JP6801845B2 - キラル分割のための方法及びそのためのデバイス - Google Patents
キラル分割のための方法及びそのためのデバイス Download PDFInfo
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- JP6801845B2 JP6801845B2 JP2017506373A JP2017506373A JP6801845B2 JP 6801845 B2 JP6801845 B2 JP 6801845B2 JP 2017506373 A JP2017506373 A JP 2017506373A JP 2017506373 A JP2017506373 A JP 2017506373A JP 6801845 B2 JP6801845 B2 JP 6801845B2
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- 241000894007 species Species 0.000 claims description 118
- 239000007788 liquid Substances 0.000 claims description 48
- 230000005684 electric field Effects 0.000 claims description 21
- 230000005672 electromagnetic field Effects 0.000 claims description 2
- 230000005291 magnetic effect Effects 0.000 description 26
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012530 fluid Substances 0.000 description 8
- 238000011914 asymmetric synthesis Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
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- 230000008859 change Effects 0.000 description 6
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- 230000005526 G1 to G0 transition Effects 0.000 description 4
- 238000010568 chiral column chromatography Methods 0.000 description 4
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001012508 Carpiodes cyprinus Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000005298 paramagnetic effect Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
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- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 2
- 240000002900 Arthrospira platensis Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005292 diamagnetic effect Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- 230000005653 Brownian motion process Effects 0.000 description 1
- 241000192700 Cyanobacteria Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- 241000589902 Leptospira Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
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- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000005219 brazing Methods 0.000 description 1
- 238000005537 brownian motion Methods 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- QLGBPZDYGNOKOQ-UHFFFAOYSA-N hexadecyl-[2-[hexadecyl(dimethyl)azaniumyl]ethyl]-dimethylazanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC[N+](C)(C)CCCCCCCCCCCCCCCC QLGBPZDYGNOKOQ-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000006060 molten glass Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C1/00—Magnetic separation
- B03C1/02—Magnetic separation acting directly on the substance being separated
- B03C1/023—Separation using Lorentz force, i.e. deflection of electrically charged particles in a magnetic field
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C5/00—Separating dispersed particles from liquids by electrostatic effect
- B03C5/02—Separators
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/18—Preparation of finely divided silica neither in sol nor in gel form; After-treatment thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
− 外筒を内筒に対してある回転方向で回転させて、液体内にテイラー・クエット流れを発生させることと、
− キラル種のうちの少なくとも1つを回収することと、を含む。
− 動作中、テイラー・クエット流れが液体内に発生するように、外筒をある回転方向に回転させるためのアクチュエータと、
− キラル種のうちの少なくとも1つを回収するための回収器と、を備える。
− 外壁を内壁に対してある回転方向で回転させて、液体内にテイラー・クエット流れを発生させることと、
− キラル種のうちの少なくとも1つを回収することと、を含む。
Reo=ωoRoGν−1及びRei=ωiRiGν−1であり、
ωoは外筒の回転速度であり、Roは外筒の内面の半径であり、ωiは内筒の回転速度であり、Riは内筒の外面の半径であり、Gは2つの筒(すなわち、R0〜Ri)の間の間隙であり、νは動粘度である。
− 内壁2と、
− 内壁2と同軸上にあり、かつ内壁2と共に液体を受容するための間隙4を形成する外壁3と、を有する。
− 動作中、テイラー・クエット流れが液体内に発生するように、外筒3をある回転方向に回転させるためのアクチュエータ5と、
− キラル種のうちの少なくとも1つを回収するための回収器6と、をさらに備える。
ナノメートルサイズの種として、長さ200nm及び幅20nmのシリカナノメートルサイズのエナンチオモルフィックねじりリボンを使用した。左巻きのねじりリボンを、以後、Sリボンと記載し、右巻きのねじりリボンをRリボンと記載する。リボンを蛍光顕微鏡で画像化できるように、リボンをスルホローダミン−Bで蛍光性に標識する。ナノメートルサイズの種を、水中に分散した。
N1,N2−ジヘキサデシル−N1,N1,N2,N2−テトラメチルエタン−1,2−ジアミニウム(双性界面活性剤)に非共有結合的に結合されたD−酒石酸またはL−酒石酸のいずれかを、超分子キラル集合体のキラル構成要素として使用した。D−酒石酸及び双性界面活性剤は、ナノメートル〜マイクロメートルの長さ及び20nmの径の左巻きのねじりリボン、そして、Sリボンに自己集合し、一方で、L−酒石酸及び双性界面活性剤は、ナノメートル〜マイクロメートルの長さ及び20nmの径の右巻きのねじりリボン、そして、Dリボンに自己集合する。
螺線形のマイクロメートルサイズのスパイラルを、光照射下で通常の液体培養で培養されたスピルリナ属の藍藻類(すなわち、シアノバクテリア)から得た。スパイラル(右巻き及び左巻き両方の)は、長さ150μm、幅30μm、厚さ10.5μmであり、20μmのピッチを有した(図13参照)。
Claims (8)
- 内壁と前記内壁の少なくとも一部にわたって前記内壁を囲む外壁とによって形成されるセルの中に配置された液体中に含有されるキラル種のキラル分割のための方法であって、前記外壁及び内壁の各々が長手方向軸を中心とした回転体であり、前記外壁及び内壁が互いに同軸上にあり、前記方法が、
− 前記外壁を前記内壁に対してある回転方向で回転させて、前記液体内にテイラー・クエット流れを発生させることと、
− 前記キラル種のうちの少なくとも1つを回収することと、を含む、方法。 - その他のキラル種のうちの少なくとも1つを回収することをさらに含む、請求項1に記載の方法。
- 前記外壁と同じまたは逆方向に、前記内壁を回転することをさらに含む、請求項1または2に記載の方法。
- 前記液体が、5×10−5Pa・s〜103Pa・sの粘度を有する、請求項1〜3のいずれかに記載の方法。
- 間隙内に生み出されたせん断速度が、平均1s−1〜1012s−1である、請求項1〜4のいずれかに記載の方法。
- 前記液体内に電場を適用することをさらに含む、請求項1〜5のいずれかに記載の方法。
- 前記液体内に電磁場を適用することをさらに含む、請求項1〜6のいずれかに記載の方法。
- 前記セル内の温度を制御することをさらに含む、請求項1〜7のいずれかに記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14306261.0A EP2982662A1 (en) | 2014-08-08 | 2014-08-08 | Method for chiral resolution and device therefor |
EP14306261.0 | 2014-08-08 | ||
PCT/EP2015/068273 WO2016020532A1 (en) | 2014-08-08 | 2015-08-07 | Method for chiral resolution and device therefor |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017529323A JP2017529323A (ja) | 2017-10-05 |
JP6801845B2 true JP6801845B2 (ja) | 2020-12-16 |
Family
ID=51383682
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017506373A Active JP6801845B2 (ja) | 2014-08-08 | 2015-08-07 | キラル分割のための方法及びそのためのデバイス |
Country Status (5)
Country | Link |
---|---|
US (1) | US10597339B2 (ja) |
EP (2) | EP2982662A1 (ja) |
JP (1) | JP6801845B2 (ja) |
CN (1) | CN106660893B (ja) |
WO (1) | WO2016020532A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017003909A2 (en) * | 2015-06-29 | 2017-01-05 | Mirianas Chachisvilis | Chiral separation and analysis by molecular propeller effect |
CN113826003A (zh) | 2019-05-16 | 2021-12-21 | 公立大学法人大阪 | 手性检测装置、手性检测方法、分离装置、分离方法和手性物质装置 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3587885T2 (de) * | 1984-03-21 | 1994-11-03 | Mclaughlin William F | Filtration einer flüssigen Suspension. |
JPH0255769A (ja) * | 1988-08-23 | 1990-02-26 | Univ Tohoku | 可溶性フタロシアニン錯体の製造方法 |
US4900421A (en) * | 1988-09-02 | 1990-02-13 | Purdue Research Foundation | Vortex stabilized electrophoretic separation apparatus |
US5888748A (en) * | 1995-07-13 | 1999-03-30 | Immucell Corporation | Methods and articles of manufacture for the detection of cryptosporidium occysts |
WO1999025463A1 (en) * | 1997-11-14 | 1999-05-27 | Massachusetts Institute Of Technology | Apparatus and method for treating whole blood |
US6344121B1 (en) * | 1998-11-25 | 2002-02-05 | University Of Cincinnati | Preparative chiral separations |
GB0211931D0 (en) * | 2002-05-23 | 2002-07-03 | Univ Liverpool | Methods & device utilizing adsorption of molecules at a surface or interface |
DE60322385D1 (de) * | 2002-05-30 | 2008-09-04 | Kkj Inc | Filtratonsvorrichtung und -verfahren mit verbesserten wirbeln |
WO2004037301A2 (en) * | 2002-10-24 | 2004-05-06 | Georgia Tech Research Corporation | Systems and methods for disinfection |
JP2005145887A (ja) * | 2003-11-14 | 2005-06-09 | Japan Science & Technology Agency | 鏡像異性粒子の分離装置および分離方法、並びに、分離シミュレーション方法 |
US7459121B2 (en) * | 2004-07-21 | 2008-12-02 | Florida State University Research Foundation | Method for continuous fabrication of carbon nanotube networks or membrane materials |
US7935906B2 (en) * | 2007-04-17 | 2011-05-03 | Dynamic Connections, Llc | Separation and manipulation of a chiral object |
US20130046086A1 (en) * | 2009-11-19 | 2013-02-21 | E. I. Du Pont De Nemours And Company | Method for separating carbon nanotubes |
US20140166545A1 (en) * | 2011-03-17 | 2014-06-19 | Joseph W. Lyding | Asymmetric magnetic field nanostructure separation method, device and system |
US9308172B2 (en) * | 2012-10-26 | 2016-04-12 | Board Of Trustees Of Michigan State University | Device and method for encapsulation of hydrophilic materials |
US9926201B1 (en) * | 2014-07-18 | 2018-03-27 | Iowa State University Research Foundation, Inc. | Method, apparatus, and system for producing buckypaper or similar sheet or layer of elongated nanostructures with a degree of nanostructure alignment |
WO2017003909A2 (en) * | 2015-06-29 | 2017-01-05 | Mirianas Chachisvilis | Chiral separation and analysis by molecular propeller effect |
-
2014
- 2014-08-08 EP EP14306261.0A patent/EP2982662A1/en not_active Withdrawn
-
2015
- 2015-08-07 WO PCT/EP2015/068273 patent/WO2016020532A1/en active Application Filing
- 2015-08-07 EP EP15750370.7A patent/EP3177582B1/en active Active
- 2015-08-07 US US15/501,674 patent/US10597339B2/en active Active
- 2015-08-07 JP JP2017506373A patent/JP6801845B2/ja active Active
- 2015-08-07 CN CN201580042045.8A patent/CN106660893B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
EP2982662A1 (en) | 2016-02-10 |
CN106660893A (zh) | 2017-05-10 |
EP3177582A1 (en) | 2017-06-14 |
JP2017529323A (ja) | 2017-10-05 |
US20170226027A1 (en) | 2017-08-10 |
EP3177582B1 (en) | 2018-08-29 |
CN106660893B (zh) | 2020-06-23 |
WO2016020532A1 (en) | 2016-02-11 |
US10597339B2 (en) | 2020-03-24 |
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