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Preparation method of capecitabine

A capecitabine and compound technology, applied in the field of medicinal chemistry synthesis, can solve problems such as tediousness, and achieve the effects of sufficient reaction, high yield and few by-products

Active Publication Date: 2014-07-23
四川弘远药业有限公司
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0010] However, in this reaction, the hydroxyl group needs to be protected by benzyl group to form the corresponding inosine derivative, and then debenzylated, and then use propylidene to protect the 2 and 3 hydroxyl groups for iodination, deiodination, and then remove the propylidene protecting group. There are 8 steps in the whole step, which is rather cumbersome, and the whole reaction yield is only 22%

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  • Preparation method of capecitabine
  • Preparation method of capecitabine
  • Preparation method of capecitabine

Examples

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Embodiment Construction

[0025] The examples of the present invention provide a complete process for synthesizing capecitabine, but the present invention is not limited to this specific embodiment.

[0026] Synthesis of 1, 2’, 3’, 5’-tri-O-acetyl-5-fluorocytidine

[0027]

[0028] Add 30g (232mmol) 5-fluorocytosine, 37.49g (232mmol) hexamethylamine (HMDS), 0.47g (3.5mmol) ammonium sulfate to 120ml of toluene, reflux to clear, continue to reflux for 1 hour and spin The toluene was evaporated, 74g (232mmol) 2,3,5-tri-O-acetyl-D-ribose, 350ml 1,2-dichloroethane were added, 35ml containing 73g (279mmol) anhydrous SnCl was added dropwise under ice bath 4 1,2-dichloroethane solution, naturally warm to room temperature, after the reaction is complete, add the reaction solution to 500ml containing 118g (1405mmol) NaHCO 3 Adjust the pH value of the aqueous solution to 8, add diatomaceous earth, stir for 2 hours, filter, and extract the water layer with 1,2-dichloroethane twice, using 120ml of 1,2-dichloroethane each...

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Abstract

The invention relates to a preparation method of capecitabine, comprising the following steps of: synthesizing the capecitabine by utilizing low-cost D-ribose and 5-fluctyosine as raw materials; generating a formula II compound by reacting a formula III compound with iodine or NBS (N-bromosuccinimide); and then carrying out hydrogenation reduction on the hydrogenation to prepare a formula I compound. The novel synthesizing method of the capecitabine has the advantages of low-cost and easy-obtaining raw materials, few synthesis process sequence without complex post processing, few side product, high yield and low cost, and is suitable for industrialized production.

Description

Technical field [0001] The invention relates to the field of pharmaceutical chemical synthesis, in particular to a method for preparing capecitabine. Background technique [0002] Capecitabine (trade name: Xeloda) is a new type of 5-fluorouracil (5-FU) prodrug developed by Roche, Switzerland, which is an oral cell with selective effect on tumor cells Toxic preparations are non-cytotoxic, but can be converted into cytotoxic 5-fluorouracil. It is transformed by tumor-related vascular factor thymidine phosphorylase at the tumor site, thereby greatly reducing the effects of 5-fluorouracil on normal humans. Cell damage has good curative effect and strong safety for adjuvant therapy and metastatic tumor treatment. Capecitabine is also suitable for the further treatment of advanced primary or metastatic breast cancer that is ineffective against paclitaxel and anthracycline chemotherapy regimens. [0003] Due to the drug use of capecitabine and its better curative effect, the research on...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/073C07H1/00A61P35/00
CPCY02P20/55
Inventor 李会康秦欣荣李凌阳海蔡付波
Owner 四川弘远药业有限公司
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