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Pyrazine derivative and preparation method as well as application thereof to pharmacy

A technology of pyrazines and derivatives, which is applied in the field of pyrazines and can solve the problems of poor drug efficacy, large toxic and side effects, and weak antioxidant effects

Active Publication Date: 2012-01-11
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the antioxidant effect of ligustrazine is weak, and its bioavailability is low, so it needs multiple administrations to reach the effective concentration clinically.
[0009] At present, there is no specific drug for the treatment of stroke, and the few drugs that have been marketed are difficult to meet the requirements due to poor curative effect or severe side effects

Method used

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  • Pyrazine derivative and preparation method as well as application thereof to pharmacy
  • Pyrazine derivative and preparation method as well as application thereof to pharmacy
  • Pyrazine derivative and preparation method as well as application thereof to pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] The synthesis of embodiment 1, TN-2 ( figure 1 )

[0085] Add 200mL of methanol to a 500mL three-necked flask, add 2.0g (0.012mol) of 3,6-dimethyl-2,5-pyrazinedicarbaldehyde, then add 4.3g (0.048mol) of tert-butylhydroxylamine, and heat to reflux 3h. Separation by column chromatography (ethyl acetate 100%) gave 1.0 g of light yellow solid compound TN-2. Yield 26.8%, mp: 198-201°C. 1 H NMR (CDCl 3 ): 1.61(s, 18H), 2.48(s, 3H), 2.50(s, 3H), 7.83(s, 2H); ESI-MS: 307[M+H] + , 329[M+Na] + ;Anal.(C 12 H 19 N 3 O) C.H.N; found C 62.52%, H 8.73%, N 18.19%; requires: C, 65.13; H, 8.65; N, 18.99.

[0086]

Embodiment 2

[0087] The synthesis of embodiment 2, TN-2 ( figure 2 )

[0088] Add 5.6g (0.02mol) of 2,5-di-tert-butylaminomethyl-3,6-dimethylpyrazine into a 250mL round bottom flask, add an appropriate amount of methanol, and add 1.64g (0.005mol) of Na 2 WO 4 · 2H 2 O, 30% H 2 O 2 10mL, stirred at room temperature for 2h. Filter, evaporate methanol, add saturated Na 2 S 2 O 3 , extracted with ethyl acetate, and evaporated most of the ethyl acetate. After separation by column chromatography (ethyl acetate 100%), a white solid TN-21.97g was obtained with a yield of 32%, and the detection data was the same as above.

Embodiment 3

[0089] The synthesis of embodiment 3, TN-4

[0090] Add 2.88g (0.02mol) of 2-methylquinoxaline in the three-necked bottle of 250mL, 20mg benzoyl peroxide, add 80mL CCl 4 , Reflux at 70°C for 10h. After cooling and filtering, the crude product of 2-bromomethylquinoxaline was obtained. The compound was not separated, and an excess of tert-butylamine was added, and stirred at room temperature for 3h. 1.25 mg of 5-tert-butylaminomethylquinoxaline was obtained with a yield of 29.1%.

[0091] Add 60mL methanol to the 670mg (0.006mol) compound obtained above, Na 2 WO 4 · 2H 2 O 0.18g, 30%H 2 O 21.75mL, react at room temperature for 2.5h. Separation by column chromatography (ethyl acetate:petroleum ether=4:1) gave the light yellow compound TN-3, 460mg, yield 35.9%. 1 HNMR (CDCl 3 ): 1.70(s, 9H), 7.77(m, 2H), 8.03(m, 2H), 8.14(s, 1H), 10.49(s, 1H); ESI-MS: 230[M+H] + ;Anal.(C 13 H 15 N 3 O) C.H.N; found C 67.80%, H 6.90%, N 17.86%; requires: C, 68.10; H, 6.59; N, 18.33. ...

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Abstract

The invention relates to a pyrazine derivative which has a structure shown in a general formula I, and also discloses a synthesis method of the pyrazine derivative. The compound has an anti-oxidation effect and a thrombolysis effect, can be used for treating cerebral apoplexy caused by ischemia and can also be used for preparing medicaments for treating nerve system diseases, infectious diseases, metabolic system diseases, cardiac-cerebral vascular system diseases, degenerative aging diseases and the like caused by excess production of free radical and / or thrombosis.

Description

technical field [0001] The present invention relates to a kind of pyrazine compound, its preparation method and its preparation are used for the treatment and prevention of nervous system disease, heart, cerebrovascular system disease and degenerative aging disease caused by excessive production of free radicals and / or thrombosis, metabolism Application in drugs for systemic diseases, etc. Background technique [0002] Oxygen is very important to human and animal life. As part of normal metabolism, the human body produces a variety of reactive oxygen species free radicals (ROS), and the human body has a variety of mechanisms to inactivate ROS. Under normal conditions, ROS are produced at a rate that does not exceed the ability of tissues to metabolize them, but under certain circumstances ROS can rise to levels that exceed these protective mechanisms (e.g. due to radiation, environmental factors, excessive iron ion loading, etc. ), or when these mechanisms go awry (such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12C07D241/42C07D241/24A61K31/4965A61K31/498A61K31/497A61P9/00A61P25/08A61P25/16A61P25/14A61P25/28A61P9/10A61P31/18A61P25/00A61P25/04A61P11/00A61P1/00A61P3/10A61P19/02A61P29/00A61P11/06A61P1/16A61P37/06A61P1/18A61P13/12A61P37/02A61P3/04A61P27/02A61P27/06A61P27/14A61P27/12A61P35/00A61P43/00
CPCC07D495/04C07D241/12C07D241/42C07D241/24A61P1/00A61P1/04A61P1/16A61P1/18A61P3/00A61P3/04A61P3/10A61P5/00A61P9/00A61P9/10A61P11/00A61P11/06A61P13/12A61P17/00A61P19/02A61P21/02A61P25/00A61P25/04A61P25/08A61P25/14A61P25/16A61P25/28A61P27/00A61P27/02A61P27/06A61P27/12A61P27/14A61P29/00A61P31/00A61P31/18A61P35/00A61P37/02A61P37/06A61P43/00
Inventor 王玉强孙业伟于沛杜静张高小
Owner JINAN UNIVERSITY
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