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Oxadiazoles derivative, preparation method and medical application thereof

A technology of compounds and mixtures, applied in the field of oxadiazole derivatives, their preparation and their application in medicine, can solve the problems of not finding a good IDO inhibitor

Active Publication Date: 2017-08-11
JIANGSU HENGRUI MEDICINE CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] IDO inhibitors have good application prospects as drugs in the pharmaceutical industry, but no good IDO inhibitors have yet been found as marketed drugs. In order to achieve better tumor treatment effects and better meet market demand, the inventor hopes Can develop a new generation of selective IDO inhibitors with high efficiency and low toxicity

Method used

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  • Oxadiazoles derivative, preparation method and medical application thereof
  • Oxadiazoles derivative, preparation method and medical application thereof
  • Oxadiazoles derivative, preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0222] MS m / z(ESI):481.2[M+1]

[0223] 1 HNMR (400MHz, DMSO-d 6 )δ11.71(s,1H),8.96(s,1H),7.15-7.20(m,1H),7.05-7.07(m,2H),6.68-6.70(m,1H),6.56(s,2H) ,3.79-3.83(m,1H),3.70-3.76(m,1H),2.85-2.87(m,2H),2.06-2.11(m,2H).

Embodiment 2

[0225] MS m / z(ESI):481.2[M+1]

[0226] 1 HNMR (400MHz, DMSO-d 6 )δ11.72(s,1H),8.97(s,1H),7.15-7.20(m,1H),7.06-7.10(m,2H),6.71-6.73(m,1H),6.56(s,2H) ,3.99-4.06(m,2H),2.58-2.64(m,2H),2.32-2.36(m,2H).

[0227] Example 3,4

[0228] 4-(((1r,3r)-3-aminocyclobutane)thio)-N-(3-bromo-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole- 3-formamidine 3

[0229] 4-(((1s,3s)-3-aminocyclobutane)thio)-N-(3-bromo-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole- 3-formamidine 4

[0230]

[0231]

[0232] The crude product 1h (200 mg, 0.47 mmol) was dissolved in 10 mL of tetrahydrofuran, 0.38 mL of 2.5M sodium hydroxide solution was added, and the reaction was stirred for 1 hour. The reaction solution was poured into 30 mL of water, extracted with ethyl acetate (30 mL × 2), the organic phases were combined, washed with saturated ammonium chloride solution (30 mL × 2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residu...

Embodiment 3

[0234] MS m / z(ESI):402.2[M+1]

[0235] 1 HNMR (400MHz, DMSO-d 6 )δ8.96(s,1H),7.15-7.20(m,1H),7.04-7.06(m,1H),6.67-6.70(m,1H),3.65-3.69(m,1H),3.26-3.28( m,1H),2.73-2.75(m,2H),1.73-1.80(m,2H).

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Abstract

The invention relates to an oxadiazoles derivative, a preparation method and a medical application thereof, in particular to the oxadiazoles derivative of general formula 1, the preparation method, a drug composition containing the oxadiazoles derivative, and the application thereof in preparing medicines which can prevent and / or cure diseases with an IDO mediated tryptophan metabolic pathway histopathologic characteristic. The diseases comprise cancer, alzheimer disease, autoimmune disease, depression, anxiety disorder, cataract, psychologic obstacle and HIV disease. Each substituent of the general formula (1) is same with the definition in the description.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to oxadiazole derivatives, their preparation method and their application in medical research. The invention discloses oxadiazole derivatives as IDO inhibitors for treating colorectal disorders mediated by IDO. Diseases characterized by the pathology of amino acid metabolism pathways, including cancer, Alzheimer's disease, autoimmune diseases, depression, anxiety, cataracts, psychological disorders, and AIDS. Background technique [0002] Tumor biotherapy is a new treatment for tumor prevention and treatment using modern biotechnology and related products. Because of its safety, effectiveness, and low adverse reactions, it has become the fourth mode of tumor treatment after surgery, radiotherapy, and chemotherapy (ClinCancer Res, 1997; 3:2623-2629), which obtains the anti-tumor effect by mobilizing the host's natural defense mechanism, such as inhibiting the tumor immune escape mechanism media...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/08C07D413/12C07D413/14A61K31/4245A61K31/454A61P35/00A61P25/28A61P37/02A61P25/24A61P25/22A61P27/12A61P31/18A61P35/02A61P19/00
CPCC07D271/08C07D413/12C07D413/14
Inventor 吕贺军费洪博贺峰陶维康
Owner JIANGSU HENGRUI MEDICINE CO LTD