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Preparation method of capecitabine and intermediate thereof

A compound and organic solvent technology, applied in the field of pharmaceutical chemical synthesis, can solve problems such as unsuitable for industrial production, and achieve the effects of simplified post-processing, high yield, and few by-products

Inactive Publication Date: 2011-03-30
CHENGDU KANGHONG PHARMA GRP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And prior art [J.Med.Chem., 2007,50 (22), 5463-5470; J.Org.Chem., 1988, 53 (21), 5046-5050; Org.Biomol.Chem., 2006, 4, 2898-2905], the post-treatment of iodine on similar compounds is column purification, which is not suitable for industrial production

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  • Preparation method of capecitabine and intermediate thereof
  • Preparation method of capecitabine and intermediate thereof
  • Preparation method of capecitabine and intermediate thereof

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Embodiment Construction

[0029] The embodiment of the present invention provides a complete process for synthesizing capecitabine, but the present invention is not limited to this specific embodiment.

[0030] 1. Synthesis of 2', 3'-di-O-acetyl-5'-halogen-inosine

[0031] 1. Synthesis of 12', 3'-di-O-acetyl-5'-iodo-inosine

[0032]

[0033] Add 80g (298mmol) formula VI inosine, 86g (328mmol) triphenylphosphine (TPP) in 400ml pyridine, place in the ice bath for half an hour, slowly add 101.5g (400mmol) iodine in batches, react overnight at natural temperature, react Spin off part of the solvent after completion, place it in an ice bath for half an hour, add dropwise 50ml of pyridine solution containing 67g (656mmol) of acetic anhydride, rise to room temperature overnight, add ethyl acetate after the reaction is complete, precipitate a solid, filter, and the filtrate is saturated with Wash with sodium chloride solution of sodium thiosulfate, dry, spin off the solvent, add a small amount of ethyl ace...

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Abstract

The invention relates to a preparation method of capecitabine and an intermediate thereof. The material conversion rate is high with less side reaction under the condition that bicarbonate is used as alkali by changing the reaction condition of synthesizing a compound of a formula I by a 5'-deoxidized-5-gemcitabine derivative and chloroformic acid n-amyl ester. Meanwhile, the applicant researches and finds that: Since 5-deoxidized-tri-O-acetyl-D-ribose prepared by using inosine reactrion substituted by iodine and protected by hydroxyl is adopted, the post-treatment process is simplified, and the yield is improved. The 5-deoxidized-tri-O-acetyl-D-ribose is a material for synthesizing the compound of the formula I while the compound of the formula I is a significant intermediate of capecitabine. The whole capecitabine synthesis process has high yield and low cost.

Description

technical field [0001] The invention relates to the field of pharmaceutical chemical synthesis, in particular to a preparation method of capecitabine and an intermediate thereof. Background technique [0002] Capecitabine (trade name: Xeloda) is a new prodrug of 5-fluorouracil (5-FU) developed by Roche, Switzerland. Toxic preparations are non-cytotoxic in themselves, but can be converted into cytotoxic 5-fluorouracil, which is transformed at the site of the tumor through the tumor-associated vascular factor thymophosphorylase, thereby greatly reducing the effect of 5-fluorouracil on normal human body. Cell damage, adjuvant therapy and treatment of metastatic tumors has a good curative effect and strong safety. Capecitabine is also indicated for the further treatment of advanced primary or metastatic breast cancer refractory to paclitaxel and chemotherapy regimens with anthracyclines. [0003] Due to the drug use of capecitabine and its good curative effect, the research on...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/06C07H1/00
Inventor 李会康秦欣荣李凌蔡付波阳海
Owner CHENGDU KANGHONG PHARMA GRP
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