Biguanide derivatives for preventing and treating infarction diseases and their application

A biguanide derivative and infarcting technology, applied in blood diseases, extracellular fluid diseases, cardiovascular system diseases, etc., can solve the problems of ineffective effect, lack of action form and mechanism, etc.

Active Publication Date: 2021-09-14
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Evidence-based medicine has confirmed that in the treatment of diabetes, metformin can not only reduce sugar and improve blood lipid metabolism, but also reduce the morbidity and mortality of cardiovascular diseases, but there is still a lack of reports on its specific mode of action and mechanism.
In previous studies, we have preliminarily verified that metformin has the effect of inhibiting thrombosis, but its antithrombotic effect is not obvious compared with the existing antithrombotic drugs commonly used in clinical practice.

Method used

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  • Biguanide derivatives for preventing and treating infarction diseases and their application
  • Biguanide derivatives for preventing and treating infarction diseases and their application
  • Biguanide derivatives for preventing and treating infarction diseases and their application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In this example, guanidinated metformin derivatives were synthesized, specifically including compounds 1-4.

[0024] 1. Synthesis of compound 1: N-(4-dimethylaminobenzylidene) metformin

[0025] Take 1.29g (10.0mmol) of metformin, 1.49g (10.0mmol) of 4-dimethylaminobenzaldehyde, 150mL of ethanol, and 2mL of acetic acid in a 250mL flask, and carry out a stirring reaction at 78°C. The progress of the reaction was detected by TCL, and the reaction was basically complete after about 6 hours. Add sodium bicarbonate to adjust the pH value to neutral to quench the reaction, then spin dry under reduced pressure to obtain a crude product, and then use petroleum ether: ethyl acetate = 2:1 (v / v) as an eluent to pass through a silica gel column, 2.3 g of compound 1 was obtained as a white powder with a yield of 90%. R f is 0.6 (dichloromethane:methanol:glacial acetic acid=9:1:0.025).

[0026] Compound 1 was detected by proton NMR spectrum, carbon NMR spectrum and mass spectrome...

Embodiment 2

[0045] In this example, sulfonamide metformin derivatives were synthesized, specifically including compounds 11-20.

[0046] 1. Synthesis of compound 11: N-(2,2,2-trifluoroethylsulfonyl) metformin

[0047] Take 1.29g (10.0mmol) metformin, 1.82g (10.0mmol) 2,2,2-trifluoroethylsulfonyl chloride, 300mL anhydrous acetone, 0.056g (1mmol) potassium hydroxide in a 500mL flask, and stir overnight at room temperature. Use TCL to detect the reaction process. When there is no obvious change in the reaction product, add dilute hydrochloric acid to adjust the pH value to neutral to quench the reaction, then spin dry under reduced pressure to obtain the crude product, and then use petroleum ether:ethyl acetate=2:1 (v / v) was used as an eluent to pass through a silica gel column to obtain 2.5 g of compound 11 as a white powder, with a yield of 90%. R f is 0.7 (dichloromethane:methanol:glacial acetic acid=9:1:0.025).

[0048] Compound 11 was detected by H NMR spectrum, C NMR spectrum and ma...

Embodiment 3

[0097] In this example, amidated metformin derivatives were synthesized, specifically including compounds 5-10.

[0098] 1. Synthesis of compound 5: N-(2,2,2-trifluoroacetyl) metformin

[0099] Take 1.29g (10.0mmol) metformin, 2.10g (10.0mmol) trifluoroacetic anhydride, 300mL anhydrous acetone, 0.056g (1mmol) potassium hydroxide in a 500mL flask, and stir overnight at room temperature. Use TCL to detect the reaction process. When there is no obvious change in the reaction product, add dilute hydrochloric acid to adjust the pH value to neutral to quench the reaction, then spin dry under reduced pressure to obtain the crude product, and then use petroleum ether:ethyl acetate=2:1 (v / v) was used as an eluent to pass through a silica gel column to obtain 2.0 g of white powder compound 5 with a yield of 89%. R f is 0.7 (dichloromethane:methanol:glacial acetic acid=9:1:0.025).

[0100] Compound 5 was detected by proton nuclear magnetic spectrum, carbon nuclear magnetic spectrum an...

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Abstract

The invention provides biguanide derivatives for preventing and treating infarction diseases, and the application of the biguanide derivatives in preparing medicines for preventing and treating infarction diseases. The biguanide derivatives provided by the present invention have anti-platelet effects, have obvious inhibitory effects on the formation of pulmonary embolism, arterial thrombosis and venous thrombosis, and can effectively reduce the size of cerebral infarction and cardiac infarction, and have obvious effects on cerebral infarction and myocardial infarction. The improvement effect, and the effect is obviously better than the positive control drug aspirin. The biguanide derivatives provided by the present invention can also reduce the gastrointestinal side effects and bleeding risks generally present in existing clinical antithrombotic drugs.

Description

technical field [0001] The invention belongs to the field of medicines, and relates to biguanide derivatives for preventing and treating infarction diseases, and the application of the biguanide derivatives in preparing medicines for preventing and treating infarction diseases. Background technique [0002] Nowadays, with the changes in people's lifestyle and diet structure, vascular diseases based on thrombosis have become the biggest threat to human life. At present, there are about 415 million diabetic patients in the world, and about 5 million people die from diabetes and its complications every year, and about 3.2 million diabetic patients die from its thrombotic complications. At present, antithrombotic drugs used clinically generally have increasing tolerance and side effects, among which bleeding risk and gastrointestinal side effects are the most common and serious side effects. For example, aspirin, the most widely used antithrombotic drug in clinical practice, ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/26C07C311/09C07C311/14C07C311/03A61P7/02A61P9/10
Inventor 黄文
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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