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Aryl substituted piperazine carbonyl derivative as well as preparation method and application thereof

A derivative, aryl technology, applied in the pharmaceutical field, can solve the problems of poor oral bioavailability, low neurobehavioral toxicity, induced bleeding, etc.

Active Publication Date: 2014-04-16
NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The second technical problem to be solved by the present invention is to disclose the application of the above-mentioned aryl-substituted piperazine carbonyl derivatives as brain neuroprotective agents in the treatment of ischemic stroke, so as to overcome the existing problems in the prior art of inducing hemorrhage and difficulty in penetrating Defects such as blood-brain barrier, poor oral bioavailability, low selectivity and high neurobehavioral toxicity

Method used

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  • Aryl substituted piperazine carbonyl derivative as well as preparation method and application thereof
  • Aryl substituted piperazine carbonyl derivative as well as preparation method and application thereof
  • Aryl substituted piperazine carbonyl derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 Ethyl 2-methylphenoxyacetate

[0055] Add 2-methylphenol (5.3g, 0.0490mol), ethyl chloroacetate (6.3mL, 0.0588mol), acetonitrile (30mL) and potassium carbonate (6.8g, 0.0490mol) into a 100mL eggplant-shaped flask, heat up to reflux , After reacting for 5 hours, it was filtered while it was hot, and the filtrate was spin-dried. The raffinate was distilled under reduced pressure, and the fraction at 102-106°C / 0.08mmHg was collected to obtain 6.0 g of a clear oil with a yield of 63.0%, and TLC showed a pure point.

Embodiment 2

[0056] Example 2 Ethyl 4-methylphenoxyacetate

[0057] Add 4-methylphenol (5.3g, 0.0490mol), ethyl chloroacetate (6.3mL, 0.0588mol), acetonitrile (30mL) and potassium carbonate (6.8g, 0.0490mol) into a 100mL eggplant-shaped flask, heat up to reflux , After reacting for 5 hours, it was filtered while it was hot, and the filtrate was spin-dried. The raffinate was distilled under reduced pressure, and the fraction at 110-114°C / 0.08mmHg was collected to obtain 5.6g of a clear oil with a yield of 58.0%, and TLC showed a pure point.

Embodiment 3

[0058] Example 3 2-(2-naphthyloxy) ethyl acetate

[0059] Add ethyl naphthol (7.1g, 0.0490mol), ethyl chloroacetate (6.3mL, 0.0588mol), acetonitrile (30mL) and potassium carbonate (6.8g, 0.0490mol) into a 100mL eggplant-shaped bottle, raise the temperature to reflux, and react After 5 hours, it was filtered while it was hot, the filtrate was spin-dried, left to cool, and the oil was separated into a solid, which was recrystallized with absolute ethanol to obtain 10 g of a light pink solid with a yield of 88.5%, and TLC showed a pure point.

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Abstract

The invention discloses aryl substituted piperazine carbonyl derivative as well as a preparation method and application thereof. The aryl substituted piperazine carbonyl derivative is free alkali or salt of a compound adopting a general formula (I) shown in the Specification, wherein the salt is one of hydrochloride, hydrobromide, sulfate, trifluoroacetate, tartrate, lactate or mesylate; Ar independently represents aryl, substituted heterocyclic ring or substituted aryl; R1 independently represents (-O-CH2-) or (-CH=CH-); R2 and R3 can be the same or different, and respectively and independently represents H, halogen, alkyl, halogen substituted alkyl, nitro, amino, nitrile group, hydroxyl, alkoxy, aryl alkoxy, heterocyclic ring alkoxy, aryl, substituted heterocyclic ring or substituted aryl. The aryl substituted piperazine carbonyl derivative can be applied to the preparation of drugs for treating cerebral arterial thrombosis.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a substituted aryl-substituted piperazine carbonyl derivative, a preparation method thereof, and an application of the derivative in preparing a brain neuroprotective agent. Background technique [0002] Stroke is one of the diseases with the highest mortality and disability rate today, and nearly 80% of strokes are ischemic strokes. The survival of brain cells after a stroke depends on how much neurons are damaged, that is, how much blood flow to the brain that supplies cells with oxygen and nutrients is reduced. When ischemic stroke occurs, the cerebral blood flow in the ischemic core is severely reduced, and irreversible damage occurs to the brain tissue after 60-90 minutes; while the cerebral blood flow in the peripheral ischemic penumbra of the core is relatively reduced, but the cell metabolism Within a few hours after the occurrence of ischemia, the abnormal electrical activity and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/192C07D317/60A61K31/495A61K31/496A61P9/10
CPCC07D295/185C07D295/192C07D317/60
Inventor 吴斌王晶王垚许逸李萍张晓平
Owner NANJING MEDICAL UNIV
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