EP3250568A1 - Procédé perfectionné pour la préparation de linézolide - Google Patents

Procédé perfectionné pour la préparation de linézolide

Info

Publication number
EP3250568A1
EP3250568A1 EP16876979.2A EP16876979A EP3250568A1 EP 3250568 A1 EP3250568 A1 EP 3250568A1 EP 16876979 A EP16876979 A EP 16876979A EP 3250568 A1 EP3250568 A1 EP 3250568A1
Authority
EP
European Patent Office
Prior art keywords
formula
compound
preparation
isoindole
dione
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.)
Withdrawn
Application number
EP16876979.2A
Other languages
German (de)
English (en)
Other versions
EP3250568A4 (fr
Inventor
Srinavas Reddy DESI REDDY
Dnyandev Ragho Rane
Srinavasa Rao VELIVELA
Subba Reddy PEKETY
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Optimus Drugs Pvt Ltd
Original Assignee
Optimus Drugs Pvt Ltd
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 Optimus Drugs Pvt Ltd filed Critical Optimus Drugs Pvt Ltd
Publication of EP3250568A1 publication Critical patent/EP3250568A1/fr
Publication of EP3250568A4 publication Critical patent/EP3250568A4/fr
Withdrawn legal-status Critical Current

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D413/06—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 only aliphatic carbon atoms

Definitions

  • the present invention relates to an improved process for the preparation of Linezolid. More specifically, the present invention relates to an improved process for preparing(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl] phthalimide and ( ⁇ -glycidylphthalimide intermediates, which are used in the preparation of Linezolid .
  • Linezolid is a synthetic antibiotic, the first of the oxazolidinone class, used for the treatment of infections caused by multi -resistant bacteria including streptococcus and methicillin-resistant Staphylococcus aureus (MRSA).
  • MRSA methicillin-resistant Staphylococcus aureus
  • the antibacterial effect of oxazolidinones is by working as protein synthesis inhibitors, targeting an early step involving the binding of N-formylmethionyl-t-RNA to the ribosome.
  • Linezolid is marketed by Pfizer under the trade names "Zyvox”and it is chemically known as (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methyl] acetamide having the formula (I).
  • Linezolid is first disclosed in U.S. Pat. No. 5,688,792 and its process describes by using of R -glycidylbutyrate which results in the formation of (R) - N-[[3-[3-fluoro-4- morpholinyl] phenyl]-2-oxo-5-oxazolidinyl] methanol which in the subsequent stages has to be converted to various intermediary compounds to finally form Linezolid.
  • the said process also encompasses intermediary azide compound, which is difficult to handle at an industrial level, which is depicted in the scheme-I given below:
  • WO 1999/24393 Al discloses a process for the preparation of oxazolidinone derivatives, which is depicted in the scheme-II given below: Roxa- NH-CO-O-X!
  • R OXA is phenyl substituted with one fluoro and one substituted amino group, wherein the substituted amino groups include 4-(benzyloxycarbonyl)- 1-piperazinyl, 4- morpholinyl and 4-hydroxyacetylpiperazinyl
  • X l is C1-C20 alkyl
  • X 2 is CI
  • Br RN is C1-C5 alkyl
  • WO' 393 does not disclose any specific examples or suitable conditions for the preparation of Linezolid.
  • WO 2005/099353 A2 discloses a process for the preparation of Linezolid, which is depicted in the scheme-Ill given below:
  • WO 2006/008754 Al discloses a process for the preparation of Linezolid, which is depicted in scheme-IV given below
  • Scheme-IV discloses a process for preparing Linezolid by reacting a compound of structure (1) with a compound of structure (2) at a temperature range from ambient temperature to about 65 °C to provide a compound of structure (3), which is hydrolyzed and subsequently acylated to give Linezolid, which is depicted in the scheme-V below:
  • US 5,608,110 discloses process for the preparation of 2-[(2,S)-oxiran-2-ylmethyl]-lH- isoindole-l,3(2H)-dione (I) comprising, reaction of phthalimide with (S)-(+)- epichlorohydrin under reflux in nitrogen atmosphere, ethyl acetate/hexane to get (S)-l- chloro-3-phthalimido-2-propanol which is cyclized in presence of NaH/THF.
  • US 6,875,875 discloses a process for the preparation of 2-[(2,S)-oxiran-2-ylmethyl]-lH- isoindole-l,3(2H)-dione (I) comprising reaction of phthalimide with (S)- epichlorohydrin in presence of alkali metal carbonate, alkali metal hydrogen carbonate or a quaternary ammonium salt to get (,S)-l-chloro-3-phthalimido-2-propanol which is cyclized in presence of metal alkoxides.
  • the main objective of the present invention is to provide cost-effective and commercially feasible process for the preparation of Linezolid.
  • Another objective of the present invention is to provide a process for the preparation of (S)-N-[[3-[3-fluoro-4-[4-morpholinyl] phenyl]-2-oxo-5-oxazolidinyl] methyl] phthalimide and (3 ⁇ 4)-glycidyl phthalimide intermediates, which employs less expensive, easily available and eco-friendly reagents.
  • R represents hydrogen, C1-C5 alkyl, aryl, aralkyl; with (S)-glycidyl phthalimide of formula (IX)
  • R alkyl or aryl
  • the organic base is primary or secondary alkyl amines having C1-C5 carbon atoms.
  • R represents hydrogen, C1-C5 alkyl, aryl, aralkyl; with (S)-glycidyl phthalimide of formula (IX)
  • the reaction is carried using an alkali metal iodides and in the presence or absence of a solvent at a temperature in the range of 60 to 120°C.
  • the reaction is carried out for a period of 10 to 14 hours.
  • the reaction is carried using a lithium tertiary butoxide used in the range 0.2-0.4 mole equivalents in presence of a suitable solvent at a temperature in the range of 40 to 100°C.
  • the reaction is carried out for a period of 4 to 12 hours.
  • suitable alkali metal iodides used is selected from lithium iodide, sodium iodide, potassium iodide and the like ;
  • Suitable solvent used is selected from alcohols such as methanol, ethanol, isopropyl alcohol, and the like or mixture thereof; ketones, such as methyl isobutyl ketone, methyl ethyl ketone, n-butanone, and the like; halogenated solvents, such as dichloromethane, ethylene dichloride, chloroform, and the like; esters, such as ethyl acetate, n-propyl acetate, isopropyl acetate, and the like; hydrocarbon solvents, such as toluene, xylene, cyclohexane, and the like; ethers, such as 1,4-dioxane, tetrahydrofuran, and the like; and amides such as N,N-
  • step b) subjecting the compound of formula(VI) with aqueous methyl amine or hydrazine hydrate, c) acylating the product of step b), and
  • the reaction between formula (III) with (S)-Glycidyl phthalimide of formula(IX) is carried out in presence of suitable alkali metal iodides (or) metal hydrides and solvent at suitable temperature to give a compound of formula(VI); further it is subjected to deprotection with hydrazine hydrae (or) aqueous methyl amine to give (S)-5-Aminomethyl-3-(3-fluoro-4-morpholin-4-yl-phenyl)- oxazolidin-2-one, which is subsequently acylated with acetic anhydride or acetyl chloride to give (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5- oxazolidinyljmethyl] acetamide (Linezolid) of formula I.
  • the reaction between formulas (III) with (S)-Glycidyl phthalimide of formula (IX) is carried out in presence of suitable metal hydrides and solvent at suitable temperature to give a compound of formula (VI); the reaction is completed within a less span of time and provides good quantity of yield with high purity
  • the alkali metal iodides is selected from lithium iodide, sodium iodide, potassium iodide and the like; metal hydrides is selected from sodium hydride, lithium hydride or magnesium hydride.
  • the suitable solvent used is selected from alcohols such as methanol, ethanol, isopropyl alcohol, and the like or mixture thereof; ketones, such as methyl isobutyl ketone, methyl ethyl ketone, n-butanone, and the like; halogenated solvents, such as dichloromethane, ethylene dichloride, chloroform, and the like; esters, such as ethyl acetate, n-propyl acetate, isopropyl acetate, and the like; hydrocarbon solvents, such as toluene, xylene, cyclohexane, and the like; ethers, such as 1,4-dioxane, tetrahydrofuran, and the like; and amides such as N,N- dimethylformamide, N,N- dimethyl acetamide and the like or dimethyl sulfoxide or mixture of solvents thereof
  • the present invention further involves conversion of compound of
  • the acylation is carried out in presence of acetic anhydride or acetyl chloride.
  • the reaction is performed at or below boiling temperature of the solvent used, more preferably between 10°C and boiling temperature of the solvent used and even more preferably at boiling temperature of the solvent used. Time required for completion of the reaction depends on factors such as solvent used and temperature at which the reaction is carried.
  • the present invention relates to an improved process for the preparation of2-[(2,S)-oxiran-2-ylmethyl]-lH-isoindole-l,3(2H)-dione of formula IX comprising the steps of: a) Phthalimide reacted with (,S)-(+)-Epichlorohydrin in presence of organic base in an organic solvent at the temperature of 60° C to obtain (,S)-l-chloro-3- phthalimido-2-propanol.
  • the organic base is primary or secondary alkyl amines having C1-C5 carbon atoms.
  • the organic base is selected from primary or secondary alkyl amines having Ci- C5 carbon atoms such as methylamine, ethylamine, ethyl methylamine, diethylamine, dipropylamine, dibutylamine, preferably diethylamine.
  • the organic solvent is selected from the group comprising of alcohols, ethers, esters, nitriles having C1-C4 carbon atoms. Preferably alcohols.
  • the alcohol is selected from methanol, ethanol, propanol, isopropanol, butanol;
  • the ether solvents are selected from diethyl ether, tetrahydrofuran etc.;
  • the ester solvents are selected from ethyl acetate, methyl acetate, etc.;
  • nitriles are selected from acetonitrile, propionitrile, butyronitrile etc.
  • (,S)-l-chloro-3-phthalimido-2-propanol is cyclized in presence of alkali metal alkoxides to obtain 2-[(2,S)-oxiran-2-ylmethyl]-lH-isoindole-l,3(2H)-dione
  • Cyclization is carried out in presence of alkali metal alkoxides as the procedure described in US 6,875,875.
  • Linezolid produced according to the present invention may be in the form of amorphous or crystalline form I and form II.
  • the compound of formula (I) or Linezolid having HPLC purity is not less than 99%.
  • the present invention is simple, operation friendly and industrial applicable process. 2. The process is commercially viable and results the compounds in high yield, which makes the process cost effective
  • the present invention provides high purity compound of formulas (I), (VI) and (IX) with very less impurities profile.
  • reaction mixture was cooled to ambient temperature, ethyl acetate (50 ml) was added, and resultant slurry was stir for 30 min at 25-30 ° C & filtered the solid.
  • the resultant crude solid was added to ethyl acetate ( 250 ml) at 25-30°C and heated to 70-75°C, stirred for 15-20 min, cooled the slurry to 25-30°C & Stir for 30 min.
  • reaction mass was cooled to below 20°C, quenched with 25 ml of methanol to decompose the excess sodium hydride, distilled out solvent and added methanol (125 ml). The resulting slurry was stir for 30 min at 25-30° C and filtered.
  • reaction mass was cooled to below 20°C, quenched with 25 ml of methanol to decompose the excess sodium hydride, further added methanol (125 ml) and the resulting slurry was stir for 30 min at 25-30° C and filtered.
  • Methyl amine solution (50 g) was added to a mixture of methanol (100 ml), DM water (400 ml) and (5S) 2-[3-(3-Fluoro-4-mo holin-4-yl-phenyl)-2-oxo-oxazolidin-5- ylmethyl]-isoindole-l,3-dione (100 g 0.235 moles ) at 25-30°C.
  • the reaction mixture was stirred, slowly raised to 80-85°C and stirred for 2-3 hours at 80-85°C.
  • the reaction mixture was allowed to cool at 25-30°C; followed by addition of dichloromethane (500 ml) and stirred for 15 min to separate the layers.
  • Purified water 500 ml was added to the MDC layer and mixture was acidified to pH 2.0-3.0 with dilute hydrochloric acid and stirred for 10-15 min and two layers were separated and again basified with aqueous ammonia pH 10.0-11.0. to separate the MDC layer, and it was distilled out by atmospheric pressure completely to get the residual product of (5S)-5-(amino methyl)- 3-[3-fluoro-4-(morpholin-4-yl) phenyl]-l,3-oxazolidin-2-one.
  • Dichloromethane 400 ml was added to the residue and acetic anhydride (25 g) was slowly added at 25-30°C over a period of 60 min.
  • reaction mixture was stirred for 60 min at 25-30°C.After completion of reaction, 5% aqueous sodium bicarbonate solution was slowly added to reaction mixture, stirred for 15 min and the two layers were separated. The dichloromethane layer was washed with D M Water (200 ml). The dichloromethane layer was filtered through hi-flow and dichl orom ethane was distilled out completely under vacuum below 40°C. Cyclohexane (500 ml) was added to the residue and heated to 45-50°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé amélioré pour la préparation de linézolide. Plus spécifiquement, la présente invention concerne un procédé amélioré de préparation d'intermédiaires de (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phényl]-2-oxo-5-oxazolidinyl]méthyl] phthalimide et de (S)-glycidyl phthalimide qui sont utilisés dans la préparation de linézolide.
EP16876979.2A 2016-04-21 2016-05-23 Procédé perfectionné pour la préparation de linézolide Withdrawn EP3250568A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN201641013830 2016-04-21
PCT/IB2016/053003 WO2017182853A1 (fr) 2016-04-21 2016-05-23 Procédé perfectionné pour la préparation de linézolide

Publications (2)

Publication Number Publication Date
EP3250568A1 true EP3250568A1 (fr) 2017-12-06
EP3250568A4 EP3250568A4 (fr) 2018-08-01

Family

ID=60115753

Family Applications (1)

Application Number Title Priority Date Filing Date
EP16876979.2A Withdrawn EP3250568A4 (fr) 2016-04-21 2016-05-23 Procédé perfectionné pour la préparation de linézolide

Country Status (6)

Country Link
EP (1) EP3250568A4 (fr)
KR (1) KR101832115B1 (fr)
AU (1) AU2016403208B2 (fr)
NZ (1) NZ741891A (fr)
RU (1) RU2766082C9 (fr)
WO (1) WO2017182853A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999024393A1 (fr) 1997-11-07 1999-05-20 Pharmacia & Upjohn Company Procede de production d'oxazolidinones
WO2014141067A2 (fr) 2013-03-14 2014-09-18 Benova Labs Pvt Limited Procédé pour la préparation de dérivés d'oxazolidinone
IN2013CH05865A (fr) 2013-12-16 2015-06-19 Optimus Drugs P Ltd
IN2014CH00444A (fr) 2014-01-31 2015-08-07 Optimus Drugs P Ltd

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1768967B1 (fr) * 2004-07-20 2009-04-22 Symed Labs Limited Nouveaux intermediaires pour linezolide et composes correspondants
WO2011114210A2 (fr) * 2010-03-15 2011-09-22 Jubilant Life Sciences Limited Procédés de préparation de linézolide
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
SI2595968T1 (sl) * 2011-02-24 2016-01-29 Lee Pharma Limited Novi postopek za pripravo linezolida in njegovih novih intermediatov
CN103420933B (zh) * 2012-05-26 2016-03-02 鲁南制药集团股份有限公司 一种利奈唑胺的制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999024393A1 (fr) 1997-11-07 1999-05-20 Pharmacia & Upjohn Company Procede de production d'oxazolidinones
WO2014141067A2 (fr) 2013-03-14 2014-09-18 Benova Labs Pvt Limited Procédé pour la préparation de dérivés d'oxazolidinone
IN2013CH05865A (fr) 2013-12-16 2015-06-19 Optimus Drugs P Ltd
IN2014CH00444A (fr) 2014-01-31 2015-08-07 Optimus Drugs P Ltd

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
"Letters", CHEMICAL & ENGINEERING NEWS, 13 September 1982 (1982-09-13), pages 4, 5, 43, XP055581856
ANONYMOUS: "Explosives Incident Report No. 170 - Static Ignition of Sodium Hydride", EXPLOSIVES ACCIDENT/ INCIDENT ABSTRACTS SEPT. 1961 THRU JUNE 1967, October 1967 (1967-10-01), pages 2pp, XP055679866
ANONYMOUS: "Letters", CHEMICAL & ENGINEERING NEWS, 13 June 1966 (1966-06-13), pages 6 - 9, XP055581966
ANONYMOUS: "Sodium hydride", NEW JERSEY DEPARTMENT OF HEALTH AND SENIOR SERVICES HAZARDOUS SUBSTANCE FACT SHEET, March 1995 (1995-03-01), pages 1 - 6, XP055581846
PANDEY BHAWANA, FULEKAR M.H.: "Environmental Management - Strategies for chemical disaster", RESEARCH JOURNAL OF CHEMICAL SCIENCES, vol. 1, no. 1, April 2011 (2011-04-01), pages 111 - 117, XP055581853
See also references of WO2017182853A1
TREVOR LAIRD: "Special Feature Section: Safety of Chemical Processes- Safety Feature", ORGANIC PROCESS RESEARCH DEVELOPMENT, vol. 9, no. 6, 2005, pages 951, XP055581961

Also Published As

Publication number Publication date
EP3250568A4 (fr) 2018-08-01
NZ741891A (en) 2020-05-29
AU2016403208B2 (en) 2018-10-25
AU2016403208A1 (en) 2018-05-10
KR20170128485A (ko) 2017-11-22
KR101832115B1 (ko) 2018-02-23
RU2766082C9 (ru) 2022-02-22
WO2017182853A1 (fr) 2017-10-26
RU2766082C1 (ru) 2022-02-07

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