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Regadenoson purifying method and new crystal form of regadenoson

A technology of regadeson, purification method, applied in the field of preparation of pharmaceutical compounds

Active Publication Date: 2019-08-13
SHANGHAI JIANHE PHARM & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] This product cannot be effectively removed to 0.10% (the general requirement for medicinal use) using the existing technology, such as the preparation method of the A crystal form described in WO2008 / 143667, so in order to obtain better quality and safer medication Desong, it is necessary to study a kind of purification method of Regardson to remove the impurity of above-mentioned formula 6 in Regardson

Method used

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  • Regadenoson purifying method and new crystal form of regadenoson

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1 Purification of Regadesone Crude Product and Preparation of Form I

[0070] Add purified water (3450mL) and dehydrated ethanol (3450mL) in the reaction bottle, stir, add the Regardson crude product (115.0g, purity sees attached figure 1 ), heated until the solid dissolved. Then slowly lower the temperature and continue to stir and crystallize for 1-2 hours. After filtering, the filter cake was rinsed with absolute ethanol, and the filter cake was vacuum-dried (50°C, 0.1M Pa) to constant weight. 96.4g of pure product of Deregardson, yield: 83.8%, purity 99.9% (HPLC, impurity of formula 6 is less than 0.1%, see attached figure 2 ).

[0071] The structure of the substance is 1 Confirmation by HNMR (see attached image 3 ). Thermal analysis (see attached Figure 4 ) The result proves that the substance contains a part of water, which is a monohydrate.

[0072] X-ray powder diffraction tests were also carried out, see attached Figure 5 The spectrogram da...

Embodiment 2

[0074] Example 2 Purification of Regadesone Crude Product and Preparation of Form I

[0075] Add DMF (75ml) and crude Regadeson (5g) to the reaction flask, stir and heat to 70-80°C to dissolve, add water (150ml) preheated to 80°C, then cool to room temperature, stir and crystallize 1- After 2 hours, filter, rinse the filter cake with absolute ethanol, and vacuum-dry the filter cake (50°C, 0.1M Pa) to constant weight. Obtained 4.3g of pure Regadeson with a yield of 86.0% and a purity of 99.95%.

Embodiment 3

[0076] Example 3 Purification of Regadesone Crude Product and Preparation of Form I

[0077] Add DMF (75ml) and crude Regadeson (5g) to the reaction flask, stir and heat to 70-80°C to dissolve, add water (225ml) preheated to 80°C, then cool to room temperature, stir and crystallize 1- After 2 hours, filter, rinse the filter cake with absolute ethanol, and vacuum-dry the filter cake (50°C, 0.1M Pa) to constant weight. Obtained 4.4g of pure Regadeson with a yield of 88.0% and a purity of 99.98%.

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Abstract

The invention relates to a regadenoson purifying method and a new crystal form of regadenoson. The method comprises the following steps that a regadenoson crude product is heated and dissolved in a mixed solvent, and then stirring cooling, crystallization, filtering and drying are conducted, wherein the mixed solvent is selected from mixed solvents of ethanol, methanol, acetonitrile and water; orthe method comprises the following steps that the regadenoson crude product is heated and dissolved in a good solvent, then a poor solvent is added, and stirring cooling, crystallization, filtering and drying are conducted, wherein the good solvent is selected from DMF, NMP and sulfolane or a mixture of the DMF, NMP and sulfolane, and the poor solvent is selected from ethanol, methanol and water or a mixture of the ethanol, methanol and water.

Description

[0001] Technical field: [0002] The invention relates to a preparation method of a drug compound, in particular to a method for purifying Regadeson, a drug used for cardiac diagnosis, and the resulting new crystal form. [0003] Background technique: [0004] Regadeson is used in cardiac perfusion imaging tests in patients who are not sufficiently active to aid in the diagnosis of coronary artery disease. They work by dilating the coronary arteries to increase blood flow to identify plaque and other obstructions in the coronary vessels. It was approved by the FDA on April 10, 2008. Its structure is regadesone monohydrate, and its trade name is "Lexiscan". [0005] Its structure is as follows: [0006] [0007] Myocardial perfusion imaging is a test used to detect and characterize coronary artery disease, and regadeson injection is the first A drug approved as a drug stress agent for myocardial perfusion imaging so far worldwide. 2A Adenosine receptor agonists. Compared w...

Claims

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Application Information

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IPC IPC(8): C07H19/167C07H1/06G01N30/02
CPCC07H19/167C07H1/06G01N30/02C07B2200/13
Inventor 韩硕康文瑞
Owner SHANGHAI JIANHE PHARM & TECH CO LTD
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