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Non-cyclic nucleoside phosphonate compound and its composition, prepn process and use

A technology of acyclic nucleoside phosphonate and cyclic nucleoside phosphonate, which is applied in the fields of pharmacy, drug synthesis and pharmacology, and can solve problems such as unstable chemical properties, high toxicity, and low oral bioavailability

Inactive Publication Date: 2011-10-05
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, acyclic nucleoside phosphonate drugs generally have disadvantages such as unstable chemical properties, relatively high toxicity, and low oral bioavailability.

Method used

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  • Non-cyclic nucleoside phosphonate compound and its composition, prepn process and use
  • Non-cyclic nucleoside phosphonate compound and its composition, prepn process and use
  • Non-cyclic nucleoside phosphonate compound and its composition, prepn process and use

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0092] Preparation Example 1N-(Chloromethoxycarbonyl)-L-Proline Methyl Ester Preparation

[0093]

[0094] At -5~0℃, N 2 Under protection, a mixture of proline methyl ester hydrochloride (5.80g, 0.035mol), DIEA (11.3g, 0.088mol), DMAP (0.086g, 0.70mmol) and dichloromethane (20mL) was added dropwise to chlorine Chloromethyl formate (4.70g, 0.036mol) and dichloromethane (50mL) mixed solution, dropwise finished, slowly rise to room temperature, continue to react for 2 hours, add ethyl acetate (60mL) to dilute, successively wash with saturated sodium bicarbonate Aqueous solution (90mL×3), 1 equivalent of hydrochloric acid (90mL×3), washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and the residue was subjected to column chromatography (petroleum ether:ethyl acetate=4:1 ) afforded the title product (6.64 g, 85.6%). 1 H NMR (CDCl 3 ): 5.65-5.84(m, 2H), 4.43(m, 1H), 3.75(s, 3H), 3.60(m, 2H), 2.24(m, 1H), 2.03(m, ...

preparation example 2-8

[0097]

[0098] Preparation example

preparation example 9

[0099] Preparation Example 9 Preparation of 2-bromoethyl chloroformate

[0100]

[0101] After triethylamine (16.2g, 0.16mol) was mixed with dichloromethane (70mL), it was added dropwise to 2-bromoethanol (20.0g, 0.160mol), solid phosgene (15.8g, 0.053mol) and In the dried dichloromethane (320mL) mixture, react at 0°C for 2 hours, then rise to room temperature and react for 2 hours, filter, extract with dichloromethane (150mL), wash with water (80mL×2), and saturated sodium chloride solution After washing, it was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the title product (17.1 g, 57.1%). 1 H NMR (CDCl 3 ): 4.60 (t, J = 6.31 Hz, 2H), 3.56 (t, J = 6.31 Hz, 2H).

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Abstract

The present invention provides one kind of non-cyclic nucleoside phosphonate compounds with the general formula as shown and their pharmaceutically acceptable inorganic and organic salts and composition. The present invention also provides the preparation process of these compounds and their use as active matter for treating viral infectious diseases, especially infectious diseases caused by HBV and HIV.

Description

technical field [0001] The invention belongs to the field of pharmacy, relates to the fields of drug synthesis and pharmacology, more specifically, relates to acyclic nucleoside phosphonate compounds containing amino acid groups, their compositions, preparation methods and their use in the preparation of antiviral drugs use. Background technique [0002] Hepatitis B virus (HBV) infection is a global health problem. According to World Health Organization estimates, there are about 350 million HBV carriers in the world, and there are 120 million HBV carriers in China alone. Chronic HBV infection can cause related diseases such as chronic hepatitis B (CHB), liver cirrhosis, and primary hepatocellular carcinoma (HCC). At present, the main drugs for the treatment of hepatitis B are interferon and nucleoside compounds. Alpha-interferon combined with ribavirin not only has limited curative effect but also has many adverse reactions, so nucleoside compounds are the main field of ...

Claims

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Application Information

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IPC IPC(8): C07F9/6561A61K31/675A61P31/12A61P1/16A61P31/18
CPCY02P20/55
Inventor 杨玉社江赛红卢鹏李战嵇汝运
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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