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[1, 3 and 4] oxadiazoles derivative and application thereof

A technology of oxadiazole and benzisoxazole, applied in the field of medicinal chemistry, can solve problems such as QT gap prolongation

Active Publication Date: 2014-04-02
HUAZHONG UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs have adverse effects such as QT gap prolongation, hyperprolactinemia and weight gain

Method used

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  • [1, 3 and 4] oxadiazoles derivative and application thereof
  • [1, 3 and 4] oxadiazoles derivative and application thereof
  • [1, 3 and 4] oxadiazoles derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1, 2-((3-(4-(3-benzisothiazole)-1-piperazinyl)propylthio)-5-phenyl-1,3,4-oxadiazole

[0070] ①Add 6.1g of benzoic acid and 40ml of absolute ethanol to the flask, slowly add 2ml of concentrated sulfuric acid dropwise under stirring, heat, reflux for 6 hours, cool to room temperature, evaporate the solvent under reduced pressure, and use 30ml of ethyl acetate and 25ml of water Dilute, extract the aqueous layer with ethyl acetate (30mlX2), combine several layers, and wash several layers with saturated sodium bicarbonate solution until neutral, then wash with saturated NaCl, dry with anhydrous magnesium sulfate, filter, and reduce pressure The solvent was evaporated to obtain ethyl benzoate.

[0071] ②Add 40ml of ethanol and 6g of ethyl benzoate into a 100ml three-necked flask, and slowly add 12.5g of 85% hydrazine hydrate dropwise under stirring. water, solids precipitated, and stood for 30 minutes until the solids were completely precipitated, filtered and washed...

Embodiment 2

[0076] Example 2, 2-((3-(4-(3-(6-fluoro-benzoisoxazole))-1-piperidinyl)propylthio)-5-phenyl-1,3,4 -Oxadiazole

[0077] ①Put 6.1g of benzoic acid and 40ml of absolute ethanol into the flask, slowly add 2ml of concentrated sulfuric acid dropwise under stirring, heat and reflux for 6 hours, cool to room temperature, evaporate the solvent under reduced pressure, dilute with 30ml of ethyl acetate and 25ml of water , the aqueous layer was extracted with ethyl acetate (30mlX2), and several layers were combined, and several layers were washed with saturated sodium bicarbonate solution to neutrality, then washed with saturated NaCl, dried with anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. Remove the solvent to get ethyl benzoate

[0078] ②Add 40ml of ethanol and 6g of ethyl benzoate into a 100ml three-necked flask, and slowly add 12.5g of 85% hydrazine hydrate dropwise under stirring. water, solids precipitated, placed for 30 minutes, until the solids ...

Embodiment 3

[0082] Example 3, 2-((3-(4-(3-benzisothiazole)-1-piperazinyl)propylthio)-5-(4-methoxyphenyl)-1,3,4 -Oxadiazole

[0083] Using p-methoxybenzoic acid as the starting material, the target compound was obtained according to the method of Example 1.

[0084] 1 HNMR (CDCl 3 )δ2.08-2.11(m, 2H), 2.61(t, 2H, J=13.6Hz), 2.69(t, 4H, J=9.6Hz), 3.38(t, 2H, J=14.4Hz), 3.57( t, 4H, J=9.6Hz), 3.87(s, 3H), 6.99(d, 2H, J=8.8Hz), 7.35(t, 1H), 7.46(t, 1H), 7.80(d, 1H, J =8.4Hz) 7.89-7.95 (m, 3H) MS (ESI) m / z 468.2 ([M+H] + ).

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Abstract

The present invention belongs to the medicinal chemistry field, and specifically discloses a [1,3,4]oxadiazole derivative with the structure of general formula (I) and pharmaceutically acceptable salt thereof. The compound can be used to prepare a medicine for preventing or treating a disease of the central nervous system.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a novel [1,3,4]oxadiazole derivative, their preparation method and their application in treating mental and nervous diseases. Background technique [0002] Schizophrenia is a disorder characterized by deep cognitive and emotional dissociations that affect the most basic human behaviors, such as language, thought, perception, and self-awareness. The symptoms of the disease include a wide range, the most common being mental disorders, such as hallucinations, paranoia and delusions. Worldwide, about 1% of people suffer from schizophrenia, and only 5% of all treated patients eventually recover fully. Typical antipsychotic drugs (eg, chlorpromazine, haloperidol) block dopamine D2 receptors, leading to severe blockade of dopamine receptors including extrapyramidal side effects (EPS), tardive dyskinesia, and increased prolactin secretion. In addition, typical antischizop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12C07D417/14C07D413/14A61K31/496A61K31/454A61P25/18
CPCC07D413/14C07D417/14C07D417/12A61P25/18
Inventor 张桂森陈寅徐祥清刘笔锋冯晓钧赵松刘世成于民权兰昱邱印利
Owner HUAZHONG UNIV OF SCI & TECH