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WO2005073239A1 - Procede de purification de derive d'acide carboxylique de quinoline - Google Patents

Procede de purification de derive d'acide carboxylique de quinoline Download PDF

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Publication number
WO2005073239A1
WO2005073239A1 PCT/JP2005/001318 JP2005001318W WO2005073239A1 WO 2005073239 A1 WO2005073239 A1 WO 2005073239A1 JP 2005001318 W JP2005001318 W JP 2005001318W WO 2005073239 A1 WO2005073239 A1 WO 2005073239A1
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WO
WIPO (PCT)
Prior art keywords
methyl
oxo
compound
quinoline
fluoro
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.)
Ceased
Application number
PCT/JP2005/001318
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English (en)
Japanese (ja)
Inventor
Masayuki Hattori
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.)
Nippon Shinyaku Co Ltd
Original Assignee
Nippon Shinyaku Co 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 Nippon Shinyaku Co Ltd filed Critical Nippon Shinyaku Co Ltd
Priority to JP2005517543A priority Critical patent/JPWO2005073239A1/ja
Publication of WO2005073239A1 publication Critical patent/WO2005073239A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to 6-fluoro-1-methyl-7- [4_ (5-methyl-2-oxo-1,3-dioxolen-41-yl) methyl-1-piperajur] -14-year-old xo 4H- [
  • the present invention relates to a method for purifying [1,3] thiazeto [3,2-a] quinoline-l--3-carboxylic acid (hereinafter, compounds A and V).
  • Compound A has excellent antibacterial activity (see, for example, Patent Document 1), and has been mentioned as a synthetic antibacterial agent.
  • the powerful compound A is synthesized as follows.
  • the final process power The purity of the obtained compound A is in the range of 80-90%, so that it can be provided as a raw drug substance. Requires higher purity. Therefore, recrystallization may be considered to increase the purity, but the compound A cannot be sufficiently purified even if recrystallized as it is. For this reason, conventionally, a method has been adopted in which the extraction treatment is repeated three times with methylene chloride to increase the purity to 93% or more, and then recrystallized with acetonitrile.
  • methylene chloride used as a solvent in the extraction process requires a high level of environmental control, and its total amount is 50 times the volume (mL) of the weight of Compound A (g). Is also necessary.
  • the above-mentioned conventional method has a problem that a long time is required for the treatment operation, and a simple and inexpensive method for purifying Compound A with little adverse effect on the environment is required.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 1-294680
  • An object of the present invention is to provide a simple and inexpensive purification method for Compound A having excellent medicinal properties, which has a small adverse effect on the environment.
  • the inventors of the present invention have conducted intensive studies on the method of purifying Compound A. After heating and stirring the crude Compound A in a predetermined solvent, the suspension was cooled, and the precipitated crystals were collected by filtration. The present inventors have found that a novel purification method of drying achieves the above object, and have completed the present invention.
  • Compound A is converted into N, N-dimethylformamide (hereinafter, referred to as DMF), N-methylformamide (hereinafter, referred to as NMF), formamide (hereinafter, referred to as FA), dimethylacetamide (hereinafter, referred to as DMA), A group consisting of dimethylimidazole (hereinafter, referred to as DMI) and dimethylsulfoxide (hereinafter, referred to as DMSO). Heating and stirring in a selected solvent. After cooling the suspension, precipitate crystals are collected by filtration. A method for purifying Compound A, comprising a step of drying.
  • purity refers to a value measured and calculated under the following conditions.
  • Detector UV absorption spectrophotometer (275 nm) SPD-6A (Shimadzu Corporation) Sample Dissolve about 10 mg of measurement sample in 10 ml of acetonitrile and inject 2.0 ⁇ l of it, or dissolve about 25 mg of measurement sample in 2 ml of DMF and dissolve Inject 4 1
  • Measurement range / Solution force of solvent peak is also 10 times the retention time of compound A Purity calculation method Calculated by Z area percentage
  • one time volume (mL) with respect to the weight (g) of Compound A means the volume (mL) of the solvent with respect to the weight (g) of Compound A as a solute.
  • double volume (mL) means that the solvent amount is 20 mL for 10 g of Compound A.
  • the “cooling temperature” refers to the temperature of the suspension at the time of filtering the precipitated crystals from the suspension after heating and stirring.
  • cooling holding time refers to the time during which the suspension after heating and stirring is cooled to a predetermined cooling temperature, and then left or stirred while maintaining the cooling temperature.
  • Examples of the solvent used in the present invention include amide solvents such as DMF, NMF, and FA, DMI, and DMSO. Of these, DMF is more preferred. The suitability of these solvents is detailed in Test Example 1.
  • the amount of the solvent used in the present invention is suitably in the range of 0.5 to 5 times volume (mL) with respect to the weight (g) of the compound A, and in the range of 0.9 to 2.5 times volume. 1 volume is particularly preferred. The appropriate amount of the solvent in this range will be described in detail in Test Example 2.
  • the heating temperature should be different depending on the solvent used. One 100 ° C is more preferable.
  • the heating and stirring time varies depending on the solvent and the stirring device used, but is suitably in the range of 0.5 to 5 hours, more preferably 1 hour. Suitability of the heating temperature and the stirring time in this range will be described in detail in Test Example 3.
  • the cooling rate after heating and stirring hardly affects the purity.
  • the cooling hold time after reaching the specified cooling temperature does not affect the purity, but the recovery rate is poor if the set temperature is high and the time is short, so the cooling temperature is 30 or less, and the cooling hold time is 30 minutes.
  • the above is preferable. Suitability of the cooling temperature and the cooling holding time in this range will be described in detail in Test Example 4.
  • Compound A used in this purification may be one produced by the above method.However, if water is contained in Compound A, it will affect the degree of purification and the recovery rate, so it must be washed and dried in advance with isopropanol. It is preferable to remove the water by performing a treatment such as drying.
  • the purified compound A can be recrystallized using, for example, acetonitrile as a recrystallization solvent. This can increase the purity of compound A to 99% or more.
  • the recrystallization can be performed by a conventional method.
  • Test Example 4 Cooling conditions and purification effect One-fold volume of DMF was added to Compound A, and the mixture was heated and stirred at 80 ° C for 1.2 hours, cooled to a predetermined temperature at a predetermined cooling rate, stirred as it was for a predetermined time, and the precipitated crystals were collected by filtration and dried. The results are shown in Table 4.
  • the purification method by the heating and stirring treatment has a purification effect equal to or higher than the purification method by the extraction treatment.
  • the purification method according to the present invention is a simple and inexpensive purification method with less adverse effect on the environment as compared with the conventional purification method by extraction treatment. Very useful.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Il est divulgué un procédé pour la purification d'un 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolene-4-yl) methyl-1-piperazinyl]-4-oxo-4H-[1,3] thiazeto [3,2-a] quinoline-3- acide carboxylique (composé A) qui présente un effet médical excellent. Ce procédé de purification est caractérisé par le fait de comprendre une étape où le composé A est chauffé et brassé dans un solvant sélectionné parmi le groupe constitué de N,N-diméthylformamide, N-méthylformamide, formamide, diméthylacétoamide, diméthylimidazole and diméthylsulfoxyde, ensuite la suspension en résultant est refroidie et les cristaux précipités sont filtrés et séchés. Ce procédé est très utile comme procédé de purification du composé A.
PCT/JP2005/001318 2004-01-30 2005-01-31 Procede de purification de derive d'acide carboxylique de quinoline Ceased WO2005073239A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2005517543A JPWO2005073239A1 (ja) 2004-01-30 2005-01-31 キノリンカルボン酸誘導体の精製方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004022699 2004-01-30
JP2004-022699 2004-01-30

Publications (1)

Publication Number Publication Date
WO2005073239A1 true WO2005073239A1 (fr) 2005-08-11

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/001318 Ceased WO2005073239A1 (fr) 2004-01-30 2005-01-31 Procede de purification de derive d'acide carboxylique de quinoline

Country Status (2)

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JP (1) JPWO2005073239A1 (fr)
WO (1) WO2005073239A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011031745A1 (fr) 2009-09-09 2011-03-17 Achaogen, Inc. Analogues de fluoroquinolone antibactériens

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0751579B2 (ja) * 1987-11-07 1995-06-05 日本新薬株式会社 キノリンカルボン酸誘導体
JP3644998B2 (ja) * 1995-02-09 2005-05-11 塩野義製薬株式会社 ベンジリデン誘導体の結晶の選択的取得方法
JP3843490B2 (ja) * 1996-06-28 2006-11-08 昭和電工株式会社 結晶質ｌ−アスコルビン酸−２−リン酸エステルナトリウム塩の製造方法
JP4336084B2 (ja) * 2001-08-03 2009-09-30 武田薬品工業株式会社 結晶およびその製造法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Tenpu Bunsho Sword-Jo 100.", MEIJI SEIKA KAISHA., December 2002 (2002-12-01), XP002991884, Retrieved from the Internet <URL:URL:http://medical.meiji.co.jp/medical/index2.php> *
KAMEMI K. ET AL: "Chemical structure, physicochemical properties and stability of prulifloxacin.", IYAKUHIN KENKYU., vol. 28, no. 1, 1997, pages 1 - 11, XP002987035 *
SEGAWA J. ET AL: "Studies on pyridonecarboxylic acids. 1. Synthesis and antibacterial evaluation of 7-substituted-6-halo-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylic acids.", JOURNAL OF MEDICINAL CHEMISTRY., vol. 35, no. 25, 1992, pages 4727 - 4738, XP002991883 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011031745A1 (fr) 2009-09-09 2011-03-17 Achaogen, Inc. Analogues de fluoroquinolone antibactériens

Also Published As

Publication number Publication date
JPWO2005073239A1 (ja) 2008-01-10

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