CA2940918C - Substituted 4,5,6,7-tetrahydro-pyrazolo[1,5-.alpha.]pyrazine derivatives and 5,6,7,8-tetrahydro-4h-pyrazolo[1,5-.alpha.][1,4]diazepine derivatives as ros1 inhibitors - Google Patents
Substituted 4,5,6,7-tetrahydro-pyrazolo[1,5-.alpha.]pyrazine derivatives and 5,6,7,8-tetrahydro-4h-pyrazolo[1,5-.alpha.][1,4]diazepine derivatives as ros1 inhibitors Download PDFInfo
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- CA2940918C CA2940918C CA2940918A CA2940918A CA2940918C CA 2940918 C CA2940918 C CA 2940918C CA 2940918 A CA2940918 A CA 2940918A CA 2940918 A CA2940918 A CA 2940918A CA 2940918 C CA2940918 C CA 2940918C
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- substituted
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- cyano
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- 239000003112 inhibitor Substances 0.000 title abstract description 18
- 101100091501 Mus musculus Ros1 gene Proteins 0.000 title abstract 2
- 150000003216 pyrazines Chemical class 0.000 title abstract 2
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical class N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 281
- 239000003814 drug Substances 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 257
- 239000001257 hydrogen Substances 0.000 claims description 256
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 226
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 133
- 125000001424 substituent group Chemical group 0.000 claims description 132
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 129
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 116
- 150000003839 salts Chemical class 0.000 claims description 111
- 150000001204 N-oxides Chemical class 0.000 claims description 99
- 239000012453 solvate Substances 0.000 claims description 99
- -1 -CH2OH Chemical group 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 65
- 125000000623 heterocyclic group Chemical group 0.000 claims description 61
- 238000011282 treatment Methods 0.000 claims description 50
- 125000004429 atom Chemical group 0.000 claims description 45
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
- 201000003803 Inflammatory myofibroblastic tumor Diseases 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 30
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- 230000008569 process Effects 0.000 abstract description 6
- WBYKOBVKGFBQMM-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-pyrazolo[1,5-a][1,4]diazepine Chemical class C1CCNCC2=CC=NN21 WBYKOBVKGFBQMM-UHFFFAOYSA-N 0.000 abstract description 3
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 160
- 230000015572 biosynthetic process Effects 0.000 description 144
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 132
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- 229910020175 SiOH Inorganic materials 0.000 description 97
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- 235000019341 magnesium sulphate Nutrition 0.000 description 80
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- 239000012267 brine Substances 0.000 description 38
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 38
- 229910000027 potassium carbonate Inorganic materials 0.000 description 37
- 235000015320 potassium carbonate Nutrition 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 32
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 28
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 23
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 21
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229960003433 thalidomide Drugs 0.000 description 1
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- 229950009158 tipifarnib Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14161950.2 | 2014-03-27 | ||
| EP14161950 | 2014-03-27 | ||
| PCT/EP2015/056498 WO2015144799A1 (en) | 2014-03-27 | 2015-03-26 | SUBSTITUTED 4,5,6,7-TETRAHYDRO-PYRAZOLO[1,5-a]PYRAZINE DERIVATIVES AND 5,6,7,8-TETRAHYDRO-4H-PYRAZOLO[1,5-a][1,4]DIAZEPINE DERIVATIVES AS ROS1 INHIBITORS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2940918A1 CA2940918A1 (en) | 2015-10-01 |
| CA2940918C true CA2940918C (en) | 2023-10-24 |
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| EP (1) | EP3129376B1 (enExample) |
| JP (1) | JP6522646B2 (enExample) |
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| ES (1) | ES2715676T3 (enExample) |
| IL (1) | IL247947B (enExample) |
| MX (1) | MX367914B (enExample) |
| WO (1) | WO2015144799A1 (enExample) |
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| US10822357B2 (en) * | 2015-08-28 | 2020-11-03 | Sekisui Medical Co., Ltd. | Benzyl compound |
| TWI782056B (zh) | 2017-07-14 | 2022-11-01 | 日商鹽野義製藥股份有限公司 | 具有ｍｇａｔ２抑制活性的縮合環衍生物 |
| CN112204027A (zh) * | 2018-06-08 | 2021-01-08 | 贝达药业股份有限公司 | Erk 抑制剂及其应用 |
| JP7068743B2 (ja) * | 2019-01-11 | 2022-05-17 | 塩野義製薬株式会社 | Ｍｇａｔ２阻害活性を有する縮合環誘導体を含有する医薬組成物 |
| EP3909583A4 (en) * | 2019-01-11 | 2022-08-17 | Shionogi & Co., Ltd | DIHYDROPYRAZOLOPYRAZINONE DERIVATIVES WITH MGAT2 INHIBITORY ACTIVITY |
| CN114364798A (zh) | 2019-03-21 | 2022-04-15 | 欧恩科斯欧公司 | 用于治疗癌症的Dbait分子与激酶抑制剂的组合 |
| US20220401436A1 (en) | 2019-11-08 | 2022-12-22 | INSERM (Institute National de la Santé et de la Recherche Médicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN114315866B (zh) * | 2020-09-30 | 2023-10-31 | 烟台药物研究所 | 一种盐酸左旋咪唑的合成方法 |
| WO2022072634A1 (en) * | 2020-09-30 | 2022-04-07 | Scorpion Therapeutics, Inc. | Bicyclic compounds for use in the treatment cancer |
| US20250276972A1 (en) * | 2020-12-15 | 2025-09-04 | Gritscience Biopharmaceuticals Co.,Ltd. | Compounds as casein kinase inhibitors |
| CN114957259A (zh) * | 2021-02-25 | 2022-08-30 | 南京明德新药研发有限公司 | 氰基取代的芳香双环类化合物及其应用 |
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| US5356897A (en) | 1991-09-09 | 1994-10-18 | Fujisawa Pharmaceutical Co., Ltd. | 3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines |
| WO2003091256A1 (en) | 2002-04-23 | 2003-11-06 | Shionogi & Co., Ltd. | PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVE AND NAD(P)H OXIDASE INHIBITOR CONTAINING THE SAME |
| US7514441B2 (en) | 2002-08-26 | 2009-04-07 | Takeda Pharmaceutical Company Limited | Substituted pyrazolo [1,5-A]pyrimidines as calcium receptor modulating agents |
| BR0317430A (pt) * | 2002-12-20 | 2005-10-25 | Pharmacia Corp | Compostos inibidores de quinase-2 de proteìna ativada por quinase de proteìna ativada por mitógeno |
| JP2005343889A (ja) * | 2004-05-06 | 2005-12-15 | Taisho Pharmaceut Co Ltd | イミダゾピリジン誘導体 |
| WO2009076440A2 (en) | 2007-12-12 | 2009-06-18 | E.I. Du Pont De Nemours And Company | Fungicidal bicyclic pyrazoles |
| CA2710454A1 (en) | 2007-12-21 | 2009-07-09 | Wyeth Llc | Pyrazolo [1,5-a] pyrimidine compounds |
| US20100029657A1 (en) | 2008-02-29 | 2010-02-04 | Wyeth | Bridged, Bicyclic Heterocyclic or Spiro Bicyclic Heterocyclic Derivatives of Pyrazolo[1, 5-A]Pyrimidines, Methods for Preparation and Uses Thereof |
| JP5214799B2 (ja) * | 2008-04-07 | 2013-06-19 | アイアールエム・リミテッド・ライアビリティ・カンパニー | キナーゼ阻害剤としての化合物および組成物 |
| EA018282B1 (ru) | 2008-04-07 | 2013-06-28 | Айрм Ллк | Соединения и композиции в качестве ингибиторов протеинкиназы |
| JP5492194B2 (ja) * | 2008-05-13 | 2014-05-14 | アイアールエム・リミテッド・ライアビリティ・カンパニー | キナーゼ阻害剤としての縮合窒素含有ヘテロ環およびその組成物 |
| CN102459264A (zh) * | 2009-05-27 | 2012-05-16 | 雅培制药有限公司 | 激酶活性的嘧啶抑制剂 |
| WO2010138579A1 (en) | 2009-05-28 | 2010-12-02 | Wilson-Cook Medical Inc. | Tacking device and methods of deployment |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| RU2014102935A (ru) | 2011-08-02 | 2015-09-10 | Пфайзер Инк. | Кризотиниб для применения в лечении рака |
| TWI585088B (zh) * | 2012-06-04 | 2017-06-01 | 第一三共股份有限公司 | 作爲激酶抑制劑之咪唑并［１，２－ｂ］嗒衍生物 |
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Also Published As
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| MX2016012668A (es) | 2016-12-14 |
| KR20160137576A (ko) | 2016-11-30 |
| AU2015238296A1 (en) | 2016-09-08 |
| WO2015144799A1 (en) | 2015-10-01 |
| BR112016022105B1 (pt) | 2023-01-31 |
| IL247947B (en) | 2019-03-31 |
| AU2015238296B2 (en) | 2018-10-18 |
| KR102455519B1 (ko) | 2022-10-14 |
| US20170174690A1 (en) | 2017-06-22 |
| CN106164076A (zh) | 2016-11-23 |
| CA2940918A1 (en) | 2015-10-01 |
| BR112016022105A2 (enExample) | 2017-08-15 |
| ES2715676T3 (es) | 2019-06-05 |
| EP3129376B1 (en) | 2018-12-26 |
| EA032255B1 (ru) | 2019-04-30 |
| JP2017508779A (ja) | 2017-03-30 |
| JP6522646B2 (ja) | 2019-05-29 |
| MX367914B (es) | 2019-09-11 |
| EA201691930A1 (ru) | 2017-02-28 |
| CN106164076B (zh) | 2019-03-26 |
| EP3129376A1 (en) | 2017-02-15 |
| US10280170B2 (en) | 2019-05-07 |
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