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Carboxylic acid derivatives containing thiazole ring and their pharmaceutical use

A kind of technology of carboxylic acid derivatives and thiazole rings, applied in the field of new carboxylic acid derivatives

Inactive Publication Date: 2011-12-28
MITSUBISHI TANABE PHARMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, because conventional beta shows weak PPARα agonistic activity at the μmol / L level (not lower than 30 μmol / L) (EC 50 ), so its dose needs to be as high as 200-1500 mg / day

Method used

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  • Carboxylic acid derivatives containing thiazole ring and their pharmaceutical use
  • Carboxylic acid derivatives containing thiazole ring and their pharmaceutical use
  • Carboxylic acid derivatives containing thiazole ring and their pharmaceutical use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0394] tert-butyl 2-{[4-(chloroacetyl)-1,3-thiazol-2-yl]thio}-2-methylpropionate

[0395]

[0396] Dissolve 2-(1-tert-butoxycarbonyl-1-methyl-ethylthio)-thiazole-4-carboxylic acid in dichloromethane (1200 mL), add 1-ethyl-3-(3-di methylaminopropyl)carbodiimide hydrochloride (191.70 g), 4-dimethylaminopyridine (5.86 g) and methanol (19.47 mL), and the mixture was stirred at room temperature overnight. The mixture was washed with dilute hydrochloric acid (about 0.5 mol / l), saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution (500 mL each), and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was redissolved in ethyl acetate (700 mL), washed successively with dilute hydrochloric acid (about 0.2 mol / l), saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution (300 mL each) , and then dried over anhydrous sodium sulfate. The solvent was evaporated, the resulting solid wa...

Embodiment 2

[0401] 2-[(4-{2-[(4'-fluorobiphenyl-4-yl)oxy]-1-hydroxyethyl}-1,3-thiazol-2-yl)thio]-2-methanol Propionic acid

Embodiment 2-1

[0403] 2-[(4-{[(4'-fluorobiphenyl-4-yl)oxy]acetyl}-1,3-thiazol-2-yl)thio]-2-methylpropanoic acid tert-butyl ester

[0404]

[0405] tert-butyl 2-{[4-(chloroacetyl)-1,3-thiazol-2-yl]thio}-2-methylpropanoate (23.8 g) obtained in Example 1 and 4'- Fluorobiphenyl-4-ol (12.00 g) was dissolved in toluene (650 mL), and aqueous sodium hydroxide solution (1 mol / l, 71 mL), tetrabutylammonium iodide (2.62 g) and water (71 mL), and the mixture was heated at reflux for 3 hours, allowed to cool, and partitioned. The organic layer was washed twice with 1 mol / L aqueous sodium hydroxide solution (300 mL), washed twice with saturated aqueous sodium chloride solution (200 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated, and the obtained residue was purified by column chromatography (using Moritex Corporation Purif Pack SI 60 μm, specification 200. Elution solvent: hexane / ethyl acetate=95 / 151→70 / 30) to obtain as a pale yellow oily substance The title compound (1.128 ...

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Abstract

A compound represented by formula (I) or a pharmaceutically acceptable salt thereof: wherein R1 and R2 are each a hydrogen atom, an alkyl group, etc., R3 is a hydrogen atom, an alkyl group, etc., R4 is a hydrogen atom, an alkyl group, etc., and m is An integer of 0-3, X is a bond, an oxygen atom or a sulfur atom, Y is a carbonyl group or a hydroxymethylene group, etc., and Z is a halogen atom, an alkyl group, an aryl group, a heteroaryl group, etc., which have excellent PPARα agonism and lipid-lowering action, and can be used as a preventive or therapeutic drug for hyperlipidemia and the like.

Description

technical field [0001] The present invention relates to a novel carboxylic acid derivative containing a thiazole ring and a medicament containing the derivative as an active ingredient. Background technique [0002] Peroxisome proliferator-activated receptor (PPAR) is a nuclear receptor cloned in 1990 as a receptor in response to peroxisome proliferators, along with other nuclear receptors, the retinoid X receptor (RXR) forms heterodimers and acts as a transcription factor to activate various target genes. PPAR includes three subtypes (PPARα, β(δ), γ), and it has been clarified that fibrate, a therapeutic drug for hyperlipidemia, acts as a ligand of PPARα and acts as an insulin sensitizer The thiazolidine derivatives function as ligands for PPARγ. [0003] Fibrate is an agent widely used as a therapeutic drug for hyperlipidemia, and clofibrate, clofibrate, aluminum salt of clofibrate, bisfibrate, clifibrate, etc. have been used before. Currently, so-called second-generati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/20A61K31/426A61K31/4439A61P3/06A61P3/10A61P9/10C07D277/36C07D417/12
CPCC07D417/12C07D277/20C07D277/36A61P3/00A61P3/06A61P9/10A61P3/10A61K31/426
Inventor 安藤直子
Owner MITSUBISHI TANABE PHARMA CORP
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