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Imidazopyridine derivatives

A technology of imidazopyridine and derivatives, applied in the field of imidazopyridine derivatives, can solve the problems of different structures, no description, no disclosure of inhibitory activity and anticancer effect, etc.

Inactive Publication Date: 2003-06-25
ASTELLAS PHARMA INC +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the structures are all different from the compounds of the present invention, and their d PI3K inhibitory activity and anticancer effect are neither disclosed nor explained

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] To a mixture of compound c4 (0.10 g) and pyridine (2.5 ml), benzenesulfonyl chloride (0.10 g) was added, followed by stirring at 100°C for 4 hours. After concentrating the reaction solution under reduced pressure, the resultant was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0-99:1) to obtain Compound 1 (0.11 g).

Embodiment 2

[0155] To 2-methyl-5-nitrobenzoic acid (500 mg) was added thionyl chloride (5 mL). After the reaction mixture was heated to reflux for 1 hour, it was concentrated under reduced pressure and dried in vacuo. To the obtained solid were added THF (10 ml), chloroform (10 ml), TEA (2 g), and compound c1 (440 mg), followed by stirring at room temperature for 3 hours. It was diluted with chloroform, washed with water and saturated aqueous sodium bicarbonate solution. The obtained organic layer was dried with anhydrous magnesium sulfate, and dried under reduced pressure. The resulting solid was purified by silica gel column chromatography (eluent; chloroform:methanol=200:1) to obtain Compound 31 (72 mg).

Embodiment 3

[0157] To compound h1 (1.2 g) were added pyridine (10 ml) and 5-nitro-2-methylbenzenesulfonyl chloride (1.1 g) at room temperature, and stirred for 5 hours. The reaction solution was concentrated under reduced pressure, and the residue was diluted with chloroform and washed with water. The obtained organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was crystallized from chloroform, and crude crystals were collected by filtration. The resulting crude crystals were washed with hot methanol to obtain Compound 32 (1.47 g).

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Abstract

The present invention relates to novel compounds having a phosphatidylinositol 3 kinase (PI3K) inhibiting activity which are useful as medicaments, more particularly as antitumor agent. Novel 3-(imidazoÄ1,2-aÜpyridin-3-yl) derivatives or salts thereof exhibit an excellent PI3K inhibiting activity and cancer cell growth inhibiting activity, and are thus useful as medicaments, especially as PI3K inhibitors and antitumor agents.

Description

technical field [0001] The present invention relates to imidazopyridine derivatives useful as pharmaceuticals, especially phosphatidylinositol 3-kinase (PI3K) inhibitors and anticancer agents. Background technique [0002] Phosphatidylinositol (hereinafter referred to as "PI") is one of cell membrane phospholipids, which is known to play a role in intracellular information transmission. It is well understood that in particular PI(4,5) diphosphate (PI(4,5)P2) is broken down by phospholipase C into diacylglycerol and inositol (1,4,5) triphosphate, causing Activation of protein kinase C and intracellular calcium mobilization [MJ Berridge et al., Nature, 312, 315, (1984), Y Nishizuka, Science, 225, 1365 (1984)]. [0003] On the other hand, in the second half of the 1980s, PI3K was identified as an enzyme that phosphorylates the 3-position of the PI-inositol ring [D Whitman et al., Nature, 332, 664 (1988)]. [0004] PI3K was once thought to be a single enzyme when it was first ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P35/00A61P43/00C07D471/04C07D487/04
CPCC07D471/04C07D487/04A61P1/18A61P13/08A61P13/12A61P17/06A61P19/00A61P27/02A61P29/00A61P3/10A61P35/00A61P35/02A61P37/02A61P43/00A61P9/08A61P9/10
Inventor 早川昌彦贝沢弘行川口贤一松田光阳石川典子小泉智信山野真由美冈田稔太田光昭
Owner ASTELLAS PHARMA INC
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