CA2798101A1 - Processes for preparing linezolid - Google Patents
Processes for preparing linezolid Download PDFInfo
- Publication number
- CA2798101A1 CA2798101A1 CA2798101A CA2798101A CA2798101A1 CA 2798101 A1 CA2798101 A1 CA 2798101A1 CA 2798101 A CA2798101 A CA 2798101A CA 2798101 A CA2798101 A CA 2798101A CA 2798101 A1 CA2798101 A1 CA 2798101A1
- Authority
- CA
- Canada
- Prior art keywords
- fluoro
- mixing
- salt
- compound
- formula
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract 36
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 title claims abstract 4
- 229960003907 linezolid Drugs 0.000 title claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims 13
- 239000002253 acid Substances 0.000 claims 9
- -1 azide salt Chemical class 0.000 claims 9
- 239000003795 chemical substances by application Substances 0.000 claims 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 6
- 239000012320 chlorinating reagent Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 6
- 230000003213 activating effect Effects 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 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 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 239000005711 Benzoic acid Substances 0.000 claims 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 235000010233 benzoic acid Nutrition 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
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-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 compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-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
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 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 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000000543 intermediate Substances 0.000 abstract 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 | |
| US61/329,892 | 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 |
|---|---|
| CA2798101A1 true CA2798101A1 (en) | 2011-11-03 |
Family
ID=44861911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2798101A Abandoned CA2798101A1 (en) | 2010-04-30 | 2011-04-28 | Processes for preparing linezolid |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US9206141B2 (https=) |
| EP (2) | EP2563781B1 (https=) |
| JP (1) | JP5865898B2 (https=) |
| KR (1) | KR20130108975A (https=) |
| CN (1) | CN103025730A (https=) |
| AU (1) | AU2011245302A1 (https=) |
| BR (1) | BR112012027901A2 (https=) |
| CA (1) | CA2798101A1 (https=) |
| IL (1) | IL222770A0 (https=) |
| MX (1) | MX2012012627A (https=) |
| RU (1) | RU2012151303A (https=) |
| SG (1) | SG185103A1 (https=) |
| TW (1) | TWI535715B (https=) |
| WO (1) | WO2011137222A1 (https=) |
| ZA (1) | ZA201208382B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106279054A (zh) | 2011-02-24 | 2017-01-04 | 李药业有限公司 | 利奈唑胺及其新中间体的新制备方法 |
| 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 |
| US9562040B2 (en) | 2012-04-06 | 2017-02-07 | 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 |
| EP3250568A4 (en) * | 2016-04-21 | 2018-08-01 | Optimus Drugs Pvt Ltd | An improved process for the preparation of linezolid |
| 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 |
| 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 |
| 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 |
| DK1028940T3 (da) | 1997-11-07 | 2007-07-30 | Pharmacia & Upjohn Co Llc | Fremgangsmåde til fremstilling af oxazolidinoner |
| US6921825B2 (en) | 1998-09-16 | 2005-07-26 | King Pharmaceuticuals Research & Development, Inc. | Adenosine A3 receptor modulators |
| US6444813B2 (en) * | 2000-02-02 | 2002-09-03 | Pharmacia & Upjohn Company | Linezolid-crystal form II |
| AR027261A1 (es) | 2000-02-02 | 2003-03-19 | Upjohn Co | Linezolid forma cristalina ii |
| SE0001866D0 (sv) * | 2000-05-18 | 2000-05-18 | Astrazeneca Ab | A new process |
| DE60118241T2 (de) | 2000-10-17 | 2006-12-28 | Pharmacia & Upjohn Co. Llc, Kalamazoo | Verfahren zur herstellung von oxazolidinonverbindungen |
| AU2002310156A1 (en) | 2001-06-05 | 2002-12-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzo-fused cycloalkyl urea compounds |
| WO2005099353A2 (en) | 2004-04-19 | 2005-10-27 | Symed Labs Limited | A novel process for the preparation of linezolid and related compounds |
| EP1768967B1 (en) | 2004-07-20 | 2009-04-22 | Symed Labs Limited | Novel intermediates for linezolid and related compounds |
| EP1866295A2 (en) | 2005-02-24 | 2007-12-19 | Teva Pharmaceutical Industries Ltd | Processes for the preparation of linezolid intermediate |
| KR20080032186A (ko) | 2005-07-15 | 2008-04-14 | 시클릭스 코포레이션 | 열가소성 물질에 대한 운반체 및／또는 유동성 개선첨가제로서의 거대고리 폴리에스테르 올리고머 |
| EP2007740A1 (en) | 2006-04-07 | 2008-12-31 | Pfizer Products Incorporated | Process for preparing linezolid |
| 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 |
| 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 |
-
2011
- 2011-04-28 JP JP2013508243A patent/JP5865898B2/ja not_active Expired - Fee Related
- 2011-04-28 AU AU2011245302A patent/AU2011245302A1/en not_active Abandoned
- 2011-04-28 MX MX2012012627A patent/MX2012012627A/es not_active Application Discontinuation
- 2011-04-28 US US13/695,211 patent/US9206141B2/en not_active Expired - Fee Related
- 2011-04-28 WO PCT/US2011/034278 patent/WO2011137222A1/en not_active Ceased
- 2011-04-28 KR KR1020127029523A patent/KR20130108975A/ko not_active Withdrawn
- 2011-04-28 CA CA2798101A patent/CA2798101A1/en not_active Abandoned
- 2011-04-28 BR BR112012027901A patent/BR112012027901A2/pt not_active IP Right Cessation
- 2011-04-28 SG SG2012080321A patent/SG185103A1/en unknown
- 2011-04-28 EP EP11775554.6A patent/EP2563781B1/en not_active Not-in-force
- 2011-04-28 RU RU2012151303/04A patent/RU2012151303A/ru not_active Application Discontinuation
- 2011-04-28 CN CN2011800328913A patent/CN103025730A/zh active Pending
- 2011-04-28 EP EP14197369.3A patent/EP2899185B1/en not_active Not-in-force
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| EP2563781B1 (en) | 2016-10-26 |
| MX2012012627A (es) | 2013-05-09 |
| EP2563781A4 (en) | 2013-11-06 |
| US20160024032A1 (en) | 2016-01-28 |
| RU2012151303A (ru) | 2014-06-10 |
| ZA201208382B (en) | 2015-06-24 |
| TWI535715B (zh) | 2016-06-01 |
| EP2899185A1 (en) | 2015-07-29 |
| IL222770A0 (en) | 2012-12-31 |
| BR112012027901A2 (pt) | 2015-09-08 |
| EP2563781A1 (en) | 2013-03-06 |
| US9206141B2 (en) | 2015-12-08 |
| JP2013525454A (ja) | 2013-06-20 |
| EP2899185B1 (en) | 2018-01-31 |
| US20130053557A1 (en) | 2013-02-28 |
| JP5865898B2 (ja) | 2016-02-17 |
| KR20130108975A (ko) | 2013-10-07 |
| WO2011137222A1 (en) | 2011-11-03 |
| US9656973B2 (en) | 2017-05-23 |
| TW201144301A (en) | 2011-12-16 |
| CN103025730A (zh) | 2013-04-03 |
| AU2011245302A1 (en) | 2012-11-22 |
| SG185103A1 (en) | 2012-12-28 |
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| Date | Code | Title | Description |
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Effective date: 20150428 |