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7-oxopyridinopyrimidine compound as well as medicinal composition and application thereof

A technology of oxopyridines and compounds, applied in the field of chemical medicine, can solve the problems that cannot solve the clinical pressure of drug resistance, wild-type cell toxicity and side effects, poor selectivity, etc.

Active Publication Date: 2013-04-03
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In short, the current EGFR-TKI still cannot solve the clinical pressure caused by drug resistance, and most of the existing drugs are EGFR reversible or irreversible inhibitors based on quinazoline or quinolineamine Toxic side effects caused by poor selectivity of wild-type cells are also inevitable
Therefore, new types, especially compounds with novel frameworks, are urgently needed to solve the problems of drug resistance, poor selectivity, etc.

Method used

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  • 7-oxopyridinopyrimidine compound as well as medicinal composition and application thereof
  • 7-oxopyridinopyrimidine compound as well as medicinal composition and application thereof
  • 7-oxopyridinopyrimidine compound as well as medicinal composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0192] As the compound of formula I-III described in the invention, those skilled in the art can make 4-chloro-2-methylmercaptopyrimidine-5-ethyl carbonate or 2,4-dichloro -5-Bromopyrimidine was synthesized by several steps reaction as the starting material. (see examples 1, 9, 32, etc. for specific synthesis steps)

[0193] In one embodiment, the present application provides a method for treating transitional proliferative diseases or symptoms such as tumors in humans or other mammals by using the compounds of formulas I-III and pharmaceutically acceptable salts thereof.

[0194] In one embodiment, the compounds designed in this application and their pharmaceutically acceptable salts can be used to treat or control non-small cell lung cancer, small cell lung cancer, lung adenocarcinoma, lung squamous cell carcinoma, pancreatic cancer, breast cancer, prostate cancer , liver cancer, skin cancer, epithelial cell carcinoma, gastrointestinal stromal tumor, leukemia, histiocytic l...

Embodiment 2

[0238] N-(3-(2-((2-methoxy-4-(4-methyl-1-piperazinyl)phenyl)amino)7-oxo-6-phenylpyrido[2,3 -d]pyrimidine-8(7hydrogen)-substituted)phenyl)acrylamide (XTF-251)

[0239]

[0240] The synthesis method is as in Example 1.

[0241] 1 H NMR(400MHz,DMSO)δ10.39(s,1H),8.81(s,1H),8.20(s,1H),8.12(s,1H),7.90(d,J=8.0Hz,1H),7.71 (d,J=7.6Hz,1H),7.66(s,1H),7.53(t,J=8.0Hz,1H),7.43(t,J=8.0Hz,1H),7.36(t,J=7.2Hz ,1H),7.33(d,J=8.8Hz,1H),7.08(d,J=7.6Hz,1H),6.53(d,J=2.0Hz,1H),6.49(dd,J=10.0,16.8Hz ,1H),6.28(dd,J=2.0,16.8Hz,1H),6.04(brs,1H),5.78(dd,J=2.0,10.0,1H),3.78(s,3H),3.06(m,4H ),2.29(m,4H)LCMS(ESI):m / z 588.0[M+H] +

Embodiment 3

[0243] N-(3-(6-benzyl-2-((4-(4-(dimethylamino)-1-piperidinyl)-2-methylphenyl)amino)-7-oxopyrido[ 2,3-d]pyrimidine-8(7hydro)-substituted)phenyl)acrylamide (XTF-230)

[0244]

[0245] The synthesis method is as in Example 1.

[0246] 1 H NMR(400MHz,DMSO)δ10.29(s,1H),8.76(s,1H),8.64(s,1H),7.75(d,J=8.4Hz,1H),7.62(s,1H),7.55 (s,1H),7.42(t,J=8.0Hz,1H),7.30-7.34(m,4H),7.06-7.24(m,1H),7.06(brs,1H),6.95(d,J=7.6 Hz,1H),6.63(s,1H),6.48(dd,J=10.0,16.8Hz,1H),6.28(dd,J=2.0,16.8Hz,1H),5.79(dd,J=10.0,2.0Hz ,1H),3.81(s,2H),3.56(d,J=6.4Hz,2H),2.50-2.57(m,2H),2.12-2.18(m,7H),2.06(s,3H),1.77- 1.80(m,2H),1.38-1.46(m,2H).LCMS(ESI):m / z 614.3[M+H] +

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Abstract

The invention discloses a 7-oxopyridinopyrimidine compound with a structure shown by formula (I) and a pharmaceutically acceptable salt or a stereoisomer or prodrug molecule thereof. The compound or pharmaceutically acceptable salt provided by the invention can effectively suppress the growth of multiple tumor cells and generate an inhibition effect on other proteases of the Her family of EGFR (epidermal growth factor receptor), can be used for preparing anti-tumor drugs and can overcome the drug resistance induced by the existing drugs gefitinib, erlotinib and the like.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and in particular relates to 7-oxopyridopyrimidine compounds and their pharmaceutical composition and application. Background technique [0002] Whether in the world or in China, chronic diseases (or non-communicable diseases) represented by malignant tumors (cancer), cardiovascular diseases, and diabetes are becoming more important long-term threats. On May 19, 2008, the World Health Organization clearly pointed out in its latest report that non-communicable diseases are becoming the deadliest "killer" of human beings. Among them, cancer ranks first. In 2004, 7.4 million people died of cancer worldwide, and the situation in China was even more serious. According to the third national retrospective survey on causes of death released at the end of April 2008, the cancer death rate among urban and rural residents in China has increased by more than 80% in the past 30 years; among them, one o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/519A61P35/00A61P35/02
CPCC07D471/04A61K31/519A61P35/00A61P35/02A61P35/04
Inventor 丁克徐田锋丁芳张连文陆小云李伟华丁健耿美玉
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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