JP6180705B2 - ハロゲン化環式化合物の合成方法 - Google Patents
ハロゲン化環式化合物の合成方法 Download PDFInfo
- Publication number
- JP6180705B2 JP6180705B2 JP2011529509A JP2011529509A JP6180705B2 JP 6180705 B2 JP6180705 B2 JP 6180705B2 JP 2011529509 A JP2011529509 A JP 2011529509A JP 2011529509 A JP2011529509 A JP 2011529509A JP 6180705 B2 JP6180705 B2 JP 6180705B2
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- JP
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- Prior art keywords
- formula
- compound
- alkyl group
- addition product
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- 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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- 0 FC(C1=N*CC=C1)(F)F Chemical compound FC(C1=N*CC=C1)(F)F 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08165547 | 2008-09-30 | ||
| EP08165547.4 | 2008-09-30 | ||
| PCT/EP2009/062462 WO2010037688A1 (en) | 2008-09-30 | 2009-09-25 | Process for the synthesis of halogenated cyclic compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015125708A Division JP6511346B2 (ja) | 2008-09-30 | 2015-06-23 | ハロゲン化環式化合物の合成方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012504153A JP2012504153A (ja) | 2012-02-16 |
| JP2012504153A5 JP2012504153A5 (https=) | 2012-10-11 |
| JP6180705B2 true JP6180705B2 (ja) | 2017-08-16 |
Family
ID=40351699
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011529509A Active JP6180705B2 (ja) | 2008-09-30 | 2009-09-25 | ハロゲン化環式化合物の合成方法 |
| JP2015125708A Expired - Fee Related JP6511346B2 (ja) | 2008-09-30 | 2015-06-23 | ハロゲン化環式化合物の合成方法 |
| JP2017225725A Active JP6647268B2 (ja) | 2008-09-30 | 2017-11-24 | ハロゲン化環式化合物の合成方法 |
| JP2019186868A Pending JP2020023533A (ja) | 2008-09-30 | 2019-10-10 | ハロゲン化環式化合物の合成方法 |
| JP2021184880A Pending JP2022028792A (ja) | 2008-09-30 | 2021-11-12 | ハロゲン化環式化合物の合成方法 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015125708A Expired - Fee Related JP6511346B2 (ja) | 2008-09-30 | 2015-06-23 | ハロゲン化環式化合物の合成方法 |
| JP2017225725A Active JP6647268B2 (ja) | 2008-09-30 | 2017-11-24 | ハロゲン化環式化合物の合成方法 |
| JP2019186868A Pending JP2020023533A (ja) | 2008-09-30 | 2019-10-10 | ハロゲン化環式化合物の合成方法 |
| JP2021184880A Pending JP2022028792A (ja) | 2008-09-30 | 2021-11-12 | ハロゲン化環式化合物の合成方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8431710B2 (https=) |
| EP (1) | EP2334645B1 (https=) |
| JP (5) | JP6180705B2 (https=) |
| KR (3) | KR20190080972A (https=) |
| CN (2) | CN106083710B (https=) |
| CA (1) | CA2735921C (https=) |
| WO (1) | WO2010037688A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018058869A (ja) * | 2008-09-30 | 2018-04-12 | ソルヴェイ(ソシエテ アノニム) | ハロゲン化環式化合物の合成方法 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010000871A2 (en) | 2008-07-04 | 2010-01-07 | Solvay Sa | Process for the manufacture of alkenones |
| GB0903749D0 (en) * | 2009-03-04 | 2009-04-15 | Syngenta Participations Ag | Chemical process |
| US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
| MX2012000379A (es) | 2009-07-06 | 2012-03-07 | Solvay | Proceso para la fabricacion de precursores halogenados de alquenonas en presencia de un solvente. |
| EP2662359A1 (en) | 2012-05-08 | 2013-11-13 | Solvay Sa | Ionic Liquids, Method for manufacturing thereof, and Electrochemical Devices Comprising the Same |
| US9365480B2 (en) * | 2012-08-22 | 2016-06-14 | Solvay Sa | Process for the manufacture of alkenones |
| EP2936607B1 (en) | 2012-12-20 | 2017-02-22 | Solvay SA | Salts of n-containing heterocyclic anions as components in electrolytes |
| US20160137624A1 (en) * | 2013-06-20 | 2016-05-19 | Basf Se | Process for preparing pyridylpyrazole compounds and derivatives thereof from pyridylhydrazine |
| EP2987782A1 (en) | 2014-08-22 | 2016-02-24 | Solvay SA | Distillation process comprising at least two distillation steps to obtain purified halogenated carboxylic acid halide, and use of the purified halogenated carboxylic acid halide |
| WO2016079122A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | A method for producing a chemical compound and apparatus therefor |
| JP2017533941A (ja) | 2014-11-17 | 2017-11-16 | ソルヴェイ(ソシエテ アノニム) | 精製ハロゲン化カルボン酸ハロゲン化物を得るための少なくとも2つの蒸留ステップを含む蒸留プロセス、および精製ハロゲン化カルボン酸ハロゲン化物の使用 |
| EP3031791A1 (en) | 2014-12-10 | 2016-06-15 | Solvay SA | Halogenation process of 1,1-dihaloethene |
| EP3199522A1 (en) | 2016-02-01 | 2017-08-02 | Solvay SA | Aminothioate derivatives, production thereof and use |
| JP2020532524A (ja) | 2017-09-04 | 2020-11-12 | ソルヴェイ(ソシエテ アノニム) | ジフルオロアセチルクロリドの製造方法及び製造中間体 |
| JP6911143B2 (ja) | 2018-11-07 | 2021-07-28 | 福建永晶科技股▲ふん▼有限公司Fujian Yongjing Technology Co., Ltd | ピラゾール又はピリミジノンの新しい製造方法 |
| EP3902786B1 (en) * | 2018-12-27 | 2022-12-14 | Corteva Agriscience LLC | Preparation of sulfonamide herbicide process intermediates |
| WO2021152055A1 (en) | 2020-01-31 | 2021-08-05 | Solvay Sa | Process for the manufacture of haloalkyl substituted pyridine compounds |
| JP2021079146A (ja) * | 2021-02-22 | 2021-05-27 | 株式会社三洋物産 | 遊技機 |
| JP7315071B2 (ja) * | 2021-03-03 | 2023-07-26 | 株式会社三洋物産 | 遊技機 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3420166A1 (de) | 1984-05-30 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | Pyrimidylphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| DE69230335T2 (de) | 1991-03-07 | 2000-05-11 | E.I. Du Pont De Nemours & Co., Inc. | Herbizide pyridin-sulfonamide |
| US5235060A (en) * | 1991-07-11 | 1993-08-10 | E. I. Du Pont De Nemours And Company | Certain three component ionic substituted pyridine compounds as intermediates for preparation as herbicides |
| DE4128828A1 (de) | 1991-08-30 | 1993-03-04 | Basf Ag | Ammonium- oder harnstoffhaltige duengemittel und verfahren zu ihrer herstellung |
| AU5150393A (en) | 1992-10-13 | 1994-05-09 | Smithkline Beecham Plc | Heterocyclic -esters or -amides used as 5-ht4 receptor antagonists |
| EP0659729B1 (de) | 1993-12-23 | 1998-06-24 | Solvay Fluor und Derivate GmbH | Verfahren zur Herstellung von Polyfluorchlor- und Perfluorcarbonsäurechloriden unter Chlorzusatz |
| JP3843152B2 (ja) * | 1995-08-08 | 2006-11-08 | 石原産業株式会社 | 4−アルコキシ−1,1,1−トリフルオロ−3−ブテン−2−オンの製造方法 |
| GB2305174A (en) * | 1995-09-15 | 1997-04-02 | Zeneca Ltd | Chemical process |
| GB9711114D0 (en) * | 1997-05-29 | 1997-07-23 | Merck Sharp & Dohme | Therapeutic agents |
| DE19821088A1 (de) | 1998-05-12 | 1999-11-18 | Basf Ag | Modifizierte Polykondensate der Asparaginsäure, Verfahren zu ihrer Herstellung und ihre Verwendung in Düngemitteln |
| AU2002235247A1 (en) | 2000-12-29 | 2002-07-16 | Honeywell International, Inc. | Halogenated-alpha,beta-unsaturated-beta-(substituted-amino) carboxylate esters |
| CN100357273C (zh) | 2003-03-07 | 2007-12-26 | 辛根塔参与股份公司 | 取代的烟酸酯的制备方法 |
| DE10325715A1 (de) * | 2003-06-06 | 2004-12-23 | Solvay Fluor Und Derivate Gmbh | Vereinfachte Herstellung von Alkenonen |
| US20060128702A1 (en) | 2004-11-23 | 2006-06-15 | Manojit Pal | Heterocyclic and bicyclic compounds, compositions and methods |
| DE102004061593A1 (de) | 2004-12-21 | 2006-06-22 | Abbott Gmbh & Co. Kg | Substituierte N-heterocyclische Verbindungen und ihre therapeutische Verwendung |
| BRPI0616463A2 (pt) | 2005-09-29 | 2011-06-21 | Merck & Co Inc | composto, composição farmacêutica, e, uso de um composto |
| WO2007088876A1 (ja) * | 2006-02-02 | 2007-08-09 | Kumiai Chemical Industry Co., Ltd. | ピリドン誘導体及び除草剤 |
| EP2422790A1 (en) * | 2007-02-09 | 2012-02-29 | Emory University | Paramyxovirus family inhibitors and methods of use thereof |
| EP1987717A1 (de) | 2007-04-30 | 2008-11-05 | Bayer CropScience AG | Pyridoncarboxamide, diese enthaltende nutzpflanzenschützende Mittel und Verfahren zu ihrer Herstellung und deren Verwendung |
| EP2008996A1 (en) | 2007-06-27 | 2008-12-31 | Syngeta Participations AG | Process for the production of pyrazoles |
| BRPI0915365B8 (pt) | 2008-07-01 | 2022-06-28 | Dow Agrosciences Llc | Processo para a preparação de 2-triflúor-metil-5-alquil-piridinas substituídas na posição 1 |
| WO2010000871A2 (en) | 2008-07-04 | 2010-01-07 | Solvay Sa | Process for the manufacture of alkenones |
| EP2154167A1 (de) * | 2008-07-30 | 2010-02-17 | Bayer MaterialScience AG | Elektromechanischer Wandler mit einem Polymerelement auf Polyisocyanat-Basis |
| US8431710B2 (en) * | 2008-09-30 | 2013-04-30 | Solvay Sa | Process for the synthesis of halogenated cyclic compounds |
| KR101782175B1 (ko) | 2009-07-06 | 2017-09-26 | 솔베이(소시에떼아노님) | 알케논의 제조 방법 |
| MX2012000379A (es) | 2009-07-06 | 2012-03-07 | Solvay | Proceso para la fabricacion de precursores halogenados de alquenonas en presencia de un solvente. |
| AU2010270359A1 (en) | 2009-07-06 | 2012-02-02 | Solvay Sa | Process for the manufacture of halogenated precursors of alkenones under specific conditions |
| JP6194245B2 (ja) * | 2013-12-27 | 2017-09-06 | 株式会社Subaru | 信号機認識装置 |
-
2009
- 2009-09-25 US US13/120,505 patent/US8431710B2/en not_active Expired - Fee Related
- 2009-09-25 CN CN201610380671.4A patent/CN106083710B/zh active Active
- 2009-09-25 JP JP2011529509A patent/JP6180705B2/ja active Active
- 2009-09-25 EP EP09783436.0A patent/EP2334645B1/en active Active
- 2009-09-25 WO PCT/EP2009/062462 patent/WO2010037688A1/en not_active Ceased
- 2009-09-25 KR KR1020197018768A patent/KR20190080972A/ko not_active Ceased
- 2009-09-25 KR KR1020117009786A patent/KR20110066201A/ko not_active Ceased
- 2009-09-25 CN CN2009801384364A patent/CN102164898A/zh active Pending
- 2009-09-25 CA CA2735921A patent/CA2735921C/en not_active Expired - Fee Related
- 2009-09-25 KR KR1020167031136A patent/KR20160131129A/ko not_active Ceased
-
2013
- 2013-04-29 US US13/872,860 patent/US8981115B2/en not_active Expired - Fee Related
-
2015
- 2015-06-23 JP JP2015125708A patent/JP6511346B2/ja not_active Expired - Fee Related
-
2017
- 2017-11-24 JP JP2017225725A patent/JP6647268B2/ja active Active
-
2019
- 2019-10-10 JP JP2019186868A patent/JP2020023533A/ja active Pending
-
2021
- 2021-11-12 JP JP2021184880A patent/JP2022028792A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018058869A (ja) * | 2008-09-30 | 2018-04-12 | ソルヴェイ(ソシエテ アノニム) | ハロゲン化環式化合物の合成方法 |
| JP2020023533A (ja) * | 2008-09-30 | 2020-02-13 | ソルヴェイ(ソシエテ アノニム) | ハロゲン化環式化合物の合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102164898A (zh) | 2011-08-24 |
| US8431710B2 (en) | 2013-04-30 |
| US8981115B2 (en) | 2015-03-17 |
| JP6511346B2 (ja) | 2019-05-15 |
| EP2334645A1 (en) | 2011-06-22 |
| KR20160131129A (ko) | 2016-11-15 |
| US20130237710A1 (en) | 2013-09-12 |
| JP2012504153A (ja) | 2012-02-16 |
| CN106083710A (zh) | 2016-11-09 |
| CN106083710B (zh) | 2021-03-12 |
| CA2735921C (en) | 2017-03-21 |
| US20110178297A1 (en) | 2011-07-21 |
| EP2334645B1 (en) | 2019-11-06 |
| JP2018058869A (ja) | 2018-04-12 |
| WO2010037688A1 (en) | 2010-04-08 |
| JP2022028792A (ja) | 2022-02-16 |
| KR20190080972A (ko) | 2019-07-08 |
| JP2015227339A (ja) | 2015-12-17 |
| CA2735921A1 (en) | 2010-04-08 |
| KR20110066201A (ko) | 2011-06-16 |
| JP2020023533A (ja) | 2020-02-13 |
| JP6647268B2 (ja) | 2020-02-14 |
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