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Heterocyclic compound

A technology of compounds and heterocycles, applied in the fields of active ingredients of heterocycles, digestive system, organic chemistry, etc., can solve the problem of no selective inhibition of PI3Kδ

Active Publication Date: 2015-09-16
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, there is no record of selective inhibition of PI3Kδ in all literatures

Method used

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Examples

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Embodiment ）

[0306] Hereinafter, the manufacturing method of the compound of formula (I) and its raw material compound is demonstrated further in detail based on an Example. It should be noted that the present invention is not limited to the compounds described in the following examples. In addition, the production method of the raw material compound is shown in the production example. In addition, the production method of the compound of formula (I) is not limited to the production method of the specific examples shown below, the compound of formula (I) can also be produced by a combination of these production methods, or a method obvious to those skilled in the art .

[0307] In addition, the following abbreviations are sometimes used in Production Examples, Examples, and Tables described below.

[0308] PEx: Manufacturing example number, Ex: Example number, Syn: Example number manufactured by the same method, PSyn: Manufacturing example number manufactured by the same method, Str: Str...

manufacture example 1

[0311] Add potassium carbonate (5.3g) and 2-(difluoroform )-1H-benzimidazole (3.9 g), and the mixture was stirred at room temperature for 5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (hexane: ethyl acetate) to obtain 1-[6-chloro-2-(methylsulfanyl)pyrimidin-4-yl ]-2-(Difluoromethyl)-1H-benzimidazole (5.49 g).

manufacture example 2

[0313] N,N-dimethyl Potassium carbonate (1.4 g) and morpholine (0.88 mL) were added to the formamide (11 mL) solution, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 2-(difluoromethyl)-1-[2-(methylsulfanyl) as a white powder -6-morpholin-4-ylpyrimidin-4-yl]-1H-benzimidazole (2.1 g).

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PUM

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Abstract

[Problem] A novel and excellent compound which is useful as an agent for preventing and / or treating rejection reactions in various organ transplantations, allergy diseases, autoimmune diseases, and hematologic tumor, and based on a PI3K´ selective inhibitory action and / or an IL-2 production inhibitory action and / or a B cell proliferation inhibitory action (including an activation inhibitory action). [Means for Solution] The present inventors have investigated a compound having a PI3K´ selective inhibitory action and / or an IL-2 production inhibitory action and / or a B cell proliferation inhibitory action (including an activation inhibitory action), and have found that the heterocyclic compound of the present invention has a PI3K´ selective inhibitory action and / or and IL-2 production inhibitory action and / or a B cell proliferation inhibitory action (including an activation inhibitory action), thereby completing the present invention.

Description

technical field [0001] The present invention relates to heterocyclic compounds useful as active ingredients of pharmaceutical compositions, for example, pharmaceutical compositions for the prevention and / or treatment of diseases associated with phosphatidylinositol-3-kinase δ (PI3Kδ). Background technique [0002] Phosphatidylinositol-3-kinase (PI3K) is a lipid signaling kinase ubiquitous in plants, yeast and mammals represented by humans beyond species. PI3K is an enzyme that phosphorylates the 3-hydroxyl group of phosphatidylinositol, phosphatidylinositol-4-phosphate, and phosphatidylinositol-4,5-bisphosphate, which are cell membrane phospholipids, and produces phosphatidylinositol from their respective substrates. Alcohol-3-phosphate, phosphatidylinositol-3,4-bisphosphate and phosphatidylinositol-3,4,5-triphosphate (PIP3). These produced phosphorylated phosphatidylinositols function as intracellular second messengers. In particular, PIP3 moves various molecules having a...

Claims

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Application Information

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IPC IPC(8): C07D401/14A61K31/5377A61K31/541A61K31/55A61P1/04A61P11/06A61P17/06A61P19/02A61P29/00A61P35/02A61P37/02A61P37/06A61P37/08A61P43/00C07D403/04C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14C07D471/04C07D471/10
CPCC07D409/14C07D417/14C07D405/14A61K31/541C07D471/04A61K31/5377C07D413/14C07D403/04C07D401/14C07D403/14C07D487/04C07D471/10A61K31/55A61K31/497A61P1/04A61P11/06A61P17/06A61P19/02A61P29/00A61P35/02A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00
Inventor 盐饱雅彦高桥史江今田直浅野亨上月祥弘前田顺子加藤浩二深堀英彦
Owner ASTELLAS PHARMA INC
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