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Tetrahydro-indolone derivative and tetrahydro-indazolone derivatives and their use

A compound, alkyl technology, applied in the field of derivatives of tetrahydroindolinone, can solve problems such as not mentioned

Active Publication Date: 2009-12-30
广州少伯控股集团有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This patent emphasizes the substitution of tetrahydroindazolone core, without mentioning any carbamyl, or cyano substituted benzene ring structure or benzamide structure

Method used

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  • Tetrahydro-indolone derivative and tetrahydro-indazolone derivatives and their use

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0054] 5,5-Dimethyl-2-(2-oxo-propyl)-1,3-cyclohexanedione (5,5-dimethyl-2-(2-oxo-propyl)-cyclohexane-1,3- dione) synthesis. (Intermediate I)

[0055]

[0056] In a reaction flask, add 5,5-dimethylcyclohexane-1,3-dione (3.5 g, 25 mmol) dissolved in THF (250 mL) and sodium hydride (1g, 40mmol), under ice-bath cooling, chloroethylketone (2.3g, 25mmol) was added dropwise in the reaction flask, after stirring at room temperature for 2h, water (400mL) was added, and the reaction product was extracted with dichloromethane, and after washing with water, no dried over magnesium sulfate. After removing the desiccant, the solvent was evaporated under reduced pressure to obtain a colorless liquid, 2.8 g, with a yield of 57%. This compound was used in the following reaction without purification.

example 2

[0058] 5,5-Dimethyl-2-(2-propionyl)-1,3-cyclohexanedione (5,5-dimethyl-2-(1-methyl-2-oxo-ethyl)-cyclohexane-1 , 3-dione) synthesis. (Intermediate II)

[0059]

[0060] Add 5,5-dimethylcyclohexane-1,3-dione (5,5-dimethylcyclohexane-1,3-dione) (3.5 g, 25 mmol) dissolved in THF (200 mL) and 2N NaOH ( 15mL, 30mmol), under ice bath cooling, 2-chloropropionaldehyde dimethyl acetal (2-chloro-1, 1-dimethoxypropane) (3.5g, 25mmol) THF (50mL) was added dropwise in the reaction flask, at room temperature After stirring for 2 hours, 1N HCl (200 mL) was added and stirred for 1 hour. The reaction product was extracted with ethyl acetate, washed with saturated sodium chloride water and dried over anhydrous sodium sulfate. After removing the desiccant, the solvent was evaporated under reduced pressure to obtain 1.9 g of a colorless liquid with a yield of 39%. This compound was used in the following reaction without purification.

example 3

[0062] Synthesis of 2-acetyl-5,5-dimethyl-1,3-cyclohexanedione (2-acetyl-5,5-dimethyl-cyclohexane-1,3-dione). (Intermediate III)

[0063]

[0064] Acetyl chloride (8.8 mL) was added dropwise to a solution of 5,5-dimethyl-1,3-cyclohexanedione (16.8 g, 120 mmol) and pyridine (9.2 mL) in chloroform (400 mL). After the addition was complete, the reaction was stirred at room temperature for an additional 1.5 hours. The reaction solution was extracted with chloroform, washed with 0.1N hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried overnight over sodium sulfate.

[0065] The crude product obtained as a colorless liquid after filtration and solvent removal was added to a solution of anhydrous aluminum chloride (32 g, 240 mmol) in chloroform (400 mL) at 0 °C. After the addition was complete, the reaction was stirred at 0°C for 10 minutes, then at room temperature for 2 hours. The reaction solution was poured into a ...

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Abstract

A tetrahydroindolone derivative and its use are disclosed. It can inhibit malignant tumor cell growth. It can be used for mammary gland cancer, lung cancer, uterus neck cancer, rectum cancer, liver cancer and blood cancer.

Description

technical field [0001] The present invention relates to tetrahydroindolinone derivatives and tetrahydroindolinone derivatives and their application in the preparation of antitumor drugs. Background technique [0002] In the past ten years, great progress has been made in tumor treatment, and new anticancer drugs enter the market every year, which improves the survival and quality of life of cancer patients. However, cancer is still the number one killer that endangers people's health. Anticancer drugs currently used clinically have defects such as high toxicity and poor drug resistance. Many of these drugs stop cancer cell growth by inhibiting DNA synthesis. However, these drugs not only kill cancer cells, but also have the same killing effect on normal cells. As a result, these drugs often also cause irreversible toxicity and side effects to patients. [0003] Recently, some new anticancer drugs are considered to have the characteristics of low toxicity and high efficie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07D209/10C07D209/30C07D231/54C07D231/56C07D403/10C07D403/12C07D401/10C07D401/12C07D401/14A61K31/404A61K31/416A61K31/4192A61K31/454A61K31/496A61K31/5355A61P35/00
Inventor 夏敏张同祥王一飞邢国文
Owner 广州少伯控股集团有限公司
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