KR20080044358A - 리네졸리드 결정 형태 ⅱ - Google Patents
리네졸리드 결정 형태 ⅱ Download PDFInfo
- Publication number
- KR20080044358A KR20080044358A KR1020087010742A KR20087010742A KR20080044358A KR 20080044358 A KR20080044358 A KR 20080044358A KR 1020087010742 A KR1020087010742 A KR 1020087010742A KR 20087010742 A KR20087010742 A KR 20087010742A KR 20080044358 A KR20080044358 A KR 20080044358A
- Authority
- KR
- South Korea
- Prior art keywords
- linezolide
- solvent
- methyl
- crystal form
- linezolid
- 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.)
- Ceased
Links
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 title abstract description 26
- 229960003907 linezolid Drugs 0.000 title abstract description 22
- 239000013078 crystal Substances 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000003242 anti bacterial agent Substances 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FKZUTWSVQLXKQE-OAHLLOKOSA-N 2-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione Chemical compound FC1=CC(N2C(O[C@@H](CN3C(C4=CC=CC=C4C3=O)=O)C2)=O)=CC=C1N1CCOCC1 FKZUTWSVQLXKQE-OAHLLOKOSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- 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
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17983700P | 2000-02-02 | 2000-02-02 | |
| US60/179,837 | 2000-02-02 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077016678A Division KR100864745B1 (ko) | 2000-02-02 | 2001-01-29 | 리네졸리드 결정 형태 ⅱ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080044358A true KR20080044358A (ko) | 2008-05-20 |
Family
ID=22658183
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087010742A Ceased KR20080044358A (ko) | 2000-02-02 | 2001-01-29 | 리네졸리드 결정 형태 ⅱ |
| KR1020027009923A Expired - Fee Related KR100781815B1 (ko) | 2000-02-02 | 2001-01-29 | 리네졸리드 결정 형태 ⅱ |
| KR1020077016678A Expired - Fee Related KR100864745B1 (ko) | 2000-02-02 | 2001-01-29 | 리네졸리드 결정 형태 ⅱ |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027009923A Expired - Fee Related KR100781815B1 (ko) | 2000-02-02 | 2001-01-29 | 리네졸리드 결정 형태 ⅱ |
| KR1020077016678A Expired - Fee Related KR100864745B1 (ko) | 2000-02-02 | 2001-01-29 | 리네졸리드 결정 형태 ⅱ |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1255754B1 (https=) |
| JP (1) | JP5235256B2 (https=) |
| KR (3) | KR20080044358A (https=) |
| CN (1) | CN1221547C (https=) |
| AR (1) | AR027261A1 (https=) |
| AT (1) | ATE297920T1 (https=) |
| AU (1) | AU782138B2 (https=) |
| BR (1) | BR0107667A (https=) |
| CA (1) | CA2395603C (https=) |
| CO (1) | CO5261555A1 (https=) |
| CZ (1) | CZ302292B6 (https=) |
| DE (1) | DE60111497T2 (https=) |
| DK (1) | DK1255754T3 (https=) |
| EA (1) | EA004434B1 (https=) |
| EE (1) | EE05197B1 (https=) |
| ES (1) | ES2242728T3 (https=) |
| HU (1) | HUP0301076A3 (https=) |
| IL (1) | IL151010A0 (https=) |
| MX (1) | MXPA02007471A (https=) |
| MY (1) | MY122829A (https=) |
| NO (2) | NO323459B1 (https=) |
| NZ (1) | NZ520541A (https=) |
| PE (1) | PE20011086A1 (https=) |
| PL (1) | PL356433A1 (https=) |
| PT (1) | PT1255754E (https=) |
| SI (1) | SI1255754T1 (https=) |
| SK (1) | SK287025B6 (https=) |
| TW (1) | TWI297687B (https=) |
| WO (1) | WO2001057035A1 (https=) |
| ZA (1) | ZA200205162B (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100490643B1 (ko) * | 2002-10-29 | 2005-05-19 | 한국과학기술연구원 | 새로운 메틸리덴 피페리딘일 옥사졸리딘온 유도체 및이들의 제조방법 |
| PT1673370E (pt) | 2003-10-16 | 2009-11-05 | Symed Labs Ltd | Forma cristalina de linezolida |
| WO2005099353A2 (en) | 2004-04-19 | 2005-10-27 | Symed Labs Limited | A novel process for the preparation of linezolid and related compounds |
| CA2572207A1 (en) * | 2004-06-29 | 2006-10-19 | Teva Pharmaceutical Industries Ltd. | Solid forms of linezolid and processes for preparation thereof |
| EP2174935A1 (en) * | 2004-06-29 | 2010-04-14 | Teva Pharmaceutical Industries Ltd | Linezolid Compositions |
| EP1866295A2 (en) | 2005-02-24 | 2007-12-19 | Teva Pharmaceutical Industries Ltd | Processes for the preparation of linezolid intermediate |
| BRPI0605901A (pt) * | 2005-06-22 | 2007-12-18 | Teva Pharma | formas polimórficas de maleato de tegaserode |
| DK1749517T3 (da) * | 2005-07-20 | 2008-11-03 | Teva Pharma | Stabil farmaceutiske sammensætning af linezolid form IV |
| WO2007102082A1 (en) * | 2006-03-09 | 2007-09-13 | Glenmark Pharmaceuticals Limited | High oxazolidinone content solid dosage forms |
| JP5302200B2 (ja) * | 2006-10-23 | 2013-10-02 | コンサート ファーマシューティカルズ インコーポレイテッド | オキサゾリジノン誘導体および使用方法 |
| WO2011050826A1 (en) | 2009-10-28 | 2011-05-05 | Synthon B.V. | Process for making crystalline form a of linezolid |
| JP5865898B2 (ja) | 2010-04-30 | 2016-02-17 | インディアナ ユニバーシティー リサーチ アンド テクノロジー コーポレーションＩｎｄｉａｎａ Ｕｎｉｖｅｒｓｉｔｙ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐｏｒａｔｉｏｎ | リネゾリドを調製するためのプロセス |
| EP2690100A1 (en) | 2010-08-11 | 2014-01-29 | Synhton B.V. | Process for making linezolid |
| EP2603505A1 (en) | 2010-08-11 | 2013-06-19 | Synthon BV | Process for making linezolid |
| US20140114065A1 (en) * | 2011-02-24 | 2014-04-24 | Lee Phama Limited | Anhydrous linezolid crystalline form-ii |
| EP2683696A1 (en) | 2011-03-09 | 2014-01-15 | Synthon BV | Process for making crystalline form a of linezolid |
| CN102731341A (zh) * | 2011-04-13 | 2012-10-17 | 上海医药工业研究院 | 用于制备利奈唑胺的中间体及其制备方法 |
| CN105461648B (zh) * | 2011-05-03 | 2018-01-12 | 江苏豪森药业集团有限公司 | 利奈唑胺的晶型及其制备方法 |
| CN102399200B (zh) * | 2011-12-14 | 2013-12-04 | 浙江新东港药业股份有限公司 | 一种利用悬浮结晶法制备利奈唑胺晶型ⅰ的方法 |
| WO2013111048A1 (en) | 2012-01-24 | 2013-08-01 | Jubilant Life Sciences Limited | Improved process for the preparation of stable crystalline form-i of linezolid, substantially free of residual solvent |
| WO2013120496A1 (en) | 2012-02-14 | 2013-08-22 | Pharmathen S.A. | Process for the preparation of linezolid in crystalline form and salts thereof |
| CN102643245A (zh) * | 2012-04-10 | 2012-08-22 | 杭州华东医药集团生物工程研究所有限公司 | 一种利奈唑胺晶型及其制备方法 |
| WO2014071990A1 (en) | 2012-11-09 | 2014-05-15 | Synthon Bv | Process for making linezolid |
| JP7101694B2 (ja) | 2016-11-16 | 2022-07-15 | ペルシカ ファーマシューティカルズ リミテッド | 腰痛のための抗生物質製剤 |
| EP3709970B1 (en) * | 2017-11-16 | 2025-05-14 | Persica Pharmaceuticals Ltd. | Linezolid formulations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
| US5688792A (en) * | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
| MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| ES2166073T3 (es) * | 1996-04-11 | 2002-04-01 | Upjohn Co | Procedimiento para preparar oxazolidinonas. |
| DK1028940T3 (da) * | 1997-11-07 | 2007-07-30 | Pharmacia & Upjohn Co Llc | Fremgangsmåde til fremstilling af oxazolidinoner |
-
2001
- 2001-01-22 AR ARP010100269A patent/AR027261A1/es not_active Application Discontinuation
- 2001-01-25 PE PE2001000080A patent/PE20011086A1/es not_active Application Discontinuation
- 2001-01-26 CO CO01005901A patent/CO5261555A1/es not_active Application Discontinuation
- 2001-01-29 DK DK01904805T patent/DK1255754T3/da active
- 2001-01-29 SK SK994-2002A patent/SK287025B6/sk not_active IP Right Cessation
- 2001-01-29 EE EEP200200420A patent/EE05197B1/xx not_active IP Right Cessation
- 2001-01-29 PT PT01904805T patent/PT1255754E/pt unknown
- 2001-01-29 KR KR1020087010742A patent/KR20080044358A/ko not_active Ceased
- 2001-01-29 CN CNB018034489A patent/CN1221547C/zh not_active Expired - Fee Related
- 2001-01-29 DE DE60111497T patent/DE60111497T2/de not_active Expired - Lifetime
- 2001-01-29 CZ CZ20022635A patent/CZ302292B6/cs not_active IP Right Cessation
- 2001-01-29 CA CA2395603A patent/CA2395603C/en not_active Expired - Lifetime
- 2001-01-29 ES ES01904805T patent/ES2242728T3/es not_active Expired - Lifetime
- 2001-01-29 MY MYPI20010371A patent/MY122829A/en unknown
- 2001-01-29 MX MXPA02007471A patent/MXPA02007471A/es active IP Right Grant
- 2001-01-29 AU AU32755/01A patent/AU782138B2/en not_active Ceased
- 2001-01-29 KR KR1020027009923A patent/KR100781815B1/ko not_active Expired - Fee Related
- 2001-01-29 EP EP01904805A patent/EP1255754B1/en not_active Expired - Lifetime
- 2001-01-29 KR KR1020077016678A patent/KR100864745B1/ko not_active Expired - Fee Related
- 2001-01-29 BR BR0107667-1A patent/BR0107667A/pt not_active Application Discontinuation
- 2001-01-29 AT AT01904805T patent/ATE297920T1/de active
- 2001-01-29 SI SI200130405T patent/SI1255754T1/sl unknown
- 2001-01-29 PL PL01356433A patent/PL356433A1/xx unknown
- 2001-01-29 HU HU0301076A patent/HUP0301076A3/hu unknown
- 2001-01-29 EA EA200200819A patent/EA004434B1/ru not_active IP Right Cessation
- 2001-01-29 WO PCT/US2001/000657 patent/WO2001057035A1/en not_active Ceased
- 2001-01-29 JP JP2001557867A patent/JP5235256B2/ja not_active Expired - Lifetime
- 2001-01-29 IL IL15101001A patent/IL151010A0/xx active IP Right Grant
- 2001-01-29 NZ NZ520541A patent/NZ520541A/en not_active IP Right Cessation
- 2001-02-02 TW TW090102231A patent/TWI297687B/zh not_active IP Right Cessation
-
2002
- 2002-06-27 ZA ZA200205162A patent/ZA200205162B/en unknown
- 2002-08-01 NO NO20023654A patent/NO323459B1/no not_active IP Right Cessation
-
2006
- 2006-12-15 NO NO20065836A patent/NO20065836L/no not_active Application Discontinuation
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Legal Events
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| A107 | Divisional application of patent | ||
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| PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 20080502 |
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| PA0201 | Request for examination | ||
| PG1501 | Laying open of application | ||
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
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