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Pyrrolopyridine compounds containing biarylamide structure, preparation method and application thereof

A technology of pyrrolopyridine and arylamide, applied in the field of pyrrolopyridine compounds containing biarylamide structure and its preparation

Inactive Publication Date: 2018-07-27
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, there are few reports on pyrrolopyridine compounds, and no related drugs have been listed yet.

Method used

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  • Pyrrolopyridine compounds containing biarylamide structure, preparation method and application thereof
  • Pyrrolopyridine compounds containing biarylamide structure, preparation method and application thereof
  • Pyrrolopyridine compounds containing biarylamide structure, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0151] N-(4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl)-4-phenylpyridineamide

[0152] Step A Synthesis of 4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine (IV)

[0153] In a 250mL three-necked flask, preheat diphenyl ether (51.843g) until completely dissolved, then add 4-chloro-7-azaindole (9.996g) and 2-fluoro-4-nitrophenol (16.862 g), heat up to 190°C and react for about 1 hour. When the temperature rises to about 130°C, all solids dissolve and the solution appears light yellow. As the temperature rises, the color of the solution deepens and the appearance is dark brown. After the reaction was completed, the reaction liquid was cooled, slowly added dropwise into 400 mL of ethyl acetate and stirred for 2 h, the precipitated solid was suction filtered, and the filter cake was dried to obtain 8.285 g of khaki powder with a yield of 46.3%.

[0154] Step B Synthesis of 4-((1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-3-fluoroaniline (V)

[0155] Add 100mL of ethanol to a 250...

Embodiment 2

[0164] N-(4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl)-4-m-tolylpyridinamide

[0165] ESI-MS[M+H](m / z):439.5

[0166] 1 H NMR(400MHz,DMSO)δ11.85(s,1H),11.13(s,1H),8.90(d,J=4.5Hz,1H),8.51(s,1H),8.23(t,J=11.2Hz ,1H),8.18(d,J=5.3Hz,1H),8.11(s,1H),7.99(d,J=8.2Hz,1H),7.82(s,1H),7.78(d,J=7.6Hz ,1H),7.57(d,J=7.3Hz,1H),7.54–7.50(m,1H),7.49–7.42(m,2H),6.50(d,J=5.1Hz,1H),6.37(s, 1H),2.53(s,3H).

Embodiment 3

[0168] N-(4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl)-4-p-tolylpyridinamide

[0169] ESI-MS[M+H](m / z):439.5

[0170] 1 H NMR (400MHz, DMSO) δ11.40 (d, J = 24.5Hz, 1H), 11.22–11.00 (m, 1H), 8.89 (d, J = 4.7Hz, 1H), 8.50 (s, 1H), 8.25 (d, J=13.1Hz, 1H), 8.18(d, J=5.2Hz, 1H), 8.10(d, J=3.2Hz, 1H), 7.99(d, J=8.7Hz, 1H), 7.91(d ,J=7.6Hz,1H),7.52(d,J=6.8Hz,1H),7.48(d,J=7.2Hz,3H),6.49(d,J=5.1Hz,1H),6.36(s,1H ),6.36(s,1H),2.49(s,3H).

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Abstract

The invention discloses a pyrrolopyridine compound containing a biaryl amide structure, its geometric isomer and its pharmaceutically acceptable salt, hydrate, solvate or prodrug, and a preparation method thereof. The pyrrolopyridine compound containing biarylamide structure of the present invention, and its pharmaceutically acceptable salt, hydrate or solvate are used as active ingredients, mixed with pharmaceutically acceptable carriers or excipients to prepare a composition, And be prepared into a clinically acceptable dosage form. Application of the compound of the present invention in the preparation of medicines for treating and / or preventing proliferative diseases, in the preparation of medicines for treating and / or preventing cancer, in the preparation of medicines for treating and / or preventing prostate cancer, lung cancer and breast cancer .

Description

technical field [0001] The invention relates to a pyrrolopyridine compound containing a biaryl amide structure, in particular to a pyrrolopyridine compound containing a biaryl amide structure and a preparation method and application thereof. Background technique [0002] Malignant tumor is a disease that seriously endangers human life and health. With the change of external factors such as environmental pollution, the number of cancer patients worldwide is increasing year by year. According to the statistics of the World Health Organization (WHO), in the next 20 years, the number of cancer patients worldwide will It is expected to surge by 57%; the number of new cancer patients per year will increase from 14 million in 2012 to 22 million; the number of cancer deaths is expected to increase from 8.2 million in 2012 to 13 million. Moreover, cancer presents a trend of three modernizations and second-tier cancers—development, rejuvenation, and aging, and the "second-tier" trend ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/437A61K31/506A61P35/00A61P35/02
CPCC07D471/04
Inventor 朱五福郑鹏武王文惠唐启东徐珊王林啸武春江涂远彪王勤勤
Owner JIANGXI SCI & TECH NORMAL UNIV