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WO2001096321A1 - Elaboration de derives de thiazolidinedione - Google Patents

Elaboration de derives de thiazolidinedione Download PDF

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Publication number
WO2001096321A1
WO2001096321A1 PCT/JP2001/004989 JP0104989W WO0196321A1 WO 2001096321 A1 WO2001096321 A1 WO 2001096321A1 JP 0104989 W JP0104989 W JP 0104989W WO 0196321 A1 WO0196321 A1 WO 0196321A1
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
reaction
mol
general formula
derivative
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/JP2001/004989
Other languages
English (en)
Japanese (ja)
Inventor
Michiro Ohnota
Kazuo Orita
Yasuhiro Aizawa
Noriyuki Yoshida
Takashi Sakamaki
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.)
Kyorin Pharmaceutical Co Ltd
Original Assignee
Kyorin Pharmaceutical 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 Kyorin Pharmaceutical Co Ltd filed Critical Kyorin Pharmaceutical Co Ltd
Priority to AU2001274502A priority Critical patent/AU2001274502A1/en
Publication of WO2001096321A1 publication Critical patent/WO2001096321A1/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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members

Definitions

  • the present invention is useful as a hypoglycemic agent and an insulin sensitivity enhancer.
  • the present invention relates to a method for producing a benzylthiazolidinedione derivative represented by the general formula (2), which is a synthetic intermediate for producing an N-benzyldioxothiazolidinyl benzamide derivative.
  • the N-benzyldioxothiazolidinyl benzamide derivative is known as a compound having an excellent hypoglycemic effect and hypolipidemic effect (Japanese Patent Application Laid-Open No. Hei 9-48771).
  • Japanese Patent Application Laid-Open No. Hei 9-48771 Japanese Patent Application Laid-Open No. Hei 9-48771.
  • a high-pressure catalytic reduction method using palladium carbon as a catalyst has been known (Japanese Patent Application Laid-Open No. H08-106468). It was done.
  • the present inventors have conducted intensive studies on the production of raw materials for establishing an industrial production method of an N-benzyldioxothiazolidinyl benzamide derivative.
  • R represents hydrogen or a lower alkyl group.
  • the present inventors have found that a benzylthiazolidinedione derivative represented by the formula (1) can be obtained with good yield, high purity and stability, and have completed the present invention.
  • the compound represented by the general formula (1) of the present invention can be synthesized by the method described in JP-A-9-48771.
  • the group defined as R is hydrogen or a lower alkyl group, which is a methyl group, an ethyl group, or an isopropyl group.
  • R of the compound of the general formula (1), which is a raw material may be either hydrogen or a lower alkyl group.
  • hydrolysis proceeds easily in the reaction system, and as a result, carboxylic acid is produced. Changes to acid groups.
  • reaction solvent in the production method of the present invention examples include aqueous solutions of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like, and these aqueous solutions and dimethylformamide, tetrahydrofuran.
  • a mixed solvent with an organic solvent such as drofuran, methanol, ethanol, and isopropyl alcohol can be used.
  • it is a 0.5 to 1 mol / L aqueous sodium hydroxide solution.
  • the temperature range of the reaction is 0-50 ° C. Preferably, it is 20 to 40 ° C.
  • Co complex catalyst used in the present invention examples include, for example, black (pyridyl) covaloxime (III) synthesized by the method described in In 0 rg. Synth. 11, 61 (19668). Can be used, but there is the trouble of separately preparing the catalyst.
  • the feature of the present invention is the same reaction In the system, C 0 ( ⁇ ) and dimethylglyoxime are used to form a C 0 complex catalyst within a specific pH range, and a reduction reaction is performed.
  • the donor of the Co (II) ion is preferably cobalt chloride, and the preferred ligand is dimethylglyoxime. This ligand is preferably used in an amount of about 4 mol% with respect to cobalt.
  • the preparation amount of the C0 catalyst used in the reaction is 0.1 to 1.5 fflol% based on the compound represented by the general formula (1). Preferably, it is 0.5 to 1.0 mol%.
  • borohydride compounds such as sodium borohydride, lithium borohydride, and borohydride can be used.
  • sodium borohydride can be used at low cost.
  • the pH of the reaction system can be set arbitrarily, but the reaction speed or the like changes significantly depending on the pH, which greatly affects the result of the reaction.
  • the compound of the present invention for example, although the reduction reaction proceeds even at pH 9.5 or more, the raw material compound (1) does not completely disappear. In order to completely eliminate the raw materials, it is necessary to add a catalyst and a reducing agent again, and it takes a long time to complete the reaction.
  • the thiazolidine-2,4-dione ring is relatively unstable under basic conditions, and therefore, it is disadvantageous to leave it under strong basic conditions for a long time.
  • the compound of the general formula (1) is prepared in a reaction system at a pH of 8.0 to 9.5 with a C 0 complex catalyst, and the reduction reaction is carried out.
  • This is a major feature of the invention.
  • the reduction reaction is completed in a short time, and the compound of the general formula (2) is produced with good reproducibility and good quality, which is an excellent method for industrial production. .
  • the precipitated crystals were collected by filtration and washed with water, ethanol, and getyl ether (50 mL each). The crystals were dried under reduced pressure at room temperature to obtain kuroguchi (pyridine) kovaloxim (III) 8.6.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

La présente invention concerne un procédé industriellement intéressant d'élaboration d'un dérivé de benzylthiazolidinedione convenant comme intermédiaire pour l'élaboration de N-benzyldioxothiazolidinyl-benzamide utilisés comme antihyperglycémiants. L'invention concerne plus particulièrement un procédé d'élaboration d'un dérivé de thiazolidinedione représenté par la formule (II). Ce procédé implique la formation d'un catalyseur à base d'un complexe de Co dans une place de pH défini dans un système de réaction dans lequel devra s'effectuer la réduction qui s'ensuit, puis la réduction d'un composé représenté par la formule générale (I) au moyen d'un réducteur dans le système de réaction résultant (I) dans lequel R est hydrogène ou alkyle inférieur.
PCT/JP2001/004989 2000-06-14 2001-06-13 Elaboration de derives de thiazolidinedione Ceased WO2001096321A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001274502A AU2001274502A1 (en) 2000-06-14 2001-06-13 Process for the preparation of thiazolidinedione derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000-178135 2000-06-14
JP2000178135 2000-06-14

Publications (1)

Publication Number Publication Date
WO2001096321A1 true WO2001096321A1 (fr) 2001-12-20

Family

ID=18679610

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2001/004989 Ceased WO2001096321A1 (fr) 2000-06-14 2001-06-13 Elaboration de derives de thiazolidinedione

Country Status (2)

Country Link
AU (1) AU2001274502A1 (fr)
WO (1) WO2001096321A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993013095A1 (fr) * 1991-12-20 1993-07-08 The Upjohn Company Procede de reduction pour la fabrication de 5-methylene triazolidinediones substituees
JPH08277279A (ja) * 1995-04-05 1996-10-22 Nitto Chem Ind Co Ltd ベンジルチアゾリジンジオン誘導体の製造方法
WO1996038428A1 (fr) * 1995-06-02 1996-12-05 Kyorin Pharmaceutical Co., Ltd. Derives de n-benzyldioxothiazolidylbenzamide et leur procede de production

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993013095A1 (fr) * 1991-12-20 1993-07-08 The Upjohn Company Procede de reduction pour la fabrication de 5-methylene triazolidinediones substituees
JPH08277279A (ja) * 1995-04-05 1996-10-22 Nitto Chem Ind Co Ltd ベンジルチアゾリジンジオン誘導体の製造方法
WO1996038428A1 (fr) * 1995-06-02 1996-12-05 Kyorin Pharmaceutical Co., Ltd. Derives de n-benzyldioxothiazolidylbenzamide et leur procede de production

Also Published As

Publication number Publication date
AU2001274502A1 (en) 2001-12-24

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