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A kind of preparation method of ribavirin

A technology of ribavirin and catalyst is applied in the field of preparation of ribavirin, and can solve the problems of many operation steps, no application, low yield of by-products, etc.

Active Publication Date: 2011-12-21
STAR LAKE BIOSCI CO INC ZHAOQING GUANGDONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has some shortcomings such as the yield is significantly lower than the theoretical value, and there are a large number of by-products, making it almost useless.
However, this type of method has many operating steps, many by-products, low yield and high cost.

Method used

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  • A kind of preparation method of ribavirin
  • A kind of preparation method of ribavirin
  • A kind of preparation method of ribavirin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Acylation:

[0012] Take a 1000mL flask, add 50g of inosine, 200ml of acetic anhydride and heat to reflux under stirring. 3 with Na 2 HPO 4 Mix according to 2:1) 10g at 110°C for 2 hours, connect to a Vickers fractionation column, evaporate the mixture of acetic acid and acetic anhydride under slight negative pressure, and evaporate 100ml of acid for about 100min. Continue to incubate at 110°C for 6 hours, and track the end point with a TLC plate until triacetyl inosine basically disappears. Cool down to 30°C, filter, combine the filtrates, evaporate the mixed acetic anhydride in a rotary evaporator in a vacuum, cool the residue to 90-100°C, add distilled water, 150ml, crystallize under stirring, and precipitate tetraacetyl ribose. The rate is 94.8%. The validation experimental data in Table 1 also yielded this level of yield.

Embodiment 2

[0014] condensation

[0015] 500ml there-necked flask, heated to 110°C, put in 50g of tetraacetyl ribose, stirred, melted until the temperature rose to 120°C, then put in 20.5g of 1,2,4-triazole-3-carboxylate methyl ester, stirred evenly, Raise the temperature to 130°C, put in the catalyst, turn on the vacuum immediately, react at 110-130°C until no acetic anhydride is drawn out, stop heating and cool down to 80°C, add 80ml of methanol, stir and pour it out to crystallize, put it in the refrigerator freezer and pump it out Filter, wash with 10ml of methanol, and dry to obtain the crude product of the condensate. The yield of the crude condensate was 92.5%. The validation experimental data in Table 2 also yielded this level of yield.

Embodiment 3

[0017] Ammonolysis

[0018] Add 50g of condensate and 175ml of methanol into the three-necked bottle, stir evenly, cool down to below 5°C, receive the ammonia gas discharged from another three-necked bottle, and control the reaction temperature so that it cannot be too high. Dissolve the ammonia completely, stop passing the ammonia, leave it at room temperature for more than 12 hours, and drain the ammonia with hot water, and the discharged ammonia is received by another three-necked bottle containing the condensate-methanol mixture. Cool below 5°C, filter with suction, wash the filter cake with an appropriate amount of 95% ethanol, and dry to obtain the crude product of ribavirin, with an ammonolysis yield of 96.7%.

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Abstract

The invention discloses a preparation method of ribavirin, comprising the following steps: A, by taking inosine as a raw material, adding acid and a catalyst I for acylation reaction to generate ribofuranose tetraacetate; B, respectively treating the ribofuranose tetraacetate obtained in the step A and 1,2,4-triazole-3-carboxylic acid methyl ester by using active carbon firstly, then uniformly mixing the ribofuranose tetraacetate and the 1,2,4-triazole-3-carboxylic acid methyl ester, and then adding a catalyst II for condensation reaction to obtain a condensation compound; C, subjecting the condensation compound obtained in the step B to ammonolysis in ammonia and methyl alcohol to generate crude ribavirin; and D, carrying out refinement on the crude ribavirin obtained in the step C to obtain pure ribavirin. The method is simple in operation, good in selectivity, clean and environment friendly and high in yield of ribavirin.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a preparation method of ribavirin. Background technique [0002] Ribavirin, its chemical name is 1-β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide. It mainly inhibits the activity of mononitrate and inosine dehydrogenase, interferes with the synthesis of DNA, prevents virus replication, has obvious inhibitory effect on various DNA viruses and RNA viruses, has no cross-resistance, and does not induce interferon It has immunosuppressive effect and is a broad-spectrum antiviral drug. It was synthesized by Witkowski et al. in 1972. It was approved by the US FDA in 1986. It is limited to the treatment of syncytial virus infection in infants and young children in an aerosol mask. It was approved to expand in July 1998. Indications. [0003] There are three methods for the production of ribavirin: fermentation, enzymatic and chemical methods. For the fermentation method, see literature (Jo...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H1/00
Inventor 郑明英鲁立宁异真李建军何建华梁健富
Owner STAR LAKE BIOSCI CO INC ZHAOQING GUANGDONG
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