CN102186833A - Mif调节剂 - Google Patents
Mif调节剂 Download PDFInfo
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- CN102186833A CN102186833A CN200980141108XA CN200980141108A CN102186833A CN 102186833 A CN102186833 A CN 102186833A CN 200980141108X A CN200980141108X A CN 200980141108XA CN 200980141108 A CN200980141108 A CN 200980141108A CN 102186833 A CN102186833 A CN 102186833A
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Classifications
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- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
- C07D405/02—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 two hetero rings
- C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Biotechnology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
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Applications Claiming Priority (3)
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| US61/189,327 | 2008-08-18 | ||
| PCT/US2009/004704 WO2010021693A2 (en) | 2008-08-18 | 2009-08-18 | Mif modulators |
Publications (1)
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| CN102186833A true CN102186833A (zh) | 2011-09-14 |
Family
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Family Applications (1)
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| EP (1) | EP2326631A4 (enExample) |
| JP (1) | JP2012500260A (enExample) |
| KR (1) | KR20110042374A (enExample) |
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| AU (1) | AU2009283195A1 (enExample) |
| BR (1) | BRPI0917394A2 (enExample) |
| CA (1) | CA2733554A1 (enExample) |
| CL (1) | CL2011000352A1 (enExample) |
| EA (1) | EA201170349A1 (enExample) |
| IL (1) | IL211170A0 (enExample) |
| MX (1) | MX2011001872A (enExample) |
| PE (1) | PE20110368A1 (enExample) |
| WO (1) | WO2010021693A2 (enExample) |
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| CN103172579A (zh) * | 2011-12-20 | 2013-06-26 | 天津市国际生物医药联合研究院 | 三氮唑苯胺类化合物的制备和用途 |
| CN103172578A (zh) * | 2011-12-20 | 2013-06-26 | 天津市国际生物医药联合研究院 | 4-环末端取代2-1,2,3-三氮唑苯胺类化合物的制备和用途 |
| CN105473581A (zh) * | 2013-06-21 | 2016-04-06 | 齐尼思表观遗传学公司 | 作为溴结构域抑制剂的新取代的双环化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007044622A1 (en) | 2005-10-07 | 2007-04-19 | Yale University | Use of mif and mif pathway agonists |
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| RU2478636C2 (ru) | 2008-08-05 | 2013-04-10 | Дайити Санкио Компани, Лимитед | ПРОИЗВОДНЫЕ ИМИДАЗОПИРИДИН-2-ОНА, ОБЛАДАЮЩИЕ mTOR ИНГИБИРУЮЩЕЙ АКТИВНОСТЬЮ |
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| TR201807207T4 (tr) | 2012-06-11 | 2018-06-21 | Ucb Biopharma Sprl | Tnf-alfa modüle edici benzimidazol bileşikleri. |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| HK1220451A1 (zh) * | 2013-03-15 | 2017-05-05 | Bioelectron Technology Corporation | 用於治疗氧化应激障碍的烷基-杂芳基取代醌衍生物 |
| WO2014200872A1 (en) | 2013-06-09 | 2014-12-18 | Rjs Biologics Llc | Pharmaceutical compounds targeted by mif affinity-tethered moieties |
| GB201317363D0 (en) | 2013-10-01 | 2013-11-13 | Eisai Ltd | Novel compounds |
| US9382245B2 (en) | 2013-10-11 | 2016-07-05 | Yale University | Compounds and methods for treating HIV infections |
| WO2015095052A1 (en) | 2013-12-17 | 2015-06-25 | Controlled Chemicals, Inc. | Isoindolin-1-ones as macrophage migration inhibitory factor (mif) inhibitors |
| RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
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| MD3519416T2 (ro) | 2016-09-27 | 2021-09-30 | Merck Sharp & Dohme | Derivați croman, izocroman și dihidroizobenzofuran ca modulatori alosterici negativi ai mGluR2, compoziții și utilizarea lor |
| EP3634417B1 (en) | 2017-05-17 | 2023-07-12 | Arcus Biosciences, Inc. | Quinazoline-pyrazole derivatives for the treatment of cancer-related disorders |
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| AU2022215844A1 (en) | 2021-02-02 | 2023-09-14 | Liminal Biosciences Limited | Gpr84 antagonists and uses thereof |
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Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU517587A1 (ru) * | 1971-08-23 | 1976-06-15 | Медицинска Академие (Инопредприятие) | Способ получени производных 2оксфенилмочевины |
| FR2244506B1 (enExample) * | 1973-06-26 | 1977-02-25 | Inst Nat Sante Rech Med | |
| DD111637A1 (enExample) * | 1974-05-13 | 1975-03-05 | ||
| DE2550959C3 (de) * | 1975-11-13 | 1980-12-04 | Hoechst Ag, 6000 Frankfurt | Tetrazolyl-imidazole und Tetrazolyl--benzimidazole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| EP0200345A3 (en) * | 1985-03-30 | 1988-03-02 | Beecham Group Plc | Anti-allergic or anti-inflammatory substituted (hetero)-aralkylamino-ortho-phenols |
| US6774227B1 (en) | 1993-05-17 | 2004-08-10 | Cytokine Pharmasciences, Inc. | Therapeutic uses of factors which inhibit or neutralize MIF activity |
| US6231833B1 (en) * | 1999-08-05 | 2001-05-15 | Pfizer Inc | 2,7-substituted octahydro-1H-pyrido[1,2-A]pyrazine derivatives as ligands for serotonin receptors |
| JPH09124620A (ja) * | 1995-10-11 | 1997-05-13 | Bristol Myers Squibb Co | 置換ビフェニルスルホンアミドエンドセリン拮抗剤 |
| WO1997038665A2 (en) * | 1996-04-03 | 1997-10-23 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| CO5011061A1 (es) * | 1996-05-15 | 2001-02-28 | Bayer Corp | Inhibicion de las metaloprotesas de matriz por acidos biariloxobutiricos sustituidos y composiciones farmaceuticas que los contienen |
| JP3783810B2 (ja) * | 1997-01-14 | 2006-06-07 | 第一製薬株式会社 | 新規ベンゾフラノン誘導体及びその製造方法 |
| US6242461B1 (en) * | 2000-01-25 | 2001-06-05 | Pfizer Inc. | Use of aryl substituted azabenzimidazoles in the treatment of HIV and AIDS related diseases |
| ATE314363T1 (de) * | 2000-06-05 | 2006-01-15 | Austria Wirtschaftsserv Gmbh | Heterocyclische hydrazone als anti-krebs- wirkstoffe |
| GB0017676D0 (en) * | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
| ES2261463T3 (es) * | 2000-08-14 | 2006-11-16 | Ortho-Mcneil Pharmaceutical, Inc. | Pirazoles sustituidos. |
| US6774134B2 (en) * | 2000-12-20 | 2004-08-10 | Bristol-Myers Squibb Company | Heterocyclic substituted 2-methyl-benzimidazole antiviral agents |
| YU52403A (sh) * | 2000-12-26 | 2006-03-03 | Dr.Reddy's Research Foundation | Heterociklična jedinjenja koja imaju antibakterijsko dejstvo, postupak za njihovo dobijanje i farmaceutske smeše koje ih sadrže |
| AR035230A1 (es) * | 2001-03-19 | 2004-05-05 | Astrazeneca Ab | Compuestos de bencimidazol, proceso para su preparacion, composicion farmaceutica, proceso para la preparacion de dicha composicion farmaceutica, y usos de estos compuestos para la elaboracion de medicamentos |
| US6515176B1 (en) * | 2001-12-03 | 2003-02-04 | Eastman Kodak Company | 6-Acylamino-5-substituted-benzoxazol-2-one compounds and method for using them |
| AR038536A1 (es) * | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| CN101675927A (zh) * | 2002-06-07 | 2010-03-24 | 科蒂科股份有限公司 | 治疗分子及方法-1 |
| TWI347946B (en) * | 2002-10-11 | 2011-09-01 | Otsuka Pharma Co Ltd | 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound |
| FR2845998A1 (fr) * | 2002-10-18 | 2004-04-23 | Servier Lab | Nouveaux composes benzoxazoles ou oxazolopyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2860235A1 (fr) * | 2003-09-29 | 2005-04-01 | Yang Ji Chemical Company Ltd | Utilisation d'un compose de formule (i) inhibiteur de l'aromatase a des fins therapeutiques et composes de formule (i) en tant que tels |
| EA200700243A1 (ru) * | 2004-07-14 | 2007-08-31 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения гепатита с |
| EP1807399A2 (en) * | 2004-10-19 | 2007-07-18 | Novartis Vaccines and Diagnostics, Inc. | Indole and benzimidazole derivatives |
| GB0423405D0 (en) * | 2004-10-21 | 2004-11-24 | Novartis Ag | Organic compounds |
| WO2006090169A1 (en) * | 2005-02-25 | 2006-08-31 | Kudos Pharmaceuticals Limited | 2,4-diamino-pyridopyrimidine derivatives and their use as mtor inhibitors |
| US7576099B2 (en) * | 2005-02-28 | 2009-08-18 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
| BRPI0608910A2 (pt) * | 2005-05-09 | 2010-02-17 | Achillion Pharmaceuticals Inc | uso de um composto da fórmula ou um sal ou hidrato farmaceuticamente aceitável desse, composto ou sal ou hidrato do mesmo, composição farmacêutica e composição farmacêutica embalada |
| JP2008542355A (ja) * | 2005-05-31 | 2008-11-27 | ファイザー株式会社 | Vr1アンタゴニストとしての置換アリールオキシ−n−ビシクロメチルアセトアミド化合物 |
| KR20080090435A (ko) * | 2005-12-21 | 2008-10-08 | 코티컬 피티와이 리미티드 | Mif 저해제 |
| WO2007076161A2 (en) * | 2005-12-27 | 2007-07-05 | Myriad Genetics, Inc | Compounds with therapeutic activity |
| EP1981884B1 (en) * | 2006-01-18 | 2012-06-13 | Amgen, Inc | Thiazole compounds as protein kinase b (pkb) inhibitors |
| GB0603041D0 (en) * | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| AU2007223797A1 (en) * | 2006-03-08 | 2007-09-13 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole derivatives with anti-HCV activity |
| WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| RU2009117701A (ru) * | 2006-10-12 | 2010-11-20 | Новартис АГ (CH) | Производные пирролидина в качестве ингибиторов iap |
| DE102007026341A1 (de) * | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| TWI428091B (zh) * | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
| WO2009094445A2 (en) * | 2008-01-25 | 2009-07-30 | E. I. Du Pont De Nemours And Company | Fungicidal hetercyclic compounds |
| JP2011513242A (ja) * | 2008-02-25 | 2011-04-28 | アミラ ファーマシューティカルズ,インク. | プロスタグランジンd2受容体アンタゴニスト |
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2009
- 2009-08-18 EA EA201170349A patent/EA201170349A1/ru unknown
- 2009-08-18 KR KR1020117006166A patent/KR20110042374A/ko not_active Withdrawn
- 2009-08-18 PE PE2011000163A patent/PE20110368A1/es not_active Application Discontinuation
- 2009-08-18 AU AU2009283195A patent/AU2009283195A1/en not_active Abandoned
- 2009-08-18 CN CN200980141108XA patent/CN102186833A/zh active Pending
- 2009-08-18 BR BRPI0917394A patent/BRPI0917394A2/pt not_active IP Right Cessation
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- 2009-08-18 WO PCT/US2009/004704 patent/WO2010021693A2/en not_active Ceased
- 2009-08-18 EP EP09808499A patent/EP2326631A4/en not_active Withdrawn
- 2009-08-18 CA CA2733554A patent/CA2733554A1/en not_active Abandoned
- 2009-08-18 US US13/059,762 patent/US20120040974A1/en not_active Abandoned
- 2009-08-18 JP JP2011523805A patent/JP2012500260A/ja active Pending
-
2011
- 2011-02-10 IL IL211170A patent/IL211170A0/en unknown
- 2011-02-18 CL CL2011000352A patent/CL2011000352A1/es unknown
Non-Patent Citations (1)
| Title |
|---|
| WEN-CHUNG SHIEH, ET AL.: "DABCO- and DBU-accelerated green chemistry for N-, O-, and S-benzylation with dibenzyl carbonate", 《TETRAHEDRON LETTERS》 * |
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Also Published As
| Publication number | Publication date |
|---|---|
| MX2011001872A (es) | 2011-05-23 |
| EP2326631A2 (en) | 2011-06-01 |
| BRPI0917394A2 (pt) | 2019-09-24 |
| WO2010021693A3 (en) | 2010-07-01 |
| US20120040974A1 (en) | 2012-02-16 |
| EP2326631A4 (en) | 2012-03-21 |
| IL211170A0 (en) | 2011-04-28 |
| KR20110042374A (ko) | 2011-04-26 |
| CA2733554A1 (en) | 2010-02-25 |
| EA201170349A1 (ru) | 2011-08-30 |
| JP2012500260A (ja) | 2012-01-05 |
| CL2011000352A1 (es) | 2011-09-23 |
| PE20110368A1 (es) | 2011-06-13 |
| WO2010021693A2 (en) | 2010-02-25 |
| AU2009283195A1 (en) | 2010-02-25 |
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