗兰家纺科技股份有限公司 | 基于乳木果油的双层微胶囊及其整理到纺织面料中的方法 |
| CN111920782B (zh) * | 2019-05-13 | 2025-11-18 | 中国医学科学院药物研究所 | 复合脂质纳米囊组合物及其制备方法和应用 |
| CN112300767B (zh) * | 2020-09-22 | 2022-04-05 | 山东大学 | 一种绿色靶向微胶囊及制备体系、制备方法和应用 |
| EP4321175B1 (en) | 2022-08-11 | 2025-07-16 | CHDE Polska S.A. | Magnetic polymer nanocapsules suitable for use in therapy, especially anti-cancer ones |
| PL446441A1 (pl) * | 2023-10-20 | 2025-04-22 | Chde Polska Spółka Akcyjna | 2-metylo-3-fitylo-1,4-naftochinon do stosowania w leczeniu lub zapobieganiu chorób przebiegających z dysfunkcją śródbłonka naczyniowego |
Family Cites Families (11)
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|---|---|---|---|---|
| ES2093562B1 (es) | 1995-05-26 | 1997-07-01 | Univ Santiago Compostela | Estabilizacion de sistemas coloidales mediante formacion de complejos ionicos lipido-polisacarido. |
| US20060063676A1 (en) | 2004-09-17 | 2006-03-23 | Brigance Mickey R | Method for enhancing deposition of an agrochemical |
| CA2618974C (en) | 2005-08-09 | 2014-01-28 | Nanobio Corporation | Nanoemulsion compositions having anti-inflammatory activity |
| EP2026771B1 (en) * | 2006-01-23 | 2009-10-21 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Microspheres comprising nanocapsules containing a lipophilic drug |
| ATE515260T1 (de) * | 2006-03-13 | 2011-07-15 | Advanced In Vitro Cell Technologies S L | Stabile nanokapselsysteme für die verabreichung von wirkstoffen |
| EP2266546A1 (en) | 2009-06-08 | 2010-12-29 | Advancell Advanced in Vitro Cell Technologies,S.A. | Process for the preparation of colloidal systems for the delivery of active compounds |
| CN102161729B (zh) * | 2011-02-25 | 2013-01-16 | 上海交通大学 | 水溶性多糖与疏水性单体形成纳米粒子的制备方法 |
| ES2366255B2 (es) | 2011-06-27 | 2012-08-08 | Universidade De Santiago De Compostela | Nanocomposiciones sacarídicas para la liberación de vacunas. |
| RU2494728C1 (ru) | 2012-08-16 | 2013-10-10 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" (ФГУП "ГНЦ "НИОПИК") | Наноэмульсия, содержащая биологически активное вещество |
| 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 |
| JP2016531112A (ja) | 2013-07-25 | 2016-10-06 | ネムコア メディカル イノベーションズ インコーポレイテッド | 疎水性白金誘導体のナノエマルジョン |
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2015
- 2015-07-17 PL PL413155A patent/PL229276B1/pl unknown
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2016
- 2016-07-12 JP JP2018501907A patent/JP6971217B2/ja active Active
- 2016-07-12 AU AU2016295949A patent/AU2016295949A1/en not_active Abandoned
- 2016-07-12 CA CA2992705A patent/CA2992705A1/en active Pending
- 2016-07-12 EP EP16757368.2A patent/EP3324939A1/en active Pending
- 2016-07-12 KR KR1020187004688A patent/KR20180025318A/ko not_active Ceased
- 2016-07-12 WO PCT/PL2016/050032 patent/WO2017014655A1/en not_active Ceased
- 2016-07-12 US US15/743,728 patent/US10821083B2/en active Active
- 2016-07-12 RU RU2018103323A patent/RU2723374C1/ru active
- 2016-07-12 MX MX2018000637A patent/MX387005B/es unknown
- 2016-07-12 CN CN201680042159.7A patent/CN107847441B/zh active Active
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2020
- 2020-07-17 US US16/932,369 patent/US20200345651A1/en not_active Abandoned
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2021
- 2021-09-30 AU AU2021240279A patent/AU2021240279A1/en not_active Abandoned
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2024
- 2024-02-27 AU AU2024201288A patent/AU2024201288A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017014655A1 (en) | 2017-01-26 |
| MX2018000637A (es) | 2018-09-06 |
| CN107847441A (zh) | 2018-03-27 |
| AU2016295949A1 (en) | 2018-02-01 |
| PL413155A1 (pl) | 2017-01-30 |
| RU2723374C1 (ru) | 2020-06-10 |
| AU2024201288A1 (en) | 2024-03-14 |
| US20180200197A1 (en) | 2018-07-19 |
| EP3324939A1 (en) | 2018-05-30 |
| US20200345651A1 (en) | 2020-11-05 |
| MX387005B (es) | 2025-03-12 |
| PL229276B1 (pl) | 2018-06-29 |
| CN107847441B (zh) | 2021-08-13 |
| AU2021240279A1 (en) | 2021-10-28 |
| US10821083B2 (en) | 2020-11-03 |
| JP2018523642A (ja) | 2018-08-23 |
| KR20180025318A (ko) | 2018-03-08 |
| HK1251154A1 (zh) | 2019-01-25 |
| JP6971217B2 (ja) | 2021-11-24 |
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