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Indometacin 2-arylmorpholine ethyl, preparation method and application thereof

A technology of aryl morpholino ethyl ester and aryl morpholino ethyl ester, which is applied in the field of new compounds and their preparation, and can solve problems such as gastrointestinal side effects

Inactive Publication Date: 2012-03-21
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional NSAIDs inhibit both cyclooxygenase-1 (COX-1) and COX-2, causing gastrointestinal side effects

Method used

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  • Indometacin 2-arylmorpholine ethyl, preparation method and application thereof
  • Indometacin 2-arylmorpholine ethyl, preparation method and application thereof
  • Indometacin 2-arylmorpholine ethyl, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1 The preparation of indomethacin 2-(2-phenylmorpholinyl) ethyl ester and its hydrochloride

[0026] (1) Preparation of Indomethacryloyl Chloride

[0027] Dissolve 3 mmol of indomethacin in 8 mL of dichloromethane, add 1 mL of oxalyl chloride, stir in an ice bath for 3 h, evaporate the solvent under reduced pressure, and separate the residual oxalyl chloride to obtain indomethacin as a yellow solid.

[0028] (2) Preparation of indomethacin 2-(2-phenylmorpholinyl) ethyl ester and its hydrochloride

[0029]

[0030] Dissolve indomethanoyl chloride prepared in 8 mL of tetrahydrofuran, add dropwise 2 mmol of 2-phenyl-4-hydroxyethylmorpholine in tetrahydrofuran, 1 mL of triethylamine as an acid-binding agent, stir at room temperature for 6 hours, and filter after completion of the reaction. The filtrate was decompressed to remove the solvent tetrahydrofuran, washed away excess indomethacin with 1.0mol / L sodium hydroxide solution, extracted with ethyl acetate t...

Embodiment 2

[0032] Embodiment 2 Preparation of indomethacin 2-[2-(4-methylphenyl)morpholinyl] ethyl ester and hydrochloride thereof

[0033]

[0034]

[0035] Dissolve the obtained indomethacryloyl chloride in 8 mL of tetrahydrofuran, add dropwise 2 mmol of 2-(4-methylphenyl)-4-hydroxyethylmorpholine in tetrahydrofuran, 1 mL of triethylamine as an acid-binding agent, and stir at room temperature for 6 h , the reaction was completed, filtered, and the filtrate was decompressed to remove the solvent tetrahydrofuran, washed off excess indomethacin with 1.0mol / L sodium hydroxide solution, extracted with ethyl acetate to obtain an organic layer, evaporated to remove ethyl acetate, and column chromatography Indomethacin 2-[2-(4-methylphenyl)morpholinyl]ethyl ester.

[0036] Dissolve indomethacin 2-[2-(4-methylphenyl)morpholinyl]ethyl ester with a small amount of anhydrous ether, and pass through dry hydrogen chloride to obtain indomethacin 2-[2-(4-methylbenzene Base) morpholino] ethyl es...

Embodiment 3

[0037] Embodiment 3 Preparation of Indomethacin 2-[2-(4-ethylphenyl)morpholinyl]ethyl ester and its hydrochloride

[0038]

[0039] Dissolve the obtained indomethacryloyl chloride in 8 mL of tetrahydrofuran, add dropwise 2 mmol of 2-(4-ethylphenyl)-4-hydroxyethylmorpholine in tetrahydrofuran, 1 mL of triethylamine as an acid-binding agent, and stir at room temperature for 6 h , the reaction was completed, filtered, and the filtrate was decompressed to remove the solvent tetrahydrofuran, washed off excess indomethacin with 1.0mol / L sodium hydroxide solution, extracted with ethyl acetate to obtain an organic layer, evaporated to remove ethyl acetate, and column chromatography Indomethacin 2-[2-(4-ethylphenyl)morpholinyl]ethyl ester.

[0040] Dissolve indomethacin 2-[2-(4-ethylphenyl)morpholinyl]ethyl ester with a small amount of anhydrous ether, and pass through dry hydrogen chloride to obtain indomethacin 2-[2-(4-ethylphenyl Base) morpholino] ethyl ester hydrochloride, yiel...

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Abstract

The invention discloses indometacin 2-arylmorpholine ethyl or a salt thereof has a structural formula in the specification. The preparation method for the indometacin 2-arylmorpholine ethyl (I) comprises the following steps: dissolving indometacin chloride into tetrahydrofuran to obtain solution; adding the solution of 4-hydroxyethyl-2-arylmorpholine tetrahydrofuran into the solution dropwise with stirring; and after finishing reaction, distilling for recovering the tetrahydrofuran so as to obtain the indometacin 2-arylmorpholine ethyl. The preparation method for the salt of the indometacin 2-arylmorpholine ethyl comprises the following steps: dissolving the indometacin 2-arylmorpholine ethyl into absolute ethyl ether or ethanol; and introducing dry HCl gas or performing a reaction with acid (HY) to obtain the salt of the indometacin 2-arylmorpholine ethyl (II). The indometacin 2-arylmorpholine ethyl or the salt thereof is applied to preparing anti-inflammatory analgesics.

Description

technical field [0001] The present invention relates to a new class of compound and its preparation method and application, in particular indomethacin 2-arylmorpholine ethyl ester or its salt and its preparation method and application. Background technique [0002] Traditional non-steroidal anti-inflammatory drugs (NSAIDs) have inhibitory effects on both COX-1 and COX-2. The effective therapeutic effect of NSAIDs stems from its inhibition of COX-2, while adverse reactions are attributed to Inhibition of COX-1. There are 30 million to 40 million patients in the world taking NSAIDs every day, and there are as many as 200,000 cases of adverse reactions or complications caused by these drugs every year, of which the fatality rate is >20%. Adverse reactions of NSAIDs appear clinically. [0003] Traditional non-steroidal anti-inflammatory drugs inhibit both cyclooxygenase-1 (COX-1) and COX-2, and have gastrointestinal side effects. In contrast, COX-2 selective inhibitors ret...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12A61K31/5377A61P29/00
Inventor 胡艾希石磊徐江平叶姣蒋毅萍林焕冰周溪
Owner HUNAN UNIV
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