Aminocarboxylic acid derivative and medicinal use thereof

A technology of azetidine carboxylic acid and objects, applied in the field of aminocarboxylic acid derivatives and their medical applications, can solve the problem of no EDG-6 agonist or antagonist

Inactive Publication Date: 2008-01-30
ONO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no description that EDG-6 agonists or antagonis...

Method used

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  • Aminocarboxylic acid derivative and medicinal use thereof
  • Aminocarboxylic acid derivative and medicinal use thereof
  • Aminocarboxylic acid derivative and medicinal use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0445] Example 1: 6-(Benzyloxy)-3,4-dihydronaphthalene-1(2H)-one

[0446] To a solution of 6-hydroxy-3,4-dihydronaphthalen-1(2H)-one (24.3 g) in acetone (160 mL) was added benzyl bromide (29.4 mL) and potassium carbonate (31.1 g) at room temperature, followed by Stir at 40°C for 3.5 hours. After filtering off insolubles and concentrating the filtrate, the residue was washed with a mixed solvent of tert-butylmethyl ether-hexane (1:4) to obtain the title compound (34.5 g) having the following physical properties.

[0447] TLC: Rf0.38 (hexane: ethyl acetate = 3: 1)

Embodiment 2

[0448] Example 2: 7-(Benzyloxy)-4-methyl-1,2-dihydronaphthalene

[0449] To a solution of the compound prepared in Example 1 (34.5 g) in tetrahydrofuran (300 mL) was added methylmagnesium bromide (3 mol / L ether solution, 55 mL) at 0°C, followed by stirring at room temperature for 1 hour. The reaction mixture was cooled to 0°C and poured into ice-saturated aqueous ammonium chloride. After adding 2 mol / L hydrochloric acid, the mixture was stirred at room temperature for 3 hours. Thereafter, the product was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, dried, and then concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain the title compound (24.8 g) having the following physical properties.

[0450] TLC: Rf0.57 (hexane: ethyl acetate = 15:1)

Embodiment 3

[0451] Example 3: 6-(Benzyloxy)-1-methyl-3,4-dihydronaphthalene-2-carbaldehyde

[0452] N,N-Dimethylformamide (60 mL) was added dropwise to phosphorus oxychloride (26.7 g) at 0°C, followed by stirring for 20 minutes. Thereafter, a dichloromethane (60 mL) solution of the compound (24.8 g) prepared in Example 2 was slowly dropped thereinto, followed by stirring at room temperature for 90 minutes. The reaction liquid was cooled to 0° C., then poured into ice and left for a period of time. Next, the product was extracted with a mixed solvent of hexane-ethyl acetate (1:2). The organic layer was washed successively with water and brine, dried and concentrated. The obtained solid was washed with tert-butyl methyl ether to obtain the title compound (19.9 g) having the following physical properties.

[0453] TLC: Rf0.50 (hexane: ethyl acetate = 3: 1)

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Abstract

A compound represented by the general formula (I), a salt thereof, an N-oxide form thereof, a solvate thereof, or a prodrug of any of these; and a drug containing any of these. (I) (In the formula, all the symbols are as defined in the description.) The compound represented by the general formula (I) has the ability to combine with an S1P receptor (especially EDG-1, EDG-6, and/or EDG-8). It is useful for the prevention and/or treatment of rejection reactions to transplantation, graft versus host diseases, autoimmune diseases, allergic diseases, neurodegenerative diseases, etc.

Description

technical field [0001] The present invention relates to a compound having a sphingosine-1-phosphate (hereinafter sometimes abbreviated as "S1P") receptor-binding ability useful as a medicine, and a medicine containing the same as an active ingredient. [0002] More specifically, the invention relates to: [0003] (1) compounds represented by general formula (I), salts thereof, N-oxides thereof, solvates thereof or their prodrugs, [0004] [0005] In the formula, all the symbols represent the same meaning as described below; and [0006] (2) A medicine containing the general formula (I), its salt, its N-oxide body, its solvate or its prodrug as an active ingredient. Background technique [0007] Sphingosine-1-phosphate (S1P) represented by the general formula (A) is a lipid synthesized by the intracellular metabolic cycle of sphingolipids and the extracellular action of secretory sphingosine kinase. It has been pointed out in the literature that S1P acts as an intercel...

Claims

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Application Information

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IPC IPC(8): C07C229/14A61K31/12A61K31/166A61K31/197A61K31/215A61K31/397A61K31/4035A61K31/41A61K31/437A61K31/4409A61K31/4412A61K31/4439A61K31/4725A61K31/55A61K45/00A61P1/04A61P3/10A61P7/00A61P11/00A61P11/06A61P17/00A61P17/06A61P19/02A61P19/04A61P25/00A61P29/00A61P37/06A61P43/00C07C257/18C07D205/04C07D209/44C07D211/22C07D211/70C07D211/74C07D211/80C07D223/16C07D271/06C07D401/04C07D409/04C07D413/04C07D471/04C07F5/04
Inventor 巾下广仓田晴登中出真嗣
Owner ONO PHARMA CO LTD
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