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Novel derivative of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl and application of novel derivative

A technology of propylsulfonamide and bromophenyl, applied in the field of compound derivatives, can solve problems such as poor metabolism, less toxic and side effects, and achieve the effects of less side effects, reduced toxicity and other side effects, and reduced drug toxicity

Inactive Publication Date: 2014-04-16
ZHENJIANG SAN AN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The object of the present invention is to overcome the defects in the prior art, providing N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy] -A novel derivative of 4-pyrimidinyl]-N'-propylsulfonamide and its application, the derivative has good drug activity, can solve the problem of poor metabolism of the drug, and has little toxic and side effects in the course of medication

Method used

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  • Novel derivative of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl and application of novel derivative
  • Novel derivative of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl and application of novel derivative
  • Novel derivative of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl and application of novel derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Preparation of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-heptafluoropropane Sulfonamide.

[0020] The preparation of the derivative of the present invention includes two steps of sulfonamidation and etherification.

[0021] The preparation steps are as follows:

[0022] (1) Preparation of N-[5-(4-bromophenyl)-6-[2-hydroxyethoxy]-4-pyrimidinyl]-N'-heptafluoropropylsulfonamide by sulfonamidation:

[0023]

[0024] Under anhydrous, oxygen-free and argon protection, add 4-chloro-[5-(4-bromophenyl)-6-[2-hydroxyethoxy]pyrimidine and DMSO in a dry flask, and add seven Fluoropropylsulfonamide sodium salt, stirred and reacted at room temperature for 48 hours, then added saturated brine to quench the reaction, and then added chloroform. The organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography to obtain N-[5-(4-...

Embodiment 2

[0028] Preparation of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-(1, 1-Difluoropropyl)sulfonamide.

[0029]

[0030] The preparation method is the same as in Example 1, except that the sodium heptafluoropropylsulfonamide salt in Example 1 is replaced by N-(1,1-difluoropropyl)sulfonamide sodium salt.

Embodiment 3

[0032] Preparation of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-(3, 3,3-trifluoropropyl)sulfonamide.

[0033]

[0034] The preparation method is the same as in Example 1, except that the sodium heptafluoropropylsulfonamide salt in Example 1 is replaced by N-(3,3,3-trifluoropropyl)sulfonamide sodium salt.

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Abstract

The invention discloses a novel derivative of N-[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]-N'-propyl and application of the novel derivative. The novel derivative has good medicine activity, can greatly prolong the half-life period of a medicine, prolongs the retention time of the medicine in a human body, and meanwhile, improves the concentration of the medicine in blood; therefore, a better curative effect is achieved. As the half-life period of the medicine is greatly prolonged, activity concentration of the medicine in the blood can be maintained for a longer period of time; under the cure condition of dose constrain, the curative effect is maintained and the dosage of the medicine is reduced, so that the problem of bad metabolism of the medicine is eliminated, the medicine toxicity is reduced, and the toxic and side effects in the medicine use process are reduced.

Description

technical field [0001] The invention relates to a compound derivative and its application, belonging to the technical field of medicine. Background technique [0002] Pulmonary arterial hypertension (PAH) is a chronic disease that can be progressive and debilitating, leading to death or the need for lung transplantation in severe cases. Pulmonary hypertension is high blood pressure in the arteries that connect the heart to the lungs. It causes the right heart to work harder than normal, which can lead to limited ability to exercise and shortness of breath. The disease is characterized by abnormally high blood pressure in the arteries between the heart and the lungs in affected individuals, and symptoms can range from mild dyspnea and fatigue to severely limited exercise capacity and ultimately shortened lifespan. On October 13, 2013, the US Food and Drug Administration (FDA) approved a drug for the treatment of patients with pulmonary arterial hypertension. The chemical nam...

Claims

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Application Information

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IPC IPC(8): C07D239/47A61K31/506A61P9/12A61P11/00
CPCC07D239/47
Inventor 陈兴海
Owner ZHENJIANG SAN AN PHARMA
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