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N<6>-substituted adenosine derivative, preparation method thereof, drug composition and application

A technology of adenosine derivatives and adenosine, which is applied in the field of medicine and can solve problems that have not been reported yet

Active Publication Date: 2014-04-30
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this component was also isolated from Gastrodia elata recently, it was found that it can prevent PC12 cell apoptosis and interact with adenosine A 2A However, there is no report on the effects of this compound and similar components on the central nervous system such as sedation and hypnosis.

Method used

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  • N&lt;6&gt;-substituted adenosine derivative, preparation method thereof, drug composition and application
  • N&lt;6&gt;-substituted adenosine derivative, preparation method thereof, drug composition and application
  • N&lt;6&gt;-substituted adenosine derivative, preparation method thereof, drug composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: N 6 Preparation of -(3,4-dihydroxybenzyl)-adenosine

[0066] In the first step, 2.76g of 3,4-dihydroxybenzaldehyde, 2.52g of hydroxylamine hydrochloride, and 3.26g of anhydrous sodium acetate were weighed and dissolved in 80ml of ethanol. The reaction was stirred for 6 hours at room temperature. The solvent was evaporated to dryness, dissolved in 40ml of water, extracted with ethyl acetate (40×3ml), and the ethyl acetate was evaporated to obtain 2.72g of light yellow solid (3,4-dihydroxybenzaldehyde oxime).

[0067] Second step, 2.72g 3,4-dihydroxybenzaldehyde oxime is dissolved in 70ml ethanol, adds 700mg 10%Pd / C, 8ml concentrated hydrochloric acid, hydrogenates under normal pressure, obtains white crystal (3,4-dihydroxybenzylamine Hydrochloride) 2.98g.

[0068] The third step, 2.98g 3,4-dihydroxybenzylamine hydrochloride was dissolved in 70ml n-propanol, add 1g 6-chloropurine nucleoside and 14ml N,N-diisopropylethylamine, heated to 70°C, react for 8 hou...

Embodiment 2

[0070] Example 2: N 6 Preparation of -(3-methoxy-4-hydroxybenzyl)-adenosine

[0071] In the first step, 3.04g of 3-methoxy-4-hydroxybenzaldehyde, 2.52g of hydroxylamine hydrochloride, and 3.26g of anhydrous sodium acetate were weighed and dissolved in 80ml of ethanol. The reaction was stirred for 6 hours at room temperature. The solvent was evaporated to dryness, dissolved in 40ml of water, extracted with ethyl acetate (40×3ml), and the ethyl acetate was evaporated to obtain 2.99g of light yellow solid (3-methoxy-4-hydroxybenzaldehyde oxime).

[0072] In the second step, 2.99g 3-methoxyl-4-hydroxybenzaldehyde oxime was dissolved in 70ml ethanol, added 700mg 10% Pd / C, 8ml concentrated hydrochloric acid, and hydrogenated at normal pressure to obtain white crystals (3-methoxyl- 4-hydroxybenzylamine hydrochloride) 3.31g.

[0073] In the third step, dissolve 3.31g of 3-methoxy-4-hydroxybenzylamine hydrochloride in 70ml of n-propanol, add 1g of 6-chloropurine nucleoside and 14ml ...

Embodiment 3

[0075] Example 3: N 6 Preparation of -(4-hydroxybenzyl)-adenosine

[0076]In the first step, 2.55g of 4-hydroxybenzaldehyde, 2.60g of hydroxylamine hydrochloride, and 3.40g of anhydrous sodium acetate were weighed and dissolved in 80ml of ethanol. The reaction was stirred for 6 hours at room temperature. The solvent was evaporated to dryness, dissolved in 40ml of water, extracted with ethyl acetate (40×3ml), and the ethyl acetate was evaporated to obtain 2.66g of light yellow solid (4-hydroxybenzaldehyde oxime).

[0077] In the second step, 2.66g of 4-hydroxybenzaldehyde oxime was dissolved in 70ml of ethanol, 300mg of 10% Pd / C was added, 8ml of concentrated hydrochloric acid was hydrogenated under normal pressure to obtain 3.02g of white crystals (4-hydroxybenzylamine hydrochloride) .

[0078] In the third step, dissolve 3.02g of 4-hydroxybenzylamine hydrochloride in 70ml of n-propanol, add 1g of 6-chloropurine nucleoside and 14ml of N,N-diisopropylethylamine, heat to 70°C...

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PUM

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Abstract

The invention discloses an N*-substituted adenosine derivative, a preparation method, a medicine composition and application thereof, in particular relates to an N6-substituted adenosine derivative shown as the general formula (I), two preparation methods of the derivative, a medicine composition using the derivative as effective components, and application of the derivative for preparing medicines and health care products for sedative-hypnotic, anticonvulsion, anti-epileptic, and anti-Parkinson's disease and anti-stupid. The formula (I) is shown in the description.

Description

technical field [0001] The present invention relates to a class of N6-substituted adenosine derivatives, a preparation method of such compounds, a pharmaceutical composition containing such compounds, and a method for preparing and treating sedative-hypnotic, anticonvulsant, antiepileptic, anti-Parkinson's disease and dementia The application in medicines and health care products belongs to the field of medical technology. Background technique [0002] N 6 -Substituted purine and adenosine derivatives are substances with important biological activity, and some structures exist in natural plants in trace forms. As plant cytokinins, they can promote the division and differentiation of plant cells, and have the functions of promoting seed germination, The differentiation of buds, the formation of branches, and the production of chlorophyll and starch are important biological functions, and they are widely used in the research of plant bioengineering technology. Recent studies...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/167A61K31/7076A61P25/20A61P25/16A61P25/08A61P25/28
Inventor 张建军石建功李敏訾佳辰朱承根王亚芳杨永春徐瑞明樊晓娜
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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