New type of phosphonate-nucleotide compound

A compound and phosphonate technology, applied in the field of chemistry, can solve the problems of low seroconversion rate, inability to absorb, and difficulties in drug resistance, and achieve good safety, high antiviral activity, and high oral absorbability

Inactive Publication Date: 2007-12-19
上海韵德日化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although lamivudine (3TC) is available for the treatment of HBV infection, it is resistant and has low seroconversion rates
While 9-(2-phosphonomethoxy)ethyladenine PMEA, 9-(2-phosphonomethoxy)propyladenine PMPA, 9-(2-phosphonomethoxy)ethyl-2 , phosphonate-nucleotide compounds such as 6-diaminopurine PMDAP, becaus

Method used

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  • New type of phosphonate-nucleotide compound
  • New type of phosphonate-nucleotide compound
  • New type of phosphonate-nucleotide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of compound No.1

[0026] The structural formula of No.1 compound is shown in the figure below, in which the carbon atom C1 is a left-handed structure:

[0027]

[0028]Add 10 g of 9-(2-phosphonomethoxyethyl) adenine (PMEA), 7 g of phenol, 5 g of triethylamine and 30 g of tetrahydrofuran into the reactor, and heat to reflux. Then add N, N'-carbonylbisimidazole 15g. The reflux reaction was continued for 24 hours. The reaction solution was cooled to 25°C. The reaction solution was concentrated under reduced pressure into a yellow-brown slurry, then 18 g of water was added, and the pH value was adjusted to 11 with 25% NaOH solution. Suspended solids were removed by filtration through 1.5 g of celite followed by rinsing with 3 g of water. The combined filtrates were extracted with ethyl acetate. The aqueous phase was adjusted to pH 3.1 with 37% HCl solution, and the 9-(2-phenoxyphosphonomethoxyethyl)adenine precipitate was separated by fi...

Embodiment 2

[0031] Embodiment 2: the synthesis of compound No.2

[0032] The structural formula of the No.2 compound is shown in the figure below, in which the carbon atom C1 is a left-handed structure:

[0033]

[0034] According to the same method as in Example 1, 10 g of 9-(2-phosphonomethoxyethyl) adenine (PMEA), 7 g of phenol, 5 g of triethylamine and 30 g of tetrahydrofuran were added to the reactor, and heated to reflux. Then add N, N'-carbonylbisimidazole 15g. The reflux reaction was continued for 24 hours. The reaction solution was cooled to 25°C. The reaction solution was concentrated under reduced pressure into a yellow-brown slurry, then 18 g of water was added, and the pH value was adjusted to 11 with 25% NaOH solution. Suspended solids were removed by filtration through 1.5 g of celite followed by rinsing with 3 g of water. The combined filtrates were extracted with ethyl acetate. The aqueous phase was adjusted to pH 3.1 with 37% HCl solution, and the 9-(2-phenoxypho...

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PUM

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Abstract

The present invention relates to chemical technology, and is especially one kind of phosphonate-nucleotide compounds in the structure as shown, and their salts, hydrates and solvates. These compounds and their salts, hydrates and solvates have broad spectrum and high antiviral activity, effect of treating HBV infection with lamivudine resistance, high safety, and high orally taken absorption rate, and may be used as antiviral medicine for treating hepatitis B, herpes and other diseases and as antitumor medicine.

Description

[0001] the field [0002] The present invention relates to the field of chemistry, in particular to a novel phosphonate-nucleotide compound, in particular to a phosphonate-nucleotide compound, its salt, hydrate or its solvent, which has antiviral activity and is used as a medicine compounds, and their pharmaceutical compositions. Background technique [0003] Currently, HBV infection is a major threat to human health and is associated with severe liver diseases, including liver cirrhosis and hepatocellular carcinoma. More than 2 billion people in the world are infected with HBV, accounting for about 1 / 3 of the world's total population. Among them, 350 million people are chronic virus carriers, and about 1 / 4 of them die from HBV infection. Therefore, inventing a drug with strong antiviral activity and no inhibitory effect on the growth of normal cells for the treatment of HBV infection and other diseases will make a huge contribution to human health. Although lamivudine (3TC...

Claims

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Application Information

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IPC IPC(8): C07F9/6561A61K31/675A61K9/00A61P1/16A61P31/12A61P37/00A61P35/00
Inventor 程伟红
Owner 上海韵德日化有限公司
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