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Nitrogen-containing heterocyclic compound for treating brain injury and application thereof

A compound and brain injury technology, applied in the direction of organic chemistry, drug combination, medical preparations containing active ingredients, etc., to achieve the effect of prevention and treatment of brain injury, good therapeutic activity, and broaden the scope

Inactive Publication Date: 2021-07-16
THE SECOND PEOPLES HOSPITAL OF SHENZHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] To sum up, although various chemical and natural medicines are at different research stages, there is no drug that combines cinnamoyl and cannabinoid fragments among the currently marketed drugs for the treatment of brain injury

Method used

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  • Nitrogen-containing heterocyclic compound for treating brain injury and application thereof
  • Nitrogen-containing heterocyclic compound for treating brain injury and application thereof
  • Nitrogen-containing heterocyclic compound for treating brain injury and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of compound 6

[0026] (1) Dissolve compound 1 (166g, 1mol) in dry dichloromethane (500mL) in a reaction flask, add triethylamine (10mol), and add compound 2 (345g, 1.2mol) di Chloromethane (600mL) solution was added dropwise to room temperature and reacted until the reaction was detected by TLC. The reaction solution was suction filtered, the filtrate was concentrated, and silica gel column chromatography (ethyl acetate / petroleum ether=3:1) gave compound 3. The yield was 89%, HPLC purity 98%;

[0027] (2) Add compound 3 (206g, 0.5mol), palladium catalyst Pd(t-Bu 3 P) 2 (6.4g, 0.0125mol) and hexamethyltin (197g, 0.6mol) and 500mL of toluene, heated to reflux and reacted until TLC detected that the reaction of raw materials was complete, quenched with water, extracted and separated, retained the organic phase, and used fluorinated organic phase Washed twice with potassium-saturated ammonia solution, dried over anhydrous magnesium sulfate, f...

Embodiment 2

[0031] Embodiment 2: the effect of the compound shown in formula 6 in treating brain injury

[0032] 1. Animals and materials

[0033] Compound 6, self-made, HPLC purity 99.0%; DW-2000 brain stereotaxic apparatus (Chengdu Taimeng Software Co., Ltd.); SD male rats, SPF grade, 180-220g, 6-8 weeks old (Zhejiang Experimental Animal Center) ; Neonatal mice (Zhejiang Experimental Animal Center); IL-6, IL-1, TNF-α kit (USA eBio-science company); neuron β-tubulin III antibody (USA Co-vanc company); Alexa Fluor 488 goat anti mouse IgG dye and Hoeschst dye (Invitrogen, USA); FBS (Gibco, USA).

[0034] 2. Experimental method

[0035] 2.1 Transwell experiment

[0036] Newborn mice within 1 day were taken out, and the cerebral cortex was separated in an ice bath, digested with 1% trypsin into a single cell suspension, microglial cells were cultured with 10% FBS+DMEM / F12, and neurons were cultured with 2% FBS+DMEM / F12 culture, change the medium every 3 days, purify after 2 weeks, divid...

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PUM

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Abstract

The invention relates to a nitrogen-containing heterocyclic compound for preventing and treating brain injury, which has a protection effect on ICH rat brain injury, can relieve neurological function defects of cerebral hemorrhage rats and reduce the water content of brain tissues, and can be used for preventing and treating brain injury caused by cerebral hemorrhage and the like.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a compound for preventing and treating brain damage, and also relates to a preparation method, pharmaceutical composition and use of the compound. Background technique [0002] Intracerebral hemorrhage (ICH) is one of the main diseases of acute cerebrovascular disease, and it is a common disease in neurology and surgery. It has the characteristics of critical onset, high disability rate and high mortality rate. It occurs within a few hours after the hemorrhage, and the hematoma spreads very quickly after the hematoma appears in the brain. If it is not treated in time, cerebral edema may occur and damage the nerve function. Neurological function further declines in most cases due to secondary injury. [0003] The current drug treatment of brain injury caused by stroke aims to block the neuronal necrosis caused by ischemia, prolong the time of tolerable ischemia and the treatmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185A61K31/495A61P9/10A61P25/00
CPCC07D295/185A61P9/10A61P25/00
Inventor 谭回李维平黄国栋黄贤键
Owner THE SECOND PEOPLES HOSPITAL OF SHENZHEN