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Preparation method and use of istradefylline

A technology of istradefylline and its compounds, which is applied in the field of preparation of istradefylline, can solve the problems of large-scale production of istradefylline, complex process, high product cost, etc., and achieve low production cost, simple synthetic route, The effect of high production efficiency

Inactive Publication Date: 2017-03-15
合肥美利康医药技术股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the process of istradefylline is relatively complicated, and neurotoxic methylating reagents, such as methyl iodide, etc., will be produced during the preparation process, which hinders the large-scale production of istradefylline, making The cost of the product is relatively high, which brings a greater burden to patients

Method used

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  • Preparation method and use of istradefylline
  • Preparation method and use of istradefylline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1) Put 180g of 1,3-diethylformamide and 125g of cyanoacetic acid in 185ml of acetic anhydride for ring formation reaction. The reaction condition is to heat and reflux at 78°C for 2 hours. After the reaction is completed, add sodium hydroxide, adjust the pH to neutral and pump filtered, washed three times with water, and the resulting white solid was compound Ⅰ;

[0024] 2) Add 260 g of compound I to 1 L of acetic acid, stir for 30 minutes, and then add sodium nitrite for nitration reaction. The reaction time is 1.5 hours. After the reaction is completed, the solid obtained by suction filtration and drying is compound II;

[0025] 3) Pass hydrogen through 260 g of compound II and 2.2 L of methanol for reduction reaction. The reaction time is 20 h. After the reaction is completed, the yellow solid obtained by HPLC detection and spin-drying is compound III;

[0026] 4) Under dark and oxygen-free conditions, 150g of compound III, 200g of 3-(3,4-dimethoxy-phenolyl)-acryloyl...

Embodiment 2

[0030] 1) Put 180g of 1,3-diethylformamide and 120g of cyanoacetic acid in 180ml of acetic anhydride for ring formation reaction. The reaction condition is to heat and reflux at 75°C for 1.5h. After the reaction is completed, add sodium hydroxide to adjust the pH to neutral After suction filtration and washing with water three times, the obtained white solid was compound Ⅰ;

[0031] 2) Add 260 g of compound I to 1 L of acetic acid, stir for 30 minutes, and then add sodium nitrite for nitration reaction. The reaction time is 1. After the reaction is completed, the solid obtained by suction filtration and drying is compound II;

[0032] 3) Pass hydrogen through 260 g of compound II and 2.5 L of methanol for reduction reaction. The reaction time is 24 hours. After the reaction is completed, the yellow solid obtained by HPLC detection and spin-drying is compound III;

[0033] 4) Under dark and oxygen-free conditions, 150g of compound III, 200g of 3-(3,4-dimethoxy-phenolyl)-acryloy...

Embodiment 3

[0037] 1) Put 180g of 1,3-diethylformamide and 122g of cyanoacetic acid in 182ml of acetic anhydride for ring formation reaction. The reaction condition is to heat and reflux at 83°C for 2 hours. After the reaction is completed, add sodium hydroxide and adjust the pH to neutral. Suction filtration, washing with water three times, the obtained white solid is compound Ⅰ;

[0038] 2) Add 260 g of compound I to 1 L of acetic acid, stir for 30 minutes, and then add sodium nitrite for nitration reaction. The reaction time is 1.5 hours. After the reaction is completed, the solid obtained by suction filtration and drying is compound II;

[0039] 3) Pass hydrogen through 260 g of compound II and 2.6 L of methanol for reduction reaction. The reaction time is 26 hours. After the reaction is completed, the yellow solid obtained by HPLC detection and spin-drying is compound III;

[0040] 4) Under dark and anaerobic conditions, 150g of compound III, 200g of 3-(3,4-dimethoxy-phenolyl)-acrylo...

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Abstract

The invention relates to the technical field of pharmaceutical chemistry, and particularly relates to a preparation method and use of istradefylline; specifically, with 1,3-diethyl formamide and cyanoacetic acid as raw materials, istradefylline is prepared through cyclization, nitration, reduction, condensation, cyclization, methylation reaction and other steps; the preparation method provided by the invention is simple, high in production efficiency and wide in application prospect.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a preparation method and application of istradefylline. Background technique [0002] PD is a progressive disease, mainly caused by the degeneration of dopamine receptors in the basal ganglia. It involves many clinical symptoms, among which the four main clinical symptoms are bradykinesia, rigidity, resting tremor and postural instability. Among them, the presence of 2 symptoms was used as the diagnostic feature. [0003] As an innovative drug for the treatment of Parkinson's disease, istradefylline is used as an adjuvant drug in combination with levodopa and other anti-Parkinson drugs to improve the motor symptoms of patients with Parkinson's disease. In the prior art, the process of istradefylline is relatively complicated, and neurotoxic methylating reagents, such as methyl iodide, etc., will be produced during the preparation process, which hinders the large-scal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/06
CPCC07D473/06
Inventor 孙明哲方存杰赵冬生方从彬孙延标徐奎
Owner 合肥美利康医药技术股份有限公司
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