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Method for purifying and refining lamivudine and emtricitabine

A refining method and technology of emtricitabine, applied in organic chemistry and other directions, can solve problems such as increasing impurities and causing ear poisoning, and achieve the effects of reducing pollution, improving product quality, and safe and reliable operation.

Inactive Publication Date: 2011-04-13
刘建红
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although domestic reports use the resin method to separate and purify emtricitabine, such as the report of the patent CN200910070765.1, the method of the patent CN200910070765.1 should be a derivative of the salicylic acid method, and the process still introduces salicylic acid, triethyl Amines, a chemical reaction occurs during the process, and new impurities will be added to the product at the same time. Salicylic acid is a strictly controlled impurity in medicines. It is reported that it can cause ototoxicity. After the reduction reaction of emtricitabine, it is also salted with acid first. Desalting with alkali to obtain relatively pure emtricitabine, the route is similar to lamivudine

Method used

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  • Method for purifying and refining lamivudine and emtricitabine

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Embodiment 1

[0029] Embodiment 1: see figure 1 , a method for purifying and refining lamivudine, the steps are as follows:

[0030] 1. Add 100ml of ethanol and 25ml of water to reactor A, then add 8.6 grams of dipotassium hydrogen phosphate and stir to dissolve; then add 10 grams of (2R, 5S)-5-(cytosine-1-yl)-1,3-oxo Thiolane-2-carboxylic acid-L-menthyl ester was stirred for 1 hour and the temperature was started to drop. Add 10-15 ml of water, 2.1 grams of sodium borohydride and 0.05-0.1 gram of sodium hydroxide into reactor B, stir to dissolve, and cool down for later use;

[0031] 2. When the temperature of reactor A is 15°C, start adding the solution in reactor B dropwise, and control the reaction temperature to ≤25°C for about 3-5 hours;

[0032] 3. Keep the temperature at 15-25°C for reaction, take a sample to measure (2R,5S)-5-(cytosine-1-yl)-1,3-oxathiolane-2-carboxylic acid-L after adding 1h -Residue of menthyl ester, the residual amount of 0.5% is the reaction end point;

[0...

Embodiment 2

[0046] Example 2: see figure 2 , a method for purifying and refining emtricitabine, the steps are as follows

[0047] 1. Add 100ml of ethanol and 25ml of water to reactor A, then add 8.6 grams of dipotassium hydrogen phosphate and stir to dissolve; then add 10 grams of (2R, 5S)-5-(5'-fluoro-cytosine-1-yl)- 1,3-Oxathiolane-2-carboxylic acid-L-menthyl ester was stirred for 1 hour and the temperature was started to drop. Add 10-15 ml of water, 2.1 grams of sodium borohydride and 0.05-0.1 gram of sodium hydroxide into reactor B, stir to dissolve, and cool down for later use;

[0048] 2. When the temperature of reactor A is 15°C, start adding the solution in reactor B dropwise, and control the reaction temperature to ≤25°C for about 3-5 hours;

[0049] 3. Keep the temperature at 15-25°C for reaction, and take a sample to measure (2R,5S)-5-(5'-fluoro-cytosine-1-yl)-1,3-oxathiolane-2 after 1 hour of addition -Carboxylic acid-L-menthyl ester residue, 0.5% residue is the reaction ...

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Abstract

The invention discloses a method for purifying and refining lamivudine and emtricitabine. In the method, the lamivudine or the emtricitabine in a material system after reduction reaction is purified and refined by a physical method. The method comprises the following basic steps: flocculation, filtration, adsorption, desorption, decoloration, crystallization and the like, and finally the high-purity lamivudine or emtricitabine product is obtained. The method disclosed by the invention is safe and reliable to operate, is simple and feasible and is applicable to large-scale production. By using the method, the product quality is improved and environmental pollution is reduced.

Description

technical field [0001] The invention relates to a purification method of lamivudine and emtricitabine. technical background [0002] Lamivudine [(2R,5S)-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone] is used for Medicines to treat hepatitis and AIDS. Lamivudine is the main treatment component in the four first-line treatment AIDS programs recommended by the World Health Organization (WHO). Emtricitabine is used in combination with other antiretroviral drugs to treat HIV-infected patients. It is a drug similar to lamivudine, and its drug effect, structure and synthesis method are very close. From a structural point of view, emtricitabine, like lamivudine, also belongs to nucleosides, and its chemical structure differs from other nucleoside analogs widely used in clinical practice in that it has a fluorine group at the 5-carbon position, The mechanism of action is similar to that of lamivudine, but the in vitro activity exceeds that of lamivudine, so ma...

Claims

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Application Information

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IPC IPC(8): C07D411/04
Inventor 彭春林
Owner 刘建红
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