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Method for preparing (Z)-istradefylline

A technology of istradefylline and acetonitrile, applied in the field of medicinal chemistry, can solve the problems of cumbersome operation, waste of materials, and low yield

Inactive Publication Date: 2019-09-20
SHANDONG XINHUA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method requires a long time, complicated operation, many waste materials, and low yield (document yield: 16%)

Method used

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  • Method for preparing (Z)-istradefylline
  • Method for preparing (Z)-istradefylline
  • Method for preparing (Z)-istradefylline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Weigh 100 mg of istradefylline into a test tube, and add 20 ml of solvent (acetonitrile-water=4:1 (volume ratio)). Close the lid tightly, shake to dissolve, and place under sunlight for 1 to 1.5 hours;

[0030] (2) Separation and preparation are carried out by reverse high performance liquid chromatography preparation method, and the elution fraction of (Z)-istradefylline is collected;

[0031] The conditions of the reverse high performance liquid chromatography preparative method are:

[0032] Sample: solution after light treatment

[0033] Chromatographic column: Hanbang Dubhe C18, Φ30×250mm, 10um

[0034] Detection wavelength: 355nm

[0035] Mobile phase: acetonitrile-water=70:30 (volume ratio)

[0036] Flow rate: 30ml / min

[0037] Injection volume: 5ml;

[0038] (3) The collected solution was evaporated to remove acetonitrile under reduced pressure at 30-35°C, transferred to a petri dish, put into a lyophilizer and freeze-dried according to the procedure t...

Embodiment 2

[0040] (1) Weigh 100 mg of istradefylline into a test tube, and add 20 ml of solvent (acetonitrile-water=3:1 (volume ratio)). Close the lid tightly, shake to dissolve, and place under sunlight for 1 to 1.5 hours;

[0041] (2) Separation and preparation are carried out by reverse-phase high-performance liquid chromatography preparation method, and the elution fraction of (Z)-istradefylline is collected; the conditions of the reverse-phase high-performance liquid chromatography preparation method are the same as in Example 1;

[0042] (3) The collected liquid was evaporated to remove acetonitrile under reduced pressure at 25-30°C, transferred to a petri dish, put into a lyophilizer and freeze-dried according to the procedure to obtain 63 mg of the target substance, HPLC: 99.5% (area normalization method) .

Embodiment 3

[0044] (1) Weigh 100 mg of istradefylline into a test tube, and add 20 ml of solvent (acetonitrile-water=2:1 (volume ratio)). Close the lid tightly, shake to dissolve, and place under sunlight for 1 to 1.5 hours;

[0045] (2) Separation and preparation are carried out by reverse-phase high-performance liquid chromatography preparation method, and the elution fraction of (Z)-istradefylline is collected; the conditions of the reverse-phase high-performance liquid chromatography preparation method are the same as in Example 1;

[0046] (3) The collected liquid was evaporated to remove acetonitrile under reduced pressure at 28-32°C, transferred to a petri dish, put into a lyophilizer and freeze-dried according to the procedure to obtain 59 mg of the target substance, HPLC: 99.0% (area normalization method) .

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Abstract

The invention provides a method for preparing (Z)-istradefylline, wherein acetonitrile-water is used as a solvent, separation preparation is performed through a reverse high performance liquid chromatography preparation method after light irradiation, and after acetonitrile is distilled off, post-treatment is performed by using a freeze-drying technology. According to the present invention, the post-treatment is simple, and high temperature is not required, such that the generation of side reactions and impurities is avoided, and the prepared target has high purity; the yield is high, and reaches more than 60%; and the method has characteristics of controllable process and easy operation.

Description

technical field [0001] The present invention relates to a method for preparing (Z)-istradefylline (that is, (Z)-1,3-diethyl-8-(3,4-dimethoxystyryl)-7-methyl yellow The method of purine, which is the isomer of istradefylline, belongs to the technical field of medicinal chemistry. Background technique [0002] Itradefylline is a new type of selective adenosine A2A receptor antagonist developed by Japan Kyowa Hakko Kogyo Co., Ltd., for the treatment of Parkinson's disease. The drug was approved by PMDA in May 2013 and launched in Japan. It is the world's first marketed adenosine A for the treatment of Parkinson's disease (PD) 2A receptor inhibitors. As a PD treatment drug, istradefylline has definite curative effect and strong tolerance. The biggest advantage is that it does not cause dyskinesia caused by levodopa (L-DOPA). On the contrary, it can significantly alleviate this adverse reaction. Compared with traditional PD therapeutic drugs, istradefylline has multiple advan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/06
CPCC07D473/06
Inventor 徐豪杰刘胜高郭统山
Owner SHANDONG XINHUA PHARMA CO LTD
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