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Pyrroline-2-one derivative capable of inhibiting cell to release tumor necrotic factor and its preparation and application

A cell-inhibiting, tetrahydropyrrole-based technology, used in anti-tumor drugs, extracellular fluid diseases, anti-bacterial drugs, etc., can solve the problems of difficult production and high drug prices for antibody drugs

Inactive Publication Date: 2011-05-18
TIANJIN HEMAY BIO TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, antibody drugs have disadvantages such as high drug price, difficult production, and immunotoxicity.

Method used

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  • Pyrroline-2-one derivative capable of inhibiting cell to release tumor necrotic factor and its preparation and application
  • Pyrroline-2-one derivative capable of inhibiting cell to release tumor necrotic factor and its preparation and application
  • Pyrroline-2-one derivative capable of inhibiting cell to release tumor necrotic factor and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment

[0222] abbreviation

[0223] CDI: 1,1'-carbonyldiimidazole; DCM: dichloromethane; DCE: 1,2-dichloroethane; THF: tetrahydrofuran; TFA: trifluoroacetic acid; DMAP: 4-(N,N-dimethyl amino)pyridine; TEA: triethylamine; DMF: N,N-dimethylformamide; DMSO: dimethylsulfoxide.

Embodiment 1

[0225] 3,4-Dicyanothiophene

[0226] Add 96.8 grams of 3,4-dibromothiophene, 104 grams of cuprous cyanide and 100 ml of dry DMF to a 2000ml three-neck flask equipped with mechanical stirring, reflux condensing device and inert gas conduit, heat to reflux for 4 hours, and cool to room temperature , add 400 grams of FeCl to the reaction solution 3 ·6H 2 O was dissolved in 700ml of 1.7M hydrochloric acid, and kept at 60-70°C for 30 minutes, and after cooling sufficiently, 500ml of DCM was added. The resulting reaction mixture was divided into 300ml portions, extracted with DCM (300ml x 2), and all DCM layers were combined. Divide the extract into 600ml portions, and use 50ml×2 6N hydrochloric acid, water, saturated Na 2 CO 3 Wash with aqueous solution and saturated saline solution, anhydrous MgSO 4 Dry, filter, evaporate the solvent to dryness to obtain a yellow solid, wash with a mixed solvent of ethyl acetate:petroleum ether=1:1, and filter to obtain 21 g of a white solid....

Embodiment 2

[0228] Thiophene-3,4-dicarboxylic acid

[0229] In a 500ml round bottom flask equipped with electromagnetic stirring and reflux condenser, add 15.978g of 3,4-dicyanothiophene, 43.997g of KOH and 174ml of ethylene glycol, and reflux for 4 hours. After cooling, add 350ml of water to the reaction mixture, extract with diethyl ether (100ml×2), discard the diethyl ether layer, add excess concentrated hydrochloric acid to the water layer under ice-cooling until a white precipitate appears, and dissolve the solid in Diethyl ether (need about 2000ml), the filtrate was extracted with diethyl ether (300ml×3), all ether layers were combined, anhydrous MgSO 4 After drying, filtering, and evaporating the solvent to dryness, 15 g of white solid was obtained, which was recrystallized from water. 1 H NMR (DMSO-d 6 ): δ10.35 (brs, 2H), 8.17 (s, 2H); MS (m / z): 171 [M-1] + .

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PUM

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Abstract

The invention relates to a compound with the function for retraining cell to release TNF alpha, which is represented as formula (I) or (II), relative salt or hydrate used in pharmacy, relative preparation method and application, wherein A, B, E respectively represent CH2, and CO, D represents S, NH, NC1-6 hydrocarbyl group, R represents H, R<3>, R<1> represents 1-4 same or different F, CI, Br, C1-4 hydrocarbyl group, OH, OC1-4 hydrocarbyl group, NO2, NHC(O)C1-4 hydrocarbyl group, NH2, NH(C1-4 hydrocarbyl group, N(C1-4 hydrocarbyl group)2, R<2> represents F, CF3, H, C1-4 hydrocarbyl group.

Description

technical field [0001] The present invention relates to pyrrolin-2-one derivatives which have the activity of inhibiting cell release of tumor necrosis factor (TNF), their preparation method and their application as pharmaceutical active ingredients. Background technique [0002] Tumor necrosis factor (TNFα) is the major cytokine released by monocytes in response to immune stimuli. Administration of TNFα to animals and humans can cause inflammation, fever, abnormal cardiovascular function, hemorrhage, coagulation and a series of acute reactions similar to acute infection and shock state. Excessive or uncontrolled production of TNFα in animals or humans often indicates the following diseases: [0003] 1. Endotoxemia and / or toxic shock syndrome [Tracey et al., Nature 330, 662-4 1987; Hinshaw et al., Circ Shock 30, 279-92 (1990)]; [0004] 2. Cachexia [Dezube et al., Laucet, 335(8690), 662(1990))]; [0005] 3. Adult Respiratory Stress Syndrome (ARDS) [Millar et al., Laucet 2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61K31/454A61P29/00A61P31/00A61P37/00A61P35/00A61P9/00C07D333/00C07D207/00
CPCC07D487/04C07D495/04A61P1/04A61P1/16A61P13/12A61P17/00A61P17/06A61P19/02A61P29/00A61P3/14A61P31/00A61P31/04A61P35/00A61P35/02A61P37/00A61P37/02A61P37/06A61P43/00A61P5/00A61P7/00A61P9/00A61P9/10A61P3/10
Inventor 张和胜曾广怀陈英伟高翳飞张玉梅
Owner TIANJIN HEMAY BIO TECH CO LTD
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