JP2009521467A5 - - Google Patents
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- JP2009521467A5 JP2009521467A5 JP2008547546A JP2008547546A JP2009521467A5 JP 2009521467 A5 JP2009521467 A5 JP 2009521467A5 JP 2008547546 A JP2008547546 A JP 2008547546A JP 2008547546 A JP2008547546 A JP 2008547546A JP 2009521467 A5 JP2009521467 A5 JP 2009521467A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidine
- carboxylic acid
- pharmaceutically acceptable
- aminoacetyl
- compound
- 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
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- -1 2-aminoacetyl Chemical group 0.000 claims description 54
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- 238000000034 method Methods 0.000 claims description 4
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Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA96283C2 (uk) * | 2005-12-23 | 2011-10-25 | Зіланд Фарма А/С | Модифіковані міметики лізину |
| EP2074087A2 (en) | 2006-12-21 | 2009-07-01 | Wyeth | Synthesis of pyrrolidine compounds |
| US20100298225A1 (en) * | 2007-07-15 | 2010-11-25 | Bjarne Due Larsen | Peptide gap junction modulators |
| US8377968B2 (en) | 2008-06-02 | 2013-02-19 | Zalicus Pharmaceuticals, Ltd. | N-piperidinyl acetamide derivatives as calcium channel blockers |
| US20120220564A1 (en) * | 2009-09-18 | 2012-08-30 | Zalicus Pharmaceuticals Ltd. | Selective calcium channel modulators |
| EP2804605A4 (en) * | 2012-01-20 | 2015-07-08 | Acucela Inc | SUBSTITUTED HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF DISEASES |
| EP2961403A4 (en) | 2013-03-01 | 2016-11-30 | Zalicus Pharmaceuticals Ltd | HETEROCYCLIC INHIBITORS OF SODIUM CHANNEL |
| ES2687481T3 (es) | 2013-03-15 | 2018-10-25 | Chromocell Corporation | Moduladores del canal de sodio para el tratamiento del dolor |
| AU2014318979B2 (en) * | 2013-09-10 | 2019-03-28 | Chromocell Corporation | Sodium channel modulators for the treatment of pain and diabetes |
| WO2015116846A1 (en) * | 2014-01-30 | 2015-08-06 | The Board Of Trustees Of The Leland Stanford Junior University | Modulation of tissue transglutaminase activation in disease |
| EP3110795A4 (en) * | 2014-02-28 | 2017-10-04 | Hikal Limited | Novel economic process for vildagliptin |
| CN110709096B (zh) | 2017-05-05 | 2023-10-31 | 泽兰德制药公司 | 细胞间隙连接通讯调节剂及其在糖尿病性眼病治疗中的应用 |
| WO2019028362A1 (en) | 2017-08-04 | 2019-02-07 | Dyax Corp. | INHIBITORS OF PLASMATIC KALLIKREIN AND USES THEREOF |
| CN118239937A (zh) | 2017-08-09 | 2024-06-25 | 戴纳立制药公司 | 化合物、组合物及方法 |
| DK3676297T3 (da) | 2017-09-01 | 2023-08-14 | Denali Therapeutics Inc | Forbindelser, sammensætninger og fremgangsmåder |
| US11358948B2 (en) | 2017-09-22 | 2022-06-14 | Kymera Therapeutics, Inc. | CRBN ligands and uses thereof |
| WO2019060742A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc | AGENTS FOR DEGRADING PROTEINS AND USES THEREOF |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| WO2019140380A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2019140387A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| CA3119773A1 (en) | 2018-11-30 | 2020-06-04 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| MA54953A (fr) * | 2019-02-13 | 2021-12-22 | Denali Therapeutics Inc | Composés, compositions et procédés |
| US12091392B2 (en) | 2019-02-13 | 2024-09-17 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| CN120574283A (zh) | 2019-04-05 | 2025-09-02 | 凯麦拉医疗公司 | Stat降解剂和其用途 |
| WO2020251972A1 (en) | 2019-06-10 | 2020-12-17 | Kymera Therapeutics, Inc. | Smarca degraders and uses thereof |
| PH12022500002A1 (en) | 2019-06-28 | 2023-04-03 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| CN112142823B (zh) * | 2019-06-28 | 2022-08-05 | 深圳翰宇药业股份有限公司 | 一种zp-1609的合成方法 |
| EP3996746A4 (en) | 2019-07-11 | 2023-08-23 | Praxis Precision Medicines, Inc. | T-TYPE CALCIUM CHANNEL MODULATOR FORMULATIONS AND METHODS OF USE THEREOF |
| WO2021011868A1 (en) | 2019-07-17 | 2021-01-21 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| WO2021119159A1 (en) | 2019-12-10 | 2021-06-17 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| KR20220145325A (ko) | 2019-12-17 | 2022-10-28 | 카이메라 쎄라퓨틱스 인코포레이티드 | Irak 분해제 및 이의 용도 |
| EP4076524A4 (en) | 2019-12-17 | 2023-11-29 | Kymera Therapeutics, Inc. | IRAQ DEGRADERS AND USES THEREOF |
| EP4081308A4 (en) | 2019-12-23 | 2024-01-24 | Kymera Therapeutics, Inc. | Smarca degraders and uses thereof |
| KR20230005160A (ko) | 2020-03-19 | 2023-01-09 | 카이메라 쎄라퓨틱스 인코포레이티드 | Mdm2 분해제 및 이의 용도 |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| WO2022120355A1 (en) | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead degraders and uses thereof |
| EP4259144A4 (en) | 2020-12-09 | 2025-08-20 | Kymera Therapeutics Inc | SMARCA DEGRADING AGENTS AND THEIR USES |
| CN116867758A (zh) | 2020-12-30 | 2023-10-10 | 凯麦拉医疗公司 | Irak降解剂和其用途 |
| CA3207724A1 (en) | 2021-02-10 | 2022-08-18 | Paul SQUIRES | Danegaptide for use in the treatment or prevention of a kidney disease |
| US12171768B2 (en) | 2021-02-15 | 2024-12-24 | Kymera Therapeutics, Inc. | IRAK4 degraders and uses thereof |
| KR20240020735A (ko) | 2021-05-07 | 2024-02-15 | 카이메라 쎄라퓨틱스 인코포레이티드 | Cdk2 분해제 및 그 용도 |
| EP4423086A1 (en) | 2021-10-25 | 2024-09-04 | Kymera Therapeutics, Inc. | Tyk2 degraders and uses thereof |
| CA3236265A1 (en) | 2021-10-29 | 2023-05-04 | William Leong | Irak4 degraders and synthesis thereof |
| JP2025500123A (ja) | 2021-12-22 | 2025-01-09 | ブルイエ・セラピューティクス・アー・ペー・エス | ギャップ結合モジュレーターおよび加齢黄斑変性の処置のためのその使用 |
| CA3243560A1 (en) | 2022-01-31 | 2023-08-03 | Kymera Therapeutics, Inc. | Iraqi Degradation Agents and Their Uses |
| WO2026009141A1 (en) * | 2024-07-01 | 2026-01-08 | Seqirus Inc. | Ionizable cationic compound |
Family Cites Families (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1125587B (de) * | 1957-03-06 | 1962-03-15 | Schering Ag | Roentgenkontrastmittel |
| US4462943A (en) * | 1980-11-24 | 1984-07-31 | E. R. Squibb & Sons, Inc. | Carboxyalkyl amino acid derivatives of various substituted prolines |
| ZA817601B (en) * | 1980-11-24 | 1982-10-27 | Squibb & Sons Inc | Carboxyalkyl amino acid derivatives of various substituted prolines |
| CA1276392C (en) | 1981-08-03 | 1990-11-13 | Donald S. Karanewsky | Phosphonamidate compounds |
| EP0088350B1 (en) | 1982-03-08 | 1985-02-20 | Schering Corporation | Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them |
| US4514391A (en) | 1983-07-21 | 1985-04-30 | E. R. Squibb & Sons, Inc. | Hydroxy substituted peptide compounds |
| US5684016A (en) * | 1984-04-12 | 1997-11-04 | Hoechst Aktiengesellschaft | Method of treating cardiac insufficiency |
| US4560506A (en) | 1984-05-25 | 1985-12-24 | E. R. Squibb & Sons, Inc. | Mercaptocycloalkylcarbonyl and mercaptoarylcarbonyl dipeptides |
| US4746676A (en) * | 1984-09-12 | 1988-05-24 | Rorer Pharmaceutical Corporation | Carboxyalkyl dipeptide compounds |
| EP0175266B1 (en) * | 1984-09-12 | 1996-03-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Antihypertensive derivatives |
| JPS61148198A (ja) * | 1984-12-22 | 1986-07-05 | Ajinomoto Co Inc | 新規トリペプチド化合物および甘味剤 |
| JPS6259296A (ja) | 1985-09-10 | 1987-03-14 | Green Cross Corp:The | ペプタイド誘導体 |
| EP0254032A3 (en) | 1986-06-20 | 1990-09-05 | Schering Corporation | Neutral metalloendopeptidase inhibitors in the treatment of hypertension |
| EP0566157A1 (en) | 1986-06-20 | 1993-10-20 | Schering Corporation | Neutral metalloendopeptidase inhibitors in the treatment of hypertension |
| US4849525A (en) | 1987-09-21 | 1989-07-18 | E. R. Squibb & Sons, Inc. | Phosphinylcycloalkylcarbonyl and phosphinylcycloalkenylcarbonyl dipeptides |
| US5120859A (en) * | 1989-09-22 | 1992-06-09 | Genentech, Inc. | Chimeric amino acid analogues |
| FR2700166B1 (fr) * | 1993-01-07 | 1995-02-17 | Rhone Poulenc Rorer Sa | Dérivés de pyrrolidine, leur préparation et les médicaments les contenant. |
| KR960705808A (ko) | 1993-11-09 | 1996-11-08 | 조셉 에프. 디프리마 | 성장 호르몬의 방출을 촉진시키는 피페리딘, 피롤리딘 및 헥사하이드로-1H-아제핀(Piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone) |
| DE4408531A1 (de) | 1994-03-14 | 1995-09-28 | Hoechst Ag | PNA-Synthese unter Verwendung einer gegen schwache Säuren labilen Amino-Schutzgruppe |
| GB9409150D0 (en) | 1994-05-09 | 1994-06-29 | Black James Foundation | Cck and gastrin receptor ligands |
| JPH0892207A (ja) * | 1994-07-26 | 1996-04-09 | Sankyo Co Ltd | ピロリジン誘導体 |
| US5491164A (en) | 1994-09-29 | 1996-02-13 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| WO1997036873A1 (en) | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| ATE226193T1 (de) | 1996-08-28 | 2002-11-15 | Procter & Gamble | Substituierte zyklische amine als metalloproteaseinhibitoren |
| AU723268B2 (en) | 1996-09-09 | 2000-08-24 | Zealand Pharma A/S | Improved solid-phase peptide synthesis and agent for use in such synthesis |
| WO1998010653A1 (en) | 1996-09-13 | 1998-03-19 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| KR100509388B1 (ko) * | 1996-10-18 | 2005-08-23 | 버텍스 파마슈티칼스 인코포레이티드 | 세린 프로테아제, 특히 간염 ｃ 바이러스 ｎｓ３ 프로테아제의 저해제 |
| AU4722197A (en) * | 1996-10-22 | 1998-05-15 | Daiichi Pharmaceutical Co., Ltd. | Novel remedies for infectious diseases |
| WO1998025897A1 (en) | 1996-12-12 | 1998-06-18 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| US6864250B1 (en) | 1997-08-22 | 2005-03-08 | Kaken Pharmaceutical Co., Ltd. | N-acylated lipophilic amino acid derivatives |
| US6399629B1 (en) * | 1998-06-01 | 2002-06-04 | Microcide Pharmaceuticals, Inc. | Efflux pump inhibitors |
| RU2243214C2 (ru) * | 1998-06-04 | 2004-12-27 | Астразенека Аб | Новые производные и аналоги 3-арилпропионовой кислоты |
| US6426331B1 (en) * | 1998-07-08 | 2002-07-30 | Tularik Inc. | Inhibitors of STAT function |
| US6242422B1 (en) | 1998-10-22 | 2001-06-05 | Idun Pharmacueticals, Inc. | (Substituted)Acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases |
| CN1420882A (zh) | 1999-07-28 | 2003-05-28 | 阿温蒂斯药物公司 | 取代的氧代氮杂杂环基化合物 |
| US6552016B1 (en) | 1999-10-14 | 2003-04-22 | Curis, Inc. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| ATE324876T1 (de) | 1999-10-14 | 2006-06-15 | Curis Inc | VERMITTLER VON ßHEDGEHOGß ÜBERMITTELNDEN BAHNEN, DAZUGEHÖRIGE ZUSAMMENETZUNGEN UND VERWENDUNGEN |
| JP2003535034A (ja) | 1999-11-12 | 2003-11-25 | ギルフォード ファーマシューティカルズ インコーポレイテッド | ジペプチジルペプチダーゼｉｖ阻害剤並びにジペプチジルペプチダーゼｉｖ阻害剤の製造及び使用法 |
| DE60107803T2 (de) | 2000-02-23 | 2006-01-19 | Zealand Pharma A/S | Neue antiarrythmische peptide |
| AU2001251147A1 (en) | 2000-03-31 | 2001-10-15 | Dupont Pharmaceuticals Company | Succinoylamino heterocycles as inhibitors of abeta protein production |
| EP1276717A2 (en) | 2000-04-17 | 2003-01-22 | Idun Pharmaceuticals, Inc. | Inhibitors of the ice/ced-3 family of cysteine proteases |
| WO2001083517A1 (en) | 2000-05-03 | 2001-11-08 | Tularik Inc. | Stat4 and stat6 binding dipeptide derivatives |
| AU7549501A (en) | 2000-06-16 | 2002-01-02 | Biogen Inc | Angiogenesis-modulating compositions and uses |
| DK1385870T3 (da) | 2000-07-21 | 2010-07-05 | Schering Corp | Peptider som inhibitorer af NS3-serinprotease fra hepatitis C-virus |
| US7244721B2 (en) | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| AR029851A1 (es) | 2000-07-21 | 2003-07-16 | Dendreon Corp | Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c |
| CA2418199A1 (en) | 2000-07-21 | 2002-01-31 | Corvas International, Inc. | Peptides as ns3-serine protease inhibitors of hepatitis c virus |
| EP1311501B1 (en) * | 2000-08-17 | 2005-11-02 | Eli Lilly And Company | Antithrombotic agents |
| US20040060568A1 (en) | 2000-10-13 | 2004-04-01 | Henryk Dudek | Hedgehog antagonists, methods and uses related thereto |
| US6376514B1 (en) | 2000-10-17 | 2002-04-23 | The Procter & Gamble Co. | Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof |
| FR2816838B1 (fr) * | 2000-11-17 | 2004-12-03 | Oreal | Utilisation de derives de l'acide 2-oxothiazolidine- 4-carboxylique comme agents prodesquamants |
| JP2005506295A (ja) | 2001-02-22 | 2005-03-03 | ジーランド ファーマ アクティーゼルスカブ | 細胞間連絡促進化合物の新規医薬使用 |
| ATE409181T1 (de) | 2001-05-08 | 2008-10-15 | Univ Yale | Proteomimetische verbindungen und verfahren |
| AU2002331064B2 (en) | 2001-08-10 | 2007-08-23 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
| US6894072B2 (en) | 2002-01-23 | 2005-05-17 | Schering Corporation | Compounds as NS3-serine protease inhibitors of hepatitis C virus |
| WO2003072528A2 (en) | 2002-02-08 | 2003-09-04 | Idun Pharmaceuticals, Inc. | (substituted)acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases |
| WO2004005248A1 (en) * | 2002-07-02 | 2004-01-15 | Novartis Ag | Peptide inhibitors of smac protein binding to inhibitor of apoptosis proteins (iap) |
| WO2004020599A2 (en) | 2002-08-29 | 2004-03-11 | Curis, Inc. | Hedgehog antagonists, methods and uses related thereto |
| WO2004032834A2 (en) * | 2002-10-04 | 2004-04-22 | Merck & Co., Inc. | Thrombin inhibitors |
| WO2004045518A2 (en) | 2002-11-15 | 2004-06-03 | Bristol-Myers Squibb Company | Open chain prolyl urea-related modulators of androgen receptor function |
| US20060194947A1 (en) * | 2002-11-25 | 2006-08-31 | Larsen Bjarne D | Peptide gap junction modulators |
| PL377633A1 (pl) | 2003-04-03 | 2006-02-06 | Merck Patent Gmbh | Związki karbonylowe |
| EP1622870A2 (en) | 2003-05-05 | 2006-02-08 | Prosidion Ltd. | Glutaminyl based dp iv-inhibitors |
| WO2005037214A2 (en) | 2003-10-14 | 2005-04-28 | Intermune, Inc. | Macrocyclic carboxylic acids and acylsulfonamides as inhibitors of hcv replication |
| CN1528745A (zh) | 2003-10-21 | 2004-09-15 | 山东大学 | 吡咯烷类基质金属蛋白酶抑制剂及其制备方法 |
| US7507760B2 (en) | 2004-01-22 | 2009-03-24 | Neuromed Pharmaceuticals Ltd. | N-type calcium channel blockers |
| EP1742914A1 (en) | 2004-02-27 | 2007-01-17 | Schering Corporation | Cyclobutenedione groups-containing compounds as inhibitors of hepatitis c virus ns3 serine protease |
| AU2005224091B2 (en) * | 2004-03-15 | 2012-02-02 | Janssen Pharmaceutica, N.V. | Novel compounds as opioid receptor modulators |
| AP2006003763A0 (en) | 2004-03-30 | 2006-10-31 | Intermune Inc | Macrocyclic compounds as inhibitors of viral replication |
| CA2565599C (en) * | 2004-05-18 | 2012-07-31 | Schering Corporation | Substituted 2-quinolyl-oxazoles useful as pde4 inhibitors |
| EP1604977A1 (en) | 2004-06-02 | 2005-12-14 | Faust Pharmaceuticals | CIS pyrrolidinyl derivatives and their uses |
| RS51974B (sr) | 2004-07-16 | 2012-02-29 | Gilead Sciences Inc. | Antivirusna jedinjenja |
| US7820699B2 (en) | 2005-04-27 | 2010-10-26 | Hoffmann-La Roche Inc. | Cyclic amines |
| US7399869B2 (en) | 2005-05-19 | 2008-07-15 | Genentech, Inc. | Fibroblast activation protein inhibitor compounds and methods |
| UA96283C2 (uk) * | 2005-12-23 | 2011-10-25 | Зіланд Фарма А/С | Модифіковані міметики лізину |
| EP2074087A2 (en) | 2006-12-21 | 2009-07-01 | Wyeth | Synthesis of pyrrolidine compounds |
-
2006
- 2006-12-21 UA UAA200808527A patent/UA96283C2/uk unknown
- 2006-12-21 WO PCT/US2006/048790 patent/WO2007078990A2/en not_active Ceased
- 2006-12-21 RU RU2008126246/04A patent/RU2494095C2/ru active
- 2006-12-21 KR KR1020087018182A patent/KR101397915B1/ko not_active Expired - Fee Related
- 2006-12-21 PL PL06849152T patent/PL1966130T3/pl unknown
- 2006-12-21 JP JP2008547546A patent/JP5473334B2/ja active Active
- 2006-12-21 NZ NZ569293A patent/NZ569293A/en not_active IP Right Cessation
- 2006-12-21 US US11/643,192 patent/US7622496B2/en active Active
- 2006-12-21 EP EP06849152.1A patent/EP1966130B1/en active Active
- 2006-12-21 CN CN2006800518550A patent/CN101336229B/zh active Active
- 2006-12-21 BR BRPI0620436A patent/BRPI0620436B8/pt active IP Right Grant
- 2006-12-21 CA CA2634743A patent/CA2634743C/en active Active
- 2006-12-21 DK DK06849152.1T patent/DK1966130T3/da active
- 2006-12-21 AU AU2006332945A patent/AU2006332945C1/en active Active
- 2006-12-21 SI SI200631729T patent/SI1966130T1/sl unknown
- 2006-12-21 ES ES06849152.1T patent/ES2443242T3/es active Active
- 2006-12-21 EP EP11166328.2A patent/EP2386539B1/en active Active
- 2006-12-21 CN CN201210106810.6A patent/CN102690221B/zh active Active
- 2006-12-21 PT PT68491521T patent/PT1966130E/pt unknown
- 2006-12-21 SG SG201102116-9A patent/SG170767A1/en unknown
- 2006-12-22 TW TW095148422A patent/TWI411597B/zh active
- 2006-12-22 PE PE2006001691A patent/PE20070849A1/es not_active Application Discontinuation
- 2006-12-26 AR ARP060105793A patent/AR058748A1/es not_active Application Discontinuation
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2008
- 2008-06-19 CR CR10089A patent/CR10089A/es not_active Application Discontinuation
- 2008-06-20 HN HN2008000957A patent/HN2008000957A/es unknown
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- 2008-06-23 IL IL192395A patent/IL192395A/en not_active IP Right Cessation
- 2008-07-18 EC EC2008008633A patent/ECSP088633A/es unknown
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