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Spiro compound used for treating cerebral apoplexy

A technology of compounds and hydrates, applied in the field of medicine

Inactive Publication Date: 2018-09-07
HEILONGJIANG UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is currently no drug that is very effective in the treatment of ischemic stroke

Method used

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  • Spiro compound used for treating cerebral apoplexy
  • Spiro compound used for treating cerebral apoplexy
  • Spiro compound used for treating cerebral apoplexy

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment approach

[0053] Hereinafter, the present invention is described in more detail to facilitate understanding of the present invention.

[0054] 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

[0055] Example 1: 7-methoxy-2-(1'-methylspiro[chroman-2,4'-piperidin]-6-yl)quinazolin-4(1H)-one (SPQU-1)

[0056]

[0057] Add 50ml of dioxane to a 150ml flask, and add 2-bromo-7-methoxyquinazolin-4(1H)-one (2.0mmol) while stirring, 1'-methylspiro[chroman Pyran-2,4'-piperidine]-6-boronic acid pinacol ester (3.0mmol), then add Pd(dppf)Cl 2 (15 mg), potassium acetate (4.0 mmol). Under the protection of nitrogen, it was heated to 90° C. to react overnight. After filtration, the solvent was distilled off from the filtrate under reduced pressure, and the residue was purified by silica gel column (cyclohexane / ethyl acetate=10:1) to obtain 661 mg of the target compound, 84.6%.

[0058] Mass Spectrum (ESI): 392.19[M+H] +

[0059] Elemental analysis: theoretical value C, 70.57; H, 6.44; N, 10.73; O, 12.26

[0060] Found value C, 70.88; H, 6.35; N, 10.39; O, 12.38

[0061] Hydrogen spectrum (400MHz, DMSO) δ7.65(s,1H),7.54(d,1H),7.31(d,1H),7.09(d,1H),6.58(d,1H),6.30(s,1H) , 4....

Embodiment 2

[0062] Example 2: 4-hydroxyl-6-(4-oxo-7-(trifluoromethyl)-1,4-dihydroquinazolin-2-yl)spiro[chroman-2, 4'-piperidine]-1'-tert-butyl carboxylate (SPQU-2)

[0063]

[0064] Add 50ml of dioxane to a 150ml flask, and add 2-bromo-7-trifluoromethylquinazolin-4(1H)-one (2.0mmol) while stirring, 4-hydroxy-1'-tert-butoxy Carbonyl-spiro[chroman-2,4'-piperidine]-6-boronic acid pinacol ester (3.0mmol), then add Pd(dppf)Cl 2 (15 mg), potassium acetate (4.0 mmol). Under the protection of nitrogen, it was heated to 90° C. to react overnight. After filtration, the solvent was distilled off from the filtrate under reduced pressure, and the residue was purified by silica gel column (petroleum ether / ethyl acetate=10:1) to obtain 661 mg of the target compound, 84.6%.

[0065] Mass Spectrum (ESI): 532.20[M+H] +

[0066] Elemental analysis: theoretical value C, 61.01; H, 5.31; F, 10.72; N, 7.91; O, 15.05

[0067] Measured value C, 61.25; H, 5.08; F, 10.91; N, 7.83; O, 14.93

[0068] Proton...

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Abstract

The invention relates to a spiro compound used for treating cerebral apoplexy. Shown by a test result, the compound can remarkably improve nerve injury caused by ischemia reperfusion of rice undergoing ischemia reperfusion, can remarkably reduce the cerebral infarction percentage and relieve the edema degree of brain tissue of the rice and can lower the water content. Therefore, the compound has an excellent treatment effect for cerebral apoplexy, especially cerebral arterial thrombosis.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular, the invention relates to a spirocyclic compound for treating cerebral apoplexy, especially ischemic apoplexy. Background technique [0002] Cerebrovascular disease is one of the three major diseases that cause human death. Its high mortality and disability rate have brought heavy burdens to society and families. Stroke is one of the most serious diseases, and it is mainly divided into hemorrhagic stroke and ischemic stroke. [0003] Ischemic stroke accounts for about 80% of all strokes, and its incidence increases with age. The occurrence of ischemic stroke is mainly due to the formation of cerebral embolism and local thrombus, which may be vascular narrowing and thromboembolism caused by atherosclerosis, or emboli from the heart flow to the brain with blood and cause cerebral infarction. Embolism; and vascular injury and vascular inflammation caused by various reasons are also ...

Claims

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Application Information

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IPC IPC(8): C07D491/107A61K31/517A61P9/10
CPCA61P9/10C07D491/107
Inventor 周海纯韩东卫王艳丽丁莹郭蕊珠马育轩张晓娟隋思逸
Owner HEILONGJIANG UNIV OF CHINESE MEDICINE
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