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Urapidil oxidation product and preparation method thereof

An oxidation product, urapidil technology, applied in the direction of organic chemistry, can solve the problem of the degradation product not being identified, and achieve the effect of improving the quality standard

Active Publication Date: 2015-04-22
REYOUNG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] To date, little has been reported on how to avoid the presence of oxidation products in urapidil substances, nor have degradation products of urapidil been previously identified

Method used

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  • Urapidil oxidation product and preparation method thereof
  • Urapidil oxidation product and preparation method thereof
  • Urapidil oxidation product and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation and isolation of compound I

[0037] In the there-necked flask, add the urapidil raw material (2g, 5.0mmol) and 20ml of dimethylformamide and heat to 70°C. After the raw material is completely dissolved, add 15% hydrogen peroxide (100ml) dropwise, and react at 70°C for 5 hours and stop heating. , the reaction solution was added to a saturated sodium sulfite solution (100ml) to quench the reaction, the reaction solution was concentrated and passed through a preparative column to obtain the target product, which was subjected to preparative chromatography.

[0038] Preparative Chromatography: Separation of oxidative degradation products was performed on reversed-phase chromatography. In order to obtain pure compounds, separations were carried out using chromatographic separations with different mobile phases.

[0039] The separation of urapidil oxidation products was performed on a preparative HPLC chromatogram equipped with an Innoval ODS-DAC column (250*250...

Embodiment 2

[0052] In the there-necked flask, add urapidil raw material (1g, 2.5mmol) and 40 milliliters of methanol and heat to 50°C. After the raw materials are completely dissolved, add 20% hydrogen peroxide (8ml) dropwise, and react at 50°C for 4 hours to stop heating. The reaction was quenched by adding saturated sodium sulfite solution (10 ml), and the reaction solution was concentrated and passed through a preparative column to obtain the target product.

[0053] Adopt the method of embodiment 1 to carry out preparation and separation.

Embodiment 3

[0055]In the there-necked flask, add urapidil raw material (2g, 5.0mmol) and 20 milliliters of toluene and heat to 60°C, after the raw material is completely dissolved, add 30% hydrogen peroxide (10ml) dropwise, and the reaction solution is reacted at 60°C for 6 hours to stop heating, and the reaction solution The reaction was quenched by adding saturated sodium sulfite solution (10 ml), and the reaction solution was concentrated and passed through a preparative column to obtain the target product.

[0056] Adopt the method of embodiment 1 to carry out preparation and separation.

[0057] Structural illustration of compound I:

[0058] Mass spectrometry:

[0059] Conditions: Linear ion trap electrostatic field orbitrap combined mass spectrometer LTQ Orbitrap XL mass spectrometer to obtain high-resolution mass spectra. Electrospray ionization was used.

[0060] NMR spectroscopy:

[0061] Conditions: H and C were performed on a BRUKER AVANCE 600 NMR spectrometer.

[0062] s...

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Abstract

The invention relates to an urapidil oxidation product and a reparation method thereof. The product is 6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]nitroxyl]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione. According to the invention, the compound is obtained, and is subjected to structure confirmation, such that the structure of the compound is confirmed. The compound is adopted as an impurity reference substance in urapidil related substance inspection, such that impurity change situations of urapidil can be directly effectively monitored. The implementation of the invention assists in improving urapidil quality standard, such that urapidil product quality can be better controlled.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to an oxidation product of urapidil and a preparation method thereof. Background technique [0002] New drug research and development must abide by the basic principles of "safety, effectiveness, and quality controllable"; adhering to the principles of "scientific design, standardized production, process monitoring, and formulation of reasonable drug quality standards" can ensure the quality of drugs is controllable. In the process of drug quality research, in addition to paying attention to the indicators of active ingredients, more and more attention has been paid to the research on its impurities and toxic and harmful substances in recent years. Impurities in drugs can be simply divided into related substances (organic impurities), residual solvents, metal impurities, crystal impurities, isomer impurities, genotoxic impurities and some other specific substances. These substances g...

Claims

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Application Information

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IPC IPC(8): C07D239/545
CPCC07D239/545
Inventor 胡清文王宏光赵磊安飞曹燕
Owner REYOUNG PHARMA
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