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Oxadiazole compound and preparation method thereof, medicine composition and application thereof

A technology of oxadiazoles and compounds, applied in the field of synthesis of pharmaceutical compounds

Active Publication Date: 2013-05-15
SHANGHAI JIAOTONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] At present, there is no drug for the treatment of diseases caused by Coxsackie virus. Therefore, it is urgent to find anti-Coxsackie virus active compounds with better therapeutic effect, lower toxicity, and better safety, and develop treatments for diseases caused by Coxsackie virus. disease

Method used

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  • Oxadiazole compound and preparation method thereof, medicine composition and application thereof
  • Oxadiazole compound and preparation method thereof, medicine composition and application thereof
  • Oxadiazole compound and preparation method thereof, medicine composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0212] Embodiment 1: Intermediate Ia of the present invention 1 Synthesis

[0213]

[0214] 50g of 3,5-dimethyl-4-hydroxybenzonitrile and 47g of hydroxylamine hydrochloride were added to 1000ml of ethanol, heated to reflux for 4 hours, detected by thin layer chromatography, 3,5-dimethyl-4-hydroxybenzonitrile The basic reaction is complete. After distilling off ethanol, add 1000ml of tetrahydrofuran, slowly add 286g of trifluoroacetic anhydride, heat and reflux for 4 hours, after cooling, filter to obtain 30g of compound Ia of the present invention 1 , namely 2,6-dimethyl-4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl-)phenol, which is a solid.

[0215] Ia 1 of 1 HNMR (DMSO, 400 MHz) δ: 3.942 (s, 6H), 7.299 (s, 2H).

Embodiment 2

[0216] Embodiment 2: Intermediate 2,6-dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl-)phenol Ia of the present invention 2 Synthesis

[0217] Adopt the preparation method of embodiment 1, replace trifluoroacetic anhydride with acetic anhydride, obtain 27g intermediate Ia 2 , namely 2,6-dimethyl-4-(5-methyl-1,2,4-oxadiazol-3-yl-)phenol.

[0218] Ia 2 of 1 HNMR (DMSO, 400 MHz) δ: 3.942 (s, 6H), 3.845 (s, 3H), 7.299 (s, 2H).

Embodiment 3

[0219] Embodiment 3: the synthesis of compound 1 of the present invention

[0220] 20g compound Ia 1 , 1,2 dibromoethane 102g, potassium carbonate 5.6g (40.8mmol), was added to 500ml of acetonitrile, heated to reflux, reacted overnight, cooled to room temperature. Filtration, the filter cake was washed with methanol, and the filtrate was concentrated to obtain 3-[3,5-dimethyl-4-(2-bromoethoxy)phenyl]-5-(trifluoromethyl)-1,2 , 22g of 4-oxadiazole white solid compound.

[0221] 5g of 3-[3,5-dimethyl-4-(2-bromoethoxy)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole, 3-hydroxy- 2.3 g of 5-methylisoxazole and 5.5 g of potassium carbonate were added to 100 ml of acetonitrile, heated to reflux, monitored by thin-layer chromatography, and cooled to room temperature after the disappearance of raw materials. After filtration, the filtrate was concentrated to obtain 4.9 g of compound 1 of the present invention, namely 3-[3,5-dimethyl-4-[2-(5-methylisoxazole-3-oxyl)ethoxy] Phenyl]-5-(trif...

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Abstract

The invention provides an oxadiazole compound, a pharmaceutically acceptable salt of the oxadiazole compound, a preparation method of oxadiazole, a medicine composition and application of oxadiazole. The oxadiazole compound contains coxsackie virus and has the structure as shown in formula (I), wherein R is CH3 or CF3, R' and R'' are respectively H, alkyl or halogen; A is O and S; n ranges from 1 to 6; X is O, S or NH; Y is alkyl, unsubstituted naphthenic base, monosubstituted naphthenic base, disubstituted naphthenic base, polysubstituted naphthenic base, unsubstituted aromatic base, monosubstituted aromatic base, disubstituted aromatic base, polysubstituted aromatic base, unsubstituted 5-6 membered heterocyclic radical, monosubstituted 5-6 membered heterocyclic radical, disubstituted 5-6 membered heterocyclic radical or polysubstituted 5-6 membered heterocyclic radical. Compared with the prior art, the oxadiazole compound provided by the invention has high anti-coxsackie virus effect, low toxicity and high safety.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical compounds, and in particular relates to oxadiazole compounds and a preparation method thereof, as well as pharmaceutical compositions containing oxadiazole compounds and applications thereof. Background technique [0002] Infectious diseases caused by enteroviruses occur frequently worldwide. Enteroviruses belong to the Picornaviridae family, including Polio viruses, Cosxackie viruses, EHCO viruses (Enteric cytopathogenic human orphan virus) and New enteroviruses, etc. Viruses have multiple serotypes, and at least 70 types can invade various tissues, such as nerves, myocardium, muscles, skin and conjunctiva, etc., causing many infectious diseases all over the world. Picornaviruses can invade various tissue systems such as the respiratory tract, intestinal tract, skin, muscle, heart, liver, adrenal gland, and central nervous system, leading to diverse clinical manifestations. Common cli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D413/14C07D417/12C07D417/14C07D403/12C07D487/04C07D498/04C07D473/00C07D473/18C07D473/30C07D473/32C07D473/34A61K31/4245A61K31/427A61K31/425A61K31/433A61K31/501A61K31/506A61K31/519A61K31/52A61K31/53A61P31/14
CPCC07D413/14A61K31/433C07D417/14A61K31/506A61K31/427C07D417/12A61K31/425A61K31/501A61K31/4245C07D271/06A61K31/14C07D413/12A61P31/14
Inventor 罗先金叶伟东
Owner SHANGHAI JIAOTONG UNIV
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