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Ketorolac impurity C and preparation method and application thereof

A technology for ketorolac and impurities, which is applied in the field of preparation of ketorolac impurities and achieves the effects of less by-products, good reproducibility and simple operation

Pending Publication Date: 2021-06-04
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is currently no research on the analysis of the synthesis method of this impurity in ketorolac raw materials and its preparations, and there is a lack of detection methods and judgment basis for the production and drug safety of ketorolac

Method used

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  • Ketorolac impurity C and preparation method and application thereof
  • Ketorolac impurity C and preparation method and application thereof
  • Ketorolac impurity C and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of Compound 3

[0032]

[0033] Pyrrol (10.0 g, 149 mmol), tetrabutylammonium sulfate (5.0 g, 14.9 mmol) was added to the reaction bottle, and 200 mlNOH 50% solution was added: in a mixed solution of dichloromethane (1: 2.5V / v), 0 Benzulfonyl chloride (29.0 g, 164 mmol) was slowly added dropwise, and 15 min was added dropwise, and 200 ml of dichloromethane was added to the room temperature. The organic phase was washed with water, and the filtrate was dried. EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc EtOAc.

Embodiment 2

[0034] Example 2: Preparation of Compound 4

[0035]

[0036] Anhydrous aluminum chloride (20.0 g, 150 mmol) was dissolved in 100 mL of dichloroethane, and then stirred slowly with benzoyl chloride (21.0 g, 150 mmol), stirred at room temperature for 10 min, and finally added Compound 3 (25.0 g, 120 mmol), at room temperature 1H; 200 mL of dichloromethane, phase phase, washed with water, washed with 10% NaHCO3, dry NASO4, filtered, concentrated filtrate, obtained white solid is Compound 4 36.0g, yield 95.8%.

Embodiment 3

[0037] Example 3 Preparation of Compound 5

[0038]

[0039] Compound 4 (35.0 g, 112 mmol), sodium hydroxide (18.0 g, 450 mmol) was added to the reaction flask, and then 200 ml of dioxane: water (4: 1V / V) mixed solvent was added, and the reaction was stirred at room temperature for 12 h. 200 ml of ethyl acetate was added, phased, and the organic phase was washed with water, waterless NASO4 dried, filtered, concentrated filtrate, the obtained white solid was compound 5, 18.0 g, yield 93.3%.

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PUM

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Abstract

The invention discloses a ketorolac impurity C and a preparation method and application thereof. According to the method, the ketorolac impurity C is prepared by taking pyrrole as an initial raw material through a series of reactions such as substitution, oxidation and alkaline hydrolysis, and the ketorolac impurity C is one of important impurities of ketorolac drugs or preparations thereof and can be used for toxicological and pharmacological researches such as in-vivo absorption and metabolism of ketorolac, and can also be applied to research on stability and quality control of ketorolac preparations. The preparation method of the ketorolac impurity C has the advantages of simplicity in operation, safety in reaction and high purity and yield, and can be widely applied to the fields of impurity analysis, toxicological research, safety detection, stability judgment and the like of ketorolac bulk drugs and preparations thereof.

Description

Technical field [0001] The present invention belongs to the field of organic synthesis, and more particularly to the preparation method and application of ketole acid impurities. Background technique [0002] Ketorolac is a derivative of pyrridic acid, a non-steroidal anti-inflammatory analgesic. For prostaglandin synthase inhibitors, there is a strong pain relief and moderate anti-inflammatory, heat-resistant effect, which is mainly to block the synthesis of prostaglandin by blocking the metabolism of peanatlic acid. In a standard analgesic animal model, the analgesic activity of this product is 800 times aspirin, which is quite or better than Bondong, which is strong, quite or better than Bugong. In many trials, the anti-inflammatory activity is equivalent to or stronger than the indomethacin, stronger than naphthane, which is obviously better than Buganong. Multiple trials for eye diseases have shown that the anti-inflammatory activity of this product is strong without deterio...

Claims

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Application Information

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IPC IPC(8): C07D487/04G01N33/15
CPCC07D487/04G01N33/15
Inventor 简勇刘晟丁茹徐梅段炼
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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