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7-alkoxy-[1,2,4]triazolo[3,4-b]benzothiazol-3(2h)-one derivatives used as antiepileptic drugs and preparation methods thereof

An anti-epileptic drug, drug technology, applied in drug combination, nervous system diseases, organic chemistry, etc., can solve problems such as side effects and discomfort

Inactive Publication Date: 2016-08-24
全哲山
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are a variety of antiepileptic drugs available in clinical application, such as phenobarbital, phenytoin, carbamazepine, valproic acid, lamotrigine, felbamate, topiramate, etc., although these drugs can be used in different degrees Protect patients from various types of epileptic convulsions, but their side effects and discomfort prevent their use in long-term treatment

Method used

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  • 7-alkoxy-[1,2,4]triazolo[3,4-b]benzothiazol-3(2h)-one derivatives used as antiepileptic drugs and preparation methods thereof
  • 7-alkoxy-[1,2,4]triazolo[3,4-b]benzothiazol-3(2h)-one derivatives used as antiepileptic drugs and preparation methods thereof
  • 7-alkoxy-[1,2,4]triazolo[3,4-b]benzothiazol-3(2h)-one derivatives used as antiepileptic drugs and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0018] Taking 7-butoxyl-[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one (compound Id) as an example to introduce the synthetic general method of compound I

[0019] Compound II (10 mmol) and urea (80 mmol) were heated to melt. The reaction was tracked by TLC. After the reaction was complete, the reactant was poured into hot water and stirred for 0.5 hours to obtain the crude product, which was separated by column chromatography (dichloromethane:methanol, 50:1) to obtain compound Id. Melting point 162-164°C, yield 63.5%; 1 H NMR (300MHz, CDCl 3 ): δ10.15(s, 1H, -NH), 7.89(d, J=8.8Hz, 1H, Ar-H), 7.06(s, 1H, Ar-H), 6.95(d, J=8.8Hz, 1H, Ar-H), 3.99(t, J=6.3Hz, 2H, -OCH 2 -), 1.90-1.67 (m, 2H, -CH 2 -), 1.62-1.39 (m, 2H, -CH 2 -), 0.99(t, J=7.2Hz, 3H, -CH 3 ).IR(KBr, cm -1 ): 3152 (N-H), 1697 (C=O). MS m / z 264 (M+1). Anal. Calcd. for C 12 h 13 N 3 o 2 S: C, 54.74; H, 4.98; N, 15.96. Found: C, 54.83; H, 4.79; N, 16.01.

Embodiment A

[0020] Example A: Anticonvulsant Pharmacological Experiment and Neurotoxicity Experiment

[0021] Taking 7-butoxy-[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one (compound Id) as an example to introduce the pharmacological experiment method of compound I

[0022] The anticonvulsant activity of the compounds was evaluated using the maximal electroshock test (MES). Get 9 Kunming mice (male and female) and be divided into 3 groups, 3 in every group, respectively oral administration 30mg / kg, 100mg / kg, the compound Id of 300mg / kg dosage, carry out 60 to experiment mice after 0.5 hour Hertz, 110 volts, 0.3 second single electrical stimulation, observe the protection of the compound 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 the modified Cole's method. The measured half effective dose of compound Id was 34.08 mg / kg. The m...

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Abstract

The invention provides 7-alkoxy-[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones of formula (I), and a preparation method thereof. The invention also relates to the use of the compounds in the preparation of antiepileptic medicines.

Description

technical field [0001] The present invention relates to a preparation method of 7-alkoxy-[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-one derivatives and their use in the preparation of antiepileptic drugs the use of. Background technique [0002] Epilepsy is a collective term used to describe a group of chronic convulsive disorders that are characterized by transient seizures accompanied by loss or disturbance of consciousness. Epilepsy, as the second most common disease in neurology after cerebrovascular disease, not only harms patients physically and mentally, but also seriously affects study, work and daily life, and even leads to accidental death. It is a common disease that seriously threatens people's lives and health. [0003] According to WHO statistics, there are about 50 million people with epilepsy worldwide, 80% of whom are in developing countries, and 2 million new epilepsy patients appear every year. The incidence rate of epilepsy is different in different count...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04A61K31/429A61P25/08
Inventor 全哲山邓先清刘大川
Owner 全哲山
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