JP6067725B2 - Fgfrキナーゼモジュレーターとしてのキノリン - Google Patents
Fgfrキナーゼモジュレーターとしてのキノリン Download PDFInfo
- Publication number
- JP6067725B2 JP6067725B2 JP2014537724A JP2014537724A JP6067725B2 JP 6067725 B2 JP6067725 B2 JP 6067725B2 JP 2014537724 A JP2014537724 A JP 2014537724A JP 2014537724 A JP2014537724 A JP 2014537724A JP 6067725 B2 JP6067725 B2 JP 6067725B2
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- alkyl
- substituted
- cancer
- formula
- compound
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- 0 CC=CC=C(*N*)C=CC Chemical compound CC=CC=C(*N*)C=CC 0.000 description 9
- LUEJLLPHHIRCHZ-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CC=C1c1cc(cc(cc2)N)c2nc1)=O Chemical compound CC(C)(C)OC(N(CC1)CC=C1c1cc(cc(cc2)N)c2nc1)=O LUEJLLPHHIRCHZ-UHFFFAOYSA-N 0.000 description 1
- OQSNYFGJJQIIQC-UHFFFAOYSA-N CC(C)NCCN(c(cc1)cc2c1ncc(-c1c[n](C)nc1)c2)c1cc(OC)cc(OC)c1F Chemical compound CC(C)NCCN(c(cc1)cc2c1ncc(-c1c[n](C)nc1)c2)c1cc(OC)cc(OC)c1F OQSNYFGJJQIIQC-UHFFFAOYSA-N 0.000 description 1
- FUGPFOLVQHEHIR-UHFFFAOYSA-N CC(C)NCCN(c1ccc2ncc(-c3c[n](C4OCCCC4)nc3)cc2c1)c1cc(OC)cc(OC)c1 Chemical compound CC(C)NCCN(c1ccc2ncc(-c3c[n](C4OCCCC4)nc3)cc2c1)c1cc(OC)cc(OC)c1 FUGPFOLVQHEHIR-UHFFFAOYSA-N 0.000 description 1
- LNIQDISDLPPVRW-UHFFFAOYSA-N COc1cc(OC)cc(N(CCO)c(cc2)cc3c2ncc(-c2ccccc2)c3)c1 Chemical compound COc1cc(OC)cc(N(CCO)c(cc2)cc3c2ncc(-c2ccccc2)c3)c1 LNIQDISDLPPVRW-UHFFFAOYSA-N 0.000 description 1
- HDUSFDPVRUFAKP-UHFFFAOYSA-N COc1cc(OC)cc(N(Cc2ncc[nH]2)c2cc3cc(C4CCNCC4)cnc3cc2)c1 Chemical compound COc1cc(OC)cc(N(Cc2ncc[nH]2)c2cc3cc(C4CCNCC4)cnc3cc2)c1 HDUSFDPVRUFAKP-UHFFFAOYSA-N 0.000 description 1
- FHDFIWPSZWQWRO-UHFFFAOYSA-N COc1ccnc(N2CC(CO)CC2)n1 Chemical compound COc1ccnc(N2CC(CO)CC2)n1 FHDFIWPSZWQWRO-UHFFFAOYSA-N 0.000 description 1
- NOYGZPRZBHMEBB-UHFFFAOYSA-N C[n](cc1)cc1-c1cnc(ccc([N+]([O-])=O)c2)c2c1 Chemical compound C[n](cc1)cc1-c1cnc(ccc([N+]([O-])=O)c2)c2c1 NOYGZPRZBHMEBB-UHFFFAOYSA-N 0.000 description 1
- AFROKUMWVBXWIB-UHFFFAOYSA-N C[n]1ncc(-c2cc(cc(C(CCO)c3cc(OC)cc(OC)c3)cc3)c3nc2)c1 Chemical compound C[n]1ncc(-c2cc(cc(C(CCO)c3cc(OC)cc(OC)c3)cc3)c3nc2)c1 AFROKUMWVBXWIB-UHFFFAOYSA-N 0.000 description 1
- BSLJXDGIIBJJOD-UHFFFAOYSA-N C[n]1ncc(-c2cc(cc(cc3)Nc(c(F)c(cc4OC)OC)c4F)c3nc2)c1 Chemical compound C[n]1ncc(-c2cc(cc(cc3)Nc(c(F)c(cc4OC)OC)c4F)c3nc2)c1 BSLJXDGIIBJJOD-UHFFFAOYSA-N 0.000 description 1
- XPXWYVCQCNFIIJ-UHFFFAOYSA-N Cc1nnc(N)[o]1 Chemical compound Cc1nnc(N)[o]1 XPXWYVCQCNFIIJ-UHFFFAOYSA-N 0.000 description 1
- ROMYKZIUOIXCRR-UHFFFAOYSA-N [O-][N+](c1cc(Br)c2ncccc2c1)=O Chemical compound [O-][N+](c1cc(Br)c2ncccc2c1)=O ROMYKZIUOIXCRR-UHFFFAOYSA-N 0.000 description 1
- DWXUBYDSYWIVHM-UHFFFAOYSA-N [O-][N+](c1cc2cc(-c3ccncc3)cnc2cc1)=O Chemical compound [O-][N+](c1cc2cc(-c3ccncc3)cnc2cc1)=O DWXUBYDSYWIVHM-UHFFFAOYSA-N 0.000 description 1
- XIGQUURJVUSYBF-UHFFFAOYSA-N [O-][N+](c1cc2cc(Br)cnc2cc1)=O Chemical compound [O-][N+](c1cc2cc(Br)cnc2cc1)=O XIGQUURJVUSYBF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161552880P | 2011-10-28 | 2011-10-28 | |
| GB1118652.5 | 2011-10-28 | ||
| GBGB1118652.5A GB201118652D0 (en) | 2011-10-28 | 2011-10-28 | New compounds |
| US61/552,880 | 2011-10-28 | ||
| PCT/GB2012/052666 WO2013061074A1 (en) | 2011-10-28 | 2012-10-26 | Quinolines as fgfr kinase modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014530896A JP2014530896A (ja) | 2014-11-20 |
| JP2014530896A5 JP2014530896A5 (enExample) | 2015-12-17 |
| JP6067725B2 true JP6067725B2 (ja) | 2017-01-25 |
Family
ID=45373580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014537724A Active JP6067725B2 (ja) | 2011-10-28 | 2012-10-26 | Fgfrキナーゼモジュレーターとしてのキノリン |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US9439896B2 (enExample) |
| EP (1) | EP2776397B1 (enExample) |
| JP (1) | JP6067725B2 (enExample) |
| KR (1) | KR102072869B1 (enExample) |
| CN (1) | CN104011025B (enExample) |
| AU (1) | AU2012328164B2 (enExample) |
| BR (1) | BR112014010177B1 (enExample) |
| CA (1) | CA2853366C (enExample) |
| DK (1) | DK2776397T3 (enExample) |
| ES (1) | ES2661003T3 (enExample) |
| GB (1) | GB201118652D0 (enExample) |
| HU (1) | HUE037458T2 (enExample) |
| IN (1) | IN2014MN00988A (enExample) |
| MX (1) | MX353806B (enExample) |
| RU (1) | RU2625303C2 (enExample) |
| WO (1) | WO2013061074A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| GB201118656D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118654D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201209609D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201209613D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| EP2909189B8 (en) | 2012-10-16 | 2017-04-19 | Janssen Pharmaceutica NV | Heteroaryl linked quinolinyl modulators of ror-gamma-t |
| TWI606045B (zh) | 2012-10-16 | 2017-11-21 | 健生藥品公司 | RORγt之亞甲基聯結的喹啉基調節劑 |
| WO2014062667A1 (en) | 2012-10-16 | 2014-04-24 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of ror-gamma-t |
| AR094812A1 (es) | 2013-02-20 | 2015-08-26 | Eisai R&D Man Co Ltd | Derivado de piridina monocíclico como inhibidor del fgfr |
| GB201307577D0 (en) | 2013-04-26 | 2013-06-12 | Astex Therapeutics Ltd | New compounds |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| WO2015057629A1 (en) * | 2013-10-15 | 2015-04-23 | Janssen Pharmaceutica Nv | ALKYL LINKED QUINOLINYL MODULATORS OF RORyt |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| WO2015057206A1 (en) * | 2013-10-15 | 2015-04-23 | Janssen Pharmaceutica Nv | SECONDARY ALCOHOL QUINOLINYL MODULATORS OF RORyt |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| EP3057422B1 (en) | 2013-10-15 | 2019-05-15 | Janssen Pharmaceutica NV | Quinolinyl modulators of ror(gamma)t |
| KR102479696B1 (ko) | 2014-03-26 | 2022-12-22 | 아스텍스 테라퓨틱스 리미티드 | Fgfr 억제제 및 igf1r 억제제의 조합물 |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| HUE053654T2 (hu) | 2014-03-26 | 2021-07-28 | Astex Therapeutics Ltd | FGFR- és CMET-inhibitorok kombinációi a rák kezelésére |
| BR112017002268B1 (pt) | 2014-08-18 | 2022-11-08 | Eisai R&D Management Co., Ltd | Sal de derivado de piridina monocíclica e cristal do mesmo |
| JOP20200201A1 (ar) | 2015-02-10 | 2017-06-16 | Astex Therapeutics Ltd | تركيبات صيدلانية تشتمل على n-(3.5- ثنائي ميثوكسي فينيل)-n'-(1-ميثيل إيثيل)-n-[3-(ميثيل-1h-بيرازول-4-يل) كينوكسالين-6-يل]إيثان-1.2-ثنائي الأمين |
| RU2712222C2 (ru) | 2015-03-25 | 2020-01-27 | Нэшнл Кэнсер Сентер | Терапевтическое средство против рака желчных протоков |
| US10478494B2 (en) | 2015-04-03 | 2019-11-19 | Astex Therapeutics Ltd | FGFR/PD-1 combination therapy for the treatment of cancer |
| CA2996857C (en) * | 2015-09-23 | 2024-05-21 | Janssen Pharmaceutica Nv | Quinoxaline, quinoline and quinazolinone derivative compounds for the treatment of cancer |
| EP3353164B1 (en) * | 2015-09-23 | 2021-11-03 | Janssen Pharmaceutica, N.V. | Bi-heteroaryl substituted 1,4-benzodiazepines and uses thereof for the treatment of cancer |
| WO2017104739A1 (ja) | 2015-12-17 | 2017-06-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 乳がん治療剤 |
| CN108264510A (zh) * | 2017-01-02 | 2018-07-10 | 上海喆邺生物科技有限公司 | 一种选择性抑制激酶化合物及其用途 |
| BR112020017922A2 (pt) | 2018-03-28 | 2020-12-22 | Eisai R&D Management Co., Ltd. | Agente terapêutico para carcinoma hepatocelular |
| CN113087696A (zh) * | 2019-12-23 | 2021-07-09 | 江苏开元药业有限公司 | 喹啉类化合物及其应用 |
| JP2023512482A (ja) * | 2020-01-17 | 2023-03-27 | ベータ・ファーマ・インコーポレイテッド | Fgfrキナーゼ阻害剤としてのピリダジンおよび1,2,4-トリアジン誘導体 |
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| WO2000042026A1 (en) | 1999-01-15 | 2000-07-20 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
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| US10039759B2 (en) | 2018-08-07 |
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| US20170000781A1 (en) | 2017-01-05 |
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| EP2776397B1 (en) | 2017-11-29 |
| AU2012328164A1 (en) | 2014-05-15 |
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| BR112014010177A2 (pt) | 2017-04-25 |
| US20140296236A1 (en) | 2014-10-02 |
| CN104011025B (zh) | 2017-04-05 |
| RU2014121494A (ru) | 2015-12-10 |
| AU2012328164B2 (en) | 2017-08-03 |
| MX2014004857A (es) | 2014-08-26 |
| GB201118652D0 (en) | 2011-12-07 |
| US9439896B2 (en) | 2016-09-13 |
| BR112014010177B1 (pt) | 2023-01-31 |
| EP2776397A1 (en) | 2014-09-17 |
| WO2013061074A1 (en) | 2013-05-02 |
| ES2661003T3 (es) | 2018-03-27 |
| HUE037458T2 (hu) | 2018-09-28 |
| CA2853366C (en) | 2021-04-20 |
| CN104011025A (zh) | 2014-08-27 |
| KR102072869B1 (ko) | 2020-03-02 |
| RU2625303C2 (ru) | 2017-07-13 |
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