Unlock instant, AI-driven research and patent intelligence for your innovation.
Anilinoquinazoline compound containing nitroimidazole group and preparation method and application thereof
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A compound and nitro technology, applied in the field of aniline quinazoline compounds and their preparation, can solve the problems of insignificant curative effect, lack of similar compounds and the like
Active Publication Date: 2017-04-19
INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
View PDF2 Cites 5 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
[0005] The present invention aims at the technical defects of the prior art, and provides a kind of anilinequinazoline compound containing nitroimidazole group and its preparation method and application, so as to solve the technical problem of lacking a similar compound in the prior art
[0007] Another technical problem to be solved by the present invention is that the curative effect of drugs used to inhibit the EGFR signaling pathway in the prior art is not obvious
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
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 14
[0060] Example 1 Preparation of 4-hydroxymethylpiperidine-1-carboxylate tert-butyl ester
[0061] Synthesized with reference to the literature J.Med.Chem., 2002, 45, 1300. White solid; melting point 74.3-76.1°C; yield 93.8%. MS M / z: 214.77 [M-1]; 1 H NMR (400MHz, DMSO-d 6 )δ0.95(ddd, J 1 =24.8Hz, J 2 =12.8Hz, J 3 =4.4Hz, 2H), 1.37(s, 9H), 1.49(m, 1H), 1.59(d, J=13.2Hz, 2H), 2.65(s, 2H), 3.23(t, J=6.0Hz, 2H) ), 3.93 (d, J=12.4 Hz, 2H), 4.42 (t, J=5.2 Hz, 1H).
Embodiment 24
[0062] Example 2 Preparation of 4-methylbenzenesulfonic acid-(1-tert-butoxycarbonylpiperidin-4-yl)methyl ester
[0063] Synthesized with reference to the literature J.Med.Chem., 2002, 45, 1300. White solid; melting point 72.4-73.6°C; yield 85.2%. MS M / z: 370.18[M+1]; 1 H NMR (400MHz, DMSO-d 6 )δ0.96(ddd, J 1 =24.4Hz, J 2 =12.4Hz, J 3 =4.4Hz, 2H), 1.36(s, 9H), 1.53(d, J=11.2Hz, 2H), 1.76(m, 1H), 2.41(s, 3H), 2.63(s, 2H), 3.87(d , 4H), 7.47(d, J=8.0Hz, 2H), 7.77(d, J=8.0Hz, 2H).
Embodiment 34
[0064] Example 3 Preparation of 4-p-toluenesulfonyloxymethylpiperidine methanesulfonate
[0065] Synthesized with reference to J.Org.Chem.2010, 75, 8117. White solid; melting point 113.0-114.5°C; yield 84.3%. MS M / z: 270.38[M+1]; 1 H NMR (400MHz, DMSO-d 6)δ1.31(m, 2H), 1.72(d, J=12.8Hz, 2H), 1.93(m, 1H), 2, 32(s, 3H), 2.42(s, 3H), 2.83(m, 2H) ), 3.23(d, J=12.8Hz, 2H), 3.92(d, J=6.0Hz, 2H), 7.48(d, J=8.4Hz, 2H), 7.78(d, J=8.4Hz, 2H), 8.12(br s, 1H), 8.50(br s, 1H).
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
Login to View More
Abstract
The invention provides a brand new anilinoquinazoline compound of the structure in the formula (I). The anilinoquinazoline compound has a tyrosinekinase inhibiting effect. Real-time fluorogenic quantitative PCR measurement results indicate that the VEGF expression quantity is reduced by 1000 times or more through the target compound, the inhibiting effect on VEGF expression is quite obvious, and the inhibiting activity is far higher than that of vandetanib. Further experiments indicate that the target compound has the better antineoplastic activity compared with vandetanib under the anoxia condition and is expected to be the medicine for treating tumors.
Description
technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a nitroimidazole group-containing anilinequinazoline compound and a preparation method and application thereof. Background technique [0002] The following descriptions of the background related to the present invention are provided to assist an understanding of the present invention and should not be considered as prior art to the present invention. All cited publications are incorporated by reference in their entirety. [0003] Tumor cells grow with blood vessels as the center. Cells that are more than 180 μm away from blood vessels are prone to form necrotic areas due to decreased oxygen concentration and lack of nutrients. The low oxygen concentration area at the front of the necrotic area is hypoxic tissue. Hypoxic cells account for about 10-50% of tumor cells. %, most of them are in the G0 phase of cell dynamics, showing no proliferation or slow proliferation,...
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
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More
IPC IPC(8): C07D401/14A61K31/517A61P35/00
CPCC07D401/14
Inventor 李祎亮魏会强李德冠唐卫生段玉清尚海花樊赛军
Owner INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
Login to View More 
Login to View More 
