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Preparation and application of 6,7-disubstituted-4-aromatic quinoline compound

A compound, quinoline technology, applied in the field of 6,7-disubstituted-4-aryl heteroquinoline compounds, can solve problems affecting tumor metastasis, neovascularization process, tumor drug resistance, etc.

Inactive Publication Date: 2018-07-24
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that the interaction between c-Met and membrane receptors affects the role of signaling molecules, further affecting tumor invasion, metastasis and angiogenesis, leading to the emergence of tumor drug resistance

Method used

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  • Preparation and application of 6,7-disubstituted-4-aromatic quinoline compound
  • Preparation and application of 6,7-disubstituted-4-aromatic quinoline compound
  • Preparation and application of 6,7-disubstituted-4-aromatic quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Example 1 N-(3-fluoro-4-((6-methoxy-7-(3-morpholino)quinolin-4-yl)oxy)phenyl)-1-(4-fluorobenzene base)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

[0082] ESI-MS m / z:693.71; 1 H NMR (400MHz, DMSO-d 6 )δ11.95(s, 1H), 9.17(s, 1H), 8.63(s, 1H), 8.61(d, J=2.3Hz, 1H), 8.58(d, J=5.5Hz, 1H), 8.11( dd, J=12.9, 2.1Hz, 1H), 7.67(d, J=8.9Hz, 1H), 7.62(s, 1H), 7.51(dd, J=8.8, 3.7Hz, 2H), 7.50–7.47(m ,2H),7.46–7.42(m,2H),6.63(d,J=5.2Hz,1H),4.28(d,J=5.7Hz, 2H),3.98(s,3H),3.51(d,J= 11.8Hz, 2H), 2.99–2.87(m, 2H), 2.32(s, 2H), 1.80(d, J=13.4Hz, 2H), 1.55–1.42(m, 2H), 0.93(d, J=6.3 Hz,2H).

[0083] Step 1 Preparation of 1-(4-(3-chloropropoxy)-3-methoxy)acetophenone (II)

[0084] Add 3-methoxy-4-hydroxyacetophenone (249g, 1.5mol) and anhydrous potassium carbonate (579.6g, 2.1mol) into 1250mL acetone, control the temperature below 25°C, and slowly add 1-bromo -3-Chloropropane (661.3g, 4.2mol) / acetone (1200mL), dropwise, stirred overnight at room temperature. After the reacti...

Embodiment 2

[0113] N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl )-1-(4-fluorophenyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

[0114] ESI-MS m / z:706.27.

Embodiment 3

[0116] N-(3-fluoro-4-((6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-1- (4-Fluorophenyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

[0117] ESI-MS m / z:693.27.

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Abstract

The invention relates to a 6,7-disubstituted-4-aromatic quinoline derivative shown as a general formula I as well as pharmaceutically-acceptable salt, a hydrate, a solvate and pro-drug thereof, wherein substituents R1, X and Y have meanings given in the description. The invention further relates to a compound with a strong effect on inhibiting c-Met kinase shown as the general formula I and further relates to application of the compound and pharmaceutically-acceptable salt, a hydrate, a solvate and pro-drug thereof to preparation of a drug for treating a disease caused by the abnormally-high expression of the c-Met kinase, in particular to application to preparation of a drug for treating and / or preventing a cancer.

Description

technical field [0001] The present invention relates to 6,7-disubstituted-4-aryl heteroquinoline compounds, their geometric isomers and their pharmaceutically acceptable salts, hydrates, solvates or prodrugs, their preparation methods and containing said The pharmaceutical composition of the compound, and its use in the preparation of medicines for treating and / or preventing cancer. Background technique [0002] Malignant tumor is a disease that seriously endangers human health and life. The receptor tyrosine kinase c-Met is an important target for antitumor therapy. c-Met is not only abnormally expressed in a variety of malignant tumors, but also regulates the process of tumor cell growth, invasion, metastasis and apoptosis, and also interacts with a variety of membrane receptors. Studies have shown that the interaction between c-Met and membrane receptors affects the role of signaling molecules, further affecting tumor invasion, metastasis and angiogenesis, resulting in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D519/00A61K31/5377A61K31/496A61K31/4709A61P35/00
CPCC07D471/04C07D519/00
Inventor 唐启东郑鹏武朱五福段永丽熊荷花赵兵兵贾双庄迎梅梅瀚汤晟
Owner JIANGXI SCI & TECH NORMAL UNIV
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