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Flunarizine derivative, preparation method and use thereof

A technology of flunarizine and derivatives, which is applied in the field of pharmacy and can solve problems such as clinical use restrictions

Inactive Publication Date: 2013-06-05
王化录
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, flunarizine may cause central nervous system side effects such as extrapyramidal system reactions. Although this side effect can disappear after drug withdrawal, it is very limited in clinical use.

Method used

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  • Flunarizine derivative, preparation method and use thereof
  • Flunarizine derivative, preparation method and use thereof
  • Flunarizine derivative, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment one: the preparation of triflunarizine

[0065] Dissolve 9g of p-fluorocinnamyl chloride in 150ml of ethanol, 18g of di-p-fluorobenzylpiperazine in 150ml of ethanol, add them together to the reactor, heat to reflux, keep reflux for 2 hours, evaporate the ethanol to dryness, and dissolve the residue in ethyl acetate Esters—extracted with water, washed the organic phase with water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain triflunarizine C as a light yellow solid 26 h 25 f 3 N 2 . Elemental analysis results: C: 73.80%; H: 5.95%; F: 13.51%; N: 6.67%. Calculated values: C: 73.92%; H: 5.96%; F: 13.49%; N: 6.63%. Proton NMR spectrum: 7.01-7.30 (6H); 7.53-7.62 (6H); 6.75 (1H); 6.44 (1H); 4.50 (1H); 3.92 (2H); 2.53-2.8098H).

[0066] The corresponding salt can be obtained by further reaction of triflunarizine with acid.

Embodiment 2

[0067] Embodiment two: replace the p-fluorocinnamyl chloride in embodiment one with p-chlorocinnamyl chloride, use similar method, can obtain chloroflunarizine C 26 h 25 CIF 2 N 2. Elemental analysis results: C: 71.20%; H: 5.68%; Cl: 8.12%; F: 8.65%; N: 6.35%. Calculated: C: 71.15%; H: 5.73%; Cl: 8.08%; F: 8.66%; N: 6.68%. Proton NMR spectrum: 7.21-7.52 (12H); 6.71 (1H); 6.45 (1H); 4.5 (1H); 3.42 (2H); 2.5-2.8 (8H). Chlorflunarizine can be further reacted with acid to obtain the corresponding salt.

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Abstract

The invention discloses flunarizine derivative, a preparation method and use of the flunarizine derivative. The flunarizine derivative, the preparation method and the use of the flunarizine derivative are specially characterized in that halogen is used to replace hydrogen, tri-flunarizine and chlorine flunarizine on specific loca, wherein the tri-flunarizine is (E)-1-[double(4- fluorinated phenyl)methyl]4-[2-allyl-3-(4-fluorinated phenyl)]-piperazine, and the chlorine flunarizine is (E)-1-[double(4-fluorinated phenyl)methyl]4-[2-allyl-3-(4-chlorphenyl)]-piperazine. Hydroxylation metabolism of carbon atoms on corresponding loca is blocked. Compared with the flunarizine, the derivative has stronger antagonism of calcium ion and weak antagonism of 5-hydroxytryptamine receptor, and extrapyramidal system reaction and other side effects in a clinical using process are avoided under the premise of improving pharmaceutical activity.

Description

technical field [0001] The invention belongs to the field of pharmacy, and specifically relates to a compound with calcium ion antagonism effect of increasing tissue and organ blood supply, a preparation method and application. Background technique [0002] Ischemic cerebrovascular disease (ICVD) accounts for the majority of cerebrovascular diseases and has become a major disease that threatens human health and social development. Dilation of carotid arteries, vertebrobasilar arteries, and capillaries to increase blood supply to the brain is one of the most important means of treating cerebral ischemia. The most direct effect of ischemia is brain tissue ischemia, and Ca 2+ Overloading and a series of harmful metabolisms triggered by it are the final common pathway leading to cell death. Therefore, reducing calcium influx into brain tissue cells is one of the important means for the treatment of ischemic cerebrovascular diseases. [0003] The calcium ion antagonist flunariz...

Claims

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Application Information

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IPC IPC(8): C07D295/073A61P9/10A61P3/14A61P39/06A61P9/08
Inventor 王化录
Owner 王化录
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