Process method for synthesizing rifampicin

A process method, rifampicin technology, applied in the field of compound preparation, can solve the problems of difficult source of raw materials, high toxicity, etc.

Pending Publication Date: 2020-10-30
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this process, tetrahydrofuran, MnO 2 , Vitamin C and other raw materials are difficult to source, and the toxicity is relatively high.

Method used

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  • Process method for synthesizing rifampicin
  • Process method for synthesizing rifampicin
  • Process method for synthesizing rifampicin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] A process for synthesizing rifampicin, comprising the following steps:

[0061] (1) Cyclization reaction: Take 1.0kg of rifamycin S in a three-necked jacketed bottle, add DMF to dissolve under stirring, heat in a constant temperature water bath and maintain at 55°C, add acetic acid and 3A molecular sieve, add dimethylol tert-butylamine, the reaction time is 90min, and the ratio of each material is V (DMF): V (dimethylol tert-butylamine): V (acetic acid): M (3A molecular sieve): M (rifamycin S) = 1.0L: 0.2 L: 0.4L: 0.06kg: 1.0kg.

[0062] (2) Dissolution and crystallization conditions: after the cyclization reaction, ethanol preheated to 40° C. was slowly added to the reaction solution. The amount of ethanol added was 9.0 L / kg rifamycin S, and the volume fraction of DMF was 10%. Cool down and crystallize under the stirring state, turn off the stirring when the temperature drops to 5°C, let it stand for 2 hours, and then filter with suction to obtain the crude product of...

Embodiment 2

[0066] A kind of processing method of synthesizing rifampicin, reference figure 1 , including the following steps:

[0067] (1) Cyclization reaction: Take 5g of rifamycin S in a 150ml three-necked jacketed bottle, add a certain volume of DMF to dissolve it under stirring, heat it in a constant temperature water bath and maintain it at 60°C, add a certain amount of acetic acid and 3A Molecular sieve, add dimethylol tert-butylamine, the reaction time is 80min, in the cyclization reaction, each material ratio is V (DMF): V (dimethylol tert-butylamine): V (acetic acid): M (3A molecular sieve): M ( Rifamycin S)=(1L):(0.2L):(0.4L):(0.06kg):(1.0kg).

[0068] (2) Dissolution and crystallization conditions: after the cyclization reaction, ethanol preheated to 20° C. was slowly added to the reaction solution, the amount of ethanol added was 19 L / kg rifamycin S, and the volume fraction of DMF was 5%. Cool down and crystallize under the stirring state, turn off the stirring when the te...

Embodiment 3

[0072] A kind of processing method of synthesizing rifampicin, reference figure 1 , including the following steps:

[0073] (1) Cyclization reaction: Take rifamycin S 5g in a 150ml three-necked jacketed bottle, add a certain volume of DMF to dissolve it under stirring, heat it in a constant temperature water bath and maintain it at 40°C, add a certain amount of acetic acid and 3A Molecular sieve, add dimethylol tert-butylamine, the reaction time is 70min, in the cyclization reaction, each material ratio is V (DMF): V (dimethylol tert-butylamine): V (acetic acid): M (3A molecular sieve): M ( Rifamycin S)=(1L):(0.2L):(1L):(0.06kg):(1.0kg).

[0074] (2) Dissolution and crystallization conditions: after the cyclization reaction, slowly add ethanol preheated to 30°C to the reaction solution, the amount of ethanol added is 9L / kg rifamycin S, and the volume fraction of DMF is 10%. Cool down and crystallize under agitation, turn off the agitation when the temperature drops to 5°C, ...

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Abstract

The invention relates to a process method for synthesizing rifampicin, wherein the process method mainly comprises the steps: by using rifamycin S as a raw material, carrying out cyclization reactionto obtain a rifamycin oxazine-containing solution, and carrying out solventing-out crystallization on the rifamycin oxazine-containing solution to obtain a rifamycin oxazine crude product; carrying out condensation reaction on the crude rifamycin oxazine product and 1-amino-4-methylpiperazine to obtain a reaction solution containing rifampicin; and cooling and crystallizing the reaction solution containing rifampicin to obtain a rifampicin product. Compared with the prior art, the method has the advantages that the reaction steps are few, the product yield is high, the reaction raw material cost is low, meanwhile, the production is more environmentally friendly, the consumption of raw materials is reduced by 30% (the consumption of dimethylol tert-butylamine required by every 1 kg of rifamycin S is reduced by about 28%, and the consumption of 1-amino-4-methylpiperazine is reduced by about 30%). The method overcomes the defect that a large amount of sewage is generated in production byadopting an elution method, and reduces the influence of impure reaction products on the yield due to the fact that rifamycin S-Na is used as a raw material.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and in particular relates to a process for synthesizing rifampicin. Background technique [0002] Rifamycin (Rifamycin) is a class of low toxicity, high efficacy, broad-spectrum antibiotics, mainly used in the treatment of tuberculosis, Gram-positive infection, trachoma, leprosy and meningococcal carriers. In the treatment of tuberculosis, compared with isoniazid and streptomycin, rifampicin has a better effect and is one of the varieties with the largest clinical use. [0003] Rifamycin belongs to the ANSA class of antibiotics in structure, which is a large class of naturally occurring or semi-synthetic antibiotics. Among the many semi-synthetic derivatives of rifamycin, rifampicin has been widely used clinically because of its broad-spectrum antibacterial effect, high curative effect, less toxic and side effects, convenient administration and low price. The synthesis of rifampici...

Claims

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Application Information

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IPC IPC(8): C07D493/08
CPCC07D493/08
Inventor 吴艳阳陈葵马智慧李汝真武斌纪利俊朱家文
Owner EAST CHINA UNIV OF SCI & TECH
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