Synthetic method for pranoprofen

A technology for compounds and intermediates, applied in the field of propionic acid non-steroidal anti-inflammatory drugs, can solve the problems of reduced yield, unreacted solidification, etc., and achieves the effects of shortening synthesis steps, improving raw material utilization, and high safety

Active Publication Date: 2014-06-18
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the key intermediate reacts with sodium methoxide, the concentration of sodium methoxide should be well controlled. If it is too high, the system will solidify and cannot react. If it is too low, the yield will decrease.
Finally, acylation with sulfonyl chloride is used to rearrange to obtain the reaction of pranoprofen, and the reported yield is 45%, which is relatively low

Method used

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  • Synthetic method for pranoprofen
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  • Synthetic method for pranoprofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The preparation of embodiment 12-(4-ethylphenoxy)nicotinic acid (3)

Embodiment 1a

[0045] Example 1a: Add 51g of sodium hydroxide and 600mL of methanol into a 1000mL three-neck flask, stir mechanically until completely dissolved, then add 232g of 4-ethylphenol in batches, and add 100g of 2-chloronicotinic acid after cooling down to room temperature. The reaction mixture is heated to evaporate most of the methanol, and then continue to heat to 170~180 o C, after removing all low boilers, heat preservation reaction for 1.5 hours. After cooling down to room temperature, 1000 mL of water was added to dissolve the residue, and extracted with ethyl acetate (300 mL×3). The aqueous phase was collected and the pH was adjusted to about 4 with 6N HCl aqueous solution, and a large amount of solids precipitated out of the system. Suction filtration, washing with water, and drying of the filter cake gave 138 g of light brown solid 3, with a yield of 90%.

Embodiment 1b

[0046] Example 1b: Add 51g of potassium hydroxide and 600mL of absolute ethanol into a 1000mL three-necked flask, stir mechanically until completely dissolved, add 232g of 4-ethylphenol in batches, and add 100g of 2-chloronicotinic acid after cooling down to room temperature. The reaction mixture is heated to steam most of the ethanol, and then heated to 200 oC, after removing all low boilers, heat preservation reaction for 2 hours. After cooling down to room temperature, 1000 mL of water was added to dissolve the residue, and extracted with ethyl acetate (300 mL×3). The aqueous phase was collected and the pH was adjusted to about 5 with aqueous acetic acid, and a large amount of solids precipitated out of the system. Suction filtration, washing with water, and drying of the filter cake gave 130 g of brown solid 3, with a yield of 85%.

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Abstract

The invention provides a synthetic method for pranoprofen and a novel compound structure which can be used for preparation of pranoprofen. More specifically, 2-chloronicotinic acid and paraethyl phenol are used as raw materials, and nucleophilic substitution, ring closure, halogenation, carbonyl group reduction, hydroxyl group elimination, a Grignard reaction and CO2 carbonyl group insertion are carried out so as to prepare pranoprofen.

Description

technical field [0001] The invention relates to a new intermediate of propionate non-steroidal anti-inflammatory drug pranoprofen and a new preparation method thereof. Background technique [0002] 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 Pharmaceuticals) in 1981, and then Senshou Pharmaceutical Co., Ltd. developed it as eye drops, and it was listed in Japan in 1988. The trade name is Punan Puling , mainly used for symptomatic treatment of outer eye and anterior segment inflammation. Pranoprofen has a good therapeutic effect on ocular inflammation, high effective rate, good tolerance, will not increase intraocular pressure, and the incidence of side effects is only 1.35%. [0003] [0004] There are few related documents about the synthesis process ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 李强李金禄王淑丽
Owner TIANJIN JINYAO GRP
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