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Antiviral activity possessed compound and preparation method thereof

A compound and composition technology, applied in the field of antiviral new compounds and their preparation, can solve the problems of cumbersome, long synthesis steps, harsh synthesis conditions, etc., and achieve improved absorption and bioavailability, reduced number of synthesis steps, good anti-inflammatory The effect of viral activity

Inactive Publication Date: 2006-12-13
CHENGDU DIAO JIUHONG PHARMA FAB
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But, the dissolubility of entecavir in water is very poor, has limited the preparation of its aqueous solution dosage form and the application in treatment, although the salt of above-mentioned structural formula also can increase water-solubility according to the understanding of those skilled in the art, but due to its synthesis The conditions are harsh and the cost is very high, so far there is no report of the salt of the above structural formula
[0005] The preparation method of entecavir disclosed in the patent publication CN91110831 adopts a step-by-step synthesis method, and the synthesis steps are long and cumbersome; a large amount of benzyl bromide that seriously pollutes the environment will be used; different reaction conditions will be used during deprotection, Step by step, and a large amount of boron trichloride is used as a deprotection agent, the reaction conditions of this step are harsh, and the industrial production cost is high

Method used

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  • Antiviral activity possessed compound and preparation method thereof
  • Antiviral activity possessed compound and preparation method thereof
  • Antiviral activity possessed compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Preparation of [1S-(1α, 2α, 3β, 5α)-2-hydroxymethyl]-6-oxabicyclo]3.1.0]hexan-3-ol (compound 3):

[0045] [1S-(1α, 2α, 3β, 5α)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexan-3-ol 16g (67.8mmol) was dissolved in 0.5 g of 10% palladium carbon was added to 100 ml of tetrahydrofuran, and catalytic hydrogenation was carried out at room temperature for 8 hours. The catalyst was filtered off, and the solvent was evaporated to dryness under reduced pressure to obtain 9.8 g of pure compound 3.

Embodiment 2

[0046] Example 2 Preparation of Compound 4:

[0047]Dissolve 9.5 g of [1S-(1α, 2α, 3β, 5α)-2-hydroxymethyl]-6-oxabicyclo[3.1.0]hexan-3-ol in 100ml of anhydrous acetone, then add 2 , 10 ml of 2-dimethoxypropane and a catalytic amount of p-toluenesulfonic acid. Stir at room temperature for 24 hours. The solvent was evaporated under reduced pressure, then dissolved in 100ml of dichloromethane, washed with saturated sodium bicarbonate (20ml×2), saturated brine (20ml×2), and dried over anhydrous sodium sulfate to obtain 11g of pure compound 4.

Embodiment 3

[0048] Example 3 6-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy--9H-purin-9-yl]-2,2-di Preparation of methylhexahydro-cyclopentyl[1,3]dioxan-5-ol (compound 5):

[0049] Under nitrogen protection, [2-[[(4-methoxyphenyl) diphenylmethyl]amino]-6-benzyloxy--9H-purine 36.5g and sodium hydride (60%) 2.85g Dissolve in DMF200ml. Stir at room temperature for 2 hours. Then, a solution of 10 g of compound 4 in 20 ml of DMF was added, the temperature was raised to 120° C., and the mixture was stirred for 10 hours. After concentration under reduced pressure, the residue was chromatographed on a silica gel column and eluted with petroleum ether-ethyl acetate (2:1) to obtain 29.3 g of pure compound 5.

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Abstract

The invention discloses a novel compound having a general formula discloses in the specification, a process for preparing the compound, and novel intermediate compound related in the compound synthesizing flow path. The compound provided by the invention can be used for preparing multiple pharmaceutical preparations for treating a plurality of diseases caused by virus infection.

Description

technical field [0001] The present invention relates to a novel compound, in particular, the present invention relates to a novel antiviral compound and a preparation method thereof. Background technique [0002] Entecavir (Entecavir) is an antiviral agent, its chemical name is:] 1S-(1α, 3α, 4β)-2-amino-1,9-dihydro-9-]4-hydroxy-3- (Hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one, the patent publication CN91110831 discloses the preparation method of the compound, and the patent publication CN1310999A discloses the preparation of low-dose entecavir and its application, the patent publication CN91110831 also discloses the compound of the following formula. [0003] [0004] But, the dissolubility of entecavir in water is very poor, has limited the preparation of its aqueous solution dosage form and the application in treatment, although the salt of above-mentioned structural formula also can increase water-solubility according to the understanding of those skilled in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/04C07F1/06C07F3/04C07D473/30A61K31/52A61P31/12A61P31/22A61P31/18A61P1/16
Inventor 王学超刘忠荣李伯刚吴逢伟钟朝斌何民黄瑜
Owner CHENGDU DIAO JIUHONG PHARMA FAB
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