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Compound in category of dihydro quinolines, preparation method, and composition of medication

A compound and mixture technology, applied in the fields of medicinal chemistry and pharmacotherapy, can solve the problems of unknown toxicity of 4-anilinoquinazoline compounds, and achieve the effects of abundant raw materials, mild reaction conditions and easy availability of raw materials

Inactive Publication Date: 2007-05-09
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] There are still many problems in the development of EGFR inhibitors, such as the unknown toxicity of 4-anilinoquinazoline compounds that have attracted people's attention, the problem of enzyme selectivity, etc.

Method used

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  • Compound in category of dihydro quinolines, preparation method, and composition of medication
  • Compound in category of dihydro quinolines, preparation method, and composition of medication
  • Compound in category of dihydro quinolines, preparation method, and composition of medication

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 2-Chloro-quinoline-3-carbaldehyde (II-1)

[0052] Add 4.6 g of DMF into a 50 ml round-bottomed flask, and slowly add 26.8 g of POCl dropwise under cooling and stirring in an ice bath 3 . After the dropwise addition, 3.4 g of N-acetanilide was added at one time, and after stirring for 5 minutes, the temperature was raised to 75° C. and refluxed for 16 hours. The reaction solution was poured into 150 ml of ice water, stirred for 30 minutes, a large amount of solids were precipitated, filtered with suction, washed with water, and dried to obtain 3.1 g of 2-chloro-quinoline-3-carbaldehyde as a yellow solid product, with a yield of 64.8%. Mp 144-146°C (lit. 148-149°C).

Embodiment 2

[0054] 2-oxo-1,2-dihydro-quinoline-3-carbaldehyde (III-1)

[0055] Put 3.1 g of 2-chloro-quinoline-3-carbaldehyde (II-1) into 55 ml of 4M hydrochloric acid, stir and reflux for 1 hour, cool to room temperature, a large amount of solid precipitated, suction filtered, washed with water, and dried to obtain a yellow solid product 2.6 grams, yield 92.8%. Mp 300°C. MS-EI 173(M), 144 (100%).

Embodiment 3

[0057] 3-[(Pyridine-3-methylimino)methyl]-1H-quinolin-2-one (IV-1)

[0058] Dissolve 0.5 g of 2-oxo-1,2-dihydro-quinoline-3-carbaldehyde and 0.32 g of 3-aminomethylpyridine in 60 ml of absolute ethanol, stir at reflux for 12 hours, and evaporate most of the The solvent was cooled to room temperature, pumped up, and washed with a small amount of absolute ethanol to obtain 0.6 g of light yellow solid with a yield of 78.9%. Mp 180-182°C; 1 H-NMR (400Hz, DMSO-d6) δ: 4.83 (2H, s), 7.21 (1H, t), 7.33 (1H, d), 7.39 (1H, m), 7.56 (1H, t), 7.76 (1H , d), 7.83 (1H, d), 8.49 (2H, m), 8.59 (1H, d), 8.73 (1H, t). MS-EI 262 (M-1, 100%).

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Abstract

This invention relates to a method for preparing 2-oxo-3-substituted aminoalkyl-1, 2-dihydroquinoline derivatives and their pharmacological applications. The general structure of the derivatives is shown in formula I, and R1, R2, R3, R4, R5, R6 and n are defined therein. The derivatives can be used as small molecular inhibitor of epithelial growth factor receptor, and can block the activity of phosphorylated functional protein of protein tyrosine kinases to regulate the cell growth, multiplication and differentiation. Therefore, the derivatives have potential applications in anti-tumor drugs.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapy, in particular to 2-oxo-3-substituted aminoalkyl-1,2-dihydroquinoline compounds, a preparation method thereof and a pharmaceutical composition containing such compounds. Background technique [0002] Cancer is a chronic disease that seriously endangers human health. There are 9 million people suffering from cancer in the world every year, and 6 million patients who die from cancer. In my country, the annual incidence of cancer is about 1.2 million, and the number of people who die from cancer every year is as high as 900,000, and more than 1.5 million patients are waiting for treatment. Overcoming the difficulty of cancer is a major task for medical workers. [0003] The drugs that have been studied and applied by people for a long time regard cancer cells as the target of drugs. Therefore, cytotoxic drugs have always been the main drugs for treating cancer, but the problem...

Claims

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Application Information

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IPC IPC(8): C07D215/22C07D401/04A61K31/4709A61K31/47A61P35/00
Inventor 罗小民李剑蒋华良沈旭柳红沈建华朱维良付莉莉李林梅长林
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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