JP2017515845A5 - - Google Patents
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- Publication number
- JP2017515845A5 JP2017515845A5 JP2016567507A JP2016567507A JP2017515845A5 JP 2017515845 A5 JP2017515845 A5 JP 2017515845A5 JP 2016567507 A JP2016567507 A JP 2016567507A JP 2016567507 A JP2016567507 A JP 2016567507A JP 2017515845 A5 JP2017515845 A5 JP 2017515845A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- carboxamide
- oxo
- triazole
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 201000010099 disease Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 11
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 10
- 230000035876 healing Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000010392 Bone Fractures Diseases 0.000 claims description 7
- 206010016654 Fibrosis Diseases 0.000 claims description 7
- 206010017076 Fracture Diseases 0.000 claims description 7
- 230000004761 fibrosis Effects 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 208000010412 Glaucoma Diseases 0.000 claims description 6
- 208000031953 Hereditary hemorrhagic telangiectasia Diseases 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 201000001474 proteinuria Diseases 0.000 claims description 6
- 230000029663 wound healing Effects 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 230000002685 pulmonary effect Effects 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 2
- MOKGJPFJPBCJGY-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-N-[1-(2-fluorophenyl)-2,3-dimethyl-5-oxopyrazol-4-yl]-5-methyltriazole-4-carboxamide Chemical compound ClC1=C(C=CC(=C1)Cl)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1=C(C=CC=C1)F)=O MOKGJPFJPBCJGY-UHFFFAOYSA-N 0.000 claims description 2
- DJCHYTWZRDUVHQ-UHFFFAOYSA-N 1-(2-chloro-4-cyclopropylphenyl)-N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-5-methyltriazole-4-carboxamide Chemical compound ClC1=C(C=CC(=C1)C1CC1)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1CCCCC1)=O DJCHYTWZRDUVHQ-UHFFFAOYSA-N 0.000 claims description 2
- ACXUNKGGFBQCSH-UHFFFAOYSA-N 1-(2-chloro-4-cyclopropylphenyl)-N-[1-(2-fluorophenyl)-2,3-dimethyl-5-oxopyrazol-4-yl]-5-methyltriazole-4-carboxamide Chemical compound ClC1=C(C=CC(=C1)C1CC1)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1=C(C=CC=C1)F)=O ACXUNKGGFBQCSH-UHFFFAOYSA-N 0.000 claims description 2
- DJCHYTWZRDUVHQ-HPRDVNIFSA-N 1-(2-chloro-4-cyclopropylphenyl)-N-[1-cyclohexyl-3-methyl-5-oxo-2-(trideuteriomethyl)pyrazol-4-yl]-5-methyltriazole-4-carboxamide Chemical compound [2H]C([2H])([2H])N1N(C2CCCCC2)C(=O)C(NC(=O)C2=C(C)N(N=N2)C2=CC=C(C=C2Cl)C2CC2)=C1C DJCHYTWZRDUVHQ-HPRDVNIFSA-N 0.000 claims description 2
- FODUFECSLYLXJO-UHFFFAOYSA-N 1-(2-chloro-4-methoxyphenyl)-N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-5-methyltriazole-4-carboxamide Chemical compound ClC1=C(C=CC(=C1)OC)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1CCCCC1)=O FODUFECSLYLXJO-UHFFFAOYSA-N 0.000 claims description 2
- ISFJQKFPHDUWPE-UHFFFAOYSA-N 1-(4-chloro-2-cyclopropylphenyl)-N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-5-methyltriazole-4-carboxamide Chemical compound ClC1=CC(=C(C=C1)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1CCCCC1)=O)C1CC1 ISFJQKFPHDUWPE-UHFFFAOYSA-N 0.000 claims description 2
- RZYISIGSIXJKBN-UHFFFAOYSA-N 1-(4-chloro-2-cyclopropylphenyl)-N-[1-(2-fluorophenyl)-2,3-dimethyl-5-oxopyrazol-4-yl]-5-methyltriazole-4-carboxamide Chemical compound ClC1=CC(=C(C=C1)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1=C(C=CC=C1)F)=O)C1CC1 RZYISIGSIXJKBN-UHFFFAOYSA-N 0.000 claims description 2
- KSOXQHSQZWSLIA-UHFFFAOYSA-N 1-(4-chlorophenyl)-N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-5-methyltriazole-4-carboxamide Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1CCCCC1)=O KSOXQHSQZWSLIA-UHFFFAOYSA-N 0.000 claims description 2
- SQLLXHARKNGURD-UHFFFAOYSA-N 1-(4-chlorophenyl)-N-[1-(2-fluorophenyl)-2,3-dimethyl-5-oxopyrazol-4-yl]-5-methyltriazole-4-carboxamide Chemical compound ClC1=CC=C(C=C1)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1=C(C=CC=C1)F)=O SQLLXHARKNGURD-UHFFFAOYSA-N 0.000 claims description 2
- WXVDTPRGJZKZPF-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethoxy)phenyl]-N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-5-methyltriazole-4-carboxamide Chemical compound ClC1=C(C=CC(=C1)OC(F)(F)F)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1CCCCC1)=O WXVDTPRGJZKZPF-UHFFFAOYSA-N 0.000 claims description 2
- JMXMZZABLCOWIP-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethoxy)phenyl]-N-[1-(2-fluorophenyl)-2,3-dimethyl-5-oxopyrazol-4-yl]-5-methyltriazole-4-carboxamide Chemical compound ClC1=C(C=CC(=C1)OC(F)(F)F)N1N=NC(=C1C)C(=O)NC=1C(N(N(C1C)C)C1=C(C=CC=C1)F)=O JMXMZZABLCOWIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- LVMFPVUIWOOJNY-UHFFFAOYSA-N N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-1-(2,4-dichlorophenyl)-5-methyltriazole-4-carboxamide Chemical compound C1(CCCCC1)N1N(C(=C(C1=O)NC(=O)C=1N=NN(C1C)C1=C(C=C(C=C1)Cl)Cl)C)C LVMFPVUIWOOJNY-UHFFFAOYSA-N 0.000 claims description 2
- LEXOBXPBMTWDHU-UHFFFAOYSA-N N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-1-(2-cyclopropyl-4-fluorophenyl)-5-methyltriazole-4-carboxamide Chemical compound C1(CCCCC1)N1N(C(=C(C1=O)NC(=O)C=1N=NN(C1C)C1=C(C=C(C=C1)F)C1CC1)C)C LEXOBXPBMTWDHU-UHFFFAOYSA-N 0.000 claims description 2
- SMEJNAIKZQKEDP-UHFFFAOYSA-N N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-1-(4-methoxy-3-methylphenyl)-5-methyltriazole-4-carboxamide Chemical compound C1(CCCCC1)N1N(C(=C(C1=O)NC(=O)C=1N=NN(C1C)C1=CC(=C(C=C1)OC)C)C)C SMEJNAIKZQKEDP-UHFFFAOYSA-N 0.000 claims description 2
- NGQWUQYESZDKHI-UHFFFAOYSA-N N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-1-[4-methoxy-2-(trifluoromethyl)phenyl]-5-methyltriazole-4-carboxamide Chemical compound C1(CCCCC1)N1N(C(=C(C1=O)NC(=O)C=1N=NN(C1C)C1=C(C=C(C=C1)OC)C(F)(F)F)C)C NGQWUQYESZDKHI-UHFFFAOYSA-N 0.000 claims description 2
- NOVSDVCDYPGXAQ-UHFFFAOYSA-N N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-8-(trifluoromethoxy)-5,6-dihydro-4H-triazolo[1,5-a][1]benzazepine-3-carboxamide Chemical compound C1(CCCCC1)N1N(C(=C(C1=O)NC(=O)C=1N=NN2C1CCCC1=C2C=CC(=C1)OC(F)(F)F)C)C NOVSDVCDYPGXAQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- -1 chloro, fluoro, cyclopropyl Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- KLJDGTASMZJZDR-UHFFFAOYSA-N 2-cyclohexyl-1,5-dimethylpyrazol-3-one Chemical compound CN1C(C)=CC(=O)N1C1CCCCC1 KLJDGTASMZJZDR-UHFFFAOYSA-N 0.000 claims 1
- 206010052428 Wound Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WGVHNCAJPFIFCR-UHFFFAOYSA-N 5-methyl-1,2-dihydropyrazol-3-one Chemical compound CC1=CC(O)=NN1 WGVHNCAJPFIFCR-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- GPKSXWTVPBSUBX-UHFFFAOYSA-N N-(1-cyclohexyl-2,3-dimethyl-5-oxopyrazol-4-yl)-1-(4-methoxyphenyl)-5-methyltriazole-4-carboxamide Chemical compound C1(CCCCC1)N1N(C(=C(C1=O)NC(=O)C=1N=NN(C1C)C1=CC=C(C=C1)OC)C)C GPKSXWTVPBSUBX-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461993046P | 2014-05-14 | 2014-05-14 | |
| EP14168319 | 2014-05-14 | ||
| EP14168319.3 | 2014-05-14 | ||
| US61/993,046 | 2014-05-14 | ||
| PCT/IB2015/001539 WO2015177646A1 (en) | 2014-05-14 | 2015-05-14 | Carboxamide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017515845A JP2017515845A (ja) | 2017-06-15 |
| JP2017515845A5 true JP2017515845A5 (OSRAM) | 2018-06-14 |
| JP6587637B2 JP6587637B2 (ja) | 2019-10-09 |
Family
ID=50735906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016567507A Active JP6587637B2 (ja) | 2014-05-14 | 2015-05-14 | カルボキサミド誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US9403833B2 (OSRAM) |
| EP (1) | EP3143014B1 (OSRAM) |
| JP (1) | JP6587637B2 (OSRAM) |
| KR (1) | KR20170003667A (OSRAM) |
| CN (1) | CN106536512B (OSRAM) |
| AP (1) | AP2016009554A0 (OSRAM) |
| AR (1) | AR100439A1 (OSRAM) |
| AU (1) | AU2015263049B2 (OSRAM) |
| CA (1) | CA2948582A1 (OSRAM) |
| EA (1) | EA201692298A1 (OSRAM) |
| MX (1) | MX2016014946A (OSRAM) |
| SG (1) | SG11201609311RA (OSRAM) |
| TN (1) | TN2016000491A1 (OSRAM) |
| TW (1) | TW201623288A (OSRAM) |
| UY (1) | UY36123A (OSRAM) |
| WO (1) | WO2015177646A1 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201623288A (zh) | 2014-05-14 | 2016-07-01 | 諾華公司 | 甲醯胺衍生物 |
| TWI714528B (zh) | 2014-05-14 | 2021-01-01 | 瑞士商諾華公司 | 甲醯胺衍生物 |
| CN108007916B (zh) * | 2017-03-16 | 2020-08-04 | 黑龙江八一农垦大学 | 希尔伯特黄法建立稻株氮含量的共聚焦显微拉曼测量模型 |
| CN110749687B (zh) * | 2019-04-04 | 2021-05-28 | 中山大学 | 一种日本血吸虫病早期诊断尿液生物标志物及筛选方法和应用 |
| CN110038012B (zh) * | 2019-05-30 | 2021-06-11 | 济南大学 | 具有1,2,3-三氮唑结构片段的生物碱化合物在制备促血管生成药物中的应用 |
| DE102020116104A1 (de) | 2020-06-18 | 2021-12-23 | Charité - Universitätsmedizin Berlin, Körperschaft des öffentlichen Rechts | Metamizolderivate zur Prävention und Therapie der pulmonalen Hypertonie |
| CN113636977B (zh) * | 2021-09-01 | 2022-12-20 | 温州大学 | 2-芳基苯并氮杂卓及其衍生物的合成方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7354722B1 (en) | 1999-06-11 | 2008-04-08 | Signal Pharmaceuticals | Modulators of Smurf and BMP/TGFβ signaling pathways |
| CN100379752C (zh) * | 1999-06-11 | 2008-04-09 | 纽约州州立大学研究基金会 | BMP和TGFβ信号转导途径的拮抗剂 |
| CA2514733A1 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| GB0312368D0 (en) | 2003-05-30 | 2003-07-02 | Univ Aston | Novel ureido- and amido-pyrazolone derivatives |
| US20060281803A1 (en) | 2003-09-23 | 2006-12-14 | Lindsley Craig W | Pyrazole modulators of metabotropic glutamate receptors |
| US7291743B2 (en) | 2005-03-29 | 2007-11-06 | Geneblue Corporation | Isoxazole derivatives and methods of treating nitric oxide mediated diseases |
| CA2627516A1 (en) * | 2005-10-31 | 2007-05-10 | Biolipox Ab | Triazole compounds as lipoxygenase inhibitors |
| WO2008121861A2 (en) | 2007-03-28 | 2008-10-09 | Xenon Pharmaceuticals Inc. | Pyrazole and pyrrole compounds useful in treating iron disorders |
| WO2009011850A2 (en) | 2007-07-16 | 2009-01-22 | Abbott Laboratories | Novel therapeutic compounds |
| JP2011511756A (ja) | 2007-08-02 | 2011-04-14 | ナームローゼ・フエンノートチヤツプ・オルガノン | Ｔｒｐｖ１モジュレータとしての５−フェニル−イソオキサゾール−３−カルボキサミド誘導体 |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| WO2011151361A1 (en) | 2010-06-03 | 2011-12-08 | Glaxo Group Limited | Novel compounds |
| TWI714528B (zh) | 2014-05-14 | 2021-01-01 | 瑞士商諾華公司 | 甲醯胺衍生物 |
| TW201623288A (zh) | 2014-05-14 | 2016-07-01 | 諾華公司 | 甲醯胺衍生物 |
-
2015
- 2015-05-13 TW TW104115286A patent/TW201623288A/zh unknown
- 2015-05-13 US US14/711,693 patent/US9403833B2/en active Active
- 2015-05-14 EA EA201692298A patent/EA201692298A1/ru unknown
- 2015-05-14 TN TN2016000491A patent/TN2016000491A1/en unknown
- 2015-05-14 AR ARP150101497A patent/AR100439A1/es unknown
- 2015-05-14 CN CN201580038374.5A patent/CN106536512B/zh active Active
- 2015-05-14 SG SG11201609311RA patent/SG11201609311RA/en unknown
- 2015-05-14 AU AU2015263049A patent/AU2015263049B2/en not_active Ceased
- 2015-05-14 EP EP15774680.1A patent/EP3143014B1/en active Active
- 2015-05-14 WO PCT/IB2015/001539 patent/WO2015177646A1/en not_active Ceased
- 2015-05-14 CA CA2948582A patent/CA2948582A1/en not_active Abandoned
- 2015-05-14 KR KR1020167034560A patent/KR20170003667A/ko not_active Withdrawn
- 2015-05-14 JP JP2016567507A patent/JP6587637B2/ja active Active
- 2015-05-14 AP AP2016009554A patent/AP2016009554A0/en unknown
- 2015-05-14 MX MX2016014946A patent/MX2016014946A/es unknown
- 2015-05-14 UY UY0001036123A patent/UY36123A/es not_active Application Discontinuation
-
2016
- 2016-06-29 US US15/197,091 patent/US9931319B2/en active Active
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