RU2012151303A - Способы получения линезолида - Google Patents
Способы получения линезолида Download PDFInfo
- Publication number
- RU2012151303A RU2012151303A RU2012151303/04A RU2012151303A RU2012151303A RU 2012151303 A RU2012151303 A RU 2012151303A RU 2012151303/04 A RU2012151303/04 A RU 2012151303/04A RU 2012151303 A RU2012151303 A RU 2012151303A RU 2012151303 A RU2012151303 A RU 2012151303A
- Authority
- RU
- Russia
- Prior art keywords
- fluoro
- mixing
- salt
- formula
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 38
- 150000003839 salts Chemical class 0.000 claims abstract 18
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 239000002253 acid Substances 0.000 claims abstract 10
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims abstract 10
- 125000003277 amino group Chemical group 0.000 claims abstract 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 8
- CSSSAKOGRYYMSA-UHFFFAOYSA-N 1-chloro-2-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(F)=C1 CSSSAKOGRYYMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000005711 Benzoic acid Substances 0.000 claims abstract 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000012190 activator Substances 0.000 claims abstract 6
- 235000010233 benzoic acid Nutrition 0.000 claims abstract 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical group 0.000 claims abstract 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000003638 chemical reducing agent Substances 0.000 claims abstract 4
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims abstract 4
- 229960003907 linezolid Drugs 0.000 claims abstract 4
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 3
- 239000011737 fluorine Substances 0.000 claims abstract 3
- RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical group [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000012320 chlorinating reagent Substances 0.000 claims 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 4
- -1 azide salt Chemical class 0.000 claims 4
- PJHUABJTDFXYRQ-UHFFFAOYSA-N benzoyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CC=CC=C1 PJHUABJTDFXYRQ-UHFFFAOYSA-N 0.000 claims 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical group N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 claims 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- QHDTZKBYJCULMO-UHFFFAOYSA-N (2,4-dichlorophenyl)methanimine Chemical compound ClC1=CC=C(C=N)C(Cl)=C1 QHDTZKBYJCULMO-UHFFFAOYSA-N 0.000 claims 1
- HGWOSZYSUGHKPI-UHFFFAOYSA-N (4-bromophenyl)methanimine Chemical group BrC1=CC=C(C=N)C=C1 HGWOSZYSUGHKPI-UHFFFAOYSA-N 0.000 claims 1
- IKTJTGWJQSDQDK-UHFFFAOYSA-N (4-chlorophenyl)methanimine Chemical group ClC1=CC=C(C=N)C=C1 IKTJTGWJQSDQDK-UHFFFAOYSA-N 0.000 claims 1
- FPENCTDAQQQKNY-UHFFFAOYSA-N 3,4-difluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1 FPENCTDAQQQKNY-UHFFFAOYSA-N 0.000 claims 1
- QPIBHIXKUQKNFP-UHFFFAOYSA-N 4-chloro-3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(F)=C1 QPIBHIXKUQKNFP-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000002466 imines Chemical group 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (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)
- Epoxy Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32989210P | 2010-04-30 | 2010-04-30 | |
| US61/328,892 | 2010-04-30 | ||
| US35985110P | 2010-06-30 | 2010-06-30 | |
| US61/359,851 | 2010-06-30 | ||
| US37557610P | 2010-08-20 | 2010-08-20 | |
| US61/375,576 | 2010-08-20 | ||
| US38953410P | 2010-10-04 | 2010-10-04 | |
| US61/389,534 | 2010-10-04 | ||
| US42144210P | 2010-12-09 | 2010-12-09 | |
| US61/421,442 | 2010-12-09 | ||
| PCT/US2011/034278 WO2011137222A1 (en) | 2010-04-30 | 2011-04-28 | Processes for preparing linezolid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2012151303A true RU2012151303A (ru) | 2014-06-10 |
Family
ID=44861911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012151303/04A RU2012151303A (ru) | 2010-04-30 | 2011-04-28 | Способы получения линезолида |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US9206141B2 (enExample) |
| EP (2) | EP2899185B1 (enExample) |
| JP (1) | JP5865898B2 (enExample) |
| KR (1) | KR20130108975A (enExample) |
| CN (1) | CN103025730A (enExample) |
| AU (1) | AU2011245302A1 (enExample) |
| BR (1) | BR112012027901A2 (enExample) |
| CA (1) | CA2798101A1 (enExample) |
| IL (1) | IL222770A0 (enExample) |
| MX (1) | MX2012012627A (enExample) |
| RU (1) | RU2012151303A (enExample) |
| SG (1) | SG185103A1 (enExample) |
| TW (1) | TWI535715B (enExample) |
| WO (1) | WO2011137222A1 (enExample) |
| ZA (1) | ZA201208382B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2760198C1 (ru) * | 2020-12-16 | 2021-11-22 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт по изысканию новых антибиотиков имени Г.Ф. Гаузе" | Однореакторный способ получения полупродукта для синтеза линезолида |
| RU2766082C1 (ru) * | 2016-04-21 | 2022-02-07 | Оптимус Драгс Пвт Лтд | Улучшенный процесс получения линезолида |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112012027901A2 (pt) * | 2010-04-30 | 2015-09-08 | Univ Indiana Res & Tech Corp | processos para preparar linezolida |
| WO2012114355A1 (en) * | 2011-02-24 | 2012-08-30 | Lee Pharma Limited | Novel process for preparation of linezolid and its novel intermediates |
| WO2013072923A1 (en) * | 2011-09-19 | 2013-05-23 | Cadila Healthcare Limited | Process for the preparation of crystalline linezolid |
| CN103254148B (zh) | 2012-02-15 | 2016-04-13 | 浙江海正药业股份有限公司 | 利奈唑胺中间体的制备方法 |
| CN103288814B (zh) * | 2012-02-24 | 2016-07-06 | 国药集团国瑞药业有限公司 | 一种利伐沙班中间体的制备方法 |
| EP2834235A1 (en) | 2012-04-06 | 2015-02-11 | Indiana University Research and Technology Corporation | Processes for preparing rivaroxaban |
| ITMI20120655A1 (it) * | 2012-04-19 | 2013-10-20 | Bioindustria Lab Italiano M Edicinali Spa | Procedimento per la preparazione di linezolid |
| AR090844A1 (es) * | 2012-04-27 | 2014-12-10 | Actelion Pharmaceuticals Ltd | Proceso para elaborar derivados de naftiridina |
| CN103626712B (zh) * | 2012-08-23 | 2016-06-01 | 重庆药友制药有限责任公司 | 一种用于制备利奈唑胺的中间体及其制备方法 |
| WO2014045292A1 (en) * | 2012-09-20 | 2014-03-27 | Symed Labs Limited | Improved process for the preparation of linezolid intermediate |
| WO2014170908A1 (en) * | 2013-04-18 | 2014-10-23 | Nosch Labs Private Limited | Process for preparation of oxazolidinone derivatives |
| CN110194750A (zh) * | 2019-06-19 | 2019-09-03 | 四川美大康华康药业有限公司 | 一种利奈唑胺的制备方法及精制方法 |
| CN112159368A (zh) * | 2020-07-07 | 2021-01-01 | 杭州杜易科技有限公司 | 一种利奈唑胺中间体的合成方法 |
| CN115684399B (zh) * | 2022-10-27 | 2024-12-20 | 贵州健安德科技有限公司 | 一种氯醇亚胺的高效液相检测及含量测定方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725450A (en) * | 1970-10-05 | 1973-04-03 | Gen Mills Chem Inc | Process for the preparation of isocyanates from acyl azides |
| US4937331A (en) * | 1988-03-25 | 1990-06-26 | President And Fellows Of Harvard College | Chiral azetidinone epoxides |
| DE4119611A1 (de) * | 1991-06-14 | 1992-12-17 | Bayer Ag | Mittel zur bekaempfung von schaedlingen auf basis substituierter oxazolidinone, neue substituierte oxazolidinone, deren herstellung und verwendung |
| TW380137B (en) * | 1994-03-04 | 2000-01-21 | Merck & Co Inc | Process for making an epoxide |
| DE19542148A1 (de) * | 1995-11-11 | 1997-05-15 | Hoechst Ag | Verfahren zur Herstellung von fluorierten Aromaten |
| CA2634657A1 (en) | 1997-11-07 | 1999-05-20 | Pharmacia & Upjohn Company | Process to produce oxazolidinones |
| US6921825B2 (en) | 1998-09-16 | 2005-07-26 | King Pharmaceuticuals Research & Development, Inc. | Adenosine A3 receptor modulators |
| AR027261A1 (es) | 2000-02-02 | 2003-03-19 | Upjohn Co | Linezolid forma cristalina ii |
| US6444813B2 (en) * | 2000-02-02 | 2002-09-03 | Pharmacia & Upjohn Company | Linezolid-crystal form II |
| SE0001866D0 (sv) * | 2000-05-18 | 2000-05-18 | Astrazeneca Ab | A new process |
| ATE321024T1 (de) | 2000-10-17 | 2006-04-15 | Pharmacia & Upjohn Co Llc | Verfahren zur herstellung von oxazolidinonverbindungen |
| WO2002098869A2 (en) | 2001-06-05 | 2002-12-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzo-fused cycloalkyl urea compounds |
| DE602004009344T2 (de) | 2004-04-19 | 2008-07-10 | Symed Labs Ltd., Hyderabad | Neues verfahren zur herstellung von linezolid und verwandten verbindungen |
| PL1768967T3 (pl) | 2004-07-20 | 2009-09-30 | Symed Labs Ltd | Nowe związki pośrednie do wytwarzania linezolidu oraz związki pokrewne |
| JP2008530028A (ja) | 2005-02-24 | 2008-08-07 | テバ ファーマシューティカル インダストリーズ リミティド | リネゾリッド中間体の調製方法 |
| WO2007011684A2 (en) | 2005-07-15 | 2007-01-25 | Cyclics Corporation | Macrocyclic polyester oligomers as carriers and/or flow modifier additives for thermoplastics |
| RU2008139612A (ru) | 2006-04-07 | 2010-04-20 | Пфайзер Продактс Инк. (Us) | Способ получения линезолида |
| CN101220001A (zh) | 2008-01-25 | 2008-07-16 | 浙江博泰化工有限公司 | 一种利奈唑酮的合成方法 |
| CN101638392B (zh) * | 2009-08-24 | 2012-05-16 | 浙江工业大学 | 一种列奈唑酮的制备方法 |
| BR112012027901A2 (pt) * | 2010-04-30 | 2015-09-08 | Univ Indiana Res & Tech Corp | processos para preparar linezolida |
-
2011
- 2011-04-28 BR BR112012027901A patent/BR112012027901A2/pt not_active IP Right Cessation
- 2011-04-28 RU RU2012151303/04A patent/RU2012151303A/ru not_active Application Discontinuation
- 2011-04-28 WO PCT/US2011/034278 patent/WO2011137222A1/en not_active Ceased
- 2011-04-28 AU AU2011245302A patent/AU2011245302A1/en not_active Abandoned
- 2011-04-28 KR KR1020127029523A patent/KR20130108975A/ko not_active Withdrawn
- 2011-04-28 SG SG2012080321A patent/SG185103A1/en unknown
- 2011-04-28 CA CA2798101A patent/CA2798101A1/en not_active Abandoned
- 2011-04-28 EP EP14197369.3A patent/EP2899185B1/en not_active Not-in-force
- 2011-04-28 EP EP11775554.6A patent/EP2563781B1/en not_active Not-in-force
- 2011-04-28 US US13/695,211 patent/US9206141B2/en not_active Expired - Fee Related
- 2011-04-28 JP JP2013508243A patent/JP5865898B2/ja not_active Expired - Fee Related
- 2011-04-28 CN CN2011800328913A patent/CN103025730A/zh active Pending
- 2011-04-28 MX MX2012012627A patent/MX2012012627A/es not_active Application Discontinuation
- 2011-04-29 TW TW100115216A patent/TWI535715B/zh not_active IP Right Cessation
-
2012
- 2012-10-30 IL IL222770A patent/IL222770A0/en unknown
- 2012-11-07 ZA ZA2012/08382A patent/ZA201208382B/en unknown
-
2015
- 2015-09-23 US US14/862,841 patent/US9656973B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2766082C1 (ru) * | 2016-04-21 | 2022-02-07 | Оптимус Драгс Пвт Лтд | Улучшенный процесс получения линезолида |
| RU2766082C9 (ru) * | 2016-04-21 | 2022-02-22 | Оптимус Драгс Пвт Лтд | Улучшенный процесс получения линезолида |
| RU2760198C1 (ru) * | 2020-12-16 | 2021-11-22 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт по изысканию новых антибиотиков имени Г.Ф. Гаузе" | Однореакторный способ получения полупродукта для синтеза линезолида |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201144301A (en) | 2011-12-16 |
| EP2563781A4 (en) | 2013-11-06 |
| TWI535715B (zh) | 2016-06-01 |
| JP5865898B2 (ja) | 2016-02-17 |
| CN103025730A (zh) | 2013-04-03 |
| US20130053557A1 (en) | 2013-02-28 |
| AU2011245302A1 (en) | 2012-11-22 |
| EP2563781B1 (en) | 2016-10-26 |
| IL222770A0 (en) | 2012-12-31 |
| JP2013525454A (ja) | 2013-06-20 |
| CA2798101A1 (en) | 2011-11-03 |
| MX2012012627A (es) | 2013-05-09 |
| US20160024032A1 (en) | 2016-01-28 |
| EP2899185A1 (en) | 2015-07-29 |
| SG185103A1 (en) | 2012-12-28 |
| BR112012027901A2 (pt) | 2015-09-08 |
| ZA201208382B (en) | 2015-06-24 |
| US9206141B2 (en) | 2015-12-08 |
| EP2899185B1 (en) | 2018-01-31 |
| KR20130108975A (ko) | 2013-10-07 |
| US9656973B2 (en) | 2017-05-23 |
| WO2011137222A1 (en) | 2011-11-03 |
| EP2563781A1 (en) | 2013-03-06 |
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