Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

N-aryl unsaturated fused ring tertiary amine compound, preparation method thereof and application thereof to tumor resistance

一种化合物、芳基的技术，应用在N-芳基不饱和稠环叔胺类化合物领域，能够解决生命健康未能达到满意的效果、抗肿瘤和抗癌药物不能满足临床需求等问题

Inactive Publication Date: 2012-11-21
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
View PDF3 Cites 17 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing anti-tumor and anti-cancer drugs are still far from meeting the clinical needs
The treatment of solid tumors, which are the most serious threat to human life and health and account for more than 90% of malignant tumors, has not achieved satisfactory results.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • N-aryl unsaturated fused ring tertiary amine compound, preparation method thereof and application thereof to tumor resistance
  • N-aryl unsaturated fused ring tertiary amine compound, preparation method thereof and application thereof to tumor resistance
  • N-aryl unsaturated fused ring tertiary amine compound, preparation method thereof and application thereof to tumor resistance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] Example 1: N 1 -[4-(2-chloro)quinazolinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (compound 1, method one)

[0143]

[0144] The reaction was refluxed for 3 hours. Yellow solid 282mg, yield 87%, melting point 136-138°C; 1 H NMR (CDCl 3 ): δppm 2.12 (2H,m,3'-CH 2 ),2.86(2H,t,J=6.8Hz,4'-CH 2 ),3.81(3H,s,OCH 3 ),4.07(2H,t,J=6.8Hz,2'-CH 2 ),6.55(1H,dd,J=8.8Hz and 2.8Hz,ArH-7'),6.70(1H,d,J=8.8Hz,ArH-8'),6.81(1H,d,J=2.8Hz, ArH-5'),7.13(1H,m,ArH-6),7.32(1H,dd,J=8.8Hz and 1.2Hz,ArH-5),7.63(1H,m,ArH-7),7.78(1H , dd, J=8.4Hz and 1.2Hz, ArH-8). MS m / z(%)326(M+H + ,100),328(M+3 + ,31).

Embodiment 2

[0145] Example 2: N 1 -[4-(2-Methyl)quinazolinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (compound 2, method 1)

[0146]

[0147] The reaction was refluxed for 3 hours. Yellow solid 242mg, yield 79%, melting point 134-136°C; 1 H NMR (CDCl 3 ): δppm 2.11 (2H,m,3'-CH 2 ),2.73(3H,s,CH 3 ),2.88(2H,t,J=6.8Hz,4'-CH 2 ),3.79(3H,s,OCH 3 ),4.05(2H,t,J=6.8Hz,2′-CH 2 ),6.53(1H,dd,J=9.2Hz and 2.8Hz,ArH-7'),6.63(1H,d,J=8.4Hz,ArH-8'),6.78(1H,d,J=2.8Hz, ArH-5'),7.12(1H,m,ArH-6),7.32(1H,dd,J=8.4Hz and 1.2Hz,ArH-5),7.62(1H,m,ArH-7),7.79(1H , d, J=8.0Hz, ArH-8). MS m / z(%)306(M+H + ,100).

Embodiment 3

[0148] Example 3: N 1 -[4-(2-Methoxy)quinazolinyl]-6-methoxy-1,2,3,4-tetrahydroquinoline (compound 3)

[0149]

[0150] 2-Chloro-4-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)quinazoline (81mg, 0.25mmol) and NaOCH 3(40mg, 0.75mmol) was added into anhydrous methanol (4.0ml), and refluxed for 2 hours. Insoluble matter was filtered off, and silica gel column chromatography (eluent: ethyl acetate and petroleum ether gradient elution, ethyl acetate 5%-80%) was separated to obtain 71 mg of a light yellow solid with a yield of 88% and a melting point of 161-163°C. 1 H NMR (CDCl 3 ): δppm 2.09 (2H,m,3'-CH 2 ),2.85(2H,t,J=6.8Hz,4'-CH 2 ),3.80(3H,s,OCH 3 ),4.03(2H,t,J=6.8Hz,2'-CH 2 ),4.09(3H,s,OCH 3 ),6.53(1H,dd,J=8.8Hz and 2.8Hz,ArH-7'),6.67(1H,d,J=8.8Hz,ArH-8'),6.79(1H,d,J=2.8Hz, ArH-5'),6.98(1H,m,ArH-6),7.32(1H,dd,J=8.4Hz and 0.8Hz,ArH-5),7.56(1H,m,ArH-7),7.68(1H , d, J=8.4Hz, ArH-8). MS m / z(%)322(M+H + ,100).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention relates to an N-aryl unsaturated fused ring tertiary amine compound, with a plurality of anticancer activities and shown as a general formula I, or a pharmaceutically acceptable salt thereof and a preparation method thereof, and a pharmaceutical composition containing the compound and application of the pharmaceutical composition to preparation of antineoplastic medicaments. R1, R2, R5, R6, X, Y, Q, W, n1 and n2 are defined as in the description.

Description

technical field [0001] The present invention relates to N-aryl unsaturated fused-ring tertiary amine compounds or pharmaceutically acceptable salts thereof with multiple anticancer activities, a preparation method thereof, a pharmaceutical composition containing the compound and its use in the preparation of antitumor drugs application. Background technique [0002] Tumors, especially cancer, are currently one of the major diseases that seriously affect people's lives. Since the 1970s, the incidence and mortality of cancer in China have been on the rise. Among urban residents, cancer has accounted for the first cause of death. According to statistics, 1 out of every 4 deaths in China is due to cancer. In recent years, international pharmaceutical companies have developed inhibitors targeting cell signal transduction molecules or new blood vessels, anti-metastasis or anti-drug resistance drugs, differentiation inducers, and guided therapy based on the molecular mechanism of...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D403/04C07D413/04C07D215/20A61K31/517A61K31/47A61K31/4709A61K31/538A61K31/55A61P35/00
CPCC07D413/04C07D403/04C07D215/20A61K31/4709A61K31/47A61K31/538A61K31/517C07D401/04A61K31/55C07D215/40C07D215/42C07D473/34A61P35/00A61P35/02C07D473/00C07D473/32C07D473/40
Inventor 谢蓝王晓锋李国雄
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com