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Imidazolopyrimidine derivatives for preventing and treating pulmonary fibrosis and application of imidazolopyrimidine derivatives

A technology for pulmonary fibrosis and its derivatives, applied in organic chemistry, drug combination, respiratory system diseases, etc., can solve the problems of pharmacokinetic performance to be improved, toxic and side effects, etc., to delay the progress of pulmonary fibrosis, low toxicity , the effect of reducing production costs

Active Publication Date: 2019-06-21
SICHUAN YIASUO PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of imidazopyrimidine derivatives for preventing and treating pulmonary fibrosis, and the application of the derivatives in the preparation of drugs for preventing and treating pulmonary fibrosis, aiming at the defects and deficiencies in the existing drugs for treating pulmonary fibrosis. In order to solve the problems that the existing drugs for the prevention and treatment of pulmonary fibrosis have relatively large toxic and side effects and the pharmacokinetic performance needs to be improved

Method used

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  • Imidazolopyrimidine derivatives for preventing and treating pulmonary fibrosis and application of imidazolopyrimidine derivatives
  • Imidazolopyrimidine derivatives for preventing and treating pulmonary fibrosis and application of imidazolopyrimidine derivatives
  • Imidazolopyrimidine derivatives for preventing and treating pulmonary fibrosis and application of imidazolopyrimidine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In this example, the steps of preparing imidazopyrimidine derivatives for preventing and treating pulmonary fibrosis are as follows:

[0020] Take 1.36g of hypoxanthine, 3mL of iodoisopropane (1.703g / mL) and 0.24g of sodium hydride, put them into a flask containing 300mL of DMSO, stir and react at 80°C for 3h, then add acid to quench, and spin dry under reduced pressure to get Isopropyl modified hypoxanthine. Take 1.5 g of isopropyl-modified hypoxanthine and 8.08 g of Lawesson reagent (Lawesson reagent), add it to a flask filled with 500 mL of toluene, heat to reflux for 3 hours, then spin dry under reduced pressure, and pass through a silica gel column to prevent and treat pulmonary fibrosis The imidazopyrimidine derivative CSA.

[0021] Carry out nuclear magnetic spectrum and nuclear magnetic carbon spectrum detection to CSA, the result is: 1 H NMR (500MHz, Chloroform-d) δ8.57(s,1H),7.76(s,1H),5.26(hept,J=6.2Hz,1H),4.86(hept,J=6.2Hz,1H),1.46 (d, J=6.1 Hz, 6H), 1.23...

Embodiment 2

[0023] In this example, the anti-pulmonary embolism activity of the CSA prepared in Example 1 was tested.

[0024] 1. Test method

[0025] (1) Animals: SPF grade c57bl / 6 mice, 25g±2g.

[0026] (2) Grouping

[0027] The animals were divided into blank control group, model control group, prevention group and treatment group, with 10 animals in each group.

[0028] The prevention group received drug intervention 14 days in advance, with a dose of 50 mg / kg / d. After modeling, the treatment group was administered with an intervention dose of 50 mg / kg / d.

[0029] (3) Inject mice intraperitoneally with 1% sodium pentobarbital at a dose of 50 mg / kg, anesthetize them, place them supine on the operating table, expose the trachea with tweezers (pull out the tongue), and slowly inject 5 mg / kg bleomycin , and then quickly erected the rat board, rotated for 5 minutes, so that the drug was evenly distributed in the lungs.

[0030] The blank control group was given intragastric administra...

Embodiment 3

[0047] In this example, a toxicity test is performed on CSA.

[0048] C57 mice were given the compound CSA by intragastric administration at a dose of 50 mg / kg / d for 180 consecutive days, and the blank control group was intragastrically administered an equal volume of isotonic saline. One hour after the last administration, the mice were anesthetized by intraperitoneal injection of pentobarbital sodium (40 mg / kg), placed on a constant temperature hot plate at 37±1°C, and blood was collected by cardiac puncture. Blood routine, liver and kidney function, electrolytes and other blood pathological indicators were measured according to the operating instructions of the instrument, and the results are shown in Table 3. It can be seen from Table 3 that CSA has no obvious adverse effects on the liver and kidney functions of mice, and has the characteristics of low toxicity.

[0049] Table 3 Mouse liver and kidney function test results (values ​​are expressed as mean ± SED, n=9-10)

...

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Abstract

The invention provides imidazolopyrimidine derivatives for preventing and treating pulmonary fibrosis and an application of the imidazolopyrimidine derivatives to preparation of drugs for preventing and treating pulmonary fibrosis. The structural formula of the derivatives is represented in the description or the derivatives are pharmaceutically acceptable salts of the compound represented as thestructural formula. The imidazolopyrimidine derivatives can obviously reduce degree of pathology of pulmonary fibrosis and delay pulmonary fibrosis development, has a remarkable function of preventingand treating pulmonary fibrosis, and has better pharmacokinetics and lower toxicity than Nintedanib as a clinical first-line anti-pulmonary fibrosis drug.

Description

technical field [0001] The invention belongs to the field of medicines, and relates to an imidazopyrimidine derivative for preventing and treating pulmonary fibrosis, and the application of the derivative in preparing medicine for preventing and treating pulmonary fibrosis. Background technique [0002] Diffuse pulmonary interstitial fibrosis (referred to as "pulmonary fibrosis") is the result of body repair after progressive and irreversible damage to lung function caused by various reasons such as chemical or physical. Pulmonary fibrosis is mainly divided into idiopathic pulmonary fibrosis and secondary pulmonary fibrosis. Usually, the main pathological features are fibroblast proliferation, extracellular matrix deposition, pulmonary interstitial inflammation, persistent alveolar epithelial damage, and alveolar structural disorder. , the compliance of the lungs will decrease, the lung capacity will decrease, and the lung function will gradually decline, and the patient ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/38A61P11/00
Inventor 黄文李为民
Owner SICHUAN YIASUO PHARM TECH CO LTD
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