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Pyrazolo[1,5-A]pyrimidine derivatives and methods of use thereof

The technology of a compound, R17, is applied in the field of pyrazolo[1, which can solve problems such as dangerous side effects and toxic anticancer agents.

Inactive Publication Date: 2009-04-08
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of anticancer agents are available, traditional chemotherapy has disadvantages
Many anticancer agents are toxic, and chemotherapy can cause significant and often dangerous side effects, including severe nausea, bone marrow suppression, liver, heart, and kidney damage, and immunosuppression

Method used

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  • Pyrazolo[1,5-A]pyrimidine derivatives and methods of use thereof
  • Pyrazolo[1,5-A]pyrimidine derivatives and methods of use thereof
  • Pyrazolo[1,5-A]pyrimidine derivatives and methods of use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0519] Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 7-[3-[[3-(trifluoromethyl)-benzoyl]amino]phenyl]-ethyl ester

[0520] MS (electrospray): m / z 455[M+H]

[0521] Step 1: 3-(Dimethylamino)-1-(3-nitrophenyl)-2-propen-1-one: Add 3-in dimethylformamide-dimethylacetal (10mL) Nitroacetophenone (5.0 g, 30.3 mmol) was heated under reflux overnight. The reaction mixture was cooled to room temperature and evaporated to remove volatiles. The residue was slurried in ether and the suspension was filtered and washed with ether to obtain 10.5 g (79%) of 3-(dimethylamino)-1-(3-nitrophenyl)-2-propene- 1-ketone, 104°C-105°C.

[0522] Step 2: 7-(3-Nitro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester: to 3-dimethylamino-1-(3-nitro-benzene 3-amino-4-ethoxycarbonylpyrazole (3.1 mmol) was added to a solution of phenyl)-propenone (3 mmol) in acetic acid and heated at 80°C overnight. The solution was concentrated and the resulting tan solid was used in the next step without further purifi...

example 2

[0528] 7-(3-{[4-Fluoro-3-(trifluoromethyl)benzoyl]amino}phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester

[0529] MS (electrospray): m / z 473[M+H]

example 3

[0531] Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 7-[3-(benzoylamino)phenyl]-ethyl ester

[0532] MS (electrospray): m / z 387[M+H]

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Abstract

The present invention relates to pyrazolo[1,5-a]pyrimidine derivatives, compositions comprising an effective amount of a pyrazolo[1,5-a]pyrimidine derivative and methods for treating or preventing cancer, comprising administering to a subject in need thereof an effective amount of a pyrazolo[1,5-a]pyrimidine derivative.

Description

Technical field [0001] The present invention relates to a pyrazolo[1,5-a]pyrimidine derivative, a composition containing an effective amount of a pyrazolo[1,5-a]pyrimidine derivative, and a method for treating or preventing cancer, the method It comprises administering an effective amount of pyrazolo[1,5-a]pyrimidine derivative to an individual in need. Background technique [0002] In the United States, cancer is the second leading cause of death after cardiovascular disease. According to the American Cancer Society (American Cancer Society) estimates, in 2004, there were 1.6 million new cancer cases and 655,000 cancer-related deaths. At present, more than 10 million existing Americans have been diagnosed with cancer, and the National Institutes of Health (NIH) estimates that the annual direct medical expenses for cancer exceed 100 billion US dollars, of which the indirect cost caused by the loss of productivity is an additional 1000 Billion US dollars, this is the largest such ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519
CPCC07D487/04A61P35/00
Inventor 阿里亚马拉·戈帕尔萨米格雷戈里·M·齐谢夫斯基石孟晓达恩·马尔滕·贝格尔南希·托里斯杰里米·I·莱温丹尼斯·威廉·鲍威尔金耿义李忠乔治·迪亚曼迪斯达林·威廉姆·霍伯爱德华·詹姆斯·萨拉斯基
Owner WYETH LLC
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