MX2018001751A - Dihidroquinolinonas aril-sustituidas, su preparacion y su uso como farmaceuticos. - Google Patents
Dihidroquinolinonas aril-sustituidas, su preparacion y su uso como farmaceuticos.Info
- Publication number
- MX2018001751A MX2018001751A MX2018001751A MX2018001751A MX2018001751A MX 2018001751 A MX2018001751 A MX 2018001751A MX 2018001751 A MX2018001751 A MX 2018001751A MX 2018001751 A MX2018001751 A MX 2018001751A MX 2018001751 A MX2018001751 A MX 2018001751A
- Authority
- MX
- Mexico
- Prior art keywords
- dihydroquinolinones
- aryl
- substituted
- pharmaceuticals
- preparation
- Prior art date
Links
- 239000003814 drug Substances 0.000 title 1
- 206010028980 Neoplasm Diseases 0.000 abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 3
- 102000001805 Bromodomains Human genes 0.000 abstract 2
- 108050009021 Bromodomains Proteins 0.000 abstract 2
- 208000035475 disorder Diseases 0.000 abstract 2
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 230000002500 effect on skin Effects 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/435—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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562203623P | 2015-08-11 | 2015-08-11 | |
| US201662356579P | 2016-06-30 | 2016-06-30 | |
| PCT/CA2016/050943 WO2017024408A1 (en) | 2015-08-11 | 2016-08-11 | Aryl-substituted dihydroquinolinones, their preparation and their use as pharmaceuticals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2018001751A true MX2018001751A (es) | 2018-08-01 |
Family
ID=57982883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2018001751A MX2018001751A (es) | 2015-08-11 | 2016-08-11 | Dihidroquinolinonas aril-sustituidas, su preparacion y su uso como farmaceuticos. |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10501438B2 (enExample) |
| EP (1) | EP3334717B1 (enExample) |
| JP (1) | JP2018527340A (enExample) |
| KR (1) | KR20180039117A (enExample) |
| CN (1) | CN108290856A (enExample) |
| AU (1) | AU2016305513A1 (enExample) |
| CA (1) | CA2994472A1 (enExample) |
| HK (1) | HK1256753A1 (enExample) |
| IL (1) | IL257347A (enExample) |
| MX (1) | MX2018001751A (enExample) |
| WO (1) | WO2017024408A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020093162A1 (en) * | 2018-11-07 | 2020-05-14 | Neomed Institute | Treatment of bet inhibitor-resistant cancers and other diseases responsive to dual bet and cbp/ep300 inhibition therapy |
| EP3938340B1 (en) * | 2019-03-11 | 2025-07-09 | Collaborative Medicinal Development, LLC | Heteroaromatic and heterobicyclic aromatic derivatives for the treatment of ferroptosis-related disorders |
| CN112239456B (zh) * | 2020-06-09 | 2021-09-07 | 浙江理工大学 | 一种取代2，3-二氢喹诺酮化合物的制备方法 |
| CN114276333B (zh) * | 2020-09-28 | 2023-05-09 | 中国科学院上海药物研究所 | 二氢喹喔啉类溴结构域二价抑制剂 |
| WO2024222147A1 (zh) * | 2023-04-23 | 2024-10-31 | 信义核新(北京)生物科技有限公司 | 喹诺酮类似物及其用途 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4550166A (en) | 1984-05-21 | 1985-10-29 | American Cyanamid Company | (Pyridinyl)-1,2,4-triazolo[4,3-a]pyridines |
| US4785005A (en) * | 1986-06-25 | 1988-11-15 | Rorer Pharmaceutical Corporation | 6-(6-alkylpyridone)-carbostyril compounds and their cardiotonic uses |
| US5093330A (en) | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| DE4237656A1 (de) | 1992-06-13 | 1993-12-16 | Merck Patent Gmbh | Benzimidazolderivate |
| US6162804A (en) | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US6465484B1 (en) | 1997-09-26 | 2002-10-15 | Merck & Co., Inc. | Angiogenesis inhibitors |
| AU760020B2 (en) | 1998-08-31 | 2003-05-08 | Merck & Co., Inc. | Novel angiogenesis inhibitors |
| MY139563A (en) | 2002-09-04 | 2009-10-30 | Bristol Myers Squibb Co | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
| CN1893950A (zh) | 2003-12-18 | 2007-01-10 | 辉瑞产品公司 | 用p38 MAP激酶抑制剂治疗动物急性炎症的方法 |
| BRPI0507653A (pt) | 2004-03-19 | 2007-07-10 | Warner Lambert Co | derivados de imidazopiridina e imidazopiridina formulação farmacêutica compreendendo os mesmos e uso |
| PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| HRP20150642T1 (hr) | 2006-12-22 | 2015-08-14 | Astex Therapeutics Limited | BICIKLIÄŚKE HETEROCIKLIÄŚKE TVARI KAO INHIBITORI FGFR-a |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| JP5456681B2 (ja) | 2007-10-17 | 2014-04-02 | ノバルティス アーゲー | ＡＬＫ阻害剤として有用なイミダゾ［１，２−ａ］ピリジン誘導体 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| GB0919423D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| EP2501232A1 (en) | 2009-11-16 | 2012-09-26 | Merck Sharp & Dohme Corp. | Imidazole derivatives and methods of use thereof |
| HRP20150571T1 (xx) | 2010-12-13 | 2015-07-03 | Array Biopharma, Inc. | Supstituirani n-(1h-indazol-4-il)imidazo[1,2-a]piridin-3-karboksamidni spojevi kao inhibitori receptora tirozin kinaze tipa iii |
| GB201114103D0 (en) | 2011-08-17 | 2011-09-28 | Glaxosmithkline Llc | Novel compounds |
| AR091790A1 (es) | 2011-08-29 | 2015-03-04 | Infinity Pharmaceuticals Inc | Derivados de isoquinolin-1-ona y sus usos |
| TR201807207T4 (tr) | 2012-06-11 | 2018-06-21 | Ucb Biopharma Sprl | Tnf-alfa modüle edici benzimidazol bileşikleri. |
| SG11201408324QA (en) | 2012-06-12 | 2015-01-29 | Abbvie Inc | Pyridinone and pyridazinone derivatives |
| ES2660051T3 (es) | 2012-09-28 | 2018-03-20 | Vanderbilt University | Compuestos heterocíclicos condensados como inhibidores selectivos de BMP |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US20140094456A1 (en) | 2012-10-02 | 2014-04-03 | Intermune, Inc. | Anti-fibrotic pyridinones |
| EP2935260A1 (de) * | 2012-12-20 | 2015-10-28 | Bayer Pharma Aktiengesellschaft | Bet-proteininhibitorische dihydropyridopyrazinone |
| CA2895905A1 (en) * | 2012-12-21 | 2014-06-26 | Zenith Epigenetics Corp. | Novel heterocyclic compounds as bromodomain inhibitors |
| WO2014128655A1 (en) | 2013-02-25 | 2014-08-28 | Aurigene Discovery Technologies Limited | Substituted imidazo[4,5-c]quinoline derivatives as bromodomain inhibitors |
| US9695179B2 (en) | 2013-03-14 | 2017-07-04 | Convergene Llc | Methods and compositions for inhibition of bromodomain-containing proteins |
| KR102244719B1 (ko) | 2013-03-15 | 2021-04-26 | 플렉시콘 인코퍼레이티드 | 헤테로시클릭 화합물 및 그의 용도 |
| WO2014152029A2 (en) | 2013-03-15 | 2014-09-25 | Epigenetix, Inc. | Oxazolo[5,4-c]quinolin-2-one compounds as bromodomain inhibitors |
| US8975417B2 (en) | 2013-05-27 | 2015-03-10 | Novartis Ag | Pyrazolopyrrolidine derivatives and their use in the treatment of disease |
| WO2015004533A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| PL3010503T3 (pl) | 2013-06-21 | 2020-08-24 | Zenith Epigenetics Ltd. | Nowe bicykliczne inhibitory bromodomen |
| JP2016523941A (ja) * | 2013-07-09 | 2016-08-12 | バイエル ファーマ アクチエンゲゼルシャフト | 改変されたｂｅｔタンパク質阻害性ジヒドロキノキサリノンおよびジヒドロピリドピラジノン |
| US20150051208A1 (en) | 2013-08-14 | 2015-02-19 | Boehringer Ingelheim International Gmbh | Pyridinones |
| WO2015049629A1 (en) | 2013-10-01 | 2015-04-09 | Piramal Enterprises Limited | Imidazoquinoline compounds as bromodomain inhibitors |
| US9399640B2 (en) | 2013-11-26 | 2016-07-26 | Incyte Corporation | Substituted pyrrolo[2,3-c]pyridines and pyrazolo[3,4-c]pyridines as BET protein inhibitors |
| WO2015081189A1 (en) | 2013-11-26 | 2015-06-04 | Incyte Corporation | Bicyclic heterocycles as bet protein inhibitors |
| GB201321729D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| US9428514B2 (en) | 2013-12-09 | 2016-08-30 | Abbvie Inc. | Bromodomain inhibitors |
| SG11201604916YA (en) | 2014-01-09 | 2016-07-28 | Orion Corp | Bicyclic heterocyclic derivatives as bromodomain inhibitors |
| JP6525437B2 (ja) | 2014-04-02 | 2019-06-05 | インターミューン， インコーポレイテッド | 抗線維性ピリジノン |
| KR102702503B1 (ko) * | 2014-04-23 | 2024-09-05 | 인사이트 홀딩스 코포레이션 | BET 단백질의 저해제로서의 1H-피롤로[2,3-c]피리딘-7(6H)-온 및 피라졸로[3,4-c]피리딘-7(6H)-온 |
| WO2016077656A2 (en) | 2014-11-13 | 2016-05-19 | Convergene Llc | Methods and compositions for inhibition of bromodomain and extraterminal proteins |
| US10710992B2 (en) | 2014-12-01 | 2020-07-14 | Zenith Epigenetics Ltd. | Substituted pyridinones as bromodomain inhibitors |
| WO2016097870A1 (en) | 2014-12-17 | 2016-06-23 | Zenith Epigenetics Corp. | Substituted bicyclic compounds as bromodomain inhibitors |
| US10231953B2 (en) | 2014-12-17 | 2019-03-19 | Zenith Epigenetics Ltd. | Inhibitors of bromodomains |
| GB201503720D0 (en) | 2015-03-05 | 2015-04-22 | Glaxosmithkline Ip No 2 Ltd | Chemical compound |
| GB201504689D0 (en) | 2015-03-19 | 2015-05-06 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| AR104259A1 (es) | 2015-04-15 | 2017-07-05 | Celgene Quanticel Res Inc | Inhibidores de bromodominio |
| GB201506660D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201506658D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| US10501459B2 (en) | 2015-10-21 | 2019-12-10 | Neomed Institute | Substituted imidazo[1,2-a]pyridines as bromodomain inhibitors |
-
2016
- 2016-08-11 AU AU2016305513A patent/AU2016305513A1/en not_active Abandoned
- 2016-08-11 US US15/751,800 patent/US10501438B2/en active Active
- 2016-08-11 CN CN201680058648.1A patent/CN108290856A/zh active Pending
- 2016-08-11 EP EP16834368.9A patent/EP3334717B1/en active Active
- 2016-08-11 KR KR1020187006580A patent/KR20180039117A/ko not_active Withdrawn
- 2016-08-11 JP JP2018506998A patent/JP2018527340A/ja active Pending
- 2016-08-11 MX MX2018001751A patent/MX2018001751A/es unknown
- 2016-08-11 HK HK18115833.9A patent/HK1256753A1/zh unknown
- 2016-08-11 CA CA2994472A patent/CA2994472A1/en not_active Abandoned
- 2016-08-11 WO PCT/CA2016/050943 patent/WO2017024408A1/en not_active Ceased
-
2018
- 2018-02-04 IL IL257347A patent/IL257347A/en unknown
-
2019
- 2019-10-28 US US16/665,198 patent/US20200299262A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP3334717A1 (en) | 2018-06-20 |
| AU2016305513A1 (en) | 2018-03-08 |
| CN108290856A (zh) | 2018-07-17 |
| HK1256753A1 (zh) | 2019-10-04 |
| US10501438B2 (en) | 2019-12-10 |
| EP3334717B1 (en) | 2020-07-01 |
| US20200299262A1 (en) | 2020-09-24 |
| US20180230130A1 (en) | 2018-08-16 |
| WO2017024408A1 (en) | 2017-02-16 |
| JP2018527340A (ja) | 2018-09-20 |
| KR20180039117A (ko) | 2018-04-17 |
| CA2994472A1 (en) | 2017-02-16 |
| IL257347A (en) | 2018-03-29 |
| EP3334717A4 (en) | 2019-02-13 |
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