CN107636019B - 水溶性酯化纤维素醚 - Google Patents
水溶性酯化纤维素醚 Download PDFInfo
- Publication number
- CN107636019B CN107636019B CN201680013934.6A CN201680013934A CN107636019B CN 107636019 B CN107636019 B CN 107636019B CN 201680013934 A CN201680013934 A CN 201680013934A CN 107636019 B CN107636019 B CN 107636019B
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- CN
- China
- Prior art keywords
- cellulose ether
- weight
- methyl cellulose
- acetic acid
- hydroxypropyl methyl
- 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.)
- Expired - Fee Related
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- 150000002148 esters Chemical class 0.000 title claims description 19
- 229920003086 cellulose ether Polymers 0.000 title abstract description 174
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 59
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims description 103
- 239000000203 mixture Substances 0.000 claims description 103
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 73
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 53
- 239000002775 capsule Substances 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 36
- 239000003085 diluting agent Substances 0.000 claims description 32
- -1 hydroxy propyloxy Chemical group 0.000 claims description 31
- 239000000470 constituent Substances 0.000 claims description 30
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 30
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 30
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 30
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 29
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 28
- 239000002552 dosage form Substances 0.000 claims description 21
- 238000006467 substitution reaction Methods 0.000 claims description 21
- 239000007962 solid dispersion Substances 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 238000005259 measurement Methods 0.000 claims description 16
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 15
- 229940079593 drug Drugs 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000007598 dipping method Methods 0.000 claims description 5
- 229920000609 methyl cellulose Polymers 0.000 claims description 5
- 239000001923 methylcellulose Substances 0.000 claims description 5
- 235000010981 methylcellulose Nutrition 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 235000015872 dietary supplement Nutrition 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 3
- 235000016709 nutrition Nutrition 0.000 claims 1
- 230000009469 supplementation Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 20
- 125000002252 acyl group Chemical group 0.000 abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 abstract description 3
- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 description 67
- 239000000243 solution Substances 0.000 description 42
- 239000002585 base Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 230000032050 esterification Effects 0.000 description 14
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- 239000012634 fragment Substances 0.000 description 14
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- 230000000052 comparative effect Effects 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
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- 229920002678 cellulose Polymers 0.000 description 9
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- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 8
- 229920013820 alkyl cellulose Polymers 0.000 description 7
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- 230000001376 precipitating effect Effects 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- 239000000047 product Substances 0.000 description 5
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
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- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000001856 Ethyl cellulose Substances 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- 239000006169 McIlvaine's buffer solution Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 229920006187 aquazol Polymers 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 238000000889 atomisation Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000005595 deprotonation Effects 0.000 description 3
- 238000010537 deprotonation reaction Methods 0.000 description 3
- 229920001249 ethyl cellulose Polymers 0.000 description 3
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
- RPZANUYHRMRTTE-UHFFFAOYSA-N 2,3,4-trimethoxy-6-(methoxymethyl)-5-[3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxyoxane;1-[[3,4,5-tris(2-hydroxybutoxy)-6-[4,5,6-tris(2-hydroxybutoxy)-2-(2-hydroxybutoxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]butan-2-ol Chemical compound COC1C(OC)C(OC)C(COC)OC1OC1C(OC)C(OC)C(OC)OC1COC.CCC(O)COC1C(OCC(O)CC)C(OCC(O)CC)C(COCC(O)CC)OC1OC1C(OCC(O)CC)C(OCC(O)CC)C(OCC(O)CC)OC1COCC(O)CC RPZANUYHRMRTTE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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- 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 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
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- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
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- 238000005804 alkylation reaction Methods 0.000 description 1
- WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B13/00—Preparation of cellulose ether-esters
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P20/00—Coating of foodstuffs; Coatings therefor; Making laminated, multi-layered, stuffed or hollow foodstuffs
- A23P20/10—Coating with edible coatings, e.g. with oils or fats
- A23P20/105—Coating with compositions containing vegetable or microbial fermentation gums, e.g. cellulose or derivatives; Coating with edible polymers, e.g. polyvinyalcohol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
- A61K9/08—Solutions
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- 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
- A61K9/4816—Wall or shell material
-
- 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
- A61K9/4833—Encapsulating processes; Filling of capsules
-
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/32—Cellulose ether-esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
- C09D101/08—Cellulose derivatives
- C09D101/32—Cellulose ether-esters
Abstract
Description
Claims (15)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US201562133508P | 2015-03-16 | 2015-03-16 | |
US62/133508 | 2015-03-16 | ||
PCT/US2016/021318 WO2016148973A1 (en) | 2015-03-16 | 2016-03-08 | Water-soluble esterified cellulose ethers |
Publications (2)
Publication Number | Publication Date |
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CN107636019A CN107636019A (zh) | 2018-01-26 |
CN107636019B true CN107636019B (zh) | 2019-02-26 |
Family
ID=55661561
Family Applications (1)
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CN201680013934.6A Expired - Fee Related CN107636019B (zh) | 2015-03-16 | 2016-03-08 | 水溶性酯化纤维素醚 |
Country Status (8)
Country | Link |
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US (1) | US10377835B2 (zh) |
EP (1) | EP3271404B1 (zh) |
JP (1) | JP6356923B2 (zh) |
KR (1) | KR20170128371A (zh) |
CN (1) | CN107636019B (zh) |
BR (1) | BR112017018232A2 (zh) |
MX (1) | MX2017011090A (zh) |
WO (1) | WO2016148973A1 (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018170062A1 (en) * | 2017-03-17 | 2018-09-20 | Dow Global Technologies Llc | Process for recovering an esterified cellulose ether from a reaction product mixture |
WO2018170060A1 (en) * | 2017-03-17 | 2018-09-20 | Dow Global Technologies Llc | Process for recovering an esterified cellulose ether from a reaction product mixture |
WO2019022822A1 (en) | 2017-07-26 | 2019-01-31 | Dow Global Technologies Llc | WATER-SOLUBLE POLYSACCHARIDES WITH IMPROVED PALABILITY |
WO2019022819A1 (en) | 2017-07-26 | 2019-01-31 | Dow Global Technologies Llc | PROCESS FOR PRODUCING HYDROGELS BASED ON LOW MOLECULAR WEIGHT HUMAN EMIER CELLULOSE ETHERS |
WO2019108264A1 (en) | 2017-11-29 | 2019-06-06 | Dow Global Technologies Llc | Hydrogels based on esterified cellulose ethers |
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- 2016-03-08 JP JP2017545916A patent/JP6356923B2/ja not_active Expired - Fee Related
- 2016-03-08 WO PCT/US2016/021318 patent/WO2016148973A1/en active Application Filing
- 2016-03-08 KR KR1020177027150A patent/KR20170128371A/ko not_active Application Discontinuation
- 2016-03-08 US US15/550,094 patent/US10377835B2/en not_active Expired - Fee Related
- 2016-03-08 CN CN201680013934.6A patent/CN107636019B/zh not_active Expired - Fee Related
- 2016-03-08 BR BR112017018232A patent/BR112017018232A2/pt not_active Application Discontinuation
- 2016-03-08 EP EP16714626.5A patent/EP3271404B1/en not_active Not-in-force
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Also Published As
Publication number | Publication date |
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CN107636019A (zh) | 2018-01-26 |
JP6356923B2 (ja) | 2018-07-11 |
EP3271404A1 (en) | 2018-01-24 |
MX2017011090A (es) | 2017-11-10 |
US10377835B2 (en) | 2019-08-13 |
EP3271404B1 (en) | 2019-01-09 |
JP2018507307A (ja) | 2018-03-15 |
WO2016148973A1 (en) | 2016-09-22 |
BR112017018232A2 (pt) | 2018-04-17 |
US20180072818A1 (en) | 2018-03-15 |
KR20170128371A (ko) | 2017-11-22 |
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