WO2011114210A3 - Processes for the preparation of linezolid - Google Patents

Processes for the preparation of linezolid Download PDF

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Publication number
WO2011114210A3
WO2011114210A3 PCT/IB2011/000527 IB2011000527W WO2011114210A3 WO 2011114210 A3 WO2011114210 A3 WO 2011114210A3 IB 2011000527 W IB2011000527 W IB 2011000527W WO 2011114210 A3 WO2011114210 A3 WO 2011114210A3
Authority
WO
WIPO (PCT)
Prior art keywords
linezolid
preparation
provides
bis
processes
Prior art date
Application number
PCT/IB2011/000527
Other languages
French (fr)
Other versions
WO2011114210A2 (en
Inventor
Ashish Kumar Gupta
Shishupal Singh
Atulya Kumar Panda
Sujay Biswas
Dharam Vir
Original Assignee
Jubilant Life Sciences Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jubilant Life Sciences Limited filed Critical Jubilant Life Sciences Limited
Publication of WO2011114210A2 publication Critical patent/WO2011114210A2/en
Publication of WO2011114210A3 publication Critical patent/WO2011114210A3/en

Links

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

Abstract

The present invention provides improved processes for the preparation of linezolid, going through a novel intermediate of formula XIa, which avoids the use of sodium azide and formation of bis-linezolid as an impurity. It also provides the process for preparation of linezolid, free of bis-linezolid through benzylamine intermediate (XIII). Also, it provides the process of preparation of linezolid by preparing azide intermediate, which further converts into linezolid in one-pot. Linezolid with high yield and high chemical purity is obtained without the use of tedious, complicated purification steps, such as chromatography or repeated recrystallization.
PCT/IB2011/000527 2010-03-15 2011-03-14 Processes for the preparation of linezolid WO2011114210A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN595/DEL/2010 2010-03-15
IN595DE2010 2010-03-15

Publications (2)

Publication Number Publication Date
WO2011114210A2 WO2011114210A2 (en) 2011-09-22
WO2011114210A3 true WO2011114210A3 (en) 2011-12-01

Family

ID=44084033

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2011/000527 WO2011114210A2 (en) 2010-03-15 2011-03-14 Processes for the preparation of linezolid

Country Status (1)

Country Link
WO (1) WO2011114210A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102491954B (en) * 2011-12-06 2014-04-23 江苏正大丰海制药有限公司 Preparation method of linezolid
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
WO2014045292A1 (en) * 2012-09-20 2014-03-27 Symed Labs Limited Improved process for the preparation of linezolid intermediate
CN103601704B (en) * 2013-11-22 2015-05-06 石家庄智恒医药科技有限公司 Preparation method of amorphous cabazitaxel
CN104262280B (en) * 2014-09-22 2016-07-20 山东华生化学股份有限公司 A kind of preparation method of linezolid
RU2766082C9 (en) * 2016-04-21 2022-02-22 Оптимус Драгс Пвт Лтд Improved process of obtaining linezolid
CN110483431A (en) * 2019-09-04 2019-11-22 桂林南药股份有限公司 Linezolid impurity compound, preparation method and its application

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5688792A (en) * 1994-08-16 1997-11-18 Pharmacia & Upjohn Company Substituted oxazine and thiazine oxazolidinone antimicrobials

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1866295A2 (en) 2005-02-24 2007-12-19 Teva Pharmaceutical Industries Ltd Processes for the preparation of linezolid intermediate
US20090093631A1 (en) 2007-09-06 2009-04-09 Ben-Zion Dolitzky Processes for the preparation of a linezolid intermediate, linezolid hydroxide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5688792A (en) * 1994-08-16 1997-11-18 Pharmacia & Upjohn Company Substituted oxazine and thiazine oxazolidinone antimicrobials

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BRICKNER S J ET AL: "SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF U-100592 AND U-100766, TWO OXAZOLIDINONE ANTOBACTERIAL AGENTS FOR THE POTERTIAL TREATMENT OF MULTIDRUG-RESISTANT GRAM-POSITIVE BACTERIAL INFECTIONS", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 39, no. 3, 2 February 1996 (1996-02-02), pages 673 - 679, XP000574381, ISSN: 0022-2623, DOI: DOI:10.1021/JM9509556 *
D'ANDREA S ET AL: "Synthesis and antibacterial activity of dihydro-1,2-oxazine and 2-pyrazoline oxazolidinones: novel analogs of linezolid", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 15, no. 11, 2 June 2005 (2005-06-02), pages 2834 - 2839, XP025313695, ISSN: 0960-894X, [retrieved on 20050602], DOI: DOI:10.1016/J.BMCL.2005.03.099 *
YU DU ET AL: "Synthesis and antibacterial activity of linezolid analogues", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 12, no. 6, 25 March 2002 (2002-03-25), pages 857 - 859, XP002963251, ISSN: 0960-894X, DOI: DOI:10.1016/S0960-894X(02)00043-4 *

Also Published As

Publication number Publication date
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