JP2009514894A5 - - Google Patents
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- JP2009514894A5 JP2009514894A5 JP2008539114A JP2008539114A JP2009514894A5 JP 2009514894 A5 JP2009514894 A5 JP 2009514894A5 JP 2008539114 A JP2008539114 A JP 2008539114A JP 2008539114 A JP2008539114 A JP 2008539114A JP 2009514894 A5 JP2009514894 A5 JP 2009514894A5
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- JP
- Japan
- Prior art keywords
- membered
- ring
- cor
- compound
- nitrogen
- 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.)
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 43
- 229910052757 nitrogen Inorganic materials 0.000 claims 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 28
- 125000005842 heteroatom Chemical group 0.000 claims 28
- 229910052760 oxygen Inorganic materials 0.000 claims 28
- 239000001301 oxygen Substances 0.000 claims 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 27
- 229910052717 sulfur Inorganic materials 0.000 claims 27
- 239000011593 sulfur Substances 0.000 claims 27
- 239000000203 mixture Substances 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 229920006395 saturated elastomer Polymers 0.000 claims 19
- 125000001931 aliphatic group Chemical group 0.000 claims 18
- 125000002950 monocyclic group Chemical group 0.000 claims 15
- 125000000464 thioxo group Chemical group S=* 0.000 claims 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 14
- 150000007824 aliphatic compounds Chemical class 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 125000002723 alicyclic group Chemical group 0.000 claims 6
- 230000001580 bacterial effect Effects 0.000 claims 6
- -1 Ar 3 is —R J Chemical group 0.000 claims 5
- 208000015181 infectious disease Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims 4
- 239000012472 biological sample Substances 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 239000003242 anti bacterial agent Substances 0.000 claims 3
- 229940088710 antibiotic agent Drugs 0.000 claims 3
- 150000002222 fluorine compounds Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 241000194033 Enterococcus Species 0.000 claims 2
- 241000194032 Enterococcus faecalis Species 0.000 claims 2
- 241000588724 Escherichia coli Species 0.000 claims 2
- 241000606768 Haemophilus influenzae Species 0.000 claims 2
- 241000590002 Helicobacter pylori Species 0.000 claims 2
- 241000588621 Moraxella Species 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 241000193998 Streptococcus pneumoniae Species 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940047650 haemophilus influenzae Drugs 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229940037467 helicobacter pylori Drugs 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 206010034674 peritonitis Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims 2
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 241000193738 Bacillus anthracis Species 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 208000004672 Cardiovascular Infections Diseases 0.000 claims 1
- 208000014912 Central Nervous System Infections Diseases 0.000 claims 1
- 108010065152 Coagulase Proteins 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 241000588914 Enterobacter Species 0.000 claims 1
- 208000001860 Eye Infections Diseases 0.000 claims 1
- 208000002633 Febrile Neutropenia Diseases 0.000 claims 1
- 206010017964 Gastrointestinal infection Diseases 0.000 claims 1
- 206010048461 Genital infection Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000000913 Kidney Calculi Diseases 0.000 claims 1
- 241000589242 Legionella pneumophila Species 0.000 claims 1
- 206010024971 Lower respiratory tract infections Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 241000588655 Moraxella catarrhalis Species 0.000 claims 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 1
- 241000202934 Mycoplasma pneumoniae Species 0.000 claims 1
- 208000009525 Myocarditis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010029148 Nephrolithiasis Diseases 0.000 claims 1
- 206010068319 Oropharyngeal pain Diseases 0.000 claims 1
- 206010031252 Osteomyelitis Diseases 0.000 claims 1
- 208000005141 Otitis Diseases 0.000 claims 1
- 206010033078 Otitis media Diseases 0.000 claims 1
- 201000007100 Pharyngitis Diseases 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 241000588769 Proteus <enterobacteria> Species 0.000 claims 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims 1
- 206010037596 Pyelonephritis Diseases 0.000 claims 1
- 206010057190 Respiratory tract infections Diseases 0.000 claims 1
- 241000607715 Serratia marcescens Species 0.000 claims 1
- 206010062255 Soft tissue infection Diseases 0.000 claims 1
- 241000191967 Staphylococcus aureus Species 0.000 claims 1
- 241000191963 Staphylococcus epidermidis Species 0.000 claims 1
- 241000193996 Streptococcus pyogenes Species 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 206010046306 Upper respiratory tract infection Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 208000006374 Uterine Cervicitis Diseases 0.000 claims 1
- 206010046914 Vaginal infection Diseases 0.000 claims 1
- 201000008100 Vaginitis Diseases 0.000 claims 1
- 206010000269 abscess Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 229940065181 bacillus anthracis Drugs 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 206010008323 cervicitis Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 201000003146 cystitis Diseases 0.000 claims 1
- 238000000502 dialysis Methods 0.000 claims 1
- 208000019836 digestive system infectious disease Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000019258 ear infection Diseases 0.000 claims 1
- 206010014599 encephalitis Diseases 0.000 claims 1
- 206010014665 endocarditis Diseases 0.000 claims 1
- 206010014801 endophthalmitis Diseases 0.000 claims 1
- 229940032049 enterococcus faecalis Drugs 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 208000011323 eye infectious disease Diseases 0.000 claims 1
- 210000004392 genitalia Anatomy 0.000 claims 1
- 208000007565 gingivitis Diseases 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- 206010023332 keratitis Diseases 0.000 claims 1
- 229940115932 legionella pneumophila Drugs 0.000 claims 1
- 229940013390 mycoplasma pneumoniae Drugs 0.000 claims 1
- 206010033072 otitis externa Diseases 0.000 claims 1
- 208000008494 pericarditis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 201000007094 prostatitis Diseases 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 208000000143 urethritis Diseases 0.000 claims 1
- 208000019206 urinary tract infection Diseases 0.000 claims 1
- 0 C*(C)(*)c1ccccn1 Chemical compound C*(C)(*)c1ccccn1 0.000 description 22
- UQFQONCQIQEYPJ-UHFFFAOYSA-N C[n]1nccc1 Chemical compound C[n]1nccc1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 2
- LNJMHEJAYSYZKK-UHFFFAOYSA-N Cc1ncccn1 Chemical compound Cc1ncccn1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N O=C1NCCC1 Chemical compound O=C1NCCC1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- XCBKPJMTRNNEMG-SNAWJCMRSA-N C/C(/I)=C\C(N(C)C)O Chemical compound C/C(/I)=C\C(N(C)C)O XCBKPJMTRNNEMG-SNAWJCMRSA-N 0.000 description 1
- HZHMUSZMPOUQQA-ONEGZZNKSA-N C/C(/I)=C\C(N=C)=O Chemical compound C/C(/I)=C\C(N=C)=O HZHMUSZMPOUQQA-ONEGZZNKSA-N 0.000 description 1
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- NGETUESZTOUZJV-UHFFFAOYSA-N CC(C)C(CCN1Cc2ccccc2)CC1=O Chemical compound CC(C)C(CCN1Cc2ccccc2)CC1=O NGETUESZTOUZJV-UHFFFAOYSA-N 0.000 description 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73413905P | 2005-11-07 | 2005-11-07 | |
| PCT/US2006/043269 WO2007056330A1 (en) | 2005-11-07 | 2006-11-06 | Benzimidazole derivatives as gyrase inhibitors |
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| JP2009514894A5 true JP2009514894A5 (https=) | 2009-10-22 |
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| EP (1) | EP1948635A1 (https=) |
| JP (1) | JP2009514894A (https=) |
| CN (1) | CN101321744A (https=) |
| AU (1) | AU2006311729A1 (https=) |
| CA (1) | CA2626685A1 (https=) |
| WO (1) | WO2007056330A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7582641B2 (en) | 2003-01-31 | 2009-09-01 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US8404852B2 (en) | 2003-01-31 | 2013-03-26 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7569591B2 (en) | 2003-01-31 | 2009-08-04 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7618974B2 (en) | 2003-01-31 | 2009-11-17 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| AR042956A1 (es) | 2003-01-31 | 2005-07-13 | Vertex Pharma | Inhibidores de girasa y usos de los mismos |
| US8193352B2 (en) | 2003-01-31 | 2012-06-05 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| MX2010006237A (es) | 2007-12-07 | 2010-12-21 | Vertex Pharma | Formas solidas de 1-etil-3-(5-(5-fluoropiridin-3-il)-7-(pirimidin- 2-il)-1h-benzo[d]imidazol-2-il)urea. |
| WO2010027583A1 (en) | 2008-09-03 | 2010-03-11 | Universal Display Corporation | Phosphorescent materials |
| GB0821913D0 (en) | 2008-12-02 | 2009-01-07 | Price & Co | Antibacterial compounds |
| WO2010111058A1 (en) * | 2009-03-23 | 2010-09-30 | Merck Sharp & Dohme Corp. | P2x3, receptor antagonists for treatment of pain |
| US9221765B2 (en) | 2009-06-10 | 2015-12-29 | North Carolina State University | Inhibition and dispersion of bacterial biofilms with benzimidazole derivatives |
| BR112012024705A2 (pt) | 2010-03-31 | 2016-06-07 | Actelion Pharmaceuticals Ltd | derivados antibacterianos de isoquinolin-3-ilureia |
| WO2011151620A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| WO2011151618A2 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile-associated disease |
| WO2011151617A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| ES2568455T3 (es) | 2010-06-01 | 2016-04-29 | Summit Therapeutics Plc | Compuestos para el tratamiento de enfermedad asociada a Clostridium difficile |
| WO2011151619A1 (en) | 2010-06-01 | 2011-12-08 | Summit Corporation Plc | Compounds for the treatment of clostridium difficile associated disease |
| WO2012097270A1 (en) | 2011-01-14 | 2012-07-19 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (r)-1-ethyl-3-[5-[2-{1-hydroxy-1-methyl-ethyl}pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl}-1h-benzimidazol-2-yl]urea |
| US8476281B2 (en) | 2011-01-14 | 2013-07-02 | Vertex Pharmaceuticals Incorporated | Solid forms of gyrase inhibitor (R)-1-ethyl-3-[6-fluoro-5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl)-1H-benzimidazol-2-yl]urea |
| AU2012205415B2 (en) | 2011-01-14 | 2017-02-02 | Spero Therapeutics, Inc. | Pyrimidine gyrase and topoisomerase IV inhibitors |
| CN103384665B (zh) | 2011-01-14 | 2018-01-09 | 斯派罗吹耐姆公司 | 制备促旋酶和拓扑异构酶抑制剂的方法 |
| AR088729A1 (es) | 2011-03-29 | 2014-07-02 | Actelion Pharmaceuticals Ltd | Derivados de 3-ureidoisoquinolin-8-ilo y una composicion farmaceutica |
| CN103702994B (zh) * | 2011-06-20 | 2016-03-23 | 沃泰克斯药物股份有限公司 | 旋转酶和拓扑异构酶抑制剂的磷酸酯 |
| WO2014015105A1 (en) | 2012-07-18 | 2014-01-23 | Vertex Pharmaceuticals Incorporated | Solid forms of (r)-2-(5-(2-(3-ethylureido)-6-fluoro-7-(tetrahydrofuran-2-yl)-1h-benzo[d]imidazol-5-yl)pyrimidin-2-yl)propan-2-yl dihydrogen phosphate and salts thereof |
| US9572809B2 (en) | 2012-07-18 | 2017-02-21 | Spero Trinem, Inc. | Combination therapy to treat Mycobacterium diseases |
| US9079935B2 (en) | 2012-08-13 | 2015-07-14 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Reducing risk of contracting Clostridium-difficile associated disease |
| MX2016010057A (es) | 2014-02-03 | 2017-04-27 | Spero Gyrase Inc | Compuestos antibacterianos. |
| CN104945329B (zh) * | 2014-03-24 | 2017-09-01 | 中国医学科学院医药生物技术研究所 | 抗结核药物 |
| WO2016127102A2 (en) | 2015-02-06 | 2016-08-11 | Ernesto Abel-Santos | Inhibiting germination of clostridium perfringens spores to reduce necrotic enteritis |
| CA3057431A1 (en) | 2017-03-24 | 2018-09-27 | Taisho Pharmaceutical Co., Ltd. | 2(1h)-quinolinone derivative |
| KR102737283B1 (ko) | 2019-07-17 | 2024-12-03 | 서밋 (옥스포드) 리미티드 | 리디닐라졸 및 이의 결정 형태의 제조방법 |
| CN111658646B (zh) * | 2020-06-28 | 2021-03-02 | 河南工业大学 | 2,6-双(2-苯并咪唑基)吡啶在制备耐碳青霉烯类铜绿假单胞菌感染药物中的应用 |
| GB202100470D0 (en) | 2021-01-14 | 2021-03-03 | Summit Oxford Ltd | Solid tablet dosage for of ridinilazole |
| GB202100471D0 (en) | 2021-01-14 | 2021-03-03 | Summit Oxford Ltd | Preparation of antibacterial compounds |
| EP4398890A4 (en) | 2021-09-09 | 2025-07-30 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The Univ Of Nevada Las Ve | C. Difficile Spore Germination Inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0303494A3 (en) * | 2000-12-15 | 2009-08-28 | Vertex Pharma | Parmaceutical compositions containing bacterial gyrase inhibitors and uses thereof |
| DE60309701T2 (de) | 2002-06-13 | 2007-09-06 | Vertex Pharmaceuticals Inc., Cambridge | 2-ureido-6-heteroaryl-3h-benzoimidazol-4-carbonsäurederivate und verwandte verbindungen als gyrase und/oder topoisomerase iv inhibitoren zur behandlung von bakteriellen infektionen |
| US7569591B2 (en) * | 2003-01-31 | 2009-08-04 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7618974B2 (en) | 2003-01-31 | 2009-11-17 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| AR042956A1 (es) * | 2003-01-31 | 2005-07-13 | Vertex Pharma | Inhibidores de girasa y usos de los mismos |
| US7582641B2 (en) | 2003-01-31 | 2009-09-01 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
-
2006
- 2006-11-06 AU AU2006311729A patent/AU2006311729A1/en not_active Abandoned
- 2006-11-06 US US11/593,418 patent/US8394803B2/en not_active Expired - Fee Related
- 2006-11-06 CN CNA2006800454440A patent/CN101321744A/zh active Pending
- 2006-11-06 JP JP2008539114A patent/JP2009514894A/ja active Pending
- 2006-11-06 EP EP06827594A patent/EP1948635A1/en not_active Withdrawn
- 2006-11-06 CA CA002626685A patent/CA2626685A1/en not_active Abandoned
- 2006-11-06 WO PCT/US2006/043269 patent/WO2007056330A1/en not_active Ceased
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