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Synthesis method and application of vidarabine monophosphate

An adenosine monophosphate arabinoside and a synthesis method technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives and other directions, can solve problems such as unfavorable industrial production, improve the overall reaction yield, simplify synthesis steps, The effect of simplifying industrial production steps

Pending Publication Date: 2021-07-27
HAINAN JINRUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most intermediates and final products need to be separated by activated carbon affinity chromatography and ion exchange resin chromatography, and the reaction involves multiple protections and deprotections, which is not conducive to industrial production

Method used

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  • Synthesis method and application of vidarabine monophosphate
  • Synthesis method and application of vidarabine monophosphate
  • Synthesis method and application of vidarabine monophosphate

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0038] Embodiment 1 A kind of synthetic method of vidarabine monophosphate M1

[0039] This embodiment provides a synthetic method of adenosine vidarabine monophosphate M1, the synthetic method comprising the following steps:

[0040] 1) Weigh 53.6g 5-iodo-2-((phosphocarboxy)methyl)-4-(tosyloxy)tetrahydrofuran-3-yl acetate (2) and 30g tert-butyl ( 8-Hydroxy-9H-purin-6-yl) carbamate (3) was mixed in 220ml THF, 31.8g sodium carbonate and 5.78g tetrakis(triphenylphosphine)palladium were added at 70°C, and the condensation reaction was carried out for 8h, The progress of the reaction was monitored by TLC, and the reaction was terminated after the ultraviolet color point of the raw material (2) disappeared. The reaction solution was filtered, the filter cake was washed three times with ethanol, the filtrate was collected and concentrated under reduced pressure until no solvent was evaporated to obtain 39.54g compound (4) crude product (60% yield), which was directly used in the ne...

Embodiment 2～6

[0049] The synthetic method of embodiment 2~6 adenosine monophosphate M2~M6

[0050] Examples 2-6 provide the synthesis method of vidarabine monophosphate M2-M6, the synthesis method is roughly the same as the synthesis method of vidarabine monophosphate provided in Example 1, the only difference is that some synthesis process parameters are different , and the specific synthesis process parameters are shown in Table 1.

[0051] Table 1: Synthetic process parameters of vidarabine monophosphate M2-M6

[0052]

[0053]

[0054] All the other processing parameters are identical with embodiment 1.

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Abstract

The invention belongs to the field of medicine synthesis, and discloses a synthesis method and application of vidarabine monophosphate. According to the synthesis method, 5-iodo-2-((phosphonooxy) methyl)-4-(tosyloxy)tetrahydrofuran-3-yl acetate and tert-butyl (8-hydroxy-9H-purin-6-yl)carbamate are subjected to condensation, epoxidation, ring opening and desulfurization reaction, and the vidarabine monophosphate is synthesized. According to the synthesis method of vidarabine monophosphate, provided by the invention, the industrial production steps are further simplified, the total reaction yield is improved, and the industrial production cost is reduced. The method is suitable for synthesizing vidarabine monophosphate, and the synthesized vidarabine monophosphate is used for preparing vidarabine monophosphate for injection.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to the synthesis and preparation of an antiviral drug, in particular to a synthesis method and application of vidarabine monophosphate. Background technique [0002] Vidarabine monophosphate [chemical name: 9-(β-D-arabinofuranosyl) adenine 5'-monophosphate, I] is a nucleotide antiviral drug, and its pharmacological effect is to deoxygenate with the virus Ribonucleotide polymerase binds, 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 nucleoti...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H1/06C07H19/20A61P31/12A61K9/00
CPCC07H1/00C07H1/06C07H19/20A61P31/12A61K9/0019Y02P20/55
Inventor 韩林黄月娜王小芳
Owner HAINAN JINRUI PHARMA
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