JP2002518385A5 - - Google Patents
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- Publication number
- JP2002518385A5 JP2002518385A5 JP2000554720A JP2000554720A JP2002518385A5 JP 2002518385 A5 JP2002518385 A5 JP 2002518385A5 JP 2000554720 A JP2000554720 A JP 2000554720A JP 2000554720 A JP2000554720 A JP 2000554720A JP 2002518385 A5 JP2002518385 A5 JP 2002518385A5
- Authority
- JP
- Japan
- Prior art keywords
- product
- formula
- mol
- mixture
- piperidinylamino
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LTENEPRDFSCUHJ-UHFFFAOYSA-N 4-[2-hydroxy-3-[[1-(5-nitropyridin-2-yl)piperidin-4-yl]amino]propoxy]phenol Chemical compound C=1C=C(O)C=CC=1OCC(O)CNC(CC1)CCN1C1=CC=C([N+]([O-])=O)C=N1 LTENEPRDFSCUHJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ANWFNPNQSGHEAZ-UHFFFAOYSA-N 1-(3-ethoxy-2,4-dimethoxyphenoxy)-3-[[1-(5-nitropyridin-2-yl)piperidin-4-yl]amino]propan-2-ol Chemical compound CCOC1=C(C=CC(=C1OC)OCC(CNC2CCN(CC2)C3=NC=C(C=C3)[N+](=O)[O-])O)OC ANWFNPNQSGHEAZ-UHFFFAOYSA-N 0.000 description 1
- GJYHWMPDENJDNT-UHFFFAOYSA-N 2-[(3-bromo-4-phenylmethoxyphenoxy)methyl]oxirane Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(Br)=CC=1OCC1CO1 GJYHWMPDENJDNT-UHFFFAOYSA-N 0.000 description 1
- BYDXZYUGDXYSJY-UHFFFAOYSA-N 2-[(4-phenylmethoxyphenoxy)methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 BYDXZYUGDXYSJY-UHFFFAOYSA-N 0.000 description 1
- CRXTZLKUJSMSEL-UHFFFAOYSA-N 2-[[4-[ethoxy(methoxy)methoxy]phenoxy]methyl]oxirane Chemical compound C1=CC(OC(OC)OCC)=CC=C1OCC1OC1 CRXTZLKUJSMSEL-UHFFFAOYSA-N 0.000 description 1
- YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 1
- ZTBBDJDYGPRPIW-UHFFFAOYSA-N 4-[2-hydroxy-3-[[1-(5-methylpyridin-2-yl)piperidin-4-yl]amino]propoxy]phenol Chemical compound N1=CC(C)=CC=C1N1CCC(NCC(O)COC=2C=CC(O)=CC=2)CC1 ZTBBDJDYGPRPIW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PKJRKAHYPSGZLZ-UHFFFAOYSA-N N1=CC(C)=CC=C1N1CCC(NCC(O)COC=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC1 Chemical compound N1=CC(C)=CC=C1N1CCC(NCC(O)COC=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC1 PKJRKAHYPSGZLZ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- BZQOKLQAZVAORE-UHFFFAOYSA-N methyl 6-[[4-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]piperidin-1-yl]methyl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1CN1CCC(NCC(O)COC=2C=CC(O)=CC=2)CC1 BZQOKLQAZVAORE-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR98/07660 | 1998-06-18 | ||
| FR9807660A FR2780057B1 (fr) | 1998-06-18 | 1998-06-18 | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| PCT/FR1999/001370 WO1999065895A1 (fr) | 1998-06-18 | 1999-06-10 | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002518385A JP2002518385A (ja) | 2002-06-25 |
| JP2002518385A5 true JP2002518385A5 (enExample) | 2010-05-06 |
| JP4563581B2 JP4563581B2 (ja) | 2010-10-13 |
Family
ID=9527517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000554720A Expired - Fee Related JP4563581B2 (ja) | 1998-06-18 | 1999-06-10 | フェノキシプロパノールアミン類、それらの製法及びそれらを含有する医薬組成物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6649627B1 (enExample) |
| EP (1) | EP1087961B1 (enExample) |
| JP (1) | JP4563581B2 (enExample) |
| AR (1) | AR018639A1 (enExample) |
| AT (1) | ATE222250T1 (enExample) |
| AU (1) | AU4048299A (enExample) |
| CO (1) | CO5011052A1 (enExample) |
| DE (1) | DE69902535T2 (enExample) |
| ES (1) | ES2183557T3 (enExample) |
| FR (1) | FR2780057B1 (enExample) |
| GT (1) | GT199900102A (enExample) |
| WO (1) | WO1999065895A1 (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| FR2802533B1 (fr) | 1999-12-17 | 2002-02-15 | Sanofi Synthelabo | Phenoxypropanolamines, leur preparation et leur application en therapeutique |
| JP4782342B2 (ja) * | 1999-12-17 | 2011-09-28 | サノフィ−アベンティス | フェノキシプロパノールアミン類、それらの製造方法およびそれらを含む医薬組成物 |
| CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| US6753322B2 (en) | 2000-06-06 | 2004-06-22 | Pfizer Inc | 2-aminocarbonyl-9H-purine derivatives |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| US7005439B2 (en) | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | Compounds |
| WO2002006276A1 (en) * | 2000-07-13 | 2002-01-24 | Eli Lilly And Company | Beta3 adrenergic agonists |
| US6458817B1 (en) | 2000-07-17 | 2002-10-01 | Wyeth | Substituted arylsulfides, arylsulfoxides and arylsulfones as beta-3 adrenergic receptor agonists |
| US6395762B1 (en) | 2000-07-17 | 2002-05-28 | American Home Products Corporation | Phenyl amino squarate and thiadiazole dioxide beta-3 adrenergic receptor agonists |
| US6498170B2 (en) | 2000-07-17 | 2002-12-24 | Wyeth | Cyclamine sulfonamides as β-3 adrenergic receptor agonists |
| US6444685B1 (en) | 2000-07-17 | 2002-09-03 | Wyeth | N-(4-sulfonylaryl)Cyclylamine 2-hydroxyethylamines as beta-3 adrenergic receptor agonists |
| US6537994B2 (en) | 2000-07-17 | 2003-03-25 | Wyeth | Heterocyclic β3 adrenergic receptor agonists |
| US6451814B1 (en) | 2000-07-17 | 2002-09-17 | Wyeth | Heterocyclic β-3 adrenergic receptor agonists |
| US6514991B2 (en) | 2000-07-17 | 2003-02-04 | Wyeth | Phenyl-oxo-tetrahydroquinolin-3-yl beta-3 adrenergic receptor agonists |
| US6410734B1 (en) | 2000-07-17 | 2002-06-25 | Wyeth | 2-substituted thiazolidinones as beta-3 adrenergic receptor agonists |
| US6509358B2 (en) | 2000-07-17 | 2003-01-21 | Wyeth | Piperidino-phenyl amino squarate and thiadiazole dioxide beta-3 adrenergic receptor agonists |
| US6506901B2 (en) | 2000-07-17 | 2003-01-14 | Wyeth | Substituted 2-(S)-hydroxy-3-(piperidin-4-yl-methylamino)-propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)-ethylamine β-3 adrenergic receptor agonists |
| US6465501B2 (en) | 2000-07-17 | 2002-10-15 | Wyeth | Azolidines as β3 adrenergic receptor agonists |
| US6525202B2 (en) | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| FR2817257B1 (fr) | 2000-11-30 | 2009-03-20 | Sanofi Synthelabo | Cyclohexyl(alkyl)-propanolamines, leur preparation et compositions pharmaceutiques en contenant |
| GB0104050D0 (en) | 2001-02-19 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| 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 |
| GB0107228D0 (en) | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
| SE0101038D0 (sv) * | 2001-03-23 | 2001-03-23 | Astrazeneca Ab | Novel compounds |
| SE0103818D0 (sv) | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| HUP0200849A2 (hu) * | 2002-03-06 | 2004-08-30 | Sanofi-Synthelabo | N-aminoacetil-2-ciano-pirrolidin-származékok, e vegyületeket tartalmazó gyógyszerkészítmények és eljárás előállításukra |
| FR2840301B1 (fr) * | 2002-05-29 | 2007-03-23 | Sanofi Synthelabo | Derives de phenyl-cyclohexyl-propanolamine, leur preparation et leur applicaton en therapeutique |
| SE0301369D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| US20090062909A1 (en) | 2005-07-15 | 2009-03-05 | Micell Technologies, Inc. | Stent with polymer coating containing amorphous rapamycin |
| ES2691646T3 (es) | 2005-07-15 | 2018-11-28 | Micell Technologies, Inc. | Revestimientos poliméricos que contienen polvo de fármaco de morfología controlada |
| TW200738634A (en) | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| AR060607A1 (es) | 2006-04-21 | 2008-07-02 | Novartis Ag | Derivados de purina,composiciones farmaceuticas que los contienen, metodo de preparacion y usos en enfermedades obstructivas o inflamatorias de las vias respiratorias. |
| US8852625B2 (en) | 2006-04-26 | 2014-10-07 | Micell Technologies, Inc. | Coatings containing multiple drugs |
| US8636767B2 (en) | 2006-10-02 | 2014-01-28 | Micell Technologies, Inc. | Surgical sutures having increased strength |
| US9539593B2 (en) | 2006-10-23 | 2017-01-10 | Micell Technologies, Inc. | Holder for electrically charging a substrate during coating |
| CN101711137B (zh) | 2007-01-08 | 2014-10-22 | 米歇尔技术公司 | 具有可生物降解层的支架 |
| US11426494B2 (en) | 2007-01-08 | 2022-08-30 | MT Acquisition Holdings LLC | Stents having biodegradable layers |
| EP1947103A1 (en) * | 2007-01-22 | 2008-07-23 | 4Sc Ag | Aryloxypropanolamines, methods of preparation thereof and use of aryloxypropanolamines as medicaments |
| CN101815540B (zh) | 2007-05-25 | 2015-08-19 | 米歇尔技术公司 | 用于医疗器材涂层的聚合物膜 |
| EA020655B1 (ru) | 2008-04-17 | 2014-12-30 | Миселл Текнолоджиз, Инк. | Стенты, имеющие биорассасывающиеся слои |
| US9510856B2 (en) | 2008-07-17 | 2016-12-06 | Micell Technologies, Inc. | Drug delivery medical device |
| CA2730995C (en) | 2008-07-17 | 2016-11-22 | Micell Technologies, Inc. | Drug delivery medical device |
| US8834913B2 (en) | 2008-12-26 | 2014-09-16 | Battelle Memorial Institute | Medical implants and methods of making medical implants |
| CN102481195B (zh) | 2009-04-01 | 2015-03-25 | 米歇尔技术公司 | 涂覆支架 |
| EP3366326A1 (en) | 2009-04-17 | 2018-08-29 | Micell Technologies, Inc. | Stents having controlled elution |
| EP2531140B1 (en) | 2010-02-02 | 2017-11-01 | Micell Technologies, Inc. | Stent and stent delivery system with improved deliverability |
| US8795762B2 (en) | 2010-03-26 | 2014-08-05 | Battelle Memorial Institute | System and method for enhanced electrostatic deposition and surface coatings |
| EP2560576B1 (en) | 2010-04-22 | 2018-07-18 | Micell Technologies, Inc. | Stents and other devices having extracellular matrix coating |
| CA2805631C (en) | 2010-07-16 | 2018-07-31 | Micell Technologies, Inc. | Drug delivery medical device |
| US10464100B2 (en) | 2011-05-31 | 2019-11-05 | Micell Technologies, Inc. | System and process for formation of a time-released, drug-eluting transferable coating |
| WO2013012689A1 (en) | 2011-07-15 | 2013-01-24 | Micell Technologies, Inc. | Drug delivery medical device |
| US10188772B2 (en) | 2011-10-18 | 2019-01-29 | Micell Technologies, Inc. | Drug delivery medical device |
| US11039943B2 (en) | 2013-03-12 | 2021-06-22 | Micell Technologies, Inc. | Bioabsorbable biomedical implants |
| CA2912387C (en) | 2013-05-15 | 2019-04-16 | Micell Technologies, Inc. | Bioabsorbable biomedical implants |
| MA44037B1 (fr) | 2016-06-06 | 2020-03-31 | Arena Pharm Inc | Modulateurs du récepteur adrénergique bêta 3 utile dans le traitement ou la prévention de troubles associés à ceux-ci |
| DK3448859T3 (da) | 2017-03-20 | 2019-09-23 | Forma Therapeutics Inc | Pyrrolopyrrolsammensætninger som pyruvatkinase- (pkr) aktivatorer |
| WO2020061378A1 (en) | 2018-09-19 | 2020-03-26 | Forma Therapeutics, Inc. | Treating sickle cell disease with a pyruvate kinase r activating compound |
| JP7450610B2 (ja) | 2018-09-19 | 2024-03-15 | ノヴォ・ノルディスク・ヘルス・ケア・アーゲー | ピルビン酸キナーゼｒの活性化 |
| MX2022003254A (es) | 2019-09-19 | 2022-04-18 | Forma Therapeutics Inc | Composiciones activadoras de piruvato cinasa r (pkr). |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI76551C (fi) * | 1980-11-06 | 1988-11-10 | Sandoz Ag | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-aminopropoxifenylderivat. |
| GB2163150B (en) * | 1984-07-19 | 1988-05-25 | Sandoz Ltd | 3-aminopropoxyaryl derivatives |
| JPS6137765A (ja) * | 1984-07-19 | 1986-02-22 | サンド・アクチエンゲゼルシヤフト | ３‐アミノプロポキシアリール誘導体 |
| FR2620704B1 (fr) * | 1987-09-17 | 1991-04-26 | Sanofi Sa | Derives de (benzyl-4 piperidino)-1 propanol-2, leur preparation, leur utilisation comme antimicrobiens et les produits les contenant |
| NZ229376A (en) * | 1988-06-03 | 1991-07-26 | Lilly Co Eli | Aryloxysubstituted propanolamines and pharmaceutical compositions |
| FR2640969B1 (enExample) * | 1988-12-23 | 1991-11-22 | Midy Spa | |
| US5145967A (en) * | 1989-04-20 | 1992-09-08 | Anaquest, Inc. | Method for preparing 4-alkoxyalkyl-4-phenylaminopiperdines and derivatives thereof |
| US5340160A (en) | 1989-11-21 | 1994-08-23 | Wavin B.V. | Thermoplastic saddle in two parts for repairing or renovating a pipe line with branch pipe and repaired or renovated pipe with a saddle |
| DE69228017D1 (de) * | 1991-03-27 | 1999-02-11 | Sanofi Sa | Verwendung von 4-Amino-1-(2-Pyridyl)Piperidinen als 5-HT3-Agonisten zur Behandlung und Verhütung von serotoninergen Dysfunktionen |
| MY110227A (en) * | 1991-08-12 | 1998-03-31 | Ciba Geigy Ag | 1-acylpiperindine compounds. |
| GB9318431D0 (en) * | 1993-09-06 | 1993-10-20 | Boots Co Plc | Therapeutic agents |
| NZ264634A (en) * | 1993-10-11 | 1995-12-21 | Sanofi Sa | 1-heteroaryl-4-alkyl-4-amino-piperidines and pharmaceutical compositions thereof and piperidine precursors |
-
1998
- 1998-06-18 FR FR9807660A patent/FR2780057B1/fr not_active Expired - Fee Related
-
1999
- 1999-06-04 CO CO99035290A patent/CO5011052A1/es unknown
- 1999-06-09 AR ARP990102731A patent/AR018639A1/es unknown
- 1999-06-10 AU AU40482/99A patent/AU4048299A/en not_active Abandoned
- 1999-06-10 DE DE69902535T patent/DE69902535T2/de not_active Expired - Lifetime
- 1999-06-10 EP EP99923710A patent/EP1087961B1/fr not_active Expired - Lifetime
- 1999-06-10 US US09/719,640 patent/US6649627B1/en not_active Expired - Fee Related
- 1999-06-10 WO PCT/FR1999/001370 patent/WO1999065895A1/fr not_active Ceased
- 1999-06-10 ES ES99923710T patent/ES2183557T3/es not_active Expired - Lifetime
- 1999-06-10 AT AT99923710T patent/ATE222250T1/de not_active IP Right Cessation
- 1999-06-10 JP JP2000554720A patent/JP4563581B2/ja not_active Expired - Fee Related
- 1999-07-01 GT GT199900102A patent/GT199900102A/es unknown
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