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Indolone derivative, medicinal composition thereof and preparation method and application of indolone derivative

A compound and hydrate technology, applied in the field of medicine and chemical industry, can solve problems such as difficult large-scale production, complex molecular structure, and difficult chemical synthesis

Active Publication Date: 2012-09-19
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the resources of these natural product drugs are limited, their molecular structure is complex, chemical synthesis is difficult, and it is not easy to produce on a large scale. Therefore, it is imperative to find small-molecule anti-tumor drugs with simple structures.

Method used

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  • Indolone derivative, medicinal composition thereof and preparation method and application of indolone derivative
  • Indolone derivative, medicinal composition thereof and preparation method and application of indolone derivative
  • Indolone derivative, medicinal composition thereof and preparation method and application of indolone derivative

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0069] Preparation Example 1: Synthesis of 2-benzoyl-pyrrole

[0070] Under the protection of nitrogen, 3.00g (44.7mmol) pyrrole was dissolved in 60mL ether, 5.86g (90.1mmol) zinc powder was added under stirring at 0°C, and 5.67g (40.3mmol) benzoyl chloride was slowly added dropwise, and the reaction was completed for 1 hr. After filtration, concentration, and silica gel column chromatography, 4.00 g of a yellow-white solid was obtained, with a yield of 58.0%. 1 H-NMR (400MHz, DMSO-d6) δppm: 12.08 (brs, 1H), 7.81-7.79 (m, 2H), 7.63-7.59 (m, 1H), 7.55-7.51 (m, 2H), 7.23-7.21 ( m, 1H), 6.78-6.77 (m, 1H), 6.27-6.26 (m, 1H).

preparation example 2

[0071] Preparation Example 2: Synthesis of 2-propionyl-pyrrole

[0072] Synthesized with reference to the method of Preparation Example 1 to obtain a white solid with a yield of 61.0%. 1 H-NMR (400MHz, DMSO-d6) δppm: 11.76 (br s, 1H), 7.06-7.04 (m, 1H), 6.97-6.95 (m, 1H), 6.16-6.18 (m, 1H), 2.72-2.89 (q, 2H, J=7Hz), 1.08-1.04 (t, 3H, J=7Hz).

preparation example 3

[0073] Preparation 3: 3,5-Dimethyl-1H-pyrrole-2,4-dicarboxylic acid-2-tert-butyl-4-ethyl ester synthesis

[0074] Under cooling in an ice-water bath, dissolve 8.35g (52.8mmol) of tert-butyl acetoacetate in 15mL of glacial acetic acid, and add dropwise an aqueous solution of sodium nitrite (4.50g of sodium nitrite in 10mL of water) while stirring. over 10°C. After dropping, stir at room temperature for 3 hrs to obtain a light yellow transparent solution, which is set aside for use.

[0075] Dissolve 5.87g (45.1mmol) of ethyl acetoacetate in 20mL of glacial acetic acid and heat to 65°C. Slowly add the light yellow transparent solution prepared above dropwise, and add 10.37g of zinc powder in 5 times. The process is exothermic, and the temperature control does not exceed 80°C. After the addition was complete, the temperature was raised to 75° C. for 1 hr. After cooling to room temperature, a white solid precipitated and was filtered. Petroleum ether was recrystallized to...

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Abstract

The invention belongs to the field of pharmaceutical chemicals, relates to an indolone derivative, a medicinal composition thereof and a preparation method and application of the indolone derivative, and particularly relates to a compound shown in a formula I, a stereoisomer or pharmaceutically acceptable salt or hydrate of the compound. By the aid of the indolone derivative, a signal transmission function of a VEGF (vascular endothelial growth factor) receptor can be blocked, neovascularization ability of vascular endothelial cells is blocked, tumor neovascularization is suppressed, and malignant metastasis of tumor is stopped.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to an indolinone derivative, its stereoisomer, its cis-trans isomer, or a pharmaceutically acceptable salt thereof. The present invention also relates to a pharmaceutical composition containing the indolinone derivatives, as well as a preparation method and application of the indolinone derivatives. Background technique [0002] Cancer is a disease that seriously threatens human health. Since the advent of the first anticancer drug, nitrogen mustard, in the 1940s, scientists have isolated and extracted several natural products with potential cytotoxic activity from plants. Active compounds, among which vinblastine, etoposide, paclitaxel, etc. have been approved for clinical treatment of cancer. However, these natural product drugs have limited resources, complex molecular structures, difficult chemical synthesis, and difficult large-scale production. Therefore, it is im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06C07D209/34A61K31/5377A61K31/496A61K31/454A61K31/4045A61P35/00A61P35/02A61P35/04
CPCC07D209/34C07D403/06A61P35/00A61P35/02A61P35/04
Inventor 李松郑志兵吕凯王莉莉钟武陈伟肖军海谢云德周辛波李微李行舟
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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