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Imidazopyridine compound

A compound, pyridyl technology, applied in organic chemistry, drug combination, blood diseases, etc., can solve problems such as undisclosed or revealed sGC activators

Active Publication Date: 2015-08-05
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this document does not disclose or suggest that sGC activators

Method used

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  • Imidazopyridine compound

Examples

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Embodiment

[0276] Hereinafter, the method for producing the compound of formula (I) will be described in more detail based on examples. It should be noted that the present invention is not limited to the compounds described in the following Examples. In addition, the manufacturing method of the raw material compound is shown in the manufacturing example. In addition to the production methods described in the examples shown below, a combination of these production methods or methods obvious to those skilled in the art can be used to produce the compound of formula (I).

[0277] In addition, the following abbreviations may be used in Examples, Production Examples, and the following tables.

[0278] PEx: Manufacturing Example Number, Ex: Example Number, No.: Compound Number, Str: Structural Formula, DATA: Physical and Chemical Data (ESI+: ESI-MS[M+H] + Or ESI-MS[M] + ; ESI-: ESI-MS[M-H] - ; CI+: CI-MS[M+H] + ; EI: EI[M] + ; APCI / ESI+: APCI / ESI-MS[M+H] + Or APCI / ESI-MS[M] + (APCI / ESI refers to t...

manufacture example 1

[0291] Combine 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester 500mg, 2,3-difluorobenzyl bromide 0.35ml, potassium carbonate 650mg N,N-dimethylformaldehyde A suspension of 8.6 ml of amide (DMF) was stirred at 60°C for 1 hour. The reaction mixture was left to cool to room temperature, and then water was added and the resulting solid was filtered out, and washed with water. The solid was washed with diisopropyl ether to obtain 650 mg of ethyl 8-[(2,3-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate.

manufacture example 2

[0293] Add 4.3 ml of ethyl 2-chloro-3-oxobutyrate and 4.3 ml of triethylamine to a solution of 5.8 g of 3-(cyclohexylmethoxy)pyridine-2-amine in 100 ml of toluene, and stir overnight under heating and reflux . 1 ml of ethyl 2-chloro-3-oxobutyrate and 1 ml of triethylamine were added to the reaction mixture, and the mixture was stirred under reflux with heating for 6.5 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography. Ethyl acetate and hexane were added to the obtained purified product, heated and stirred, and then stirred under ice cooling. The produced solid was collected by filtration to obtain 4.0 g of ethyl 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate.

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Abstract

[Problem] To provide a medicinal composition which functions to activate soluble guanylate cyclase (sGC) and which is for the treatment or prevention of various cardiovascular diseases that is based on an improvement in cGMP signals. [Solution] An imidazo[1,2-a]pyridine compound represented by formula (I), which has a carbamoyl group at the 3-position of the imidazo[1,2-a]pyridine framework and has a specific ring group bonded to the 8-position through a methyleneoxy group, or a salt of the compound. The pyridine compound or salt functions to activate sGC and is useful as the active ingredient of a medicinal composition for the treatment or prevention of various cardiovascular diseases in which sGC participates, in particular, peripheral arterial diseases, intermittent claudication, critical limb ischemia, hypertension, and pulmonary hypertension. (In formula (I), A1 is cyclohexyl, phenyl substituted by 1-3 fluorine atoms, or 3-fluoropyridin-2-yl and R is a group represented by any of the formulae (i) to (vii).)

Description

Technical field [0001] The present invention relates to an imidazolium useful as an active ingredient of a pharmaceutical composition for the treatment or prevention of various cardiovascular diseases that has a soluble guanylate cyclase (sGC) activation effect and is based on the improvement of cyclic guanosine phosphate (cGMP) signal [1,2-a] Pyridine compound. Background technique [0002] cGMP is an important intracellular messenger. Through the regulation of cGMP-dependent protein kinase, phosphodiesterase and ion channels, it participates in various physiological phenomena such as relaxation and proliferation of smooth muscle cells, platelet aggregation and adhesion, and signal transmission of nerve cells. control. As a response to various extracellular and intracellular stimuli, the cGMP is catalyzed by guanosine triphosphate (GTP) by guanylate cyclase. Two groups of guanylate cyclase have been reported so far. That is, membrane-bound guanylate cyclase stimulated by pept...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61K31/444A61K31/506A61P7/02A61P9/04A61P9/08A61P9/10A61P9/12A61P11/00A61P43/00
CPCC07D471/04A61P11/00A61P43/00A61P7/02A61P9/00A61P9/04A61P9/08A61P9/10A61P9/12
Inventor 黑崎寿夫渡边翼大根和彦石冈裕贵野泽荣典花泽毅八谷俊一郎柴田洋古贺祐司沟口亮
Owner ASTELLAS PHARMA INC
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