JP2015535252A - 電位作動型ナトリウムチャネルにおいて選択的活性を有するn−置換インダゾールスルホンアミド化合物 - Google Patents
電位作動型ナトリウムチャネルにおいて選択的活性を有するn−置換インダゾールスルホンアミド化合物 Download PDFInfo
- Publication number
- JP2015535252A JP2015535252A JP2015539755A JP2015539755A JP2015535252A JP 2015535252 A JP2015535252 A JP 2015535252A JP 2015539755 A JP2015539755 A JP 2015539755A JP 2015539755 A JP2015539755 A JP 2015539755A JP 2015535252 A JP2015535252 A JP 2015535252A
- Authority
- JP
- Japan
- Prior art keywords
- indazole
- sulfonamide
- fluoro
- alkyl
- ethyl
- 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.)
- Pending
Links
- 0 CC*(*)I1=NC=CC=C1 Chemical compound CC*(*)I1=NC=CC=C1 0.000 description 7
- QLXOJLUHWBDVKZ-UHFFFAOYSA-N Cc1ncn[s]1 Chemical compound Cc1ncn[s]1 QLXOJLUHWBDVKZ-UHFFFAOYSA-N 0.000 description 1
- RQSCFNPNNLWQBJ-UHFFFAOYSA-N Cc1nnc[s]1 Chemical compound Cc1nnc[s]1 RQSCFNPNNLWQBJ-UHFFFAOYSA-N 0.000 description 1
- YFNMRKXDKJUPQG-UHFFFAOYSA-N NC1Cc2c(C[n]3nc(cc(c(S(Nc([s]4)ncc4Cl)(=O)=O)c4)F)c4c3)cccc2CC1 Chemical compound NC1Cc2c(C[n]3nc(cc(c(S(Nc([s]4)ncc4Cl)(=O)=O)c4)F)c4c3)cccc2CC1 YFNMRKXDKJUPQG-UHFFFAOYSA-N 0.000 description 1
- PRHQVIUYALYWMF-UHFFFAOYSA-N O=S(c(c(F)c1)cc2c1[nH]nc2)(Nc(nc1)ccc1F)=O Chemical compound O=S(c(c(F)c1)cc2c1[nH]nc2)(Nc(nc1)ccc1F)=O PRHQVIUYALYWMF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261719118P | 2012-10-26 | 2012-10-26 | |
| US61/719,118 | 2012-10-26 | ||
| PCT/US2013/066360 WO2014066491A1 (en) | 2012-10-26 | 2013-10-23 | N-substituted indazole sulfonamide compounds with selective activity in voltage-gated sodium channels |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015535252A true JP2015535252A (ja) | 2015-12-10 |
| JP2015535252A5 JP2015535252A5 (enExample) | 2016-12-08 |
Family
ID=50545213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015539755A Pending JP2015535252A (ja) | 2012-10-26 | 2013-10-23 | 電位作動型ナトリウムチャネルにおいて選択的活性を有するn−置換インダゾールスルホンアミド化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9388179B2 (enExample) |
| EP (1) | EP2911663B1 (enExample) |
| JP (1) | JP2015535252A (enExample) |
| KR (1) | KR20150074123A (enExample) |
| CN (1) | CN104869992A (enExample) |
| AU (1) | AU2013334664A1 (enExample) |
| BR (1) | BR112015008987A2 (enExample) |
| CA (1) | CA2891056A1 (enExample) |
| RU (1) | RU2015119640A (enExample) |
| WO (1) | WO2014066491A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドXenon Pharmaceuticals Inc. | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| ES2586213T3 (es) | 2011-10-31 | 2016-10-13 | Xenon Pharmaceuticals Inc. | Compuestos de bencenosulfonamida y su uso como agentes terapéuticos |
| BR112014029161A2 (pt) | 2012-05-22 | 2017-06-27 | Genentech Inc | benzamidas n-substituídas e seu uso no tratamento de dor |
| BR112015000187A2 (pt) | 2012-07-06 | 2017-06-27 | Genentech Inc | benzamidas substituídas com n e métodos de uso das mesmas |
| BR112015022488A2 (pt) | 2013-03-14 | 2017-07-18 | Genentech Inc | triazolopiridinas substituídas e métodos de uso das mesmas |
| BR112015023397A2 (pt) | 2013-03-15 | 2017-07-18 | Genentech Inc | benzoxazois substituídos e métodos de uso dos mesmos |
| CR20160296A (es) | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| EP3166939B1 (en) | 2014-07-07 | 2019-06-05 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| US9783527B2 (en) * | 2014-09-16 | 2017-10-10 | Abbvie Inc. | Indazole ureas and method of use |
| US9682985B2 (en) * | 2015-03-13 | 2017-06-20 | Abbvie Inc. | (Indazol-4-yl) hexahydropyrrolopyrrolones and methods of use |
| WO2016191312A1 (en) | 2015-05-22 | 2016-12-01 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| MA42683A (fr) | 2015-08-27 | 2018-07-04 | Genentech Inc | Composés thérapeutiques et leurs méthodes utilisation |
| PE20181003A1 (es) | 2015-09-28 | 2018-06-26 | Genentech Inc | Compuestos terapeuticos y sus metodos de uso |
| CN108495851A (zh) | 2015-11-25 | 2018-09-04 | 基因泰克公司 | 取代的苯甲酰胺及其使用方法 |
| TW201726637A (zh) | 2015-12-18 | 2017-08-01 | 默沙東藥廠 | 對電位閘控鈉通道具選擇活性之羥基烷基胺-及羥基環烷基胺-取代之二胺-芳基磺胺化合物 |
| EP3854782A1 (en) | 2016-03-30 | 2021-07-28 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| KR102366077B1 (ko) | 2016-05-20 | 2022-02-21 | 제논 파마슈티칼스 인크. | 벤젠술폰아미드 화합물 및 치료제로서의 그의 용도 |
| SG11201903348UA (en) | 2016-10-17 | 2019-05-30 | Genentech Inc | Therapeutic compounds and methods of use thereof |
| KR20190086772A (ko) | 2016-12-09 | 2019-07-23 | 제논 파마슈티칼스 인크. | 벤젠술폰아미드 화합물 및 치료제로서의 그의 용도 |
| WO2018175707A1 (en) | 2017-03-24 | 2018-09-27 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
| CN107247885B (zh) * | 2017-07-06 | 2020-07-03 | 中国水产科学研究院黄海水产研究所 | 一种电压-门控钠离子通道的结构预测方法 |
| EP3759098A1 (en) | 2018-02-26 | 2021-01-06 | Genentech, Inc. | Pyridine-sulfonamide compounds and their use against pain and related conditions |
| EP3774801A1 (en) | 2018-03-30 | 2021-02-17 | F. Hoffmann-La Roche AG | Fused ring hydro-pyrido compounds as sodium channel inhibitors |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| BR112020024729A2 (pt) | 2018-06-13 | 2021-03-23 | Xenon Pharmaceuticals, Inc. | compostos de benzenossulfonamida e seu uso como agentes terapêuticos |
| CA3104913A1 (en) | 2018-08-31 | 2020-03-05 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors |
| IL279810B2 (en) | 2018-08-31 | 2025-03-01 | Xenon Pharmaceuticals Inc | Heteroaryl-modified sulfonamide compounds and their use as medicinal agents |
| WO2020192553A1 (zh) * | 2019-03-22 | 2020-10-01 | 上海海雁医药科技有限公司 | 磺酰基取代的苯并杂环甲酰胺衍生物、其制法与医药上的用途 |
| AU2020392128A1 (en) | 2019-11-27 | 2022-06-09 | Praxis Precision Medicines, Inc. | Formulations of ion channel modulators and methods of preparation and use of ion channel modulators |
| KR20240159579A (ko) | 2022-02-14 | 2024-11-05 | 어레이즈 테라퓨틱스 인크. | Parg 억제제 |
| WO2023186058A1 (zh) * | 2022-03-31 | 2023-10-05 | 江苏恒瑞医药股份有限公司 | 吲唑类化合物、其制备方法及其在医药上的应用 |
| CA3250706A1 (en) | 2022-04-26 | 2023-11-02 | Praxis Precision Medicines, Inc. | TREATMENT OF NEUROLOGICAL DISORDERS |
| WO2024173234A1 (en) * | 2023-02-13 | 2024-08-22 | Arase Therapeutics Inc. | Inhibitors of parg |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008519833A (ja) * | 2004-11-11 | 2008-06-12 | アストラゼネカ・アクチエボラーグ | インダゾールスルホンアミド誘導体 |
| JP2008540539A (ja) * | 2005-05-10 | 2008-11-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャンネルの調節因子としての二環系誘導体 |
| WO2010047990A1 (en) * | 2008-10-23 | 2010-04-29 | Merck Sharp & Dohme Corp. | Fused heterocyclic m1 receptor positive allosteric modulators |
| JP2010533652A (ja) * | 2007-07-13 | 2010-10-28 | アイカジェン, インコーポレイテッド | ナトリウムチャネル阻害物質 |
| WO2012004743A1 (en) * | 2010-07-09 | 2012-01-12 | Pfizer Limited | Benzenesulfonamides useful as sodium channel inhibitors |
| WO2012095781A1 (en) * | 2011-01-13 | 2012-07-19 | Pfizer Limited | Indazole derivatives as sodium channel inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3705185A (en) | 1969-04-14 | 1972-12-05 | Minnesota Mining & Mfg | N-aroyl sulfonamides |
| US4136256A (en) | 1977-09-27 | 1979-01-23 | American Cyanamid Company | 4-(monoalkylamino)benzoic acid imidates |
| US4242273A (en) | 1977-09-27 | 1980-12-30 | American Cyanamid Company | 4-(Monoalkylamino)benzoic acid amides and imidates |
| US4309553A (en) | 1977-09-27 | 1982-01-05 | American Cyanamid Company | Aldehydes and ketones containing a 4-(monoalkylamino)-benzoyl substituent |
| US4254138A (en) | 1977-12-19 | 1981-03-03 | American Cyanamid Company | Esters of 4-(monoalkylamino)benzoic hydroxyalkanoic acids |
| US4272546A (en) | 1977-12-19 | 1981-06-09 | American Cyanamid Company | Esters of 4-(monoalkylamino)benzoic hydroxyalkanoic acids |
| US4245097A (en) | 1978-02-27 | 1981-01-13 | American Cyanamid Company | 4-[(Monosubstituted-alkyl) amino] benzoic acids and analogs as hypolipidemic and antiatherosclerotic agents |
| US4227014A (en) | 1978-02-27 | 1980-10-07 | American Cyanamid Company | 4-[(Cycloalkyl or cycloalkenyl substituted)amino, alkylamino or alkenylamino]benzoic acids and salts thereof |
| US4243609A (en) | 1978-02-02 | 1981-01-06 | American Cyanamid Company | Ring-fluorinated 4-(hexadecyl-amino) N-substituted benzamide compounds |
| US4230628A (en) | 1978-04-12 | 1980-10-28 | American Cyanamid Company | 4-[(Carboxyl- and sulfamyl-substituted alkyl)-amino] benzoic acids and analogs |
| US4211783A (en) | 1978-03-20 | 1980-07-08 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic novel 4-(aralkyl- and heteroarylalkylamino)phenyl compounds |
| US4205085A (en) | 1978-03-09 | 1980-05-27 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoroalkylamino)phenyl compounds |
| US4230878A (en) | 1978-03-08 | 1980-10-28 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-[(cyclopropyl alkyl)amino]benzoic acids and derivatives |
| US4305959A (en) | 1978-03-09 | 1981-12-15 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoro-alkylamino)phenyl compounds |
| US4310545A (en) | 1978-03-09 | 1982-01-12 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoroalkylamino) phenyl compounds |
| US4318914A (en) | 1978-03-09 | 1982-03-09 | American Cyanamid Company | Hypolipidemic and antiatherosclerotic 4-(polyfluoro-alkylamino)phenyl compounds |
| US4485105A (en) | 1978-10-12 | 1984-11-27 | American Cyanamid Company | Method of treating hyperlipidemia with 4-(monoalkylamino)benzoic acid amides |
| DK471479A (da) | 1978-12-13 | 1980-06-14 | Pfizer | Fremgangsmaade til fremstilling af imidazolderivater og salte deraf |
| US4670421A (en) | 1982-07-12 | 1987-06-02 | American Cyanamid Company | Antiatherosclerotic silanes |
| JP4316787B2 (ja) | 2000-01-11 | 2009-08-19 | 壽製薬株式会社 | エーテル又はアミド誘導体、その製法並びにそれを含有する糖尿病治療剤、 |
| HUE025013T2 (hu) | 2009-01-12 | 2016-04-28 | Pfizer Ltd | Szulfonamid-származékok |
| JP5860045B2 (ja) | 2010-07-09 | 2016-02-16 | ファイザー・リミテッドPfizer Limited | 化合物 |
| JP5872552B2 (ja) | 2010-07-09 | 2016-03-01 | ファイザー・リミテッドPfizer Limited | 化学化合物 |
| JP2013531030A (ja) | 2010-07-12 | 2013-08-01 | ファイザー・リミテッド | 電位開口型ナトリウムチャネルの阻害剤としてのn−スルホニルベンズアミド |
| WO2012007883A1 (en) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Sulfonamide derivatives as nav1.7 inhibitors for the treatment of pain |
| ES2526541T3 (es) | 2010-07-12 | 2015-01-13 | Pfizer Limited | N-sulfonilbenzamidas como inhibidores de canales de sodio dependientes de voltaje |
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| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドXenon Pharmaceuticals Inc. | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| ES2586213T3 (es) | 2011-10-31 | 2016-10-13 | Xenon Pharmaceuticals Inc. | Compuestos de bencenosulfonamida y su uso como agentes terapéuticos |
| EP2788332A1 (en) | 2011-12-07 | 2014-10-15 | Amgen, Inc. | Bicyclic aryl and heteroaryl sodium channel inhibitors |
| WO2013134518A1 (en) | 2012-03-09 | 2013-09-12 | Amgen Inc. | Sulfamide sodium channel inhibitors |
-
2013
- 2013-10-23 US US14/437,142 patent/US9388179B2/en active Active
- 2013-10-23 AU AU2013334664A patent/AU2013334664A1/en not_active Abandoned
- 2013-10-23 JP JP2015539755A patent/JP2015535252A/ja active Pending
- 2013-10-23 KR KR1020157013297A patent/KR20150074123A/ko not_active Withdrawn
- 2013-10-23 EP EP13849733.4A patent/EP2911663B1/en active Active
- 2013-10-23 BR BR112015008987A patent/BR112015008987A2/pt not_active IP Right Cessation
- 2013-10-23 CA CA2891056A patent/CA2891056A1/en not_active Abandoned
- 2013-10-23 CN CN201380068064.9A patent/CN104869992A/zh active Pending
- 2013-10-23 RU RU2015119640A patent/RU2015119640A/ru not_active Application Discontinuation
- 2013-10-23 WO PCT/US2013/066360 patent/WO2014066491A1/en not_active Ceased
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008519833A (ja) * | 2004-11-11 | 2008-06-12 | アストラゼネカ・アクチエボラーグ | インダゾールスルホンアミド誘導体 |
| JP2008540539A (ja) * | 2005-05-10 | 2008-11-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャンネルの調節因子としての二環系誘導体 |
| JP2010533652A (ja) * | 2007-07-13 | 2010-10-28 | アイカジェン, インコーポレイテッド | ナトリウムチャネル阻害物質 |
| WO2010047990A1 (en) * | 2008-10-23 | 2010-04-29 | Merck Sharp & Dohme Corp. | Fused heterocyclic m1 receptor positive allosteric modulators |
| WO2012004743A1 (en) * | 2010-07-09 | 2012-01-12 | Pfizer Limited | Benzenesulfonamides useful as sodium channel inhibitors |
| WO2012095781A1 (en) * | 2011-01-13 | 2012-07-19 | Pfizer Limited | Indazole derivatives as sodium channel inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2911663B1 (en) | 2020-03-18 |
| US20150284389A1 (en) | 2015-10-08 |
| RU2015119640A (ru) | 2016-12-20 |
| EP2911663A4 (en) | 2016-04-13 |
| AU2013334664A1 (en) | 2015-05-07 |
| CA2891056A1 (en) | 2014-05-01 |
| KR20150074123A (ko) | 2015-07-01 |
| CN104869992A (zh) | 2015-08-26 |
| BR112015008987A2 (pt) | 2017-07-04 |
| US9388179B2 (en) | 2016-07-12 |
| EP2911663A1 (en) | 2015-09-02 |
| WO2014066491A1 (en) | 2014-05-01 |
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