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CA2573129A1 - Process for preparing levofloxacin or its hydrate - Google Patents

Process for preparing levofloxacin or its hydrate Download PDF

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Publication number
CA2573129A1
CA2573129A1 CA002573129A CA2573129A CA2573129A1 CA 2573129 A1 CA2573129 A1 CA 2573129A1 CA 002573129 A CA002573129 A CA 002573129A CA 2573129 A CA2573129 A CA 2573129A CA 2573129 A1 CA2573129 A1 CA 2573129A1
Authority
CA
Canada
Prior art keywords
mixed solvent
levofloxacin
ethyl acetate
monohydrate
water
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.)
Granted
Application number
CA002573129A
Other languages
French (fr)
Other versions
CA2573129C (en
Inventor
Tai-Au Lee
Ja-Heouk Khoo
Seong-Ho Song
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.)
Yuhan Corp
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2573129A1 publication Critical patent/CA2573129A1/en
Application granted granted Critical
Publication of CA2573129C publication Critical patent/CA2573129C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/06—Peri-condensed systems
    • 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
    • A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
    • 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)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Saccharide Compounds (AREA)

Abstract

The present invention provides a process of preparing levofloxacin hemihydrate or monohydrate without impurities, i.e. Impurities B, C, D, E, and F. The process comprises (a) adding crude levofloxacin to a novel mixed solvent, (b) refluxing the mixture obtained in (a) to form a solution, and (c) recovering levofloxacin hemihydrate or monohydrate from the solution obtained in (b).

Claims (4)

  1. [1] A process of preparing levofloxacin hemihydrate or monohydrate, the process comprising:
    adding crude levofloxacin to a mixed solvent (A) containing water and an organic solvent selected from the group consisting of methyl acetate, ethyl acetate, and isobutyl methyl ketone; or a mixed solvent (B) containing water and two organic solvents selected from the group consisting of t-butanol, isopropyl acetate, methyl acetate, ethyl acetate, and isobutyl methyl ketone, refluxing the mixture obtained in the adding the crude levofloxacin to the mixed solvent (A) or (B) to form a solution, and recovering levofloxacin hemihydrate or monohydrate from the solution.
  2. [2] The process of claim 1, wherein the water content in the mixed solvent (A) or (B) is about 1.5 - 6.0 % (v/v).
  3. [3] The process of claims 1 or 2, wherein the mixed solvent (B) contains t-butanol, ethyl acetate, and water.
  4. [4] The process of claim 3, wherein the volume ratio of t-butanol, ethyl acetate and water is 32.3 : 64.7 : 3.
CA2573129A 2004-07-21 2005-07-18 Process for preparing levofloxacin or its hydrate Expired - Fee Related CA2573129C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR10-2004-0056637 2004-07-21
KR1020040056637A KR100704641B1 (en) 2004-07-21 2004-07-21 High purity levofloxacin production method
PCT/KR2005/002294 WO2006009374A1 (en) 2004-07-21 2005-07-18 Process for preparing levofloxacin or its hydrate

Publications (2)

Publication Number Publication Date
CA2573129A1 true CA2573129A1 (en) 2006-01-26
CA2573129C CA2573129C (en) 2012-10-16

Family

ID=35785447

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2573129A Expired - Fee Related CA2573129C (en) 2004-07-21 2005-07-18 Process for preparing levofloxacin or its hydrate

Country Status (4)

Country Link
JP (1) JP5065020B2 (en)
KR (1) KR100704641B1 (en)
CA (1) CA2573129C (en)
WO (1) WO2006009374A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2272781T5 (en) 2001-10-03 2010-04-06 Teva Pharmaceutical Industries Ltd. PREPARATION OF HEMIHYDRATED LEVOFLOXACINO.
US7964723B2 (en) 2008-08-02 2011-06-21 Apeloa-Kangyu And practical process for exclusively producing (S)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido-[1,2,3,de][1,4]benzoxazine-6-carboxylic acid hemihydrate
CA3059952C (en) 2017-04-23 2023-04-18 Illumina Cambridge Limited Compositions and methods for improving sample identification in indexed nucleic acid libraries
CN111855840A (en) * 2020-06-30 2020-10-30 辰欣药业股份有限公司 Method for detecting related substances in levofloxacin hydrochloride injection
CN112174981A (en) * 2020-11-03 2021-01-05 深圳市祥根生物科技有限公司 A kind of preparation method of levofloxacin defluorination impurity
CN116953096A (en) * 2022-12-24 2023-10-27 华夏生生药业(北京)有限公司 Method for detecting impurities in levofloxacin injection

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4777253A (en) * 1986-04-25 1988-10-11 Abbott Laboratories Process for preparation of racemate and optically active ofloxacin and related derivatives
JP3105572B2 (en) * 1990-03-01 2000-11-06 第一製薬株式会社 Selective production of hydrate
TW208013B (en) * 1990-03-01 1993-06-21 Daiichi Co Ltd
KR100309871B1 (en) * 1999-02-24 2001-10-29 윤종용 Process for Preparing (-)Pyridobenzoxazine Carboxylic Acid Derivatives
CN1596256A (en) * 2001-11-29 2005-03-16 特瓦制药工业有限公司 Methods for the purification of levofloxacin
JP2004099494A (en) * 2002-09-09 2004-04-02 Shiono Chemical Co Ltd Method for producing optically active tricyclic compound
CN1735620A (en) * 2002-12-16 2006-02-15 兰贝克赛实验室有限公司 Pure levofloxacin hemihydrate and its preparation method

Also Published As

Publication number Publication date
WO2006009374A1 (en) 2006-01-26
JP5065020B2 (en) 2012-10-31
CA2573129C (en) 2012-10-16
JP2008507507A (en) 2008-03-13
KR100704641B1 (en) 2007-04-06
KR20060009155A (en) 2006-01-31

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Effective date: 20220718