Supercharge Your Innovation With Domain-Expert AI Agents!

A kind of preparation method of hydroxychloroquine impurity

A technology for hydroxychloroquine and impurities is applied in the field of preparation of hydroxychloroquine impurities, and achieves the effects of reasonable design, strong operability, and simple and easy-to-obtain reagents

Active Publication Date: 2022-03-15
TLC NANJING PHARMA RANDD CO LTD
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention has studied a kind of synthetic method of hydroxychloroquine impurity (compound VIII), mainly studies its synthetic content, has not yet been reported at home and abroad

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
  • A kind of preparation method of hydroxychloroquine impurity
  • A kind of preparation method of hydroxychloroquine impurity
  • A kind of preparation method of hydroxychloroquine impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] A preparation method for hydroxychloroquine impurities, specifically comprising the following steps:

[0059]

[0060] Preparation of Compound III: Mix Compound I (30.00 g) and Compound II (57.59 g), heat up to 80°C and stir for 4 hours. Cool, add methanol and dichloromethane and stir for half an hour, and the precipitated solid is suction-filtered to obtain 45.10 g of compound III as a white solid, with a yield of 94.13%. See mass spectrometry image 3 , NMR see Figure 4 .

[0061]

[0062] Preparation of Compound IV: Dissolve Compound III (32.00 g) in 480.0 mL of dry dichloromethane, add boron tribromide (20.40 g) and mix, and stir at 0°C for 1 hour. After quenching, adding water to adjust the base and extracting with dichloromethane to obtain 35.10 g of compound IV as a white solid with a yield of 88.63%. See mass spectrometry Figure 5 .

[0063]

[0064] Preparation of Compound VI: Dissolve Compound IV (35.00 g) in tetrahydrofuran (350.00 mL), add 3...

Embodiment 2

[0070] A preparation method for hydroxychloroquine impurities, specifically comprising the following steps:

[0071]

[0072] Preparation of Compound III: Mix Compound I (470.00g) with Compound II (902.32g), heat up to 80°C and stir for 4 hours. Cool, add methanol and dichloromethane and stir for half an hour, and the precipitated solid is suction-filtered to obtain 1131.42 g of compound III as a white solid, with a yield of 93.80%. See mass spectrometry image 3 , NMR see Figure 4 .

[0073]

[0074] Preparation of Compound IV: Dissolve Compound III (312.00g) in 4680.0mL dry dichloromethane, add boron tribromide (198.6g), and stir at 0°C for 1 hour. After quenching, adding water to adjust the base and extracting with dichloromethane to obtain 354.20 g of compound IV as a white solid with a yield of 91.73%. See mass spectrometry Figure 5 .

[0075]

[0076] Preparation of Compound VI: Dissolve Compound IV (250.00 g) in tetrahydrofuran (2500.00 mL), add 250.0 m...

Embodiment 3

[0082] A preparation method for hydroxychloroquine impurities, specifically comprising the following steps:

[0083]

[0084] Preparation of Compound III: Compound I (10.00 g) was mixed with Compound II (7.91 g), heated to 50°C and stirred for 10 hours. After cooling, add methanol and dichloromethane and stir for half an hour, and the precipitated solid is suction-filtered to obtain 0.21 g of compound III as a white solid, with a yield of 8.18%. See mass spectrometry image 3 , NMR see Figure 4 .

[0085]

[0086] Preparation of Compound IV: Dissolve Compound III (8.00 g) in 40.0 mL of dry dichloromethane, add boron tribromide (1.00 g) and mix, and stir at 0°C for 1 hour. After quenching, adding water to adjust the base and extracting with dichloromethane to obtain 2.10 g of compound IV as a white solid with a yield of 21.21%. See mass spectrometry Figure 5 .

[0087]

[0088] Preparation of Compound VI: Dissolve Compound IV (2.50 g) in tetrahydrofuran (12.50 ...

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 discloses a preparation method of hydroxychloroquine impurity, which uses 4-amino-1-pentanol as a raw material to realize the synthesis of hydroxychloroquine impurity VIII through five-step reactions. The preparation method of the present invention has reasonable process design, strong operability, and can realize industrial production; and the reagents used in the synthesis method are simple and easy to obtain; the purity of the hydroxychloroquine impurities obtained by the reaction can reach more than 98%, and the total yield can reach 20% %above. The hydroxychloroquine impurity prepared by the invention provides an important basis for the scientific evaluation of the quality, safety and efficacy of the hydroxychloroquine.

Description

technical field [0001] The invention belongs to medicine synthesis technology, in particular to a preparation method of hydroxychloroquine impurity. [0002] technical background [0003] Hydroxychloroquine (Hydroxychloroquine), commonly used as its sulfate, is a 4-aminoquinoline derivative antimalarial drug and a unique antirheumatic drug. The chemical name is 2-[[4-[(7-chloroquinolin-4-yl)amino]pentyl](ethyl)amino]ethanol, the molecular weight is 335.87, and the structural formula is: [0004] [0005] Hydroxychloroquine sulfate (Hydroxychloroquine sulfate) was successfully developed by Surrey and Hammer of Winthrop Company in 1946. It was first listed in the United States in 1956 and has been listed in Japan, Denmark, Germany, Finland, France and other countries and regions. U.S. FDA approved hydroxychloroquine sulfate tablets on May 29, 1998 for the treatment of lupus erythematosus and rheumatoid arthritis. [0006] Since January 2020, the COVID-19 strain has escalat...

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): C07D215/46
CPCC07D215/46
Inventor 杨石吕冠宝张池崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com