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Preparation method of taxol anticancer drugs Cabazitaxel XRP6258

A technology of paclitaxel and anticancer drugs, which is applied in specific related fields, can solve the problems of difficult purification, long route, and long synthetic route, and achieve the effect of simple purification process, simple preparation process, and easy operation

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

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Problems solved by technology

[0011] 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 preparation of XRP6258
[0012] The above two methods for preparing XRP6258 have defects such as low yield, difficult purification (multi-step column chromatography), and too long synthetic route, which limit industrial large-scale preparation and application to a certain extent.

Method used

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

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Embodiment 1

[0047] 1. Preparation of compound II

[0048]

[0049] 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 synthesizing a second-generation taxol anticancer drugs Cabazitaxel 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, reducing C-13 bit carbonyl to obtain a mother nucleus midbody (III), carrying out butt joint with various types of side chains to obtain butt joint product midbodies (IV-1) and (IV-2), and removing a side-chain protecting group after the di-methylthio is removed or removing the di-methylthio of the nuclear parent after the side-chain protecting group is removed to obtain a product Cabazitaxel XRP6258 (V). The method disclosed by the invention has the advantages of being 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, and relates to a method for synthesizing the second-generation paclitaxel anticancer drug Cabazitaxel XRP6258, specifically, a method for synthesizing XRP6258 (V) with 10-deacetylbaccatin III (I) as a starting material The new 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 (Paclitaxel) and its semi-synthetic analog Docetaxel (Docetaxel) are the star molecules of anti-tumor drugs in the world today. Cancer, breast cancer, non-small cell lung cancer, malignant black solid tumors and some other solid tumors, especially for the treatment of metastatic ovarian cancer and breast cancer, it has a remarkable effect, and has been recognized as a very promising new anticancer drug. However, paclitaxel, like other chemoth...

Claims

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Application Information

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