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Dihydronaphthalene devivatives and drugs contanining these compounds as active ingrdeient

A technology of dihydronaphthalene derivatives and dihydronaphthalene, which can be applied in the directions of organic active ingredients, medical preparations containing active ingredients, drug combinations, etc., and can solve rare problems and the like

Inactive Publication Date: 2007-12-26
ONO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] On the other hand, there are few reports on ligands that significantly activate PPARδ or biological activities related to PPARδ

Method used

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  • Dihydronaphthalene devivatives and drugs contanining these compounds as active ingrdeient
  • Dihydronaphthalene devivatives and drugs contanining these compounds as active ingrdeient
  • Dihydronaphthalene devivatives and drugs contanining these compounds as active ingrdeient

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0328] 3-(5-Hydroxy-3,4-dihydronaphthalen-1-yl)propionic acid

[0329]

[0330] To pyridine hydrochloride (200 g) was added 3-(5-methoxy-3,4-dihydronaphthalen-1-yl)propionic acid (25.1 g; known compounds (see J.Chem.Soc.Perkin Trans.I., 1739-1742 (1987)), then stirred at 180°C for 3 hours. The reaction mixture was cooled to room temperature and diluted with water. The aqueous layer was acidified with concentrated hydrochloric acid. The aqueous layer was extracted with ethyl acetate. Extract with saturated aqueous sodium bicarbonate solution. The combined aqueous layers were acidified with concentrated hydrochloric acid, and then extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (11.8g), which has the following physical data.

[0331] TLC: Rf0.42 (chloroform: methanol = 6: 1);

[0332] NMR (CDCl 3 ): δ9.21(s, 1H), 6.98(dd, J=7...

reference example 2

[0334] Methyl 3-(5-hydroxy-3,4-dihydronaphthalen-1-yl)propionate

[0335]

[0336] Anhydrous methanol (40 ml) was cooled to -10°C, and thionyl chloride (5.92 ml) was added dropwise thereto under an argon atmosphere, followed by stirring at -10°C for 20 minutes. To this solution, the compound (11.8 g) prepared in Reference Example 1 was added, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, then azeotroped with toluene (twice). The residue was purified by silica gel column chromatography (chloroform to chloroform:methanol=50:1) to obtain the title compound (10.6 g) having the following physical data.

[0337] TLC: Rf0.72 (chloroform:methanol=10:1);

[0338] NMR (CDCl 3 ): δ7.06(dd, J=7.8, 7.6Hz, 1H), 6.88(d, J=7.6Hz, 1H), 6.70(d, J=7.8Hz, 1H), 5.88(t, J=4.4Hz , 1H), 4.93(s, 1H), 3.68(s, 3H), 2.82-2.62(m, 4H), 2.58-2.49(m, 2H), 2.26(m, 2H).

reference example 3

[0340] 5-Pivaloyloxy-1,2,3,4-tetralin-1-one

[0341]

[0342] To a solution of pyridine (180 ml) in 5-hydroxy-1-tetralone (30.0 g), 4-dimethylaminopyridine (1.13 g) was added, and pivaloyl chloride (25.0 ml) was added thereto under ice cooling , and then stirred overnight at room temperature. The reaction mixture was ice-cooled, and concentrated hydrochloric acid was added thereto, followed by extraction with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1~5:1) to obtain the title compound (45.4 g) having the following physical data.

[0343] TLC: Rf 0.42 (hexane: ethyl acetate = 5: 1);

[0344] NMR (CDCl 3 ): δ7.95(dd, J=7.8, 1.4Hz, 1H), 7.33(t, J=7.8Hz, 1H), 7.19(dd, J=7.8, 1.4Hz, 1H), 2.79(t, J= 6.0Hz, 2H), 2.65(dd, J=7.6, 6.0Hz, 2H), 2.19-2.05(m, 2H), 1.40(s, 9H).

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Abstract

Compounds represented by the following general formula (I): (I) wherein each symbol has the meaning as defined in the description; salts thereof and drugs for controlling peroxisome proliferation-activated receptor which contain these compounds as the active ingredient. Because of having an activity of controlling peroxisome proliferation-activated receptor, the compounds of the general formula (I) are useful as hypoglycemics, lipid-lowering agents, preventives and / or remedies for metabolic errors such as diabetes, obesity, syndrome X, hypercholesterolemia and hyperlipoproteinemia, preventives and / or remedies for hyperlipemia, arteriosclerosis, hypertension, circulatory diseases, over-eating, ischemic heart diseases, etc., HDL cholesterol-elevating agents, LDL cholesterol and / or VLDL cholesterol-lowering agents and risk factor relieving agents for diabetes and syndrome X.

Description

technical field [0001] The present invention relates to dihydronaphthalene derivatives. More specifically, the present invention relates to [0002] (1) dihydronaphthalene derivatives or nontoxic salts thereof represented by the following formula (I) [0003] [0004] (the definitions of all the symbols are as explained below), [0005] (2) its method of preparation, and [0006] (3) Drugs containing it as an active ingredient. Background technique [0007] Recently, in the study of transcription factors involved in marker gene expression in adipocyte differentiation, peroxisome proliferator-activated receptor (hereinafter abbreviated as PPAR), as one of nuclear receptors, has attracted much attention. Cloning the cDNA of PPAR from various animals found multiple isoform genes, specifically, three types of isoforms (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, 4...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/32C07D277/42C07D413/04C07D417/04A61K31/4439A61K31/422A61K31/454A61K31/496A61K31/541A61K31/497A61K31/4545A61K31/421A61P3/10A61P3/06A61P9/10C07D277/40C07D407/04C07D413/12
CPCC07D263/32C07D413/04C07D417/04C07D407/04C07D277/40C07D277/42C07D413/12A61P3/00A61P3/10A61P3/04A61P3/06A61P43/00A61P9/00A61P9/10A61P9/12
Inventor 田嶋久男中山孝介福岛大吉
Owner ONO PHARMA CO LTD
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