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A kind of selective copper ion chelating agent, its preparation method and its application in pulmonary fibrosis

A technology of pulmonary fibrosis and copper ions, applied in the field of medicine, can solve the problems of polymyositis and poor specificity, and achieve the effects of increasing lung blood supply, easy acceptance, improving and inhibiting the level of pulmonary fibrosis

Active Publication Date: 2022-08-09
AFFILIATED HOSPITAL OF JINING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently clinically commonly used copper ion chelating agents include penicillamine, trientine, dimercaptosuccinic acid, sodium dimercaptopropanesulfonate, and tetrathiomolybdate, but they all have the disadvantage of poor specificity. When used, it also complexes with iron, zinc, calcium, etc. in the body, so it is easy to cause side effects such as gastrointestinal reactions, lupus erythematosus, myasthenia gravis, polymyositis, etc.

Method used

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  • A kind of selective copper ion chelating agent, its preparation method and its application in pulmonary fibrosis
  • A kind of selective copper ion chelating agent, its preparation method and its application in pulmonary fibrosis
  • A kind of selective copper ion chelating agent, its preparation method and its application in pulmonary fibrosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Synthesis of JYFY-001 compound

[0050] Acetic acid (0.24 g, 4.0 mmol), DMAP (0.49 g, 4.0 mmol) and EDCI (0.77 g, 4.0 mmol) were added to 6 mL of CH 2 Cl 2 was stirred at room temperature for 10 min. 2-Bromothieno[3,2-c]pyridin-4-amine (compound 1) (0.46 g, 2.0 mmol) was added, and the reaction was continued to stir at room temperature for 6 h. Spin dry CH 2 Cl 2 , ethyl acetate was added, washed twice with water and once with saturated NaCl solution. Anhydrous Na 2 SO 4 After drying, filtration, concentration under reduced pressure, and silica gel column chromatography (dichloromethane:methanol=100:1) to obtain white powdery solid N-(2-bromothieno[3,2-c]pyridin-4-yl ) acetamide (intermediate 2) 0.43 g, yield 79.3%. Melting point: 178-180℃; 1 H NMR (400MHz, DMSO) δ 8.42 (d, J=5.5Hz, 1H), 8.16 (d, J=5.5Hz, 1H), 7.84 (s, 1H), 2.19 (s, 3H); 13 C NMR (100MHz, DMSO) δ172.32, 150.56, 146.42, 142.87, 134.16, 124.78, 118.94, 118.72, 26.53; HRMS (ESI): Calc...

Embodiment 2

[0052] Example 2 Establishment and administration of a mouse pulmonary fibrosis model

[0053] In this study, a mouse model of pulmonary fibrosis was established, and the inducer was bleomycin (BLM). In this experiment, 30 mice were randomly divided into 3 groups, 10 in the blank group and 20 in the model group. In the pulmonary fibrosis model induced by bleomycin, the mice in the model group were fasted for 16 hours before modeling. Mice in the modeling group were given BLM aqueous solution (5 mg·kg-1) via tracheal perfusion, and the blank group was perfused with the same volume of normal saline in the same way.

[0054] On the seventh day, 20 mice in the model group were randomly divided into two groups. They are: model group 10, JYFY-001 group 10, ♀♂ half and half. On the 8th day, the JYFY-001 group was given 50 mg / kg dose of tail vein administration (weighed before administration), and the blank group and the model group were given the corresponding volume of normal s...

Embodiment 3

[0055] Example 3 Histopathological evaluation of the degree of pulmonary fibrosis in lung tissue

[0056] The lung tissues of the three groups of mice treated for 2 weeks were collected, fixed, routinely dehydrated, made into paraffin tissue sections, stained with hematoxylin-eosin (HE) and Masson, and the morphological changes of the lung tissues were observed under a microscope.

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Abstract

The invention discloses a selective copper ion chelating agent, its preparation method and its application in pulmonary fibrosis. The chelating agent is N-(2-(pyridine-3-yl)thieno[3,2-c ]pyridin-4-yl)acetamide. JYFY‑001 can improve and inhibit the level of pulmonary fibrosis in the body, inhibit the excessive deposition of extracellular matrix in the lung, reduce inflammatory cells, inhibit the proliferation of fibroblasts, improve the blood supply to the lungs to relieve dyspnea, and has a good effect on pulmonary fibrosis. In addition, the drug is not only easy for patients to accept, but also has few side effects and low price. In addition, JYFY‑001 will change the market structure of existing drugs for the treatment of pulmonary fibrosis and become a clinical drug that can be taken for a long time and can effectively inhibit pulmonary fibrosis and improve lung function.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a selective copper ion chelating agent, a preparation method thereof and its application in pulmonary fibrosis. Background technique [0002] Pulmonary fibrosis is the end-stage change of a large class of lung diseases characterized by the proliferation of fibroblasts and the accumulation of a large amount of extracellular matrix, accompanied by inflammatory damage and tissue structure destruction, that is, normal alveolar tissue is damaged and then abnormally repaired to lead to structural changes. Abnormal (Karampitsakos T, et al., Eur J Pharmacol. 2017 Aug 5;808:35-43). Because its early clinical manifestations are usually nonspecific symptoms of exertional dyspnea with or without dry cough, it is often overlooked or misdiagnosed as other diseases in the early stage. Severe pulmonary fibrosis is due to structural changes in normal lung tissue, loss of function, and replace...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61P11/00A61K31/444
CPCC07D495/04A61P11/00
Inventor 刘艳荣石小龙贾孟亭李莹孙涛张苗苗
Owner AFFILIATED HOSPITAL OF JINING MEDICAL UNIV
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