Method for preparing firocoxib

A technology of firocoxib and compounds, applied in the field of medicine, which can solve the problems of high pollution, volatile, high toxicity, etc.

Active Publication Date: 2019-11-15
SHANDONG LUKANG SHELILE PHARMA
View PDF9 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The international patent whose patent number is WO9714691 discloses the synthetic method of firocoxib, which uses sulfide anisole as raw material, prepares firocoxib through F-C acylation, oxidation reaction, bromination reaction and cyclopropoxyacetic acid reaction , but this technique uses the sulfide anisole that is easy to volatilize, smelly, the big isobutyryl chloride of corrosiveness, the liquid bromine that is toxic, volatile, corrosive big and the cyclopropoxyacetic acid (raw material of unscaled production) Not easy to obtain), the whole process is highly polluting, has high requirements for equipment and environmental protection, and is not suitable for industrialized green production

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
  • Method for preparing firocoxib
  • Method for preparing firocoxib
  • Method for preparing firocoxib

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0035] The invention provides a preparation method of filocoxib, comprising the following steps:

[0036] Methyl p-methanesulfonyl phenylacetate, methylmagnesium iodide and the first organic solvent are mixed, and a methylation reaction is carried out to obtain a compound having the structure shown in formula II;

[0037] Mixing the compound with the structure shown in formula II, the dehydrating agent and the second organic solvent, and performing a dehydration reaction to obtain the compound with the structure shown in formula III;

[0038] Mixing the compound with the structure shown in the formula III, an oxidant, water and a third organic solvent, and carrying out an oxidation reaction to obtain a compound with the structure shown in the formula IV;

[0039] Mixing the compound with the structure shown in formula IV, acetoxyacetyl chloride, the first organic base and the fourth organic solvent, and carrying out an esterification reaction to obtain the compound with the st...

Embodiment 1

[0082] Methyl p-methanesulfonyl phenylacetate (228 g) was mixed with 1 L of tetrahydrofuran, and the above mixed solution was added dropwise to 1.5 L of 3M methylmagnesium iodide ether solution (5°C), and the dropwise addition was completed after 2 h. Slowly heat up to room temperature, continue to react for 8h, add dropwise 4L of saturated saline solution, extract with dichloromethane 2L*3 times, and concentrate under reduced pressure until no liquid flows out to obtain a compound with the structure shown in formula II;

[0083] After mixing the compound with the structure shown in formula II and 1 L of tetrahydrofuran, the above mixed solution was added dropwise to 150 mL of a 50% boron trifluoride THF solution, the dropwise addition was completed after 3 hours, and the mixture was heated to reflux at a temperature of 55 °C. After 5h, it was lowered to room temperature, 10L of sodium hydroxide solution with a mass concentration of 2% was added, extracted with dichloromethane ...

Embodiment 2

[0091] After mixing methyl p-methanesulfonyl phenylacetate (228 g) with 1 L of ether, the above mixed solution was added dropwise to 1.5 L of 3M methylmagnesium iodide ether solution (5°C), and the dropwise addition was completed after 2 h. Slowly warming up to room temperature, after continuing the reaction for 8h, dropwise add 4L of saturated saline solution, extract with dichloromethane 2L*3 times, and concentrate under reduced pressure until no liquid flows out to obtain a compound having the structure shown in formula II;

[0092] After mixing the compound with the structure shown in formula II and 1 L of methyl tert-butyl ether, the above mixed solution was added dropwise to 213 g of phosphorus pentoxide. , drop to room temperature, add 10L of 2% sodium methoxide solution by mass concentration, extract with dichloromethane 2L*3 times, and concentrate under reduced pressure until no liquid flows out, to obtain a compound with the structure shown in formula III;

[0093] M...

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 relates to the technical field of medicines and particularly relates to a method for preparing firocoxib. Raw materials used in the preparation method are conventional reagents in the market, thioanisole which is easily volatized and has strong odor, isobutyryl chloride with high corrosion and liquid bromine with high toxicity, easy volatilization and strong corrosion are abandoned.The method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a preparation method of filocoxib. Background technique [0002] Firocoxib is an animal-specific non-steroidal anti-inflammatory drug developed by the French company Merial, which is used for surgical pain relief, acute and chronic inflammation treatment and pain caused by osteoarthritis. The product has the characteristics of fast absorption, takes 10 minutes to take effect, and the effect lasts for more than 24 hours. The product has high safety, and no adverse reactions have been observed after taking 5 times the dose for 180 days. The product has good palatability and is a smoky barbecue flavored tablet. Because the product has excellent therapeutic effect and palatability, it has a very good market prospect. [0003] The international patent with the patent number of WO9714691 discloses a method for synthesizing filocoxib, which takes anisole as a raw material, and prepa...

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 Applications(China)
IPC IPC(8): C07D307/60
CPCC07D307/60
Inventor 郭强武茂成桑艳丽赵琪邓忠慧
Owner SHANDONG LUKANG SHELILE PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap