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Picolinamide compound containing triazole or quinolinone structure and application of picolinamide compound

A technology of compound and pyridine, applied in medical preparations containing active ingredients, organic chemistry, drug combination, etc., can solve problems such as the absence of such compounds

Active Publication Date: 2020-01-03
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at the technical defect of prior art, provides the pyridine amide compound containing triazole or quinolinone structure and application thereof, to solve existing A technical problem with such compounds does not yet exist in the technology

Method used

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  • Picolinamide compound containing triazole or quinolinone structure and application of picolinamide compound
  • Picolinamide compound containing triazole or quinolinone structure and application of picolinamide compound
  • Picolinamide compound containing triazole or quinolinone structure and application of picolinamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1 N-ethyl-4-(4-(5-(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxamido)phenoxy)picolinylmethyl Amide

[0105] 1 H NMR (400MHz, DMSO-d 6 )δ10.75(s,1H),8.83(s,1H),8.51(d,J=5.3Hz,1H),8.03(s,1H),8.01(s,1H),7.63(s,5H), 7.41(s,1H),7.23(d,J=8.5Hz,2H),7.17(d,J=3.0Hz,1H),3.28(dd,J=13.3,6.6Hz,2H),2.59(s,3H ),1.09(t,J=7.0Hz,3H).

[0106] ESI-MS m / z:442.18

[0107] Step 1: Preparation of 4-chloropyridine chloride (b)

[0108] Add picolinic acid (10g, 0.081mol), thionyl chloride (50mL) for ultrasonic dissolution and NaBr (0.1g, 0.001mol) to a 150mL round-bottom flask, gradually raise the temperature to 85°C, and reflux for 24h. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and an appropriate amount of toluene was added for use. A pale yellow liquid was obtained with a yield of about 97.5%.

[0109] Step 2: Preparation of ethyl 4-chloropicolinate (c)

[0110] Add dichloromethane (30mL), ethanol (16.43g...

Embodiment 2

[0130] Example 2 N-ethyl-4-(2-fluoro-4-(5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxamido)phenoxy)pyridine Formamide

[0131] 1 H NMR (400MHz, DMSO-d 6 )δ10.96(s,1H),8.86(s,1H),8.55(d,J=5.1Hz,1H),8.10(d,J=12.9Hz,1H),7.85(d,J=8.4Hz, 1H), 7.67(s, 5H), 7.47-7.40(m, 2H), 7.23(d, J=3.3Hz, 1H), 3.31-3.27(m, 2H), 2.59(s, 3H), 1.09(t ,J=6.8Hz,3H).

[0132] ESI-MS m / z:460.17

Embodiment 3

[0133] Example 3 N-ethyl-4-(4-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamido)phenoxy) picolinamide

[0134] 1 H NMR (400MHz, DMSO-d 6 )δ10.76(s,1H),8.84(s,1H),8.52(d,J=5.5Hz,1H),8.04(s,1H),8.02(s,1H),7.78(d,J=4.8 Hz,1H),7.76(d,J=4.7Hz,1H),7.53(d,J=8.6Hz,2H),7.42(d,J=1.9Hz,1H),7.24(d,J=8.8Hz, 2H), 7.19(d, J=2.3Hz, 1H), 3.29(dd, J=13.5, 6.7Hz, 2H), 2.59(s, 3H), 1.10(t, J=7.1Hz, 3H).

[0135] ESI-MS m / z:460.17

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PUM

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Abstract

The invention provides a picolinamide compound containing a triazole or quinolinone structure and application of the picolinamide compound. According to a technical scheme in the invention, extensiveresearch is conducted on the picolinamide compound, and a plurality of structural sites are modified and transformed, so a series of picolinamide derivatives with novel structures are synthesized. Onsuch a basis, the chemical properties and the biological properties of the derivatives are investigated, and results show that the derivatives have strong c-Met kinase inhibition effect and can achieve a treatment effect on diseases caused by abnormal high expression of c-Met kinase. Thus, the invention determines the use of the compound or its derivatives in the preparation of drugs for treatingproliferative diseases or tumors. Experimental results show that the compound has exact and remarkable inhibition effect on tumor cells, so data support is provided for pharmaceutical application of the compound.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to pyridine amide compounds containing triazole or quinolinone structures and applications thereof. Background technique [0002] Malignant tumor is a disease that seriously endangers human health and life. The death rate caused by human malignant tumors ranks second only to cardiovascular diseases. c-Met kinase widely exists in epithelial tissues and plays an important role in embryonic development and wound healing. Recent studies have reported that c-Met kinase is abnormally highly expressed in tumor tissues such as lung cancer, colon cancer, liver cancer, rectal cancer, gastric cancer, renal cancer, ovarian cancer, glioma, melanoma, breast cancer, and prostate cancer. Mutation or Altered Activity. c-Met kinase can promote the proliferation of tumor cells, regulate the migration of tumor cells, enhance the invasion ability of tumor cells and induce tumor angiogenesis...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D409/14A61K31/4439A61K31/5377A61K31/4709A61P35/00
CPCC07D401/12C07D409/14A61P35/00
Inventor 唐启东郑鹏武朱五福熊荷花张建清段永丽
Owner JIANGXI SCI & TECH NORMAL UNIV
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