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2-acylaminothiazole derivative and salt thereof

An amino and alkyl technology, which is applied in the field of 2-acylaminothiazole derivatives or their salts, can solve the problems such as ineffectiveness of urination disorder

Active Publication Date: 2015-10-28
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, adrenaline α 1 The effectiveness of receptor antagonists on voiding disorders not accompanied by benign prostatic hypertrophy is not obvious (Journal of Pharmacological Sciences,112:pp.121-127(2010))

Method used

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  • 2-acylaminothiazole derivative and salt thereof
  • 2-acylaminothiazole derivative and salt thereof
  • 2-acylaminothiazole derivative and salt thereof

Examples

Experimental program
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Embodiment

[0329] Hereinafter, based on examples, the production method of the compound of formula (I) will be described in further detail. In addition, this invention is not limited to the compound described in the following Example. In addition, the production method of the raw material compound is as shown in the production example. Furthermore, the production method of the compound of formula (I) is not limited to the production method shown in the specific examples below, and 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.

[0330] In this specification, naming software such as ACD / Name (registered trademark, Advanced Chemistry Development, Inc.) may be used for naming compounds.

[0331] In addition, the following abbreviations may be used in Examples, Production Examples, and Tables described later.

[0332] PEx: production example number, Ex: example number, PSyn: production example n...

manufacture example 1

[0339] To a solution of 1-[4-hydroxy-3-(trifluoromethyl)phenyl]ethanone (1 g) in acetonitrile (10 mL) was added 1-bromopropane (0.90 mL), potassium carbonate (1.7 g) and tetrabutyl ammonium iodide (180 mg), stirred overnight at room temperature. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1-[4-propoxy-3-(trifluoromethyl)phenyl]ethanone (1.16 g) as an oily substance.

manufacture example 2

[0341] 1-[4-Hydroxy-3-(trifluoromethyl)phenyl]ethanone (1 g), ethyl iodide (1.19 mL), cerium carbonate (1.92 g) and N,N-dimethylformamide ( 15 mL) was stirred at 60°C for 3 hours. The reaction mixture was cooled to room temperature, water was added, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1-[4-ethoxy-3-(trifluoromethyl)phenyl]ethanone (1.1 g) as a solid.

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Abstract

The present inventors achieved the present invention on the basis of the knowledge that a thiazole derivative with a pyrazine-2-carbonylamine substituent at the second carbon position is an excellent positive allosteric modulator of the muscarinic M3 receptor and is useful as a prophylactic and / or therapeutic agent against bladder / urinary tract disorders associated with bladder contractions induced by the muscarinic M3 receptor. A 2-acylaminothiazole derivative or a salt thereof according to the present invention can be used as a prophylactic and / or therapeutic agent against bladder / urinary tract disorders associated with bladder contractions induced by the muscarinic M3 receptor, including, for example, urinary disorders such as underactive bladder. (In the formula, R1 is -(N(-R11)(-R12) or an optionally substituted cyclic amine; R11 is a C1–6 alkyl; R12 is an optionally substituted C1–6 alkyl or an optionally substituted C3–8 cycloalkyl; R2 is an optionally substituted aryl, an optionally substituted monocyclic aromatic heterocycle, or an optionally substituted bicyclic aromatic heterocycle; and R3 is -H,-OH, -O-( C1–6 alkyl), or a halogen.)

Description

technical field [0001] The present invention relates to can be used as pharmaceutical composition, especially with muscarine M 3 A 2-acylaminothiazole derivative or a salt thereof as an active ingredient of a pharmaceutical composition for treating bladder and urethral diseases related to receptor-induced bladder contraction. Background technique [0002] The important functions of the lower urethra are urine storage and urination, which are regulated through the coordination of the bladder and urethra. That is, when storing urine, bladder smooth muscle relaxes and urethral sphincter contracts to maintain a high resistance state of the urethra to maintain urinary continence. On the other hand, at the time of urination, the smooth muscle of the urethra relaxes simultaneously with the contraction of the smooth muscle of the bladder, and the contraction of the external urethral sphincter is also inhibited. Lower urinary tract disorders include urinary storage disorders such a...

Claims

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Application Information

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IPC IPC(8): C07D417/14A61K31/497A61K31/5377A61P13/10A61P43/00C07D491/107
CPCA61K31/497A61K31/5377C07D417/14C07D491/08C07D491/107A61P13/10A61P43/00
Inventor 高桥泰辅前田纯稻垣勇典根来贤二田中宏明横山和宏高松肇小池贵德塚本一成
Owner ASTELLAS PHARMA INC
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