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

Novel synthetic process for levocetirizine and key intermediates

A technology of levocetirizine and compounds, applied in the direction of organic chemistry, can solve the problems of unsatisfactory purity and yield of levocetirizine, and achieve the effects of convenient use, high yield and high purity

Inactive Publication Date: 2013-10-30
HUNAN JIUDIAN PHARMA
View PDF3 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But according to this method, the purity and yield of levocetirizine in the industrialization process are unsatisfactory

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
  • Novel synthetic process for levocetirizine and key intermediates
  • Novel synthetic process for levocetirizine and key intermediates
  • Novel synthetic process for levocetirizine and key intermediates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1, the preparation of the compound of compound formula (II)

[0063] Add 50 g of 1,4-oxocyclohexane, 80 g of thionyl chloride, and 20 g of potassium hydrogen persulfide into the reaction vessel, and react at room temperature for 1 hour, then slowly add 10 g of anhydrous acetic acid, and then add 3 g of sodium hypochlorite, and react 3 hours, filtered, the filter cake was dissolved by adding 100 g of water, and extracted twice with 80 g of acetone respectively; the organic phases were combined, filtered and concentrated under reduced pressure to obtain the title compound.

Embodiment 2

[0064] Embodiment 2, the preparation of the compound of chemical formula (Ⅲ)

[0065] In the reaction vessel, 10 g of the product obtained in Example 1 was added with 100 g of anhydrous piperazine, then triethylamine was added, and 40 g of dichloromethane and 50 g of p-toluenesulfonyl chloride were added dropwise at room temperature, and the reaction 2 hours, the organic phase was separated, washed with 20 g of saturated brine, dried, filtered, and concentrated under reduced pressure to obtain the title compound.

Embodiment 3

[0066] Embodiment 3, the preparation of the compound of chemical formula (Ⅳ)

[0067] Put 20g of the product obtained in Example 2 into a reaction vessel, add 15g of bromobenzene, 60ml of acetonitrile, and 12g of cobalt bromide, then stir the mixture and heat it up to 70-80°C, keep it warm for 1.5 hours, and add p-toluenesulfonate dropwise Acyl piperazine 20g, keep warm for 5 hours after dropping, concentrate under reduced pressure, recover acetonitrile, filter and dry to obtain the title compound.

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 novel compound, namely, the compound in formula (IV), wherein, R is selected from Cl, Br, NO2, OH, tosyl, OR' or alkyl, and R' is alkyl. The invention provides applications of the compound in synthesis of levocetirizine, comprises an application of the compound in synthesis of (-)-1-[(4-chlorophenyl) benzyl] piperazine, and provides intermediates which can be used for synthesis of levocetirizine. The invention further provides compounds (II) and (III) which can be used for synthetic process for the compound (IV).

Description

Area of invention [0001] The present invention is the field of chemical drugs, which involves a new method of preparation (-) -1- [(4-chlorophenyl) benzozine] povethiazine, as well as in the process of synthesis of the method of synthesisThe key new intermediate. Background technique [0002] Levitidizine was launched in February 2001. It is the third -generation anti -allergic drug. Because it is the L -carrier of Sididizine, the pharmacological effect is similar to Sididizine.Allergic diseases, such as allergic nasal conjunctivitis, allergic skin diseases, allergic asthma, etc., have fast effect, strong effects, and long -lasting effects, but avoid the sedation and lethargy central nervous system of Setolizine.side effect. [0003] [0004] (-)-1-[(4-chlorophenyl) benzozyl] Polyzide is an important intermediate of synthetic levisizine. US patent US5478941 disclosed synthesis (-)-1- [(4-chloropene benzene phenylThe method of phenolinel] phenzide] It includes hydrolytic acid hy...

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): C07D295/22C07D295/24C07D295/28C07D295/26C07D295/073C07D295/088
Inventor 朱志宏卜振军郑霞辉谭军华杨静
Owner HUNAN JIUDIAN PHARMA
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