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Phenylacetic acid derivative, process for producing the same, and use

A technology of acetic acid and phenyl, which is applied in the field of phenylacetic acid derivatives, and can solve problems such as compounds with no reported structure

Inactive Publication Date: 2006-12-20
ONO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, some drugs in PPARγ agonists have been reported to cause liver disease, and they need to be used with caution as drugs
In addition, it is speculated that the hepatotoxic side effect is derived from the thiazolidine structure, but no structural compound has been reported to actually avoid hepatotoxicity

Method used

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  • Phenylacetic acid derivative, process for producing the same, and use
  • Phenylacetic acid derivative, process for producing the same, and use
  • Phenylacetic acid derivative, process for producing the same, and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0170] Methyl[3-(2-{5-ethyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl}ethoxy)-4-methyl Phenyl]acetate:

[0171]

[0172] To a solution of methyl(3-hydroxy-4-methylphenyl)acetate (1.00 g) in dichloromethane (22 mL) was added 2-{5-ethyl-2-[4-( Trifluoromethoxy)phenyl]-1,3-oxazol-4-yl}ethanol (2.00 g), triphenylphosphine (2.18 g) and 1,1'-(azodicarbonyl)dipiperidine ( 2.10 g), stirred at room temperature overnight. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (2.38 g) having the following physical data.

[0173] TLC: Rf 0.62 (hexane:ethyl acetate=2:1);

[0174] 1 H NMR (CDCl 3 ): δ8.05-7.99(m, 2H), 7.30-7.24(m, 2H), 7.05(d, J=7.5Hz, 1H), 6.77-6.72(m, 2H), 4.24(t, J=6.5 Hz, 2H), 3.67(s, 3H), 3.56(s, 2H), 3.00(t, J=6.5Hz, 2H), 2.75(q, J=7.5Hz, 2H), 2.15(s, 3H), 1.29(t, J=7.5Hz, 3H).

Embodiment 2

[0176] [3-(2-{5-Ethyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl}ethoxy)-4-methylphenyl ] acetic acid

[0177]

[0178] A 2N aqueous sodium hydroxide solution (10 mL) was added to a mixed solution of the compound (1.90 g) prepared in Example 1 in tetrahydrofuran (10 mL) and methanol (10 mL), followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 1N hydrochloric acid (25 mL), followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then the filtrate was concentrated to give the title compound (3.66 g) with the following physical data.

[0179] TLC: Rf 0.40 (chloroform:methanol=9:1);

[0180] 1 H NMR (CDCl 3 ): δ8.00(m, 2H), 7.25(d, J=8.1Hz, 1H), 7.05(d, J=8.1Hz, 1H), 6.76-6.71(m, 3H), 4.22(t, J= 6.6Hz, 2H), 3.58(s, 2H), 2.99(t, J=6.6Hz, 2H), 2.76(q, J=7.5Hz, 2H), 2.14(s, 3H), 1.29(t, J= 7.5Hz, 3H).

Embodiment 3- Embodiment 27

[0182] By the same procedure as described in Examples 1 and 2, using methyl(3-hydroxy-4-methylphenyl)acetate or its corresponding alcohol derivative, and methyl(3-hydroxy-4-methylbenzene) yl) acetate and the corresponding alcohol derivatives of 2-{5-ethyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl}ethanol instead of 2- {5-ethyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl}ethanol to give the following compounds of the present invention.

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PUM

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Abstract

The present invention relates to the compound represented by formula (I) (wherein R 1 and R 2 is hydrogen atom, C1-8 alkyl etc.; R 3 is C1-8 alkyl which may be substituted with 1 to 3 halogen atom(s), phenyl; R 4 is hydrogen atom etc. ; R 5 and R 6 is hydrogen atom, CI-8 alkyl etc.; X is sulfur atom or oxygen atom etc.; ringA is cyclic group which may have a substituent(s).), or a salt thereof Toxicity of the compound represented by formula (I) is very low, and it is safe enough to use as a pharmaceutical agent and since it has PPAR ' agonistic activity, it is useful as preventive and / or therapeutic agent for glucose lipid metabolic disorder, hypertension, circulatory diseases etc.

Description

Technical field [0001] The present invention relates to phenylacetic acid derivatives that can be used to treat hyperlipidemia and the like, their preparation and their uses. Background technique [0002] Recently, peroxisome proliferator-activated receptor (hereinafter abbreviated as PPAR), which is a type of nuclear receptor, has attracted attention in the study of transcription factors involved in induction of marker gene expression in adipocyte differentiation. The cDNA of PPAR was cloned from various animals and multiple isoform genes were found. In particular, three isoform types (α, δ, γ) are known in mammals (see J. Steroid Biochem. Molec. Biol., 51 , 157(1994);Gene Expression., 4 , 281 (1995); Biochem Biophys. Res. Commun., 224 , 431 (1996); Mol. Endocrinology., 6, 1634 (1992)). Furthermore, it is known that the PPARγ isoform is mainly expressed in adipose tissue, immune cells, adrenal glands, spleen, and small intestine, the PPARα isoform is mainly expressed in...

Claims

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Application Information

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IPC IPC(8): C07D263/32C07D413/10C07D277/24C07D417/02A61K31/421A61K31/422A61K31/426A61K31/454A61K31/4439A61P3/04A61P3/06A61P3/10A61P9/00A61P9/10A61P9/12A61P9/14A61P43/00
Inventor 楠田晋也中山孝介田嵨久男坂元孝彦
Owner ONO PHARMA CO LTD
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