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Compounds for treating myocardial ischemia, and application of compounds

A technology of compounds and nitrogen oxides, which is applied in the field of medicine, can solve problems that affect the quality of life of patients, the efficacy of drugs is not completely the same, and there is no effect.

Active Publication Date: 2018-11-09
XIAN PEIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, western medicine treatment often leads to some adverse reactions, such as inducing bronchial asthma, inhibiting the heart, causing heart failure, etc.
In addition, Chinese patent medicines are often used in the treatment of myocardial ischemic diseases, such as salvia miltiorrhiza preparations, compound ginkgo preparations, Suxiao Jiuxin pills, etc. These medicines have certain therapeutic effects, but there are certain problems, mainly due to different individual patients. Physiques are not exactly the same, so the curative effect of the drugs during treatment is also not the same, and some even have no effect, and some of these drugs have a certain degree of drug resistance, and patients need to take the drugs for life, which affects the quality of life of patients
[0004] It can be seen that there is still a lack of effective drugs for the treatment of myocardial ischemia clinically, so it is very urgent and of great significance to develop more anti-myocardial ischemia drugs

Method used

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  • Compounds for treating myocardial ischemia, and application of compounds
  • Compounds for treating myocardial ischemia, and application of compounds
  • Compounds for treating myocardial ischemia, and application of compounds

Examples

Experimental program
Comparison scheme
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specific Embodiment approach

[0057] Hereinafter, the present invention is described in more detail to facilitate understanding of the present invention.

[0058] Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many other compounds of the invention and that other methods for preparing the compounds of the invention are considered to be within the scope of the invention Inside. For example, the synthesis of those non-exemplified compounds according to the present invention can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by using other known reagents in addition to those described in the present invention, or by incorporating Reaction conditions with some routine modifications. In addition, reactions disclosed herein or known reaction conditions are also recognized to be applicable to the preparation of other compounds of this invention.

Embodiment 1

[0059] Example 1: (3-(5-(6-(2-methoxyethoxy)pyridin-2-yl)-1,3,4-oxadiazol-2-yl)-3,4-di Hydroquinolin-1(2H)-yl)(5-methylthiophen-2-yl)methanone (compound OADA-1)

[0060]

[0061] Step 1: Mix 1-(5-methylthiophene-2-carbonyl)-1,2,3,4-tetrahydroquinoline-3-carboxylic acid (5.0 mmol) and 6-(2-methoxyethoxy base) picidinecarbohydrazide (5.0mmol) was suspended in 50mL THF, then EDC (1.6g), HOBt (1.1g) was added, and pyridine (3mL) was added dropwise, stirred and reacted at room temperature for 24 hours, filtered, and the filter cake was After washing with tetrahydrofuran, an off-white solid was obtained, which was dried to obtain a bishydrazide intermediate, which was used in the next step without purification.

[0062] Step 2: Suspend the bishydrazide obtained in the previous step in 50 mL of dry tetrahydrofuran solution, add methyl N-(triethylammoniumsulfonyl)carbamate (Burgess reagent) (2 g), and heat up to reflux for 4 hours. Filter after cooling, collect the filtrate, evap...

Embodiment 2

[0067] Example 2: (3-(5-(3,5-dibromopyridin-2-yl)-1,3,4-oxadiazol-2-yl)-3,4-dihydroquinoline-1( 2H)-yl)(1-methylpyrrolidin-3-yl)methanone (compound OADA-2)

[0068]

[0069] Synthesized by a method similar to Example 1, using 1-(1-methylpyrrolidine-3-carbonyl)-1,2,3,4-tetrahydroquinoline-3-carboxylic acid instead of 1-(5-methyl thiophene-2-carbonyl)-1,2,3,4-tetrahydroquinoline-3-carboxylic acid, replacing 6-(2-methoxyethoxy) with 3,5-dibromopicolinylhydrazide Picolinyl hydrazide, to obtain the target compound, the two-step total yield of 79.5%.

[0070] Mass Spectrum (ESI): 546.01[M+H] +

[0071] Elemental analysis: theoretical value C, 48.28; H, 3.87; Br, 29.20; N, 12.80; O, 5.85

[0072] Found C, 48.41; H, 3.99; Br, 29.05; N, 12.71; O, 5.84.

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PUM

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Abstract

The invention relates to oxadiazole compounds for treating myocardial ischemia. The invention also relates to application of the compounds in the aspect of treatment of the myocardial ischemia. The test results show that the compounds provided by the invention can effectively reduce the myocardial infarct area of rats with myocardial infarction and significantly reduce the creatine kinase (CK), aspartate transaminase (AST) and lactate dehydrogenase (LDH) activities of the serum of the rats; therefore, the compounds are prove to have significant preventive and therapeutic effects on the myocardial infarction, thus being used for prevention and treatment of the myocardial ischemia.

Description

technical field [0001] The present invention relates to the field of medicine, specifically, the present invention relates to an oxadiazole compound for treating myocardial ischemia, and the present invention also relates to the application of said compound in treating myocardial ischemia. Background technique [0002] Myocardial ischemia is a type of cardiovascular disease with a relatively high incidence rate. During the attack, the patient feels severe paroxysmal dull pain or colic in the precordial area; when repeated attacks and reperfusion occur, it will also cause myocardial cell damage and heart failure. Functional disorders are mainly manifested as: arrhythmia, vascular injury or even blood retention, loss of myocardial function, accelerated ischemia-induced necrosis of damaged myocardial cells, and myocardial cell edema. In my country, more than 3 million patients die from cardiovascular and cerebrovascular diseases every year, and among the surviving patients, 75%...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14A61P9/10A61K31/4709
CPCA61P9/10C07D413/14
Inventor 柳蔚孟姣陈玉华
Owner XIAN PEIHUA UNIV
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