ES2686747T3 - Derivados de 4,5,6,7-tetrahidro-pirazolo[1,5-a]pirimidina y derivados de 2,3-dihidro-1H-imidazo[1,2-b]pirazol sustituidos como inhibidores de ROS1 - Google Patents
Derivados de 4,5,6,7-tetrahidro-pirazolo[1,5-a]pirimidina y derivados de 2,3-dihidro-1H-imidazo[1,2-b]pirazol sustituidos como inhibidores de ROS1 Download PDFInfo
- Publication number
- ES2686747T3 ES2686747T3 ES15712138.5T ES15712138T ES2686747T3 ES 2686747 T3 ES2686747 T3 ES 2686747T3 ES 15712138 T ES15712138 T ES 15712138T ES 2686747 T3 ES2686747 T3 ES 2686747T3
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- alkyl
- substituted
- hydrogen
- alkyloxy
- hydroxyl groups
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- 101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 title description 18
- 102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 title description 18
- 239000003112 inhibitor Substances 0.000 title description 15
- HJFZVTDRWQVFDN-UHFFFAOYSA-N 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine Chemical class C1CCNC2=CC=NN21 HJFZVTDRWQVFDN-UHFFFAOYSA-N 0.000 title description 3
- KPMVHELZNRNSMN-UHFFFAOYSA-N chembl1985849 Chemical class N1=CC=C2NCCN21 KPMVHELZNRNSMN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 302
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 292
- 239000001257 hydrogen Substances 0.000 claims abstract description 291
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 258
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 238
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 185
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 169
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 162
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 125
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 120
- 150000003839 salts Chemical class 0.000 claims abstract description 104
- 125000001424 substituent group Chemical group 0.000 claims abstract description 104
- 239000012453 solvate Substances 0.000 claims abstract description 96
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 95
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 90
- -1 -CH2OH Chemical group 0.000 claims abstract description 81
- 125000005843 halogen group Chemical group 0.000 claims abstract description 80
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 54
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 53
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 34
- 125000006682 monohaloalkyl group Chemical group 0.000 claims abstract description 34
- 125000004429 atom Chemical group 0.000 claims abstract description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 29
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 26
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical group 0.000 claims abstract description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims abstract description 7
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims abstract description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
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- 239000003814 drug Substances 0.000 claims description 19
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- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
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- 239000004480 active ingredient Substances 0.000 claims description 8
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- 206010009944 Colon cancer Diseases 0.000 claims description 6
- 208000007207 Epithelioid hemangioendothelioma Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 201000003076 Angiosarcoma Diseases 0.000 claims description 5
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- 201000003803 Inflammatory myofibroblastic tumor Diseases 0.000 claims description 5
- 206010067917 Inflammatory myofibroblastic tumour Diseases 0.000 claims description 5
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 201000006585 gastric adenocarcinoma Diseases 0.000 claims description 5
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
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- 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000025113 myeloid leukemia Diseases 0.000 claims 1
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 330
- 239000000543 intermediate Substances 0.000 description 269
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 204
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- 239000002904 solvent Substances 0.000 description 150
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 124
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- 235000019341 magnesium sulphate Nutrition 0.000 description 62
- 238000003786 synthesis reaction Methods 0.000 description 62
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- 235000019439 ethyl acetate Nutrition 0.000 description 51
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 206010028980 Neoplasm Diseases 0.000 description 39
- 229910020175 SiOH Inorganic materials 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 36
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 34
- 238000000034 method Methods 0.000 description 29
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
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- 230000005526 G1 to G0 transition Effects 0.000 description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 16
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 14
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
- C07D471/04—Ortho-condensed systems
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- 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
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Public Health (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP14161959 | 2014-03-27 | ||
| EP14161959 | 2014-03-27 | ||
| PCT/EP2015/056501 WO2015144801A1 (en) | 2014-03-27 | 2015-03-26 | SUBSTITUTED 4,5,6,7-TETRAHYDRO-PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES AND 2,3-DIHYDRO-1H-IMIDAZO[1,2-b]PYRAZOLE DERIVATIVES AS ROS1 INHIBITORS |
Publications (1)
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|---|---|
| ES2686747T3 true ES2686747T3 (es) | 2018-10-19 |
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| ES15712138.5T Active ES2686747T3 (es) | 2014-03-27 | 2015-03-26 | Derivados de 4,5,6,7-tetrahidro-pirazolo[1,5-a]pirimidina y derivados de 2,3-dihidro-1H-imidazo[1,2-b]pirazol sustituidos como inhibidores de ROS1 |
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| CN106580982B (zh) * | 2016-11-26 | 2017-09-22 | 王玉美 | 一种治疗药物流产后子宫出血的药物 |
| CN106866536A (zh) * | 2017-04-12 | 2017-06-20 | 中国农业大学 | 一种制备4‑卤代‑5‑氨基吡唑的方法 |
| JP7069295B2 (ja) * | 2017-08-17 | 2022-05-17 | エックスダブリューファルマ リミテッド | 活性酸素種スカベンジャー誘導体の調製および使用 |
| 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 |
| CN111087398A (zh) * | 2019-12-24 | 2020-05-01 | 上海万巷制药有限公司 | 一种制备拉罗替尼中间体的清洁工艺 |
| EP4105206A4 (en) | 2020-01-13 | 2024-08-14 | Aptabio Therapeutics Inc. | NOVEL PYRAZOLE DERIVATIVE |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN113416140B (zh) * | 2021-06-03 | 2023-01-13 | 万华化学集团股份有限公司 | 一种制备2-甲基戊二胺的方法 |
| US20250145628A1 (en) * | 2022-02-15 | 2025-05-08 | Novo Nordisk A/S | Pyrazolopyrimidines, compositions comprising them and uses thereof |
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| GB9204464D0 (en) * | 1992-03-02 | 1992-04-15 | Fujisawa Pharmaceutical Co | New heterocyclic derivatives |
| US5356897A (en) * | 1991-09-09 | 1994-10-18 | Fujisawa Pharmaceutical Co., Ltd. | 3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines |
| AU2003227437A1 (en) | 2002-04-23 | 2003-11-10 | Shionogi And Co., Ltd. | PYRAZOLO(1,5-a)PYRIMIDINE DERIVATIVE AND NAD(P)H OXIDASE INHIBITOR CONTAINING THE SAME |
| JP4494205B2 (ja) | 2002-08-26 | 2010-06-30 | 武田薬品工業株式会社 | カルシウム受容体調節化合物およびその用途 |
| UA80295C2 (en) * | 2002-09-06 | 2007-09-10 | Biogen Inc | Pyrazolopyridines and using the same |
| MXPA05006568A (es) | 2002-12-20 | 2005-09-22 | Pharmacia Corp | Compuestos de pirazol aciclico para la inhibicion de proteina cinasa-2 activada por proteina cinasa activada por mitogenos. |
| BRPI0822239A2 (pt) | 2007-12-21 | 2015-06-30 | Wyeth Llc | Composto de pirazolo[1,5-a] pirimidina |
| 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 |
| ES2548135T3 (es) | 2008-05-13 | 2015-10-14 | Novartis Ag | Heterociclos condensados que contienen nitrógeno y composiciones de los mismos como inhibidores de quinasa |
| JP2012528175A (ja) * | 2009-05-27 | 2012-11-12 | アボット・ラボラトリーズ | キナーゼ活性のピリミジン阻害剤 |
| WO2011153553A2 (en) * | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| JO3407B1 (ar) * | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| 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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| AU2015238298A1 (en) | 2016-09-15 |
| AU2015238298B2 (en) | 2019-04-18 |
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| KR20160137566A (ko) | 2016-11-30 |
| IL247948B (en) | 2019-03-31 |
| BR112016021507B1 (pt) | 2022-10-18 |
| WO2015144801A1 (en) | 2015-10-01 |
| EP3126366B1 (en) | 2018-06-06 |
| EA201691934A1 (ru) | 2017-01-30 |
| MX2016012669A (es) | 2016-12-14 |
| JP2017508777A (ja) | 2017-03-30 |
| CA2941206C (en) | 2022-09-20 |
| MX367913B (es) | 2019-09-11 |
| US10342795B2 (en) | 2019-07-09 |
| CA2941206A1 (en) | 2015-10-01 |
| EP3126366A1 (en) | 2017-02-08 |
| CN106132967A (zh) | 2016-11-16 |
| KR102455518B1 (ko) | 2022-10-14 |
| CN106132967B (zh) | 2019-05-28 |
| US20170173014A1 (en) | 2017-06-22 |
| JP6527167B2 (ja) | 2019-06-05 |
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