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Novel preparation method of pranoprofen

An intermediate and equivalent ratio technology, which is applied in the field of preparation of propionate non-steroidal anti-inflammatory drug pranoprofen, can solve the problems of low yield and reduction, and achieve simple operation, cost reduction and increased yield Effect

Inactive Publication Date: 2019-06-28
GUANGDONG XIANQIANG PHARMA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the concentration of sodium methoxide is too high, the system will solidify and cannot react; if it is too low, the yield will decrease

Method used

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  • Novel preparation method of pranoprofen
  • Novel preparation method of pranoprofen
  • Novel preparation method of pranoprofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] step one)

[0061] Add 5H-[1]-benzopyran[2,3-b]pyridine (50g, 0.27mol) into a one-necked flask, then add 250ml of dichloromethane, cool to 0°C, add anhydrous aluminum trichloride ( 108g, 0.81mol), and finally propionyl chloride (37g, 0.4mol) was slowly added dropwise, and the dropwise addition was completed in 15 minutes. Adjust the pH to about 4 with sodium, filter, add 250ml of dichloromethane to the filtrate for extraction, add water to the organic layer after layering, and spin dry the organic layer to obtain 57g of a light red solid, with a yield of 89%.

[0062] Step (2)

[0063] Add 7-(1-propionyl)-5H-[1]-benzopyran[2,3-b]pyridine (50g, 0.208mol) into the one-necked flask, then add 150ml of carbon tetrachloride, and then add NBS (44g, 0.24mol) was heated and refluxed for 5h. After the reaction was completed, water was added, washed twice with 250ml of water, separated into layers, and the organic layer was spin-dried to obtain a reddish-brown solid 7-(2-bromopr...

Embodiment 2

[0069] step one)

[0070] Add 5H-[1]-benzopyran[2,3-b]pyridine (50g, 0.27mol) into a one-necked flask, then add 150ml of ethyl acetate, cool to -5°C, add anhydrous aluminum chloride (72g, 0.54mol), and finally propionyl bromide (36g, 0.27mol) was slowly added dropwise, and the dropwise addition was completed in 10 minutes. The temperature control during the dropwise addition was ≤10°C, and the temperature was raised to room temperature to continue the reaction for 2 hours, and then the system was added to 250ml of ice water , adjust the pH to about 4 with sodium carbonate, filter, add 250ml of dichloromethane to the filtrate for extraction, add water to the organic layer after layering, spin dry the organic layer to obtain 55g of a light red solid, and the yield is 85%.

[0071] Step (2)

[0072] Add 7-(1-propionyl)-5H-[1]-benzopyran[2,3-b]pyridine (50g, 0.208mol) into the one-necked bottle, then add 100ml of chloroform, and then add dibromohydantoin (59.3g, 0.208mol) was he...

Embodiment 3

[0078] step one)

[0079] Add 5H-[1]-benzopyran[2,3-b]pyridine (50g, 0.27mol) into a one-necked flask, then add 500ml of dichloromethane, cool to 5°C, add anhydrous aluminum trichloride ( 180g, 1.35mol), and finally propionyl bromide (73.4g, 0.54mol) was slowly added dropwise, and the dropwise addition was completed in 30 minutes. During the dropwise addition, the temperature was controlled to be ≤10°C, and then the temperature was raised to room temperature to continue the reaction for 4 hours, and then the system was added to 250ml of ice water , adjust the pH to about 4 with sodium carbonate, filter, add 250ml of dichloromethane to the filtrate for extraction, add water to the organic layer after layering, and spin dry the organic layer to obtain 56g of a light red solid with a yield of 87%.

[0080] Step (2)

[0081] Add 7-(1-propionyl)-5H-[1]-benzopyran[2,3-b]pyridine (50g, 0.208mol) into a one-necked flask, then add 250ml of dichloromethane, and then add NBS ( 55g, 0.3...

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Abstract

The invention discloses a novel preparation method of pranoprofen. The novel preparation method of the pranoprofen has the advantages of being high in yield, having less impurities, and being safe andenvironmentally friendly. The novel preparation method of the pranoprofen comprises the following steps that step 1, 5H-[1]-benzopyran[2,3-b]pyridine and propionyl chloride are directly acylated; step 2, bromination is carried out; step 3, potassium tert-butoxide or sodium tert-butoxide is used for hydrolysis, and finally, rearrangement is carried out to obtain the pranoprofen.

Description

technical field [0001] The invention relates to a preparation method of propionate non-steroidal anti-inflammatory drug pranoprofen. Background technique [0002] Pranoprofen, CAS: 52549-17-4, the trade name is pranoprofen, and the chemical name is 2-5H-[1]benzopyran[2,3-b]pyridin-7-ylpropionic acid ( 2-(5H-chromeno[2,3-b]pyridin-7-yl)propanoic acid), the chemical structure is as follows: [0003] [0004] Pranoprofen is a propionic acid non-steroidal anti-inflammatory drug, which can inhibit the production of prostaglandins and stabilize the cell membrane. Pranoprofen was developed and listed by Welfide Company (formerly Jifu Pharmaceutical Co., Ltd., now Mitsubishi Pharmaceutical Co., Ltd.) in 1981, and then Senshou Pharmaceutical Co., Ltd. developed it as eye drops. It was listed in Japan in 1988, mainly for external eyes and Symptomatic treatment of anterior segment inflammation. Pranoprofen has good therapeutic effect on ocular inflammation, high effective rate, g...

Claims

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Application Information

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IPC IPC(8): C07D491/052
Inventor 邓军叶琼仙罗日康黄彩逢熊伟梅谭珍友
Owner GUANGDONG XIANQIANG PHARMA
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