SG11201408800VA - Manufacture of 2- (5- bromo-4-(4-cyclopropylnaphthalen-1-yl) -4h-1,2,4-triazol-3-ylthio) acetic acid - Google Patents
Manufacture of 2- (5- bromo-4-(4-cyclopropylnaphthalen-1-yl) -4h-1,2,4-triazol-3-ylthio) acetic acidInfo
- Publication number
- SG11201408800VA SG11201408800VA SG11201408800VA SG11201408800VA SG11201408800VA SG 11201408800V A SG11201408800V A SG 11201408800VA SG 11201408800V A SG11201408800V A SG 11201408800VA SG 11201408800V A SG11201408800V A SG 11201408800VA SG 11201408800V A SG11201408800V A SG 11201408800VA
- Authority
- SG
- Singapore
- Prior art keywords
- international
- llll
- san diego
- rule
- hill
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- FGQFOYHRJSUHMR-UHFFFAOYSA-N lesinurad Chemical compound OC(=O)CSC1=NN=C(Br)N1C(C1=CC=CC=C11)=CC=C1C1CC1 FGQFOYHRJSUHMR-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 102220240796 rs553605556 Human genes 0.000 abstract 2
- 241001415342 Ardea Species 0.000 abstract 1
- 241000972773 Aulopiformes Species 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000008520 organization Effects 0.000 abstract 1
- 235000019515 salmon Nutrition 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Information Retrieval, Db Structures And Fs Structures Therefor (AREA)
- Management, Administration, Business Operations System, And Electronic Commerce (AREA)
Abstract
(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 9 January 2014 (09.01.2014) WIPOIPCT (10) International Publication Number WO 2014/008295 A1 (51) International Patent Classification: C07D 249/12 (2006.01) A61P 9/00 (2006.01) A61K31/4196 (2006.01) A61P 29/00 (2006.01) (21) International Application Number: (22) International Filing Date: (25) Filing Language: (26) Publication Language: PCT/US2013/049135 2 July 2013 (02.07.2013) English (30) Priority Data: 61/667,922 3 July 2012 (03.07.2012) English US (71) Applicant: ARDEA BIOSCIENCES, INC. [US/US]; 4939 Directors Place, San Diego, CA 92121 (US). (72) Inventors: GUNIC, Esmir; 8952 Capcano Rd., San Diego, CA 92129 (US). GALVIN, Gabriel; 13222 Salmon River Rd., San Diego, CA 92129 (US). (74) Agent: HARDT, Ingo, H.; Wilson Sonsini Goodrich & Rosati, 650 Page Mill Road, Palo Alto, CA 94304 (US). (81) Designated States (unless otherwise indicated, for every kind of national protection available)'. AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available)'. ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). Declarations under Rule 4.17: — as to applicant's entitlement to apply for and be granted a patent (Rule 4.17(H)) [Continued on next page] (54) Title: MANUFACTURE OF 2- (5- BROMO-4 (-CYCLOPROPYLNAPHTHALEN-1 -YL) -4H-l,2,4-TRIAZOL-3-YLTHIO) ACETIC ACID (57) Abstract: Described herein are certain processes for the synthesis of compounds of Formula (I): o\ CJ 00 o 20 30 40 2-Theta- Scale WO 2014/008295 A11II llll IIII III III Hill III III III Hill Hill llll llll lllll 111 mill llll 111 llll u ls e ' — before the expiration of the time limit for amending the — with international search report (Art. 21(3)) claims and to be republished in the event of receipt of amendments (Rule 48.2(h))
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261667922P | 2012-07-03 | 2012-07-03 | |
| PCT/US2013/049135 WO2014008295A1 (en) | 2012-07-03 | 2013-07-02 | Manufacture of 2- (5- bromo-4 (-cyclopropylnaphthalen-1-yl) -4h-1,2,4-triazol-3-ylthio) acetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG11201408800VA true SG11201408800VA (en) | 2015-01-29 |
Family
ID=49882471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG11201408800VA SG11201408800VA (en) | 2012-07-03 | 2013-07-02 | Manufacture of 2- (5- bromo-4-(4-cyclopropylnaphthalen-1-yl) -4h-1,2,4-triazol-3-ylthio) acetic acid |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US9296709B2 (en) |
| EP (1) | EP2870142B1 (en) |
| JP (1) | JP6124226B2 (en) |
| KR (1) | KR20150028992A (en) |
| CN (1) | CN104736522B (en) |
| AR (1) | AR091651A1 (en) |
| AU (1) | AU2013286739B2 (en) |
| BR (1) | BR112015000160A2 (en) |
| CA (1) | CA2878027A1 (en) |
| CO (1) | CO7170165A2 (en) |
| ES (1) | ES2609595T3 (en) |
| HU (1) | HUE031416T2 (en) |
| IL (1) | IL236413A (en) |
| MX (1) | MX352812B (en) |
| MY (1) | MY174629A (en) |
| NZ (1) | NZ631044A (en) |
| PL (1) | PL2870142T3 (en) |
| PT (1) | PT2870142T (en) |
| RU (1) | RU2666549C2 (en) |
| SA (2) | SA115360678B1 (en) |
| SG (1) | SG11201408800VA (en) |
| SI (1) | SI2870142T1 (en) |
| TW (2) | TWI634110B (en) |
| WO (1) | WO2014008295A1 (en) |
| ZA (1) | ZA201409489B (en) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR091651A1 (en) | 2012-07-03 | 2015-02-18 | Ardea Biosciences Inc | ACID ELABORATION 2- (5-BROMO-4- (4-CICLOPROPILNAFTALEN-1-IL) -4H-1,2,4-TRIAZOL-3-ILTIO) ACETIC |
| CN105263913B (en) * | 2013-06-14 | 2017-12-15 | 广东东阳光药业有限公司 | Thio 1,2,4 triazole derivative and preparation method thereof |
| CN103524440B (en) * | 2013-10-15 | 2015-09-09 | 苏州鹏旭医药科技有限公司 | The preparation method of gout therapertics Lesinurad and Lesinurad intermediate |
| AU2014351486C1 (en) * | 2013-11-22 | 2019-06-06 | Crystal Pharmatech Co., Ltd. | Crystalline forms of lesinurad and its sodium salt |
| JP6738326B2 (en) * | 2014-06-06 | 2020-08-12 | ザ スクリプス リサーチ インスティテュート | Sulfur fluoride (VI) compound and method for producing the same |
| CN105294585B (en) * | 2014-07-02 | 2019-02-12 | 成都海创药业有限公司 | A kind of compound for treating gout |
| CN105315218A (en) * | 2014-07-17 | 2016-02-10 | 天津药物研究院 | Preparation method of lesinurad intermediate namely 1-naphthyltriazole thioketone |
| CN104311498B (en) * | 2014-10-27 | 2016-04-06 | 张远强 | Triazole sulphonyl propanedioic acid compounds, Preparation Method And The Use that alkoxyl group replaces |
| CN104341361B (en) * | 2014-10-27 | 2017-01-11 | 张远强 | Cyano-substituted triazolesulfonylmalonic acid compounds as well as preparation method and application thereof |
| CN104326999B (en) * | 2014-10-27 | 2017-01-18 | 张远强 | Alkoxy-substituted triazole sulfinyl malonate type compound, and preparation method and application thereof |
| CN105820130B (en) * | 2015-01-08 | 2018-06-22 | 天津药物研究院有限公司 | Triazole n Propanoic acid class URAT1 inhibitor, preparation method and its purposes in hyperuricemia and gout treatment |
| CN105985296B (en) * | 2015-02-13 | 2018-10-16 | 天津药物研究院有限公司 | It is a kind of can be with the process for refining of industrialized lesinurad intermediates 1- naphthalene triazolinthiones |
| CN105985295B (en) * | 2015-02-17 | 2018-11-20 | 华润赛科药业有限责任公司 | A kind of optically pure thioacetic acid class compound |
| CN104788318A (en) * | 2015-03-23 | 2015-07-22 | 爱斯特（成都）生物制药有限公司 | Method for preparing 4-nitro-cyclopropyl-naphthalene |
| CN105622531A (en) * | 2015-04-03 | 2016-06-01 | 南京明德新药研发股份有限公司 | Axial chiral isomers and preparation method and pharmaceutical application thereof |
| CN104817509B (en) * | 2015-04-13 | 2019-05-17 | 安徽省逸欣铭医药科技有限公司 | Lesinurad analog and preparation method thereof and medical usage |
| CN106187926B (en) | 2015-04-30 | 2018-11-27 | 天津药物研究院有限公司 | Carboxylic acids URAT1 inhibitor, preparation method and its purposes in hyperuricemia and gout treatment of the structure containing diarylmethanes |
| EP3112334A1 (en) | 2015-06-29 | 2017-01-04 | DPx Fine Chemicals Austria GmbH & CoKG | Process for manufacturing 1-cyclopropyl-naphthalenes |
| CN104987311A (en) * | 2015-06-30 | 2015-10-21 | 安徽万邦医药科技有限公司 | Preparing method for (4-(4-cyclopropyl-naphthalene-1-yl)-5-nitr-4H-(1, 2, 4) triazole-3-ylsulfanyl)-ethyl acetate and intermediate (5-nitr-4H-(1, 2, 4) triazole-3-sulfenyl)-ethyl acetate thereof |
| CN105017168A (en) * | 2015-07-01 | 2015-11-04 | 安徽万邦医药科技有限公司 | New preparation method of [5-bromo-4-(4-cyclopropyl-naphthalene-1-yl)-4H-[1, 2, 4]triazole-3-ylsulfanyl]-methyl acetate |
| WO2017036884A1 (en) | 2015-08-28 | 2017-03-09 | Sandoz Ag | A lesinurad, free form / lesinurad ethyl ester co-crystal |
| CN105175348A (en) * | 2015-10-16 | 2015-12-23 | 北京康立生医药技术开发有限公司 | Preparation method for lesinurad |
| CN105399694B (en) * | 2015-12-11 | 2017-09-15 | 浙江京新药业股份有限公司 | Medicine Lesinurad axial chirality enantiomers |
| WO2017147270A1 (en) * | 2016-02-24 | 2017-08-31 | Ardea Biosciences, Inc. | Atropisomers of triazole derivative |
| CN105906576B (en) * | 2016-06-12 | 2018-04-17 | 成都百裕制药股份有限公司 | It is a kind of come Si Nuolei intermediates preparation method |
| CN106083680B (en) * | 2016-06-21 | 2018-11-02 | 山东川成医药股份有限公司 | A kind of preparation method of 4- cyclopropyl -1- naphthalenylisothiocyanates |
| CN106187927B (en) * | 2016-07-26 | 2020-02-04 | 山东川成医药股份有限公司 | Preparation method of Lesinurad intermediate |
| CN106220577A (en) * | 2016-07-26 | 2016-12-14 | 苏州明锐医药科技有限公司 | The preparation method of Li Xinluode |
| EP3281941B1 (en) | 2016-08-11 | 2019-07-24 | Zentiva K.S. | Process for preparing 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4h-1,2,4-triazol-3-ylthio)acetic acid |
| CN106632108A (en) * | 2016-12-14 | 2017-05-10 | 湖南欧亚生物有限公司 | Preparation method of lesinurad |
| EP3372592A1 (en) | 2017-03-07 | 2018-09-12 | Zentiva, k.s. | Solid forms of lesinurad amine salts |
| US10351537B2 (en) | 2017-03-10 | 2019-07-16 | Apotex Inc. | Processes for the preparation of lesinurad and intermediates thereof |
| EP3315494A1 (en) | 2017-04-19 | 2018-05-02 | Química Sintética, S.A. | Amorphous form of lesinurad and processes for its preparation |
| CN108947919B (en) | 2017-05-17 | 2023-05-02 | 上海奥博生物医药股份有限公司 | A novel preparation method of anti-gout drug Lesinurad and its key intermediate |
| CN109206323A (en) * | 2017-07-07 | 2019-01-15 | 上海现代制药股份有限公司 | A kind of preparation method of naphthylamines pharmaceutical intermediate |
| CN107739344A (en) * | 2017-10-10 | 2018-02-27 | 浙江新东港药业股份有限公司 | Prepare Lesinurd method and its intermediate |
| EP3498697A1 (en) | 2017-12-12 | 2019-06-19 | Química Sintética, S.A. | Novel salts and polymorphs of lesinurad |
| CN109970667A (en) * | 2017-12-27 | 2019-07-05 | 徐州万邦金桥制药有限公司 | A kind of refining methd of the western Nader of thunder |
| CN108047148A (en) * | 2017-12-28 | 2018-05-18 | 北京沃邦医药科技有限公司 | A kind of preparation method of the western Nader's impurity of thunder |
| CN110878045A (en) * | 2018-09-05 | 2020-03-13 | 江西同和药业股份有限公司 | Compound and preparation method and application thereof |
| CN111116501B (en) * | 2019-12-30 | 2021-03-12 | 北京鑫开元医药科技有限公司海南分公司 | Synthesis method of Ravinard intermediate capable of effectively reducing impurity content |
| CN111116500B (en) * | 2019-12-30 | 2021-06-08 | 北京鑫开元医药科技有限公司海南分公司 | A kind of purification method of key intermediate of Recinade |
| CN112778223A (en) * | 2021-01-25 | 2021-05-11 | 海南鑫开源医药科技有限公司 | Preparation method of Raschindde oxidation impurities |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060135556A1 (en) | 2002-08-23 | 2006-06-22 | Jean-Luc Girardet | Non-nucleoside reverse transcriptase inhibitors |
| ATE540677T1 (en) | 2004-08-25 | 2012-01-15 | Ardea Biosciences Inc | S-TRIAZOLYL ALPHA MERCAPTOACETANILIDE AS AN INHIBITOR OF REVERSE TRANSCRIPTASE OF HIV |
| WO2007050087A1 (en) | 2004-08-25 | 2007-05-03 | Ardea Biosciences, Inc. | N[S(4-aryl-triazol-3-yl)α -mercaptoacetyl]-p-amino benozoic acids AS HIV REVERSE TRANSCRIPTASE INHIBITORS |
| EP2217577B1 (en) | 2007-11-27 | 2014-08-06 | Ardea Biosciences, Inc. | Novel compounds and compositions and methods of use |
| US8173690B2 (en) * | 2008-09-04 | 2012-05-08 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| EP2328874A4 (en) * | 2008-09-04 | 2012-05-09 | Ardea Biosciences Inc | Compounds, compositions and methods of using same for modulating uric acid levels |
| US8242154B2 (en) | 2008-09-04 | 2012-08-14 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| MY161482A (en) * | 2010-01-08 | 2017-04-14 | Ardea Biosciences Inc | Polymorphic, crystalline and mesophase forms of sodium 2-(5-bromo-4-(4-cyclopropylnapthalen-1-yl)-4h-1,2,4-triazol-3-ylthio)acetate, and uses thereof |
| EP2560642A4 (en) | 2010-03-30 | 2013-12-18 | Ardea Biosciences Inc | Treatment of gout |
| WO2011159732A1 (en) | 2010-06-15 | 2011-12-22 | Ardea Biosciences,Inc. | Treatment of gout and hyperuricemia |
| CN103249417A (en) | 2010-10-15 | 2013-08-14 | 阿迪亚生命科学公司 | Methods for treating hyperuricemia and related diseases |
| BR112013016982A2 (en) | 2010-12-30 | 2016-10-25 | Ardea Biosciences Inc | 2- (5-bromo-4- (4-cyclopropylnaphthalen-1-yl) -4h-1,2,4-triazol-3-ylthio) acetic acid polymorphic forms and uses thereof |
| AR091651A1 (en) | 2012-07-03 | 2015-02-18 | Ardea Biosciences Inc | ACID ELABORATION 2- (5-BROMO-4- (4-CICLOPROPILNAFTALEN-1-IL) -4H-1,2,4-TRIAZOL-3-ILTIO) ACETIC |
-
2013
- 2013-07-01 AR ARP130102354 patent/AR091651A1/en unknown
- 2013-07-02 KR KR20157001430A patent/KR20150028992A/en not_active Ceased
- 2013-07-02 PL PL13813122T patent/PL2870142T3/en unknown
- 2013-07-02 WO PCT/US2013/049135 patent/WO2014008295A1/en active Application Filing
- 2013-07-02 AU AU2013286739A patent/AU2013286739B2/en not_active Ceased
- 2013-07-02 SG SG11201408800VA patent/SG11201408800VA/en unknown
- 2013-07-02 MX MX2015000082A patent/MX352812B/en active IP Right Grant
- 2013-07-02 JP JP2015520662A patent/JP6124226B2/en active Active
- 2013-07-02 ES ES13813122.2T patent/ES2609595T3/en active Active
- 2013-07-02 CN CN201380045807.0A patent/CN104736522B/en not_active Expired - Fee Related
- 2013-07-02 PT PT138131222T patent/PT2870142T/en unknown
- 2013-07-02 RU RU2015102723A patent/RU2666549C2/en not_active IP Right Cessation
- 2013-07-02 EP EP13813122.2A patent/EP2870142B1/en active Active
- 2013-07-02 US US14/409,806 patent/US9296709B2/en not_active Expired - Fee Related
- 2013-07-02 CA CA2878027A patent/CA2878027A1/en not_active Abandoned
- 2013-07-02 SI SI201330470A patent/SI2870142T1/en unknown
- 2013-07-02 HU HUE13813122A patent/HUE031416T2/en unknown
- 2013-07-02 BR BR112015000160A patent/BR112015000160A2/en not_active IP Right Cessation
- 2013-07-02 NZ NZ631044A patent/NZ631044A/en not_active IP Right Cessation
- 2013-07-02 MY MYPI2015000009A patent/MY174629A/en unknown
- 2013-07-03 SA SA115360678A patent/SA115360678B1/en unknown
- 2013-07-03 SA SA113340696A patent/SA113340696B1/en unknown
- 2013-07-03 TW TW104135665A patent/TWI634110B/en not_active IP Right Cessation
- 2013-07-03 TW TW102123881A patent/TWI621615B/en not_active IP Right Cessation
-
2014
- 2014-12-23 ZA ZA2014/09489A patent/ZA201409489B/en unknown
- 2014-12-23 IL IL236413A patent/IL236413A/en active IP Right Grant
-
2015
- 2015-01-15 CO CO15007371A patent/CO7170165A2/en unknown
-
2016
- 2016-02-19 US US15/048,110 patent/US20160214947A1/en not_active Abandoned
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