Method for synthesizing dexketoprofen intermediate

A kind of technology of dexketoprofen and synthesis method, applied in the field of medicine, can solve the problems of cumbersome operation, unfavorable industrialized large-scale production, large loss of raw materials, etc.

Inactive Publication Date: 2018-12-28
NANJING ZENKOM PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dexketoprofen yield that prepares according to this method is all lower than 70%, and raw material loss is bigger, and operation is loaded down with trivial details, is unfavorable for industrialized large-scale production

Method used

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  • Method for synthesizing dexketoprofen intermediate
  • Method for synthesizing dexketoprofen intermediate
  • Method for synthesizing dexketoprofen intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Dissolve 8.67 g (0.0389 mol) of compound (1) and 15.00 g (0.0486 mol) of compound (2) in 300 ml of dichloromethane under nitrogen protection. The temperature was lowered to -30°C with stirring, 6.00 g of potassium tert-butoxide was added therein, and the temperature was controlled at -10 to -5°C for 3 hours. After the reaction was complete, water was slowly added dropwise at 0°C, stirred for 1 h, then left to stand, and the organic phase was obtained by liquid separation and washed with saturated brine. Add anhydrous sodium sulfate 30.00 to the organic phase to dry, 1h, and filter with suction. The filtrate was concentrated to dryness at 30°C to obtain the crude product. The crude product was mixed with ethyl acetate and n-hexane solution, beaten for 1 hour at 30°C, and 20.50 g of the refined product was obtained by suction filtration.

Embodiment 2

[0025]

[0026] Dissolve 9.76 g (0.044 mol) of compound (1) and 15.00 g (0.0486 mol) of compound (2) in 300 ml of dichloromethane under nitrogen protection. The temperature was lowered to -10°C while stirring, 6.00 g of potassium tert-butoxide was added therein, and the temperature was controlled at -10 to -5°C to react for 3 hours. After the reaction was complete, water was slowly added dropwise at 0°C, stirred for 1 h, then left to stand, and the organic phase was obtained by liquid separation and washed with saturated brine. Add anhydrous sodium sulfate 30.00 to the organic phase, dry it for 2 hours, and filter with suction. The filtrate was concentrated to dryness at 30°C to obtain a crude product, which was mixed with ethyl acetate and n-hexane solution, beaten for 2 hours at 40°C, and filtered with suction to obtain 22.43 g of a refined product.

Embodiment 3

[0028]

[0029] 11.93 g (0.0534 mol) of compound (1) and 15.00 g (0.0486 mol) of compound (2) were dissolved in 300 ml of dichloromethane under nitrogen protection. The temperature was lowered to -20°C with stirring, 6.00 g of potassium tert-butoxide was added therein, and the temperature was controlled at -10 to -5°C for 3 hours. After the reaction was complete, water was slowly added dropwise at 0°C, stirred for 1 h, then left to stand, and the organic phase was obtained by liquid separation and washed with saturated brine. Add anhydrous sodium sulfate 30.00 to the organic phase to dry, 3h, and filter with suction. The filtrate was concentrated to dryness at 30°C to obtain a crude product, which was mixed with ethyl acetate and n-hexane solution, beaten for 3 hours at 50°C, and filtered with suction to obtain 21.47 g of a refined product.

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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a method for synthesizing a dexketoprofen intermediate. The dexketoprofen intermediate is prepared by asymmetricsynthesis of Darzens reaction. The method can improve the selectivity of the reaction, reduce the loss of raw materials, improve the yield and simplify the operation process, and is conducive to industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a synthetic method of a dexketoprofen intermediate. Background technique [0002] Mixed ketoprofen consists of equal amounts of dexketoprofen and levoketoprofen. It has been clinically used as an anti-inflammatory and analgesic for 30 years and is considered to be the safest non-steroidal anti-inflammatory drug NSAID. And it's an over-the-counter drug. However, mixed ketoprofen still has various side effects including gastrointestinal toxicity, water and sodium retention, decreased renal perfusion, and allergic reactions, with an incidence rate of 15% to 30%. For the development of safer NSAIDs, two drugs have been proposed: cyclooxygenase (COX-2) inhibitors and pure steric counterparts of NSAIDs, especially dexketoprofen. In 1996, dexketoprofen began to be widely used in the treatment of rheumatoid arthritis in Austria. Because it is the pure spatial counterpart o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/48
CPCC07D303/48C07B2200/07
Inventor 龚青青徐卓业祁艳
Owner NANJING ZENKOM PHARMA
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