Methods for inhibiting protein kinases

Inactive Publication Date: 2007-04-12
SCHERING CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

up>is H, halo or alkyl; [0119] m is 0 to 4; </
p>is not methyl. [0125] The compounds disclosed in copending patent application Serial No. (Attorney Docket No. OC01617K3) filed of even date herewith generically fall within Formula I. The compounds disclosed in copending patent application Serial No. (Attorney Docket No. OC01618K2) filed of even date herewith generically fall within Formula II

Problems solved by technology

In the adult, however, angiogenesis is fairly limited, occurring only in the proce

Method used

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  • Methods for inhibiting protein kinases
  • Methods for inhibiting protein kinases
  • Methods for inhibiting protein kinases

Examples

Experimental program
Comparison scheme
Effect test

example 1

PREPARATIVE EXAMPLE 1

[0429]

[0430] SOCl2 (18.5 mL) was added slowly under N2 to a stirred mixture of the acid (50.0 g, 218 mmol) and pyridine (44.0 mL) in anhydrous CH2Cl2 (300 mL). The mixture was stirred at 25° C. for 20 min, then Meldrum's acid (35.0 g, 243 mmol) and DMAP (66.6 g, 546 mmol) were added and the mixture was stirred under N2 for 1 hr. Then Et2O (2 L) was added, the mixture was washed with 1 M HCl (3×500 mL), brine (500 mL), and the organic layer was dried over Na2SO4, filtered, and the solvent was evaporated. The residue was dissolved in MeOH (580 mL), and the mixture was refluxed for 4 hr. The solvent was evaporated and the residue was purified by column chromatography on silica gel with 10:1 CH2Cl2 / EtOAc as eluent. Pale yellow oil (26.5 g, 43%) was obtained.

example 2

PREPARATIVE EXAMPLE 2

[0431]

[0432] A mixture of the beta-ketoester from Preparative Example 1 (20.0 g, 70.1 mmol) and 3-aminopyrazole (5.40 g, 65.0 mmol) in anhydrous toluene (60 mL) was stirred and refluxed under N2 for 24 hr. The solvent was evaporated and the residue was purified by column chromatography on silica gel with 20:1 CH2Cl2 / MeOH as eluent. White solid (15.0 g, 73%) was obtained. LC-MS: 319 [M+H].

example 3-4

PREPARATIVE EXAMPLE 3-4

[0433] By essentially same procedure set forth in Preparative Example 2, combining 3-aminopyrazole with the corresponding beta-ketoesters, compounds given in Column 1 of Table 1A were prepared.

TABLE 1AEx.Column 1Data3LCMS: MH+ = 2364

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Abstract

The present invention provides methods for inhibiting protein kinases selected from the group consisting of AKT, Checkpoint kinase, Aurora kinase, Pim kinases, and tyrosine kinase using pyrazolo[1,5-a]pyrimidine compounds and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with protein kinases using such compounds.

Description

[0001] This application claims the benefit of priority from U.S. Provisional Patent Application Ser. No. 60 / 724,158, filed on Oct. 6, 2005.FIELD OF THE INVENTION [0002] The present invention relates to methods for inhibiting, regulating or modulating Akt kinases, Checkpoint kinases, Aurora kinases, Pim kinases, and / or tyrosine kinases using pyrazolo[1,5-a]pyrimidine compounds or pharmaceutical compositions containing the compounds, and methods of treatment using the compounds or compositions to treat diseases such as, for example, cancer, inflammation, arthritis, viral diseases, neurodegenerative diseases such as Alzheimer's disease, cardiovascular diseases, and fungal diseases. BACKGROUND OF THE INVENTION [0003] Protein kinases are a family of enzymes that catalyze phosphorylation of proteins, in particular the hydroxyl group of specific tyrosine, serine, or threonine residues in proteins. Protein kinases are pivotal in the regulation of a wide variety of cellular processes, includ...

Claims

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Application Information

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IPC IPC(8): A61K31/5377A61K31/519
CPCA61K31/519A61K31/5377A61K45/06A61P9/00A61P17/14A61P19/00A61P19/02A61P25/00A61P25/28A61P29/00A61P31/02A61P31/10A61P31/12A61P35/00A61P35/02A61P37/02A61P37/06A61P43/00A61K2300/00
Inventor GUZI, TIMOTHYPARUCH, KAMILDWYER, MICHAELPARRY, DAVID
Owner SCHERING CORP
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