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Pyrazolopyrimidinone compound and derivative as well as preparation method and application thereof

A technology of compounds and solvates, applied in the field of medicine

Active Publication Date: 2014-07-09
HUBEI BIO PHARMA IND TECHCAL INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, no AKT / PI3K inhibitor has been successfully marketed. Therefore, the development of a safer and more efficient AKT / PI3K inhibitor targeted anti-tumor drug has huge social value and economic benefits, and is currently the research of major pharmaceutical companies at home and abroad. hotspot

Method used

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  • Pyrazolopyrimidinone compound and derivative as well as preparation method and application thereof
  • Pyrazolopyrimidinone compound and derivative as well as preparation method and application thereof
  • Pyrazolopyrimidinone compound and derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Embodiment 1: the preparation of the compound shown in formula 3a-1

[0095] Add ethanol (1000mL), compound shown in formula 2a (27.8 g, 0.2 mol) and compound shown in formula 1a-1 (21.1 g, 0.1 mol) in sequence in the three-necked flask, stir and reflux the resulting solution for 12 hours, pass through a thin layer Chromatography (TLC) point plate test reaction is complete (developing agent is CH 2 Cl 2 / MeOH=10:1 (V / V)). After the reaction was complete, the mixture was concentrated under vacuum to obtain the crude product of the compound shown in formula 3a as a brownish yellow oily liquid, which was dissolved with ethanol (100mL), then stirred with ethyl acetate (300mL) for 2 hours, and the temperature was controlled at 10 Recrystallized at ~15°C, filtered, and dried the solid to obtain the compound represented by formula 3a-1 (12.4 g, yield 42.4%).

Embodiment 2

[0096] Embodiment 2: the preparation of the compound shown in formula 3a-1

[0097] Add ethanol (1000mL), the compound shown in formula 2a (16.7 g, 0.12 mol) and the compound shown in formula 1a-1 (21.1 g, 0.1 mol) in sequence in the three-necked flask, and the resulting solution was stirred and refluxed for 8 hours. Chromatography (TLC) point plate test reaction is complete (developing agent is CH 2 Cl 2 / MeOH=10:1 (V / V)). After the reaction was complete, the mixture was concentrated under vacuum to obtain the crude product of the compound shown in formula 3a as a brownish-yellow oily liquid, which was dissolved with ethanol (100mL), then stirred with ethyl acetate (300mL) for 2 hours, and the temperature was controlled at 20 Recrystallized at ~25°C, filtered, and dried the solid to obtain the compound represented by formula 3a-1 (7.83 g, yield 26.8%).

Embodiment 3

[0098] Embodiment 3: the preparation of the compound shown in formula 3a-1

[0099] Add ethanol (1000mL), compound shown in formula 2a (34.8 g, 0.25 mol) and compound shown in formula 1a-1 (21.1 g, 0.1 mol) in sequence in the three-necked flask, stir and reflux the resulting solution for 24 hours, pass through a thin layer Chromatography (TLC) point plate test reaction is complete (developing agent is CH 2 Cl 2 / MeOH=10:1 (V / V)). After completion of the reaction, the mixture was concentrated under vacuum to obtain the crude product of the compound shown in formula 3a as a brownish-yellow oily liquid, which was dissolved with ethanol (100mL), then stirred with ethyl acetate (300mL) for 2 hours, and the temperature was controlled at 15 Recrystallized at ~20°C, filtered, and dried the solid to obtain the compound represented by formula 3a-1 (9.94 g, yield 34.0%).

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Abstract

The invention provides a pyrazolopyrimidinone compound and a derivative (a compound as shown in formula I) as well as a preparation method and an application thereof. The compound is the compound as shown in a formula I or a pharmaceutically acceptable salt, a hydrate or a solvate as shown in the formula I. The compound is used as an AKT / PI3K inhibitor and can be used for treating related diseases of cancer by drug targeting. In the compound as shown in the formula I, R1, R2, R3 and R4 are designed in the specification. The formula I is as shown in the specification.

Description

technical field [0001] The present invention relates to the field of medicine, specifically, the present invention relates to pyrazolopyrimidinone compounds and their derivatives, their preparation methods and applications, more specifically, to the compounds represented by formula I or the pharmaceutically acceptable compounds represented by formula I Salts, crystalline hydrates or solvates of , their preparation methods and uses in the preparation of medicines for treating cancer, and pharmaceutical compositions. Background technique [0002] The latest WHO data predicts that by 2020, the global cancer incidence will increase by 50%, that is, 15 million new cancer patients will be added every year. Not only that, the number of cancer deaths is also rising rapidly around the world. In 2007, a total of 7.6 million people died of cancer worldwide, and this number may increase to 13.2 million in 2030. According to relevant data provided by the Cancer Prevention and Control Of...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61K31/541A61K31/5377A61P35/00A61P35/02
CPCA61K31/519A61K31/5377A61K31/541C07D487/04
Inventor 乐洋许勇黄璐郭涤亮冯权武肖强田华王家兵
Owner HUBEI BIO PHARMA IND TECHCAL INST
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