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Synthesis method of antineoplastic medicine capecitabine

An anti-tumor drug, the technology of capecitabine, applied in the field of medicinal chemistry, can solve the problems of expensive starting materials and increased production costs, and achieve the effects of easy industrial production and popularization and application, short operation time and large quantity

Inactive Publication Date: 2010-09-29
ZHENGZHOU UNIV
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AI Technical Summary

Problems solved by technology

[0011] The starting raw material price that above-mentioned four kinds of methods are used is all relatively expensive, has increased production cost

Method used

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  • Synthesis method of antineoplastic medicine capecitabine
  • Synthesis method of antineoplastic medicine capecitabine
  • Synthesis method of antineoplastic medicine capecitabine

Examples

Experimental program
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Embodiment 1

[0027] 1. Preparation of Compound 2

[0028] Add xylose (100g, 0.67mol) into 1L of acetone, add concentrated sulfuric acid (30ml, 0.55mol) dropwise, stir at room temperature for 8 hours, adjust the pH to 3 with saturated sodium bicarbonate solution, stir for 2 hours, Adjust the pH to neutral, filter and concentrate to obtain compound 2 (116.5 g), with a yield of 92.0%.

[0029] 2. Preparation of Compound 3

[0030] Compound 2 (30g, 0.16mol) was dissolved in 200ml of pyridine, p-toluenesulfonyl chloride (31.9g, 0.17mol) was added in portions within 2 hours, then stirred for 1 hour, 150ml of saturated sodium bicarbonate solution and 300ml of dichloromethane, stirred for 30 minutes, separated the organic phase, washed the organic phase with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a light yellow solid, which was crystallized by adding ether to obtain compound 4. White crystals (39.1 g)...

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Abstract

The invention discloses a synthesis method of antineoplastic medicine capecitabine, belonging to the technical field of pharmaceutical chemistry. The method takes xylose as raw material, and the capecitabine can be obtained through eight-step chemical reaction. The synthetic route uses the raw material which can be easily obtained and is low in price, has short reaction time, simple operation and high yield, and is easy for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a preparation method of an antitumor drug capecitabine. More precisely it relates to a process for the preparation of 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine. Background technique [0002] Capecitabine, a prodrug of 5-F uracil, is a new targeted drug for the treatment of breast cancer and colorectal cancer. After oral administration, capecitabine is absorbed as the original drug in the gastrointestinal tract, and then undergoes a variety of enzymatic reactions in the liver and tumor cells, and is finally converted into 5-F by the action of thymidine phosphorylase in tumor cells. uracil nucleotides. Because there is no release of 5-F uracil in the gastrointestinal tract, the typical 5-F fluorouracil-induced gastrointestinal toxicity is reduced. At the same time, due to the presence of more thymidine phosphorylase in tumor tissue cells, capecitabine has selec...

Claims

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Application Information

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IPC IPC(8): C07H19/06C07H1/00
Inventor 刘宏民赵明礼任彦甫张召钱伟邢培智
Owner ZHENGZHOU UNIV
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