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Production process of vidarabine monophosphate

A technology of vidarabine monophosphate and vidarabine monophosphate crude product, which is applied in the direction of preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc. It can solve the problems of expensive solvent acetonitrile and high toxicity of pyridine, etc. Achieve the effects of easy control, high yield and purity, and mild reaction

Active Publication Date: 2019-01-04
海南卓科制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The solvent acetonitrile used in this method is more expensive, and pyridine is highly toxic.

Method used

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  • Production process of vidarabine monophosphate

Examples

Experimental program
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Effect test

Embodiment 1

[0037] A production process of adenosine monophosphate, which comprises the steps:

[0038] S1 Mix 30 g of adenosine arabinoside in 3 mL of tetrahydrofuran, and stir to cool down to 0 °C;

[0039] S2 adds 30.83g of di-n-butylphosphoryl chloride in batches to the system after the cooling in step S1, and after the addition, the reaction is continued at 10°C until the remaining amount of adenosine vibranium does not exceed 3% of the added amount;

[0040] S3 Add 1.5 g of palladium catalyst to the reaction system after the stop of step S2, and heat up to 50 ° C and stir for 8 h, filter, and wash the filter cake with ethanol, collect the filtrate, remove the solvent under reduced pressure, and obtain the crude product of adenosine monophosphate. ;

[0041] The preparation method of described palladium catalyst comprises the steps:

[0042] Add 17.7 g of palladium chloride and 203.3 g of magnesium chloride hexahydrate to 20 mL of saturated ammonia solution, and stir until complete...

Embodiment 2

[0047] A production process of adenosine monophosphate, which comprises the steps:

[0048] S1 Mix 30 g of adenosine arabinoside in 3 mL of acetone, stir and cool down to -5°C;

[0049] S2 adds 52.12 g of bis(4-nitrophenyl) phosphoryl chloride in batches to the system cooled in step S1, and continues to react at 5°C after the addition until the remaining amount of adenosine does not exceed 3% of the added amount stop;

[0050] S3 Add 1.5 g of palladium catalyst to the reaction system after the stop of step S2, and heat up to 50 ° C and stir for 8 h, filter, and wash the filter cake with ethanol, collect the filtrate, and remove the solvent under reduced pressure to obtain the crude product of adenosine monophosphate. ; The preparation method of described palladium catalyst is with embodiment 1;

[0051]S4 after the crude adenosine monophosphate obtained in step S3 is just dissolved in water at 40°C, a mixed solution of diethyl ether, methanol and triethylamine is gradually a...

Embodiment 3

[0053] A production process of adenosine monophosphate, which comprises the steps:

[0054] S1 Mix 30 g of adenosine arabinoside in 3 mL of dioxane, stir and cool down to 8 °C;

[0055] S2 adds 32.54 g of bis(2-chloroethyl) phosphoryl chloride in batches to the system cooled in step S1, and continues to react at 15°C after the addition until the remaining amount of adenosine does not exceed 1% of the added amount stop;

[0056] S3 Add 1.5 g of palladium catalyst to the reaction system after the stop of step S2, and heat up to 50 ° C and stir for 8 h, filter, and wash the filter cake with ethanol, collect the filtrate, remove the solvent under reduced pressure, and obtain the crude product of adenosine monophosphate. ;

[0057] The preparation method of described palladium catalyst is with embodiment 1;

[0058] S4 After the crude adenosine monophosphate obtained in step S3 is just dissolved in water at 40°C, a mixed solution of ether, methanol and ethyl acetate is gradually...

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Abstract

The invention belongs to the technical field of preparation of vidarabine monophosphate and particularly relates to a production process of vidarabine monophosphate. The production process of vidarabine monophosphate comprises the following steps of S1 dissolving vidarabine into organic solvent and cooling down the mixture; S2, adding in phosphoryl chloride to perform thermal reaction until that the residual content of the vidarabine is not higher than 3% of the added amount; S3, adding in palladium catalysts for catalytic reduction, then filtering reaction products, removing the solvent fromthe obtained filter liquor to obtain crude vidarabine monophosphate; S4, recrystallizing the crude vidarabine monophosphate obtained in S3 for purification. The production process of vidarabine monophosphate introduces the phosphoryl chloride relatively low in reactivity to react with the raw vidarabine, the reaction process is mild and easy to control, so that the produced quantity of side products can be reduced from the source; meanwhile, the novel palladium catalysts can selectively reduce introduced ether groups, thereby simplifying purification processes and achieving high product yieldand purity.

Description

technical field [0001] The invention belongs to the technical field of adenosine monophosphate preparation, in particular to a production process of adenosine monophosphate. Background technique [0002] Vidarabine monophosphate (AraAMP) is a monophosphate compound of adenosine arabinosine (Ara-A), which is a synthetic adenosine antiviral drug. Currently in my country, it is mainly used for chronic viral hepatitis, herpes simplex virus, herpes zoster virus, vaccinia virus, a variety of animal herpes viruses and a few oncogenic RNA viruses. Its pharmacological effect is that it can combine with deoxyribonucleic acid polymerase to reduce its activity, thereby inhibiting DNA synthesis. After monophosphate arabinosine enters cells, it undergoes phosphorylation to generate arabinosine diphosphate and arabinosine. Triphosphate, and the antiviral effect is mainly caused by monophosphate arabinosine triphosphate, which competitively binds to DNA with deoxyadenosine triphosphate, th...

Claims

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Application Information

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IPC IPC(8): C07H19/20C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H19/20
Inventor 李强
Owner 海南卓科制药有限公司
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