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Lamivudine compound and novel preparation method thereof

A compound and intermediate technology, applied in the field of lamivudine compound and its new production method, can solve the problems of low yield and long synthesis steps, and achieve the effect of high yield, high purity and easy purification process

Inactive Publication Date: 2010-08-18
HAINAN MEILAN SMITH KLINE PHARMA
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Problems solved by technology

[0021] In order to overcome the defects of low yield and long synthetic steps in the production of lamivudine in the above-mentioned prior art, we have done a lot of experiments and adopted a new chiral inducing reagent R-(-)-glyceryl acetonide , in the process of synthesizing chiral lamivudine, no isomer impurities will be introduced, which makes the purification process easier, and the final product obtained has high purity and high yield, which is more suitable for industrial production

Method used

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  • Lamivudine compound and novel preparation method thereof
  • Lamivudine compound and novel preparation method thereof
  • Lamivudine compound and novel preparation method thereof

Examples

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Embodiment 1

[0045] The synthesis of embodiment 1 lamivudine

[0046] (1) Synthesis of glyoxylic acid-R-(-)-glycerol acetonide

[0047] Mix 74g of glyoxylic acid, 300ml of isopropyl ether, 132g of R-(-)-glycerol acetone and 15g of p-toluenesulfonic acid, heat and stir at room temperature until the solids are completely dissolved, then reflux for 10 hours, then cool to room temperature, filter, and separate Washed three times with 100ml of water, collected the organic phase, dried with anhydrous sodium sulfate for 12 hours, distilled the solvent under reduced pressure until the solid was precipitated, then added 400ml of petroleum ether, frozen, and filtered to obtain 173g of white solid, with a yield of 92%;

[0048] (2) Synthesis of (1R, 5R)-5-hydroxy-[1,3]-oxathiolane-2-carboxylic acid-R-(-)-glycerol acetonide

[0049] Mix 94g of glyoxylic acid-R-(-)-glycerol acetonide, 1000ml of toluene, 10ml of acetic acid, and 76g of 2,5-dihydroxy-1,4-dithiane, stir and reflux for 3 hours, and filter...

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Abstract

The invention relates to a lamivudine compound and a novel preparation method thereof. A novel chiral inducing reagent R-(-)-glyceryl alcohol acetonide is adopted for removing protective radicals under the alkaline condition to obtain target products of the lamivudine. The deprotection in the reaction is easier, the reaction condition is milder, and the obtained products have higher purity. Through the method of the invention, the yield of the lamivudine products can be greatly improved, because of the price of the R-(-)-glyceryl alcohol acetonide is low, the cost of the method of the invention is greatly reduced, the obtained products have high purity, and the invention is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a lamivudine compound and a new preparation method thereof, belonging to the technical field of medicine. Background technique [0002] Lamivudine, chemical name: (2R-cis)-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-1H-pyrimidine-2- Ketone, molecular formula: C 8 h 11 N 3 o 3 S, molecular weight: 229.26, structural formula: [0003] [0004] Lamivudine is a nucleoside antiviral drug. It has a strong inhibitory effect on hepatitis B virus (HBV) in vitro and in experimentally infected animals. Lamivudine can be metabolized in HBV-infected cells and normal cells to produce lamivudine triphosphate, which is the active form of lamivudine, which is both an inhibitor of HBV polymerase and a substrate of this polymerase. Lamivudine triphosphate penetrates into the viral DNA strand and blocks the synthesis of viral DNA. Lamivudine triphosphate does not interfere with the metabolism of deoxynucleosides in normal cells, it ...

Claims

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Application Information

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IPC IPC(8): C07D411/04
Inventor 胡建荣
Owner HAINAN MEILAN SMITH KLINE PHARMA
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