Novel technology for synthesis of capecitabine

A capecitabine and synthetic process technology, applied in the field of medicinal chemistry, can solve problems such as long route and complicated operation, and achieve the effects of reducing environmental pollution, convenient post-processing, and improving product yield
CN103288905AInactive Publication Date: 2013-09-11北京博时安泰科技发展有限公司
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
北京博时安泰科技发展有限公司
Publication Date
2013-09-11
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention relates to a novel technology for synthesis of capecitabine. The technology is characterized in that: 5-fluorocytosine protected by trimethyl silicon is taken as raw material; and the capecitabine is obtained after condensation, esterification and deacetylation. The Reaction sequence is more economically reasonable, the synthetic route is short, the cost is low, the operation is simplified, the yield is high, the synthetic period is short, the quality of intermediates can be controlled, solvents used in reaction are few, pollution to the environment is little, and the technology is suitable for industrial production. Comparing the technology with the prior art for capecitabine production, trimethylsilyl trifluoromethanesulfonate (TMSOTf) which replaces a heavy metal agent stannic chloride is used as a condensing agent for glycosylation (condensation), and a sodium methoxide / methanol system replaces an ammonia gas / methanol system for deacetylation, so that the production yield is increased, and heavy metal residues of the products and the environmental pollution are reduced. The overall yield of the technology of the invention reaches 59%, the purity of the production is high and meets the standards of the United States Pharmacopeia.
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Description

technical field

[0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a new process for synthesizing antitumor drug capecitabine. Background technique

[0002] Capecitabine (capecitabine, such as Figure I ), the chemical name is 5'-deoxy-5-fluoro- N -[(Pentyloxy)carbonyl]cytidine, developed by Swiss Hoffmann-LaRoche Company, was first launched in Switzerland in 1998, and was approved for marketing in my country in October 2000. The product name is Xeloda. Xeloda is the only brand in the domestic capecitabine market, which is mainly monopolized by Hoffman-Roche and Shanghai Roche. This product is a new type of oral flucytosine nucleoside analogue, which has no cytotoxicity itself, and is metabolized into 5-fluorouracil (5-FU) under the action of enzymes in the body, and then exerts anti-tumor effect. It is mainly used clinically for the treatment of advanced breast cancer Carcinoma, colorectal cancer and other solid tumors...

Claims

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