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Fluorophenyl-substituted thiazole dihydropyrimidine

A thiazolyl and benzylidene technology, applied in the field of fluorophenyl-substituted thiazole dihydropyrimidines, can solve problems such as rebound effects and side reactions, achieve good tolerance and enhance antiviral activity

Active Publication Date: 2008-12-24
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, interferon has only moderate activity and has deleterious side effects; although lamivudine (lamivudine) has good activity, it develops resistance rapidly during treatment and often has rebound effects after stopping treatment, Lamivudine (3-TC) > IC 50 Value is 300nM (Science, 299(2003), 893-896)

Method used

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  • Fluorophenyl-substituted thiazole dihydropyrimidine
  • Fluorophenyl-substituted thiazole dihydropyrimidine
  • Fluorophenyl-substituted thiazole dihydropyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Ethyl 4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate

[0118]

[0119] 10.0g (49.3mmol) of 2-chloro-4-fluorobenzaldehyde, 8.2g (63.1mmol) ethylacetoacetic acid, 10.3g (63.1mmol) 2-amidino-thiazole hydrochloride and 6.2g (75.7mmol) Sodium acetate was dissolved or suspended in 500ml of ethanol and boiled under reflux for 16 hours. Cool to room temperature, filter with suction, and wash the residue with water to remove inorganic salts. Obtain product 12.8g (53.4%)

[0120] Melting point: 162-164°C.

Embodiment 2

[0122] Methyl 4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate

[0123] The compound was synthesized by a method similar to Example 1 using methyl acetoacetic acid. Yield: 55% (melting point: 152-154°C)

Embodiment 3

[0125] Ethyl 6-chloromethyl-4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

[0126]

[0127] 4.0g (8.72mmol) ethyl 4-(2-chloro-4-fluorophenyl)-2-(thiazol-2-yl)-6-methyl-1,4-dihydro obtained in Example 1 Pyrimidine-5-carboxylate was added to 80ml of carbon tetrachloride and heated to 50°C under argon atmosphere to obtain a clear solution. At this temperature, 1.73 g (9.61 mmol) of N-bromosuccinimide were added and mixing was maintained at this temperature for 10 minutes. Cool immediately, filter under vacuum at room temperature, and concentrate under reduced pressure. The purity of the product was checked by HPLC to be higher than 90%, and it was used as the raw material for the next step.

[0128] Rf=0.70 (petroleum ether / ethyl acetate=8:2)

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Abstract

The invention relates a novel fluorophenyl-substituted thiazolyldihydropyrimidine applicable to acting against hepatitis B virus (HBV) infection and a composition of the same and other antiviral agents.

Description

technical field [0001] The present invention relates to a novel fluorophenyl-substituted thiazole dihydropyrimidine, its preparation method and its use as medicine, especially its application in treating and preventing hepatitis B virus infection. The present invention also relates to the composition of these dihydropyrimidines with other antiviral agents and, where appropriate, immunomodulators, and medicaments containing these compositions, especially for the treatment and prevention of HBV infection, such as hepatitis B. Background technique [0002] Hepatitis B virus belongs to the Hepaviridae family. It can cause acute and or persistent / progressive chronic disease. Hepatitis B virus also causes many other clinical signs in the pathomorphology - notably chronic inflammation of the liver, cirrhosis and canceration of hepatocellular cells. In addition, co-infection with hepatitis D can have detrimental effects during the development of the disease. [0003] Conventional...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A61K31/506A61K31/5377A61P1/16A61P31/12
CPCA61P1/16A61P31/12C07D417/04C07D417/14
Inventor S·戈尔德曼李静刘遗松
Owner SUNSHINE LAKE PHARM CO LTD
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