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Application of tetrazole compounds to anti-epileptic medicines

A technology of antiepileptic drugs and compounds, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, drug combination, etc., can solve the problems of side effects and tolerance

Inactive Publication Date: 2017-10-24
王增涛
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these drugs are able to protect patients from various epileptic convulsions to varying degrees, their side effects and tolerability prevent their use in long-term treatment

Method used

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  • Application of tetrazole compounds to anti-epileptic medicines
  • Application of tetrazole compounds to anti-epileptic medicines

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0020] Taking 5-(o-tolyl)-1H-tetrazole (compound I4) as an example to introduce the general synthesis method of compound I

[0021] In a round bottom flask, add sodium azide (3mmol), triethylamine hydrochloride (3mmol), toluene (5mL) and compound III4 (1mmol), heat at 120ºC, react for about 12h, follow the reaction by TLC, after the reaction is complete, drop Add 6N hydrochloric acid, filter with suction, wash with water, wash with dichloromethane and recrystallize with ethanol to obtain the pure compound I4 as light yellow solid. The melting point is 153-155°C, and the yield is 51.5%. 1 H-NMR (DMSO-d 6 , 600 MHz, δ ppm): 7.69 (d, 1H, ArH, J=7.8 Hz), 7.49 (td, 1H, ArH, J=1.2, 7.2 Hz), 7.44 (d, 1H, ArH, J=7.8 Hz ), 7.40 (td, 1H, ArH, J=1.2, 7.2 Hz), 2.48 (s, 3H, CH 3 ).

Embodiment A

[0022] Embodiment A: anticonvulsant pharmacological experiment and neurotoxicity experiment

[0023] Taking 5-(o-tolyl)-1H-tetrazole (compound I4) as an example, the maximum electroshock test (MES) was used in pharmacological experiments to evaluate the anticonvulsant activity of the compound. Get 9 Kunming mice (male and female) and divide them into 3 groups, 3 in each group, respectively intraperitoneally inject 30mg / kg, compound I4 of 100mg / kg dose, carry out electrical stimulation to the tested mice after 0.5 hours, observe Protection of compounds against electrical stimulation-induced convulsions. It is valid if the hind limbs are not stiff. For compounds that are 100% effective at a dose of 100 mg / kg, the half effective dose is further evaluated by Bliss method. The half effective dose of compound I4 was determined to be 9.6 mg / kg. The mouse rotarod ataxia test is used to evaluate the neurotoxicity of the compound. After intraperitoneal injection for 0.5 hours, the mo...

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Abstract

The invention relates to compounds serving as anti-epileptic medicines and as shown in a general formula I and a general formula II, wherein R1 is selected from substituted groups and polysubstituted group derivatives such as 2-chlorine; 3-chlorine; 4-chlorine; 2-methyl; 3-methyl; 4-methyl; 2-fluorine; 3-fluorine; 4-fluorine; 2-methoxyl; 3-methoxyl; 4-methoxyl; 2-nitryl; 3-nitryl; 4-nitryl; 2-bromine; 3-bromine; 4-bromine; 2-tertiary butyl; 3-tertiary butyl; 4-tertiary butyl; 2-amino; 3-amino; and 4-amino. R2 is selected from: cyclopropyl; 3-pyrazolyl; 4-oxazolyl; 2-pyridyl; 2-oxocyclopentane; 5-(2-methyl pyridyl); 4-thiazolyl; 7-indolyl; 5-(1H-benzimidazolyl); 1-(2,3-dihydro-1H-indenyl); 6-(1H-indazolyl); 4-isoquinolyl; and 7-(1-indenone).

Description

technical field [0001] The present invention relates to a class of tetrazole compounds used as antiepileptic drugs. Background technique [0002] Epilepsy is a group of chronic brain diseases characterized by transient central nervous system dysfunction caused by abnormal discharge of brain neurons, and has the characteristics of sudden and recurrent seizures. A variety of antiepileptic drugs have been used in clinical applications, such as phenobarbital, carbamazepine, phenytoin, and valproic acid. Although these drugs are able to protect patients from various epileptic convulsions to varying degrees, their side effects and tolerability prevent their use in long-term treatment. In order to improve the therapeutic effect and eliminate or reduce side effects, new compounds with new structural features and new mechanisms of action are needed. Contents of the invention [0003] In order to solve the disadvantages of the above problems, the present invention provides a use o...

Claims

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Application Information

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IPC IPC(8): C07D257/04A61K31/41A61P25/08
CPCC07D257/04
Inventor 王增涛王甜甜董士阳许军刘燕华
Owner 王增涛
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