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Imidazopyridine compound

A compound and group technology, applied in the direction of active ingredients of heterocyclic compounds, organic chemistry, drug combination, etc., can solve the problems of compounds not being disclosed, not enlightening, etc.

Active Publication Date: 2014-02-26
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] However, this document neither discloses nor suggests compounds having an imidazo[1,2-a]pyridine skeleton.

Method used

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  • Imidazopyridine compound
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  • Imidazopyridine compound

Examples

Experimental program
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Effect test

Embodiment

[0322] Hereinafter, the production method of the compound of formula (I) is demonstrated in more 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. The compound of formula (I) is not limited to the production methods described in the examples below, but can also be produced using a combination of these production methods or a method obvious to those skilled in the art.

[0323] In addition, the following abbreviations may be used in Examples, Production Examples, and Tables described later. PEx: Manufacturing example number, Ex: Example number, Str: Structural formula, Dat: Physical data (ESI+: ESI-MS[M+H] + or ESI-MS[M] + ;ESI-:ESI-MS[M-H] - ;FAB+: FAB-MS[M+H] + or FAB-MS[M] + ;EI+:EI[M] + ;APCI / ESI+:APCI / ESI-MS[M+H] + or APCI / ESI-MS[M] + (APCI / ESI refers to the simultaneous det...

manufacture example 1

[0329] A suspension of 1 g of 5-methyl-2-nitropyridin-3-ol, 1.35 ml of (bromomethyl)cyclohexane, and 1.79 g of potassium carbonate in 10 ml of DMF was stirred at 78° C. for 12 hours. After cooling naturally at room temperature, water and hexane / ethyl acetate were added to the reaction liquid, and a liquid separation operation was performed. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.8 g of 3-(cyclohexylmethoxy)-5-methyl-2-nitropyridine.

manufacture example 2

[0331] To a solution of 1.8 g of 3-(cyclohexylmethoxy)-5-methyl-2-nitropyridine in 16 ml of THF was added 325 mg of 10% palladium-carbon (hydrate) and stirred under a hydrogen atmosphere for 3 hours. After filtering the reaction liquid through celite, the solvent was distilled off under reduced pressure to obtain 1.38 g of 3-(cyclohexylmethoxy)-5-methylpyridin-2-amine.

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Abstract

[Problem] To provide an excellent therapeutic or prophylactic agent for cardiovascular diseases on the basis of cGMP production-increasing activity attributed to soluble guanylate cyclase-activating activity. [Solution] It was discovered that an imidazopyridine compound having a carbamoyl group at the 3-position of an imidazo[1,2-a]pyridine skeleton and having a substituent attached to the 8-position of the skeleton through an oxygen atom exhibits cGMP production-increasing activity attributed to potent soluble guanylate cyclase-activating activity and can be used in an excellent therapeutic or prophylactic agent for various cardiovascular diseases associated with soluble guanylate cyclase, and the invention was completed.

Description

technical field [0001] The present invention relates to a pharmaceutical composition, for example, an imidazopyridine useful as an active ingredient of a pharmaceutical composition for the treatment or prevention of various cardiovascular diseases, which has a soluble guanylate cyclase (sGC) activating action and is based on the improvement of cGMP signal compound. Background technique [0002] cGMP (cyclic guanosine monophosphate, cyclic guanosine monophosphate) is an important intracellular messenger, through the regulation of cGMP-dependent protein kinases, phosphodiesterases and ion channels, it participates in the relaxation and proliferation of smooth muscle cells, platelet aggregation and adhesion, and Nerve cell signaling controls various physiological phenomena. This cGMP is produced from guanosine triphosphate (GTP) catalyzed by guanylate cyclase in response to various extracellular and intracellular stimuli. Two groups of guanylate cyclases have been reported so...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61K31/439A61K31/444A61K31/4545A61K31/496A61K31/497A61K31/501A61K31/506A61K31/53A61K31/5377A61K31/541A61P7/02A61P9/00A61P9/04A61P9/10A61P9/12A61P15/10A61P43/00C07D519/00
CPCC07D471/04C07D519/00C07D453/02A61P15/10A61P29/00A61P43/00A61P7/02A61P9/00A61P9/04A61P9/10A61P9/12A61P9/14A61K31/437
Inventor 古贺祐司前野恭一佐藤一平今村佳正花泽毅饭田真依子大根和彦今村健一郎渡边翼野泽荣典柴田洋
Owner ASTELLAS PHARMA INC
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