Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

The synthetic method of 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: 2017-02-22
TIANJIN JINYAO GRP
View PDF8 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • The synthetic method of pranoprofen
  • The synthetic method of pranoprofen
  • The synthetic method of pranoprofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Preparation of 2-(4-ethylphenoxy)nicotinic acid (3)

Embodiment 1a

[0050] Example 1a: Add 51 g of sodium hydroxide and 600 mL of methanol into a 1000 mL three-necked flask, stir mechanically until completely dissolved, then add 232 g of 4-ethylphenol in batches, and then add 100 g 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

[0051]Example 1b: Add 51 g of potassium hydroxide and 600 mL of absolute ethanol to a 1000 mL three-necked flask, stir mechanically until completely dissolved, then add 232 g of 4-ethylphenol in batches, and add 100 g 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 o C, 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%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

[0001] Technical field: [0002] The invention relates to a new intermediate of propionate non-steroidal anti-inflammatory drug pranoprofen and a new preparation method thereof. [0003] Background technique: [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 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%. [0005] [0006] There are few related documents about the s...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 李强李金禄王淑丽
Owner TIANJIN JINYAO GRP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com