JP2014534227A5 - - Google Patents
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- Publication number
- JP2014534227A5 JP2014534227A5 JP2014540047A JP2014540047A JP2014534227A5 JP 2014534227 A5 JP2014534227 A5 JP 2014534227A5 JP 2014540047 A JP2014540047 A JP 2014540047A JP 2014540047 A JP2014540047 A JP 2014540047A JP 2014534227 A5 JP2014534227 A5 JP 2014534227A5
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- JP
- Japan
- Prior art keywords
- compound
- moiety
- compound according
- linker
- substituted
- 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
- 150000001875 compounds Chemical class 0.000 claims description 71
- 206010028980 Neoplasm Diseases 0.000 claims description 28
- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 25
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 25
- 239000002246 antineoplastic agent Substances 0.000 claims description 23
- 241001465754 Metazoa Species 0.000 claims description 21
- 201000011510 cancer Diseases 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 229940127089 cytotoxic agent Drugs 0.000 claims description 16
- 210000004027 cell Anatomy 0.000 claims description 14
- 208000024891 symptom Diseases 0.000 claims description 14
- 230000008685 targeting Effects 0.000 claims description 13
- 206010018338 Glioma Diseases 0.000 claims description 12
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 10
- 208000005017 glioblastoma Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 9
- 229940044683 chemotherapy drug Drugs 0.000 claims description 9
- 238000012377 drug delivery Methods 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- -1 3-chloropropyl Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims description 8
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims description 8
- 229960004961 mechlorethamine Drugs 0.000 claims description 8
- GDFYVGREOHNWMM-UHFFFAOYSA-N platinum(4+);tetranitrate Chemical compound [Pt+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GDFYVGREOHNWMM-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229940126585 therapeutic drug Drugs 0.000 claims description 8
- 241000219198 Brassica Species 0.000 claims description 7
- 235000003351 Brassica cretica Nutrition 0.000 claims description 7
- 235000003343 Brassica rupestris Nutrition 0.000 claims description 7
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 7
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 7
- 229940127093 camptothecin Drugs 0.000 claims description 7
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 7
- 210000003470 mitochondria Anatomy 0.000 claims description 7
- 235000010460 mustard Nutrition 0.000 claims description 7
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims description 6
- 208000032612 Glial tumor Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229960005243 carmustine Drugs 0.000 claims description 6
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 6
- 229960004316 cisplatin Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 210000004962 mammalian cell Anatomy 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims description 4
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229960003668 docetaxel Drugs 0.000 claims description 4
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 4
- 229960005420 etoposide Drugs 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229960004768 irinotecan Drugs 0.000 claims description 4
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229960004964 temozolomide Drugs 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 229960003048 vinblastine Drugs 0.000 claims description 4
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 4
- 206010003571 Astrocytoma Diseases 0.000 claims description 3
- 206010006143 Brain stem glioma Diseases 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- 206010014967 Ependymoma Diseases 0.000 claims description 3
- 201000010133 Oligodendroglioma Diseases 0.000 claims description 3
- 230000001086 cytosolic effect Effects 0.000 claims description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 3
- 244000144972 livestock Species 0.000 claims description 3
- 201000004058 mixed glioma Diseases 0.000 claims description 3
- 229960003552 other antineoplastic agent in atc Drugs 0.000 claims description 3
- 230000000306 recurrent effect Effects 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- KQYMFAQTZNPPGW-UHFFFAOYSA-N 1-cyclopropyl-3,6-dihydro-2h-pyridine Chemical compound C1CC1N1CC=CCC1 KQYMFAQTZNPPGW-UHFFFAOYSA-N 0.000 claims description 2
- AUFIRGPROMANKW-UHFFFAOYSA-N 1-methyl-3,6-dihydro-2h-pyridine Chemical group CN1CCC=CC1 AUFIRGPROMANKW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012623 DNA damaging agent Substances 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 101710183280 Topoisomerase Proteins 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000008499 blood brain barrier function Effects 0.000 claims description 2
- 210000001218 blood-brain barrier Anatomy 0.000 claims description 2
- 239000000824 cytostatic agent Substances 0.000 claims description 2
- 239000002254 cytotoxic agent Substances 0.000 claims description 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 2
- 230000000254 damaging effect Effects 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 210000001700 mitochondrial membrane Anatomy 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 230000000149 penetrating effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 210000000130 stem cell Anatomy 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 230000003439 radiotherapeutic effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 15
- 230000000973 chemotherapeutic effect Effects 0.000 description 5
- 239000002207 metabolite Substances 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 3
- 241000282412 Homo Species 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000002438 mitochondrial effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 241000938605 Crocodylia Species 0.000 description 1
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 238000011319 anticancer therapy Methods 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000029824 high grade glioma Diseases 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 229960002247 lomustine Drugs 0.000 description 1
- 201000011614 malignant glioma Diseases 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161553854P | 2011-10-31 | 2011-10-31 | |
| US61/553,854 | 2011-10-31 | ||
| PCT/US2012/062850 WO2013151584A1 (en) | 2011-10-31 | 2012-10-31 | Compound comprising a mao targeting/ seeker moiety for treating human gliomas |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014534227A JP2014534227A (ja) | 2014-12-18 |
| JP2014534227A5 true JP2014534227A5 (enExample) | 2015-11-12 |
| JP6118808B2 JP6118808B2 (ja) | 2017-04-19 |
Family
ID=47146760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014540047A Active JP6118808B2 (ja) | 2011-10-31 | 2012-10-31 | ヒトグリオームを治療するためのｍａｏ標的化／探索部分を含む化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10555936B2 (enExample) |
| EP (2) | EP2804604A1 (enExample) |
| JP (1) | JP6118808B2 (enExample) |
| KR (1) | KR102110794B1 (enExample) |
| CN (1) | CN104136026B (enExample) |
| AU (1) | AU2012376221A1 (enExample) |
| CA (1) | CA2887928A1 (enExample) |
| HK (1) | HK1204547A1 (enExample) |
| WO (1) | WO2013151584A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2804604A1 (en) | 2011-10-31 | 2014-11-26 | The Methodist Hospital Research Institute | Compound comprising a mao targeting/ seeker moiety for treating human gliomas |
| CN104710433B (zh) * | 2014-01-23 | 2016-08-17 | 南京友怡医药科技有限公司 | 苯丁酸氮芥衍生物、制备方法及应用 |
| WO2015153516A1 (en) * | 2014-04-04 | 2015-10-08 | University Of Florida Research Foundation | Hdac inhibitor compounds and methods of treatment |
| TWI843989B (zh) | 2021-02-19 | 2024-06-01 | 美商美威高能離子醫療系統公司 | 用於粒子治療系統之支架 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4913891A (en) * | 1986-04-17 | 1990-04-03 | The United States Of America As Represented By The United States Department Of Energy | Positron emitter labeled enzyme inhibitors |
| US5466468A (en) | 1990-04-03 | 1995-11-14 | Ciba-Geigy Corporation | Parenterally administrable liposome formulation comprising synthetic lipids |
| US5399363A (en) | 1991-01-25 | 1995-03-21 | Eastman Kodak Company | Surface modified anticancer nanoparticles |
| EP0710244A1 (en) * | 1993-06-07 | 1996-05-08 | The Wellcome Foundation Limited | Immunoreactive reagents employing monoamine oxidase |
| US5543158A (en) | 1993-07-23 | 1996-08-06 | Massachusetts Institute Of Technology | Biodegradable injectable nanoparticles |
| IE80468B1 (en) | 1995-04-04 | 1998-07-29 | Elan Corp Plc | Controlled release biodegradable nanoparticles containing insulin |
| US5612329A (en) | 1995-06-05 | 1997-03-18 | University Of Maryland At Baltimore | Diaziridinylpolyamine anti-cancer agents |
| WO1998022110A1 (en) * | 1996-11-20 | 1998-05-28 | Virginia Tech Intellectual Properties, Inc. | Prodrugs for the selective inhibition of monoamine oxidase-b |
| MXPA01008855A (es) | 1999-03-03 | 2002-07-02 | Procter & Gamble | Inhibidores de metaloproteasa que contienen alquenilo y alquinilo. |
| US6750345B2 (en) | 2000-11-07 | 2004-06-15 | Symyx Technologies, Inc. | Substituted pyridyl amine catalysts, complexes and compositions |
| US6946479B2 (en) | 2002-11-09 | 2005-09-20 | The Procter & Gamble Company | N-sulfonyl-4-methyleneamino-3-hydroxy-2-pyridones |
| WO2004110255A2 (en) | 2003-06-09 | 2004-12-23 | Gang Zheng | Antineoplastic agents targeted via glut transporters |
| WO2005111016A1 (en) * | 2004-05-14 | 2005-11-24 | Pfizer Products Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
| US7091205B2 (en) | 2004-10-08 | 2006-08-15 | Yu Show Fu | Use of tetramethylpyrazine in the treatment of brain tumor |
| GB0513297D0 (en) | 2005-06-29 | 2005-08-03 | Glaxo Group Ltd | Novel compounds |
| US20070275944A1 (en) | 2006-04-05 | 2007-11-29 | The Board Of Trustees Operating Michigan State University | Antioxidants and methods of their use |
| AR070317A1 (es) * | 2008-02-06 | 2010-03-31 | Osi Pharm Inc | Furo (3,2-c) piridina y tieno (3,2-c) piridinas |
| KR20100122505A (ko) * | 2008-02-29 | 2010-11-22 | 어레이 바이오파마 인크. | Ｒａｆ 저해물질 화합물 및 이들의 이용 방법 |
| EP2141163A1 (de) * | 2008-07-02 | 2010-01-06 | Bayer Schering Pharma AG | Substituierte Thiazolidinone, deren Herstellung und Verwendung als Arzneimittel |
| HUE046402T2 (hu) * | 2009-06-10 | 2020-03-30 | Chugai Pharmaceutical Co Ltd | Tetraciklusos vegyületek |
| US8293925B2 (en) * | 2009-09-21 | 2012-10-23 | Chemocentryx, Inc. | Pyrrolidinone carboxamide derivatives |
| EP2804604A1 (en) | 2011-10-31 | 2014-11-26 | The Methodist Hospital Research Institute | Compound comprising a mao targeting/ seeker moiety for treating human gliomas |
-
2012
- 2012-10-31 EP EP12783818.3A patent/EP2804604A1/en not_active Withdrawn
- 2012-10-31 CN CN201280064763.1A patent/CN104136026B/zh not_active Expired - Fee Related
- 2012-10-31 CA CA2887928A patent/CA2887928A1/en not_active Abandoned
- 2012-10-31 HK HK15103179.0A patent/HK1204547A1/xx unknown
- 2012-10-31 WO PCT/US2012/062850 patent/WO2013151584A1/en not_active Ceased
- 2012-10-31 JP JP2014540047A patent/JP6118808B2/ja active Active
- 2012-10-31 KR KR1020147014835A patent/KR102110794B1/ko active Active
- 2012-10-31 EP EP20189611.5A patent/EP3815685A3/en not_active Withdrawn
- 2012-10-31 AU AU2012376221A patent/AU2012376221A1/en not_active Abandoned
-
2014
- 2014-04-30 US US14/266,729 patent/US10555936B2/en active Active
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