JP2014504632A5 - - Google Patents
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- Publication number
- JP2014504632A5 JP2014504632A5 JP2013552304A JP2013552304A JP2014504632A5 JP 2014504632 A5 JP2014504632 A5 JP 2014504632A5 JP 2013552304 A JP2013552304 A JP 2013552304A JP 2013552304 A JP2013552304 A JP 2013552304A JP 2014504632 A5 JP2014504632 A5 JP 2014504632A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- optionally substituted
- methyl
- pyrrol
- propionyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 35
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 19
- -1 cyano, hydroxy Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 150000001408 amides Chemical class 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 210000000056 organ Anatomy 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- LTEZKLTYUKOFNO-UHFFFAOYSA-N 1-(4-sulfamoylphenyl)pyrrole-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C=C(C(O)=O)C=C1 LTEZKLTYUKOFNO-UHFFFAOYSA-N 0.000 claims 2
- QJZJGAGMJJSWRD-UHFFFAOYSA-N 4-[2-methyl-3-propanoyl-5-(1,4,4-trimethyl-2-oxo-3h-quinolin-6-yl)pyrrol-1-yl]benzenesulfonamide Chemical compound CC1=C(C(=O)CC)C=C(C=2C=C3C(C)(C)CC(=O)N(C)C3=CC=2)N1C1=CC=C(S(N)(=O)=O)C=C1 QJZJGAGMJJSWRD-UHFFFAOYSA-N 0.000 claims 2
- RHBODKIUOLTNRO-UHFFFAOYSA-N 4-[5-(2,2-dimethyl-3,4-dihydrochromen-6-yl)-2-methyl-3-propanoylpyrrol-1-yl]benzenesulfonamide Chemical compound CC1=C(C(=O)CC)C=C(C=2C=C3CCC(C)(C)OC3=CC=2)N1C1=CC=C(S(N)(=O)=O)C=C1 RHBODKIUOLTNRO-UHFFFAOYSA-N 0.000 claims 2
- VHWQGUPMLYQUEM-UHFFFAOYSA-N 4-[5-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-methyl-3-propanoylpyrrol-1-yl]benzenesulfonamide Chemical compound CC1=C(C(=O)CC)C=C(C=2C=C3C(C(CNC3)(C)C)=CC=2)N1C1=CC=C(S(N)(=O)=O)C=C1 VHWQGUPMLYQUEM-UHFFFAOYSA-N 0.000 claims 2
- KWJALAVCSKHXSA-UHFFFAOYSA-N 4-[5-(4,4-dimethyl-2,3-dihydro-1h-quinolin-7-yl)-2-methyl-3-propanoylpyrrol-1-yl]benzenesulfonamide Chemical compound CC1=C(C(=O)CC)C=C(C=2C=C3C(C(CCN3)(C)C)=CC=2)N1C1=CC=C(S(N)(=O)=O)C=C1 KWJALAVCSKHXSA-UHFFFAOYSA-N 0.000 claims 2
- DFOIZESJWAQQFQ-UHFFFAOYSA-N 4-[5-(4,4-dimethyl-2,3-dihydrochromen-6-yl)-2-methyl-3-propanoylpyrrol-1-yl]benzenesulfonamide Chemical compound CC1=C(C(=O)CC)C=C(C=2C=C3C(C)(C)CCOC3=CC=2)N1C1=CC=C(S(N)(=O)=O)C=C1 DFOIZESJWAQQFQ-UHFFFAOYSA-N 0.000 claims 2
- UQUQXVOBIZNVNG-UHFFFAOYSA-N 4-[5-(8-fluoro-4,4-dimethyl-2,3-dihydrochromen-6-yl)-2-methyl-3-propanoylpyrrol-1-yl]benzenesulfonamide Chemical compound CC1=C(C(=O)CC)C=C(C=2C=C3C(C)(C)CCOC3=C(F)C=2)N1C1=CC=C(S(N)(=O)=O)C=C1 UQUQXVOBIZNVNG-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 210000004204 blood vessel Anatomy 0.000 claims 2
- 230000019771 cognition Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- ATVATHGNDUETKK-UHFFFAOYSA-N 4-[5-(2,3-dihydro-1h-inden-4-yl)-2-methyl-3-propanoylpyrrol-1-yl]benzenesulfonamide Chemical compound CC1=C(C(=O)CC)C=C(C=2C=3CCCC=3C=CC=2)N1C1=CC=C(S(N)(=O)=O)C=C1 ATVATHGNDUETKK-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000015943 Coeliac disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 208000004550 Postoperative Pain Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 208000013677 cerebrovascular dementia Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 201000003146 cystitis Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 210000004558 lewy body Anatomy 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 201000001245 periodontitis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002980 postoperative effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN151/KOL/2011 | 2011-02-03 | ||
| IN151KO2011 | 2011-02-03 | ||
| PCT/IB2012/050442 WO2012104782A1 (en) | 2011-02-03 | 2012-01-31 | Pyrrole derivatives used as modulators of alpha7 nachr |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014504632A JP2014504632A (ja) | 2014-02-24 |
| JP2014504632A5 true JP2014504632A5 (enExample) | 2015-02-26 |
| JP5865397B2 JP5865397B2 (ja) | 2016-02-17 |
Family
ID=45787252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013552304A Expired - Fee Related JP5865397B2 (ja) | 2011-02-03 | 2012-01-31 | α７ｎＡＣｈＲのモジュレータとして使用されるピロール誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20130310419A1 (enExample) |
| EP (1) | EP2670744B1 (enExample) |
| JP (1) | JP5865397B2 (enExample) |
| KR (1) | KR20140041442A (enExample) |
| CN (1) | CN103443092B (enExample) |
| AU (1) | AU2012213086B2 (enExample) |
| BR (1) | BR112013019893A2 (enExample) |
| CA (1) | CA2825519A1 (enExample) |
| MX (1) | MX344701B (enExample) |
| SG (1) | SG192078A1 (enExample) |
| WO (1) | WO2012104782A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS55433B1 (sr) * | 2011-02-23 | 2017-04-28 | Lupin Ltd | Derivati heteroarila kao modulatori nachr alfa7 |
| AU2012235779B2 (en) * | 2011-03-31 | 2017-03-02 | Lupin Limited | Pyrrole derivatives as nicotinic acetylcholine receptor modulators for use in the treatment of neurodegenerative disorders such as Alzheimer's and Parkinson's disease |
| NZ629453A (en) | 2012-03-06 | 2016-04-29 | Lupin Ltd | Thiazole derivatives as alpha 7 nachr modulators |
| EP2945936A1 (en) | 2012-11-12 | 2015-11-25 | Lupin Limited | Thiazole derivatives as alpha 7 nachr modulators |
| EP2945941B1 (en) | 2013-01-16 | 2016-12-07 | Lupin Limited | Pyrrole derivatives as alpha 7 nachr modulators |
| US9617210B2 (en) | 2013-03-13 | 2017-04-11 | Lupin Limited | Pyrrole derivatives as alpha 7 NACHR modulators |
| TW201446243A (zh) | 2013-06-03 | 2014-12-16 | Lupin Ltd | 4-(5-(4-氯苯基)-2-(2-環丙基乙醯基)-1,4-二甲基-1氫-吡咯-3-基)苯磺醯胺作為α7尼古丁乙醯膽鹼受體調節劑 |
| WO2014203150A1 (en) | 2013-06-17 | 2014-12-24 | Lupin Limited | Pyrrole derivatives as alpha 7 nachr modulators |
| GB2516045A (en) * | 2013-07-09 | 2015-01-14 | Neuro Bio Ltd | Neurodegenerative disorders |
| US10759762B2 (en) * | 2014-10-10 | 2020-09-01 | High Force Research Limited | Fluorescent synthetic retinoids |
| EP3623371A1 (en) | 2014-12-16 | 2020-03-18 | Axovant Sciences GmbH | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| CA2988968A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmaceuticals, Inc. | Aminobenzisoxazole compounds as agonists of a7-nicotinic acetylcholine receptors |
| WO2017027600A1 (en) | 2015-08-12 | 2017-02-16 | Forum Pharmaceuticals, Inc. | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF α7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| US10835895B2 (en) | 2016-04-01 | 2020-11-17 | The University Of Tokyo | Compound and synthesis method therefor |
| HU231414B1 (hu) | 2018-07-13 | 2023-08-28 | Richter Gedeon Nyrt. | Tiadiazin származékok |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808597A (en) | 1983-07-05 | 1989-02-28 | Pfizer Inc. | Method for inhibiting the degradation of cartilage |
| AU626881B2 (en) | 1988-07-14 | 1992-08-13 | F. Hoffmann-La Roche Ag | Benzofused heterocyclics used as pharmaceuticals |
| US5756529A (en) * | 1995-09-29 | 1998-05-26 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides for use in veterinary therapies |
| JPH11180871A (ja) * | 1997-09-26 | 1999-07-06 | Sankyo Co Ltd | １，２−ジフェニルピロール誘導体を含有する医薬 |
| US6313107B1 (en) | 2000-08-29 | 2001-11-06 | Allergan Sales, Inc. | Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI |
| TW201245229A (en) | 2003-10-14 | 2012-11-16 | Hoffmann La Roche | Macrocyclic carboxylic acids and acylsulfonamides as inhibitors of HCV replication |
| CA2561639A1 (en) | 2004-03-29 | 2005-10-06 | Neurosearch A/S | Novel urea derivatives and their medical use |
| US20060142349A1 (en) | 2004-12-23 | 2006-06-29 | Pfizer Inc | Methods of modulating the activities of alpha-7 nicotinic acetylcholine receptor |
| EP1866314B1 (en) | 2005-02-16 | 2010-09-15 | NeuroSearch A/S | Novel diazabicyclic aryl derivatives and their medical use |
| JP2006316054A (ja) * | 2005-04-15 | 2006-11-24 | Tanabe Seiyaku Co Ltd | 高コンダクタンス型カルシウム感受性ｋチャネル開口薬 |
| NZ566036A (en) | 2005-09-13 | 2010-06-25 | Janssen Pharmaceutica Nv | 2-Aniline-4-aryl substituted thiazole derivatives that modulate the alpha7 nicotinic receptor |
| WO2007093602A1 (en) | 2006-02-16 | 2007-08-23 | Neurosearch A/S | Enantiopure quinuclidinyloxy pyridazines and their use as nicotinic acetylcholine receptor ligands |
| KR20080105092A (ko) * | 2006-02-20 | 2008-12-03 | 아스텔라스세이야쿠 가부시키가이샤 | 피롤 유도체 또는 그의 염 |
| JO3019B1 (ar) | 2006-04-19 | 2016-09-05 | Janssen Pharmaceutica Nv | ثلاثي مستبدل 4،2،1-ثلاثي زولات |
| EP2038278A2 (en) | 2006-06-27 | 2009-03-25 | Abbott Laboratories | Thiazoline and oxazoline derivatives and their methods of use |
| US7741364B2 (en) | 2006-06-27 | 2010-06-22 | Abbott Laboratories | Pyrrole derivatives and their methods of use |
| CA2692248A1 (en) | 2007-06-19 | 2008-12-24 | Kyorin Pharmaceutical Co., Ltd. | Pyridazinone derivative and pde inhibitor containing the same as active ingredient |
| AU2008285644A1 (en) | 2007-08-08 | 2009-02-12 | Neurosearch A/S | Novel 1,2,3-triazole derivatives useful as modulators of nicotinic acetylcholine receptors |
| ES2443290T3 (es) | 2007-10-04 | 2014-02-18 | F. Hoffmann-La Roche Ag | Derivados arilamida sustituidos con tetrazol y usos de los mismos |
| WO2009043784A1 (en) | 2007-10-04 | 2009-04-09 | F. Hoffmann-La Roche Ag | Cyclopropyl aryl amide derivatives and uses thereof |
| JO2784B1 (en) | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| MY152486A (en) | 2008-03-19 | 2014-10-15 | Janssen Pharmaceutica Nv | Trisubstituted 1,2,4 - triazoles as nicotinic acetylcholine receptor modulators |
| US7786171B2 (en) | 2008-04-04 | 2010-08-31 | Abbott Laboratories | Amide derivatives as positive allosteric modulators and methods of use thereof |
| CL2009000916A1 (es) | 2008-04-17 | 2010-12-31 | Glaxo Group Ltd | Compuestos derivados de 2-trifluorometil-1h-indol-5-metilcarboxamida, moduladores del receptor nicotinico de acetilcolina alfa7 (nachr); composicon farmaceutica; y uso para el tratamiento del deterioro cognitivo y de un trastorno psicotico como esquizofrenia. |
| WO2009135944A1 (en) | 2008-05-09 | 2009-11-12 | Janssen Pharmaceutica Nv | Trisubstituted pyrazoles as acetylcholine receptor modulators |
| CN102105475B (zh) | 2008-07-28 | 2014-04-09 | 卫材R&D管理有限公司 | 螺氨基二氢噻嗪衍生物 |
| AU2009296048A1 (en) | 2008-09-25 | 2010-04-01 | F. Hoffmann-La Roche Ag | 2,3-substituted indazole or 4,5,6,7-tetrahydro-indazoles as FXR modulators against dyslipidemia and related diseases |
| WO2010083444A1 (en) | 2009-01-15 | 2010-07-22 | Anvyl, Llc | Alpha7 nicotinic acetylcholine receptor allosteric modulators, their derivatives and uses thereof |
| WO2010130768A1 (en) | 2009-05-14 | 2010-11-18 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.1]octane derivatives useful as nicotinic acetylcholine receptor modulators |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| JO3078B1 (ar) | 2009-11-27 | 2017-03-15 | Janssen Pharmaceutica Nv | مورفولينوثيازولات بصفتها منظمات الوستيرية نوع الفا 7 موجبة |
-
2012
- 2012-01-31 CA CA2825519A patent/CA2825519A1/en not_active Abandoned
- 2012-01-31 MX MX2013008947A patent/MX344701B/es active IP Right Grant
- 2012-01-31 SG SG2013055769A patent/SG192078A1/en unknown
- 2012-01-31 WO PCT/IB2012/050442 patent/WO2012104782A1/en not_active Ceased
- 2012-01-31 BR BR112013019893A patent/BR112013019893A2/pt not_active IP Right Cessation
- 2012-01-31 US US13/983,362 patent/US20130310419A1/en not_active Abandoned
- 2012-01-31 AU AU2012213086A patent/AU2012213086B2/en not_active Ceased
- 2012-01-31 KR KR1020137022397A patent/KR20140041442A/ko not_active Ceased
- 2012-01-31 JP JP2013552304A patent/JP5865397B2/ja not_active Expired - Fee Related
- 2012-01-31 EP EP12706923.5A patent/EP2670744B1/en not_active Not-in-force
- 2012-01-31 CN CN201280013694.1A patent/CN103443092B/zh not_active Expired - Fee Related
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