Simple preparation method of felbinac

A technology of felbinac and ethyl biphenylacetate is applied in the field of easy preparation of felbinac, can solve problems such as industrial application limitation, toxic phosphine and POx smog, and achieves easy operation, short operation period, high yield effect

Active Publication Date: 2017-05-31
山东海佑福瑞达制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the use of triphenylphosphine in this method, toxic phosphine and POx fumes will be generated during thermal decomposition, and the operation is carried out in a fume hood. As a reaction reagent, its industrial application is limited to a certain extent

Method used

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  • Simple preparation method of felbinac
  • Simple preparation method of felbinac
  • Simple preparation method of felbinac

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A kind of convenient preparation method of felbinac comprises the steps:

[0034] (1) Preparation of biphenylphenonate

[0035] In a 500mL four-neck flask, under nitrogen protection, add 180ml of dichloroethane, 27.8g (0.18mol) of biphenyl and 36g (0.27mol) of anhydrous aluminum trichloride, stir rapidly and cool down to -5°C, and drop Add 29.5 g (0.25 mol) of monoethyl oxalyl chloride, and control the temperature at -5°C to 5°C during the dropwise addition. After dropping, react at 0°C for 6 hours. After the reaction, pour the reaction solution into concentrated hydrochloric acid / ice water 500mL, V(concentrated hydrochloric acid) / V(ice water)=1:1; Saturated sodium chloride aqueous solution, saturated sodium bicarbonate aqueous solution and purified aqueous solution were washed until neutral, dried over anhydrous sodium sulfate; filtered, and the organic solvent was evaporated to obtain the compound diphenylacetone ethyl ester;

[0036] (2) Synthesis of Felbinac

[0...

Embodiment 2

[0040] A kind of convenient preparation method of felbinac comprises the steps:

[0041] (1) Preparation of biphenylphenonate

[0042] In a 300mL four-neck flask, under nitrogen protection, add 1080ml of dichloroethane, 172.8g (1.08mol) of biphenyl and 230g (1.72mol) of anhydrous aluminum trichloride, stir rapidly and cool down to -4°C, and drop in 4 hours Add 192g (1.62mol) of monoethyl oxalyl chloride, and control the temperature at -3°C to 5°C during the dropwise addition; after the dropwise addition, react at 0°C for 9h, and after the reaction is completed, pour the reaction solution into 3000mL of concentrated hydrochloric acid / ice water, V( Concentrated hydrochloric acid) / V (ice water)=1.2:1; Stir and separate, and the organic phase layer is washed with saturated aqueous sodium chloride solution, saturated aqueous sodium bicarbonate solution and purified aqueous solution until neutral, and dried over anhydrous sodium sulfate; Filter and evaporate the organic solvent to ...

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PUM

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Abstract

The invention provides a simple preparation method of felbinac. The method comprises the following steps: taking biphenyl and ethyl oxalyl monochloride as initial raw materials; carrying out Friedel-Crafts reaction under the action of aluminum trichloride to generate biphenylethyl glyoxylate under the condition of low temperature; then carrying out alkaline hydrolysis to obtain felbinac salt; carrying out Huang-Minlon reaction reduction and acidification to obtain the felbinac. The method has the advantages of no need of intermediate separation, simplicity and convenience in operation, environment friendliness, high yield and industrial production value.

Description

technical field [0001] The invention relates to a convenient preparation method of felbinac, which belongs to the field of medicinal chemistry. Background technique [0002] Felbinac is a drug developed and marketed by Japan Lederle in 1986 as "Napageln" ointment, with the molecular formula C 14 h 12 o 2 , which is a non-steroidal anti-inflammatory drug, is a potent metabolite of ibuprofen, and its anti-inflammatory activity is similar to that of ibuprofen. At present, domestic preparations have been produced, and the main indications are: osteoarthritis, periarthritis of the shoulder, tenosynovitis, peritendinitis, muscle pain, traumatic swelling, pain, etc. [0003] The existing multiple synthetic method report of literature, so far, the processing route of synthetic felbinac mainly contains following several kinds: [0004] (1) Patent CN 104086394A discloses a synthetic route using p-bromophenylacetic acid and phenylboronic acid as starting materials: [0005] [...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/738C07C27/02C07C59/84C07C51/02C07C57/38
Inventor 宋永保魏乐坤王洪臣林治秘
Owner 山东海佑福瑞达制药有限公司
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