Hydrazone-containing pyrimidine derivatives and use thereof
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A technology of derivatives and compounds, applied in the field of hydrazone-containing pyrimidine derivatives and their uses, can solve problems such as ROS1 protein dysregulation
Active Publication Date: 2017-09-12
SHENYANG PHARMA UNIVERSITY
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Problems solved by technology
Fusion, overexpression and mutation of ROS1 gene can lead to dysregulation of ROS1 protein
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Embodiment 1
[0115] Step A Isopropyl(2-nitrophenyl)sulfide (Ⅱ)
[0116] Add 509.1g (3.61mol) of o-fluoronitrobenzene and 698.0g (5.06mol) of anhydrous potassium carbonate to 2500mL of dry N,N-dimethylformamide (DMF), slowly drop into 301.8g (3.97mol ) isopropyl mercaptan, after dropping, the temperature was raised to 110° C. for 10 h. After cooling to room temperature, the reaction solution was poured into a large amount of water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 604.6 g of a yellow liquid with a yield of 85.0%.
[0117] Step B 1-Isopropylsulfonyl-2-nitrobenzene (Ⅲ)
[0118] Add 197.1g (1.00mol) of isopropyl (2-nitrophenyl) sulfide to 1500mL of glacial acetic acid, slowly drop into 583.0g (6.00mol) of 35% hydrogen peroxide, raise the temperature to 80°C, and react for 9h. After cooling to room temperature, the reaction solution was poured into a large amount of water, stirred at room temperature for 30 min, filtered wi...
Embodiment 2
[0129] Example 2 (E)-5-chloro-N-(2-(isopropylsulfonyl)phenyl)-2-(2-(pyridin-4-ylmethylene)hydrazino)pyrimidin-4-amine
[0131] Example 3 (E)-5-chloro-N-(2-(isopropylsulfonyl)phenyl)-2-(2-(pyridin-3-ylmethylene)hydrazino)pyrimidin-4-amine
[0132] ESI-MS [M+H] (m / z): 431.1;
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Abstract
The invention relates to hydrazone-containing pyrimidine derivatives represented by general formula I, and optical isomers, pharmaceutically acceptable salts, solvates or prodrugs thereof, a preparation method of above compounds, and a medicinal composition adopting the compounds represented by the general formula I as an active component. Substituent groups R1, R2, R3, Ar and X in the general formula I are as defined in the description. The invention also relates to a strong ALK and ROS1 kinase inhibition effect of the compounds of the general formula I, and an application of the compounds, and the optical isomers and pharmaceutically acceptable salts thereof in the preparation of medicines for treating and / or preventing ALK and ROS1 abnormal expression induced disease, and especially a use in the preparation of medicines for treating and / or preventing cancers.
Description
technical field [0001] The present invention relates to hydrazone-containing pyrimidine derivatives and optical isomers, pharmaceutically acceptable salts, solvates or prodrugs, their preparation methods and pharmaceutical compositions containing the compounds. The present invention also relates to the strong ALK and ROS1 kinase inhibitory effect of the compound, and also relates to the preparation of such compounds and their optical isomers and pharmaceutically acceptable salts for the treatment and / or prevention of ALK and ROS1 abnormalities The application of the drug expressing the caused disease, especially the application in the preparation of the drug for the treatment and / or prevention of cancer. Background technique [0002] The research on kinase target drugs has become an important direction in the research and development of anticancer drugs. Among the currently discovered kinase target drugs, protein kinases are known to be the most studied class. Due to mutat...
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