Preparation method of taxol anticancer drugs XRP6258

An anticancer drug, paclitaxel technology, applied in antitumor drugs, drug combinations, organic chemistry and other directions, can solve the problems of long route, difficult purification, long synthesis route, etc., and achieves simple preparation process, simple purification process, and easy operation. Effect

Inactive Publication Date: 2013-04-03
FUDAN UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The disadvantage of this method is that the route is too long, and the C-7 hydroxy methyl etherification conversion rate of the mother nucleus is low, and the total yield is less than 10%, which is not suitable for large-scale industrial preparatio

Method used

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  • Preparation method of taxol anticancer drugs XRP6258
  • Preparation method of taxol anticancer drugs XRP6258
  • Preparation method of taxol anticancer drugs XRP6258

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Embodiment 1

[0051] 1. Preparation of Compound II

[0052]

[0053] 10-DAB(I) (27.3g, 50.0mmol) was dissolved in dry DMSO (200mL), acetic anhydride (200mL) was added, protected by argon, stirred at room temperature overnight, and after the reaction was detected by thin layer chromatography, the reaction solution was Concentrate under reduced pressure and evaporate to dryness, dilute the resulting residue with ethyl acetate (1.5L), and wash with saturated sodium bicarbonate solution (300mL×6), distilled water (200mL×3), and saturated aqueous sodium chloride solution (200mL×3) successively , dried over anhydrous sodium sulfate, and concentrated to obtain light yellow foamy solid product II (28.1 g, yield about 85.1%), which was directly carried out to the next step without purification; 1 H-NMR (400MHz, CDCl 3 ): δ8.06(d, 2H, J=7.0Hz, Ph-H), 7.62(t, 1H, J=7.6Hz, Ph-H), 7.49(t, 2H, J=7.6Hz, Ph-H ), 5.80(s, 1H, H-10), 5.67(d, 1H, J=6.7Hz, H-2), 4.94(d, 1H, J=9.2Hz, H-5), 4.84(d, 1H , J=1...

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Abstract

The invention belongs to the field of drug synthesis, and relates to a method for preparing taxol anticancer drugs XRP6258. The method comprises the following steps of: obtaining C-7 and C-10 bit hydroxy methyl mercaptan methylene (MTM) and C-13 bit oxhydryl oxydic key intermediate (II) of 10-oxhydryl baccatin III(I) by high regioselectivity, sequentially removing methylthio, reducing C-13 bit carbonyl or sequentially reducing C-13 bit carbonyl and removing methylthio to obtain a mother nucleus (IV) of the product XRP6258, carrying out butt joint with side chains with various types and removing a side-chain protecting group to obtain a product Cabazitaxel (V). The method disclosed by the invention has the advantages of being high in efficiency during a preparation process, simple in preparation process, high in yield, lower in cost, easy to operate and the like, so that the XRP6258 can be produced and prepared on a large scale.

Description

technical field [0001] The invention belongs to the field of drug synthesis, relates to paclitaxel anticancer drugs, in particular to a preparation method of paclitaxel anticancer drugs Cabazitaxel (XRP6258), specifically starting with 10-deacetylbaccatin III (I) A new method for synthesizing XRP6258(V) from raw materials, the method has the advantages of high preparation process efficiency, simple process, high yield, low cost, easy operation, etc., and is suitable for large-scale production and preparation of XRP6258. Background technique [0002] Paclitaxel and its semi-synthetic analog Docetaxel are one of the most effective anticancer drugs discovered by humans so far. After being launched in the United States at the end of 1992, they have been approved for marketing in more than 40 countries. And as a first-line anticancer drug, it is widely used in breast cancer, lung cancer, gastric cancer, esophageal cancer, ovarian cancer, etc. Despite their remarkable anticancer ...

Claims

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Application Information

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IPC IPC(8): C07D305/14A61P35/00
CPCY02P20/55
Inventor 李英霞刘珂王军飞丁宁张伟
Owner FUDAN UNIV
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