Entecavir compound prepared in novel method

A technology of entecavir and compounds, which is applied in the field of entecavir compounds, can solve the problems of high import prices, low product purity, and increased costs

Inactive Publication Date: 2010-08-18
HAINAN LINGKANG PHARMA CO LTD
View PDF2 Cites 32 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] This route is relatively short, and the intermediate product page is relatively easy to purify, but the disadvantage is that it uses dimethylphenylchlorosilane as a protecting group ...

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
  • Entecavir compound prepared in novel method
  • Entecavir compound prepared in novel method
  • Entecavir compound prepared in novel method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The synthesis of embodiment 1 entecavir

[0038] (1) Synthesis of intermediate (II)

[0039] Add 130g (1mol) [1S-(1α, 2α, 3β, 5α)-2-hydroxymethyl]-6-oxabicyclo[3.1.0]hexan-3-ol into a 3L reaction flask, then add 134g (1.2mol) of isobutylene and 1000ml of anhydrous acetone, stirred, then added 133g (1mol) of aluminum chloride, stirred at room temperature for 15 hours, then evaporated the solvent under reduced pressure, and dissolved the residue with 1500ml of dichloromethane , and then washed with water, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 220 g of intermediate (II) product with a yield of 91%.

[0040] (2) Synthesis of intermediate (III)

[0041] Under nitrogen protection, 51g (0.1mol) of [2-[[(4-methoxyphenyl) diphenylmethyl] amino]-6-benzyloxy-9H-purine and 100g of sodium hydride (Content 60%) was dissolved in the DMF of 500ml, stirred and reacted at room temp...

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 aims to provide an entecavir compound prepared in a novel method. The reaction procedures in the preparation method of the entecavir compound are simplified. Moreover, isopropyl is adopted as a protection agent. Since the steric hindrance can function as multiple types of directional substitution, the invention reduces the introduction of heterogeneous impurities. The reaction in multiple procedures needs no strict operating conditions. Therefore, the invention lays a foundation for industrial production.

Description

technical field [0001] The invention relates to a novel entecavir compound, which belongs to the technical field of medicine. Background technique [0002] Entecavir, chemical name 2-amino-9-[(1S,3S,4S)-4-hydroxy-3-hydroxymethyl-2-methylenepentyl]-1,9-hydrogen-6-H-purine- 6-keto-hydrate, molecular formula: C 12 h 15 N 5 o 3 ·H 2 O, molecular weight: 295.3, structural formula is [0003] [0004] Entecavir is a carbocyclic nucleoside anti-HBV drug developed by Bristol-Myers Squibb, which was approved by the US FDA in March 2005 for marketing in the US. Entecavir is a selective inhibitor of HBV DNA polymerase and blocks all three stages of HBV replication. Clinical studies have proved that entecavir has strong anti-HBV activity, which is significantly better than lamivudine and is still effective for patients who have failed lamivudine treatment. Entecavir is similar in safety and tolerability to lamivudine, but it is much less likely to develop clinical resistance ...

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
IPC IPC(8): C07D473/18C07D303/30
Inventor 王明
Owner HAINAN LINGKANG PHARMA CO LTD
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