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[4-(1, 3, 3-trimethyl-2-oxo-3, 4-dihydro-1h-quinoxalin-7-yl) phenoxy]ethyloxy compound or salt thereof

A compound, technology of alkylcarbonyl, applied in the field of [4-phenoxy] ethyloxy compound or its salt

Inactive Publication Date: 2018-04-17
SANTEN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there is no specific disclosure of [4-(1,3,3-trimethyl-2-oxo-3,4-dihydro-1H-quinoxalin-7-yl)phenoxy]ethyl Oxygen compound or its salt

Method used

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  • [4-(1, 3, 3-trimethyl-2-oxo-3, 4-dihydro-1h-quinoxalin-7-yl) phenoxy]ethyloxy compound or salt thereof
  • [4-(1, 3, 3-trimethyl-2-oxo-3, 4-dihydro-1h-quinoxalin-7-yl) phenoxy]ethyloxy compound or salt thereof
  • [4-(1, 3, 3-trimethyl-2-oxo-3, 4-dihydro-1h-quinoxalin-7-yl) phenoxy]ethyloxy compound or salt thereof

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0317] (S)-4-Benzyloxy-2-hydroxybutyl methanesulfonate (reference compound 1-1)

[0318] To (S)-4-benzyloxy-1,2-butanediol (10.0g, 51.0mmol) and 2,6-lutidine (59mL, 507mmol) in dichloromethane (200mL) solution, in A solution of methanesulfonyl chloride (4.1 mL, 53.0 mmol) in dichloromethane (50 mL) was added dropwise over 30 minutes at -20°C, and stirred at room temperature for 24 hours. Furthermore, a dichloromethane (30 mL) solution of methanesulfonyl chloride (1.3 mL, 16.8 mmol) was added dropwise at room temperature over 30 minutes, followed by stirring for 1.5 hours. The mixture was washed with 0.5N hydrochloric acid (200 mL×4), saturated aqueous sodium bicarbonate solution (100 mL×3), saturated brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform / methanol) to obtain the title reference compoun...

reference example 2

[0322] (S)-4-Benzyloxy-1,2-epoxybutane (reference compound 2-1)

[0323] Mix (S)-4-benzyloxy-2-hydroxybutyl methanesulfonate (reference compound 1-1, 12.3g, 44.8mmol), potassium carbonate (12.3g, 89.0mmol) and methanol (100mL) at room temperature The mixture was stirred for 75 minutes. The solvent was distilled off under reduced pressure, and then 0.5N sodium hydroxide (450 mL) and ethyl acetate (200 mL) were added. The mixture was separated, and the aqueous layer was extracted with ethyl acetate (100 mL×2). The organic layers were combined and washed with saturated brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, whereby the title reference compound (8.0 g) (quantitative) was obtained.

[0324] [Table 2]

[0325]

[0326] (R)-4-Benzyloxy-1,2-epoxybutane (reference compound 2-2)

[0327] Under ice-cooling, to a solution of (R)-4-benzyloxy-1,2-butanediol (1.24g, 6.3mmol) in...

reference example 3

[0331] (S)-7-[4-(4-Benzyloxy-2-hydroxybutyl)oxy-2-methoxyphenyl]-8-(5-fluoro-2-methylphenoxymethyl )-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (reference compound 3-1)

[0332] 8-(5-fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3, 4-Dihydro-1H-quinoxalin-2-one (Compound A (prepared with reference to the above-mentioned Patent Document 2, the same applies below), 500 mg, 1.11 mmol), (S)-4-benzyloxy-1,2-cyclo A mixture of oxybutane (reference compound 2-1, 500 mg, 2.81 mmol), potassium carbonate (600 mg, 4.34 mmol) and ethanol (5 mL) was stirred for 7 hours. Water (30 mL) was added to the mixture, followed by extraction with ethyl acetate (30 mL×2). The organic layer was washed with saturated brine (30 mL), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane / ethyl acetate), whereby the title reference co...

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Abstract

The present invention relates to a novel [4-(1, 3, 3-trimethyl-2- oxo-3, 4-dihydro-1H-quinoxalin-7-yl)phenoxy]ethyloxy compound or a salt thereof. A compound of the present invention or a salt thereofhas glucocorticoid receptor agonist activity, and is useful as a pharmaceutical product, especially as a prophylactic and / or therapeutic agent for diseases associated with a glucocorticoid receptor.

Description

technical field [0001] The present invention relates to novel [4-(1,3,3-trimethyl-2-oxo-3,4-dihydro-1H-quinoxalin-7-yl)phenoxy]ethyloxy compounds or its salt. The compound of the present invention or a salt thereof has glucocorticoid receptor agonistic activity, and is useful as a drug, especially as a prophylactic or therapeutic agent for a disease associated with a glucocorticoid receptor. Background technique [0002] The glucocorticoid receptor is a 94 kDa ligand-activating intracellular transcriptional regulator belonging to the nuclear receptor superfamily. This receptor is known to regulate the metabolism of carbohydrates, proteins, and fats, suppress immune and inflammatory responses, activate the central nervous system, regulate cardiovascular system functions, and homeostasis related to basal and stress through its transcriptional regulation etc. (Non-Patent Document 1, Patent Document 1). [0003] Therefore, compounds having binding activity to glucocorticoid r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/44A61P27/14C07D403/12A61K31/498A61K31/5377A61K31/675
CPCC07D403/12A61K31/498A61K31/5377A61K31/675C07D241/44A61P27/02A61P29/00C07F9/650994
Inventor 川岛健二山崎裕辅高冈慎治椎大介小田知子松山高央
Owner SANTEN PHARMA CO LTD
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