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A kind of preparation method of anticancer drug vorinostat

A technology of vorinostat and anticancer drugs, which is applied in the field of preparation of anticancer drug vorinostat, can solve the problems of low product yield, long reaction time, poor selectivity, etc., and achieve good selectivity and high yield , the effect of mild conditions

Inactive Publication Date: 2018-04-06
马腾 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the defects of long reaction time, poor selectivity and low product yield in the existing method for preparing vorinostat, and provide a kind of vorinostat suitable for short reaction time, good selectivity and high yield. his method of preparation
[0008] In the preparation of vorinostat, the yield is low because suberic acid reacts with two carboxyl groups without selectivity. In the prior art, it is adjusted by adjusting the reaction conditions or using a special coupling agent to control the suberic acid monocarboxyl group. reaction, and by modifying a carboxyl group in suberic acid, the problem of reaction selectivity can be fundamentally solved

Method used

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  • A kind of preparation method of anticancer drug vorinostat

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Embodiment 1

[0026] Preparation of suberic acid-substrate self-assembled film

[0027] Hydrophilic treatment of quartz sheet: place the cut substrate (quartz sheet, 10cm×10cm) in a strong acid mixed solution (H 2 SO 4 / HNO 3 , volume ratio 1:1), boiled at 90°C for 1 hour, then stood at room temperature, cleaned with deionized water and ultrasonicated for 15 minutes to obtain a hydrophilic substrate, which was stored in deionized water until use.

[0028] The specific process of self-assembly includes: adding the hydrophilic substrate to the solution of suberic acid in anhydrous toluene, keeping it warm at 50°C for 10 hours, then taking out the substrate and washing it with water to obtain the suberic acid-substrate self-assembled film . The solution concentration of suberic acid in anhydrous toluene is 1×10 -3 mol / L.

Embodiment 2

[0030] Preparation of suberic acid-substrate self-assembled film

[0031] Hydrophilic treatment of quartz wafers: place the cut substrate (silicon wafer, 10cm×10cm) in a strong acid mixed solution (H 2 SO 4 / HNO 3 , volume ratio 1:1), boiled at 90°C for 1 hour, then stood at room temperature, cleaned with deionized water and ultrasonicated for 15 minutes to obtain a hydrophilic substrate, which was stored in deionized water until use.

[0032] The specific process of self-assembly includes: adding the hydrophilic substrate to the solution of suberic acid in anhydrous toluene, keeping it warm at 60°C for 8 hours, then taking out the substrate and washing it with water to obtain the suberic acid-substrate self-assembled film . The solution concentration of suberic acid in anhydrous toluene is 1×10 -4 mol / L.

Embodiment 3

[0034] Preparation of suberic acid-substrate self-assembled film

[0035] Hydrophilic treatment of quartz sheet: place the cut substrate (glass sheet, 10cm×10cm) in a strong acid mixed solution (H 2 SO 4 / HNO 3 , volume ratio 1:1), boiled at 90°C for 1 hour, then stood at room temperature, cleaned with deionized water and ultrasonicated for 15 minutes to obtain a hydrophilic substrate, which was stored in deionized water until use.

[0036] The specific process of self-assembly includes: adding the hydrophilic substrate to the solution of suberic acid in anhydrous toluene, keeping it warm at 45°C for 10 hours, then taking out the substrate and washing it with water to obtain the suberic acid-substrate self-assembled film . The solution concentration of suberic acid in anhydrous toluene is 1×10 -3 mol / L.

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Abstract

The invention discloses a preparation method of an anti-cancer drug vorinostat. The method comprises the following steps that 1, a hydrophilic substrate and suberic acid make contact with each other to be self-assembled to obtain a suberic acid-substrate self-assembled membrane; 2, the suberic acid-substrate self-assembled membrane makes contact with hydroxylamine hydrochloride in THF in the presence of 1,3-dicyclohexylcarbodiimide, after reacting is finished, 4M of a HCl solution is added, reacting under stirring is conducted, and dichloromethane extraction is conducted to obtain N-hydroxyl-7-carboxyl-heptamide; 3, N-hydroxyl-7-carboxyl-heptamide reacts with aniline to obtain the vorinostat in the presence of 1,3-dicyclohexylcarbodiimide and alkali. According to the preparation method of the vorinostat, a novel synthesis way of the vorinostat is provided. By means of the preparation method of the vorinostat, the conditions are mild, the selectivity is good, the reacting time, especially the aniline amidation reacting time is greatly shortened, and meanwhile the yield of the vorinostat is greatly increased.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of an anticancer drug vorinostat. Background technique [0002] Vorinostat, launched in the United States in October 2006, is the first new anticancer drug that inhibits protein deacetylase, and it can play a role by inducing cell differentiation, blocking cell cycle, and inducing cell regulation . The specific structural formula is as follows: [0003] [0004] At present, there are many synthetic methods for vorinostat, most of which use suberic anhydride or suberic acid and aniline ring-opening amidation to obtain suberic acid monoanilide, and then esterification and hydroxylamine hydrochloride aminolysis to obtain. However, there are problems such as low yield and long reaction time in these methods, and the reaction conditions are quite harsh. For example J.Med.Chem., 1995,38 (9): the method for 1411-1413 report, first dioic acid and anili...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C259/06
CPCC07C259/06
Inventor 马腾马晓维
Owner 马腾
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