Synthesis process of adenosine aose monophosphate

A technology of adenosine vidarabine monophosphate and adenosine monophosphate, which is applied in the field of synthesis technology for the preparation of antiviral drug adenosine monophosphate, can solve problems such as unfavorable industrial production, achieve simplified operation, increase yield, and operate simplified effect

Active Publication Date: 2005-01-05
广东京豪生物制药有限公司
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AI Technical Summary

Problems solved by technology

[0012] The whole process of this process does not need dephosphorylation and phosphorylation, and the total yield can reach 12%. But most of the intermediates and final products need to be separated by activated carbon affinity chromatography and ion exchange resin chromatography, and the reaction involves multiple protection and Deprotection, not conducive to industrial production

Method used

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  • Synthesis process of adenosine aose monophosphate
  • Synthesis process of adenosine aose monophosphate
  • Synthesis process of adenosine aose monophosphate

Examples

Experimental program
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Embodiment

[0022] (1) Preparation of 2'-oxygen-p-toluenesulfonyl-5'-phosphate adenosine (II)

[0023] Add 34.7 grams of 5'-AMP to a mixed solution of 150 milliliters of dioxane and 350 milliliters of 1N sodium hydroxide; After stirring and reacting for 15 hours, 35 ml of 6N hydrochloric acid was added to adjust the pH to 4.0. The precipitated crystals were collected by filtration to obtain 46.4 g of crystalline powder II.

[0024] (2) Preparation of 8-bromo-2'-oxygen-p-toluenesulfonyl ester-5'-phosphate adenosine (III)

[0025] In 240 ml of 2 M sodium acetate (pH4) solution, add 46 g of II and cool to 0-5°C. Then 19 ml of bromine was added dropwise to this solution, maintaining 0-5°C. Stir at this temperature for 18 hours. At 0-5°C, 28 g of sodium bisulfite was added to the reaction solution. After stirring for 15 minutes, the pH was adjusted to 4.0 with 5 N NaOH (about 90-100 mL). Evaporated to dryness under reduced pressure, the obtained solid was directly used in the next reacti...

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Abstract

The invention provides a synthetic process of monophosphoarabonic adenosine, using monophosphoric adenosine as raw material, bromizing under the protection, making the reactions of aminating, mercapto action, hydrogenation, etc, obtaining monophosphoarabonic adenosine, after completing bromination reaction, making vacuum evaporation on the reacting substances to dryness, directly making acetylation reaction without separating, under the action of strongly acidic ion exchange resin, directly decyclizing the epoxide by sulfureted hydrogen without protecting, obtaining 8-mercapto monophosphoarabonic adenosine (VIII), which is hydrogenated to obtain object compound.

Description

technical field [0001] The invention relates to a synthesis process for preparing antiviral drug vidarabine monophosphate. technical background [0002] Adenosine monophosphate [chemical name chemical name is: 9-(β-D-arabinofuranosyl) adenosine 5'-monophosphate, I] is a nucleotide antiviral drug, and its pharmacological action is similar to that of Binding to viral deoxyribonucleic acid polymerase, reducing its activity and inhibiting DNA synthesis. After adenosine monophosphate enters the cell, it undergoes phosphorylation to generate adenosine adenosine diphosphate (Ara-ADP) and adenosine adenosine triphosphate (Ara-ATP). The antiviral activity is mainly caused by adenosine triphosphate (Ara-ATP), which competes with deoxyadenosine triphosphate (dATP) to bind to viral DNAP, thereby inhibiting the activity of enzymes and the synthesis of viral DNA , while inhibiting the activity of viral nucleotide reductase to inhibit the synthesis of viral DNA, it can also inhibit the a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/20
Inventor 胡小侠陈铁钎
Owner 广东京豪生物制药有限公司
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