Anti-hepatitis B virus drug

An anti-hepatitis B and drug technology, applied in the field of anti-hepatitis B virus drugs, can solve the problems of poor curative effect and easy rebound

Active Publication Date: 2014-05-21
BEIJING MEIBEITA DRUG RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, entecavir and lamivudine have certain cross-resistance, and the curative effect on lamivudine-resistant patients is poor
In addition, like other nucleoside anti-HBV drugs, entecavir is prone to rebound after drug withdrawal

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0019] Example 12-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxyl-3-((methoxycarbonylmethylamino-phenoxy-phosphoryl)-oxomethanol Base)-2-methylenecyclopentyl]-6H-purin-6-one (I-1) preparation

[0020]

[0021] Dissolve 2.1 g (0.01 mol) of phenol dichlorophosphate and 1.3 g (0.01 mol) of glycine methyl ester hydrochloride in 30 mL of anhydrous dichloromethane, and cool to -78°C. A solution of 2 g of triethylamine dissolved in 20 mL of anhydrous dichloromethane was added dropwise with stirring, and the rate of addition was controlled to maintain the reaction temperature at -78°C. After the addition was complete, the reaction temperature was gradually raised to room temperature, and stirring was continued for 1 hour. The solvent was distilled off under reduced pressure, and 30 ml of anhydrous diethyl ether was added to the residue, and filtered. The filtrate was evaporated to dryness under reduced pressure to obtain a colorless oily substance, namely phosphoramide intermediate IV...

Embodiment 2

[0024] Example 2 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxyl-3-((ethoxycarbonylmethylamino-phenoxy-phosphoryl)-oxygen Preparation of methyl)-2-methylenecyclopentyl]-6H-purin-6-one (I-2)

[0025]

[0026] Dissolve 2.1 g (0.01 mol) of phenol dichlorophosphate and 1.4 g (0.01 mol) of ethyl glycine hydrochloride in 30 mL of anhydrous dichloromethane, and cool to -78°C. A solution of 2 g of triethylamine dissolved in 20 mL of anhydrous dichloromethane was added dropwise with stirring, and the rate of addition was controlled to maintain the reaction temperature at -78°C. After the addition was complete, the reaction temperature was gradually raised to room temperature, and stirring was continued for 1 hour. The solvent was distilled off under reduced pressure, and 30 ml of anhydrous diethyl ether was added to the residue, and filtered. The filtrate was evaporated to dryness under reduced pressure to obtain a colorless oily substance, namely phosphoramide intermediate IV-2, whi...

Embodiment 32

[0028] Example 32-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxyl-3-((isopropoxycarbonylmethylamino-phenoxy-phosphoryl)-oxygen Preparation of methyl)-2-methylenecyclopentyl]-6H-purin-6-one (I-3)

[0029]

[0030] Dissolve 2.1 g (0.01 mol) of phenol dichlorophosphate and 1.53 g (0.01 mol) of glycine isopropyl hydrochloride in 30 mL of anhydrous dichloromethane, and cool to -78°C. A solution of 2 g of triethylamine dissolved in 20 mL of anhydrous dichloromethane was added dropwise with stirring, and the rate of addition was controlled to maintain the reaction temperature at -78°C. After the addition was complete, the reaction temperature was gradually raised to room temperature, and stirring was continued for 1 hour. The solvent was distilled off under reduced pressure, and 30 ml of anhydrous diethyl ether was added to the residue, and filtered. The filtrate was evaporated to dryness under reduced pressure to obtain a colorless oily substance, namely phosphoramide intermediate I...

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Abstract

The invention relates to a novel anti-hepatitis B virus drug represented in a formula I, and a nontoxic pharmaceutically acceptable salt and a hydrate thereof: (img file= 'DSA00000804267600011.TIF' wi= '739' he= '766' /), wherein R1 is alkyl or naphthenic base, of which the carbon number is 1-6, and R2 is H or alkyl of which the carbon number is 1-6.

Description

technical field [0001] The invention relates to a new anti-hepatitis B virus drug and its non-toxic pharmaceutically acceptable salt and hydrate. Background technique [0002] Viral hepatitis is a major disease that threatens human health. Entecavir is currently the most effective drug for hepatitis B treatment. However, Entecavir and lamivudine have certain cross-resistance, and the curative effect on lamivudine-resistant patients is poor. In addition, like other nucleoside anti-HBV drugs, entecavir is prone to rebound after drug withdrawal. Therefore, better anti-HBV drugs are needed clinically. Contents of the invention [0003] The object of the present invention is to provide new anti-hepatitis B virus medicine represented by formula I and its non-toxic pharmaceutically acceptable salt and hydrate thereof: [0004] [0005] Among them, R 1 is a carbonyl or cycloalkyl group with 1-6 carbon atoms, R 2 is H or an alkyl group with 1-6 carbon atoms. [0006] The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561A61K31/675A61P31/20
Inventor 王建明陈伟房建山张鸿
Owner BEIJING MEIBEITA DRUG RES
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