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A kind of synthetic method of antiviral drug cidofovir

The technology of an antiviral drug and a synthetic method is applied in the field of preparation of the anti-cytomegalovirus drug cidofovir and its intermediate, which can solve problems such as many side reactions, unsuitability for industrial production, unsuitable purification of products, etc., and achieve simplified yield. The effect of low yield, increased yield, and increased yield

Inactive Publication Date: 2011-12-07
扬州三友合成化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] This route uses (R)-epihalohydrin to react with cytosine. Due to the basicity of the cytosine ring, the epoxy ring is easy to ring-opening reaction, but there are many side reactions, and the product is not suitable for purification and is not suitable for industrial production.

Method used

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  • A kind of synthetic method of antiviral drug cidofovir
  • A kind of synthetic method of antiviral drug cidofovir
  • A kind of synthetic method of antiviral drug cidofovir

Examples

Experimental program
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Effect test

Embodiment 1

[0056] 1. Synthesis of 4,4'-dimethoxytriphenylmethyl-(R)-glycidol (compound III):

[0057] Dissolve 5.04 g (15 mmol) DMT-Cl and 0.20 g (1.52 mmol) 4-dimethylaminopyridine (DMAP) in 100 mL CH2Cl2, cool to 0 °C, add dropwise 10 mL TEA , Slowly added 2. 00 g ( 27 mmol) chiral hydroxymethyloxirane (compound II). After the addition, the reaction was naturally raised to room temperature. After 4-6 h, stop the reaction until the DMT-Cl disappears as detected by TLC. Filter and wash the filtrate with saturated NaHCO3 solution (50mL×2), saturated NaCl solution (50 mL×2), dry over anhydrous Na2SO4, filter and concentrate. A colorless viscous product, namely 5.08 g of 4,4'-dimethoxytriphenylmethyl-(R)-glycidol (compound III), was obtained directly, with a yield of 90% and a purity of 99% by HPLC.

[0058] 2. Synthesis of (S)-N1-[(2-hydroxy-3-(dimethoxytriphenylmethoxy)propyl]cytosine (compound IV):

[0059] Under nitrogen protection, 3.56 g (32 mmol) cytosine was added to 150 mL of a...

Embodiment 2

[0068] 1. Synthesis of triphenylmethyl-(R)-glycidol (compound III):

[0069] Dissolve 4.18 g (15 mmol) Tr-Cl and 0.20 g (1.52 mmol) 4-dimethylaminopyridine (DMAP) in CH2Cl2 (100 mL), cool to 0 °C, add dropwise TEA (10 mL), slowly added 2. 00 g (27 mmol) chiral hydroxymethyloxirane (compound II). After the addition, the reaction was naturally raised to room temperature. After 4-6 h, stop the reaction until the DMT-Cl disappears as detected by TLC. Filter and wash the filtrate with saturated NaHCO3 solution (50mL×2), saturated NaCl solution (50 mL×2), dry over anhydrous Na2SO4, filter and concentrate. A colorless viscous product, namely 4.22 g of triphenylmethyl-(R)-glycidol (compound III), was obtained directly, with a yield of 89% and a purity of 98% by HPLC.

[0070] 2. Synthesis of (S)-N1-[(2-hydroxy-3-(triphenylmethoxy)propyl]cytosine (compound IV):

[0071] Under nitrogen protection, 3.56 g (32 mmol) of cytosine was added to 150 mL of anhydrous N,N-dimethylformamide (D...

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Abstract

A method for synthesizing antiviral drug cidofovir belongs to the field of antiviral chemical drugs. The invention starts from raw material (S)-hydroxymethyl oxirane and synthesizes (S)-1-R-2,3- Propylene oxide (R is a hydrocarbyl group), prepared by etherification, acylation, condensation, deprotection, hydrolysis, acidification and other reactions to prepare cidofovir. The synthesis process is simple in operation, low in cost, high in yield, high in purity and less in pollution, and is very suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of antiviral chemical drugs, and in particular relates to a preparation method of an anti-cytomegalovirus drug cidofovir and an intermediate thereof. Background technique [0002] Cytomegalovirus (Cytomegaoviyns, CMV) is one of the most harmful herpes viruses. The infection rate in the human body is as high as 50% to 80%. The current adult infection rate in my country is over 95%. Symptoms, but under certain conditions can affect multiple organs and systems producing severe disease. The virus can invade lungs, liver, kidneys, salivary glands, mammary glands and other glands as well as multinucleated leukocytes and lymphocytes, and can excrete viruses from saliva, breast sweat, blood, urine, semen, and uterine secretions for a long time or intermittently. It is transmitted through various routes such as oral cavity, reproductive tract, placenta, blood transfusion or organ transplantation. [0003] When the immune func...

Claims

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Application Information

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IPC IPC(8): C07F9/6512
Inventor 魏开举李明成张扬张众笑
Owner 扬州三友合成化工有限公司
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