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2‑acylaminothiazole derivatives or salts thereof

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

Active Publication Date: 2017-11-10
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 derivatives or salts thereof
  • 2‑acylaminothiazole derivatives or salts thereof
  • 2‑acylaminothiazole derivatives or salts thereof

Examples

Experimental program
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Embodiment

[0327] 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.

[0328] In this specification, naming software such as ACD / Name (registered trademark, Advanced Chemistry Development, Inc.) may be used for naming compounds.

[0329] In addition, the following abbreviations may be used in Examples, Production Examples, and Tables described later.

[0330] PEx: production example number, Ex: example number, PSyn: production example n...

manufacture example 1

[0337] 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

[0339] 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 have found that thiazole derivatives substituted with pyrazine-2-carbonylamino at the 2-position are excellent muscarinic M3 receptor positive allosteric modulators and can be used as bladder contractions associated with muscarinic M3 receptors. A preventive and / or therapeutic agent for bladder and urinary tract diseases, thus completing the present invention. The 2-acylaminothiazole derivatives and salts thereof of the present invention can be used as a preventive agent and / or voiding disorder in bladder and urinary tract diseases (such as low bladder activity, etc.) associated with muscarinic M3 receptor-induced bladder contraction or therapeutic agents. (In the formula, R1 is -N(-R11) (-R12), or a cyclic amino group that may be substituted, R11 is a C1-6 alkyl group, R12 is a C1-6 alkyl group that may be substituted, or may be substituted C3-8 cycloalkyl, R2 is an aryl group that may be substituted, a monocyclic aromatic heterocycle that may be substituted, or a bicyclic aromatic heterocycle that may be substituted, and R3 is -H, -OH, -O-(C1 ‑6 alkyl), or halogen).

Description

technical field [0001] The present invention relates to compositions useful as pharmaceuticals, especially with muscarinic M 3 A 2-acylaminothiazole derivative or a salt thereof as an active ingredient of a pharmaceutical composition for the treatment of bladder / urinary tract diseases associated with receptor-induced bladder contraction. Background technique [0002] The important role of the lower urinary tract is urine storage and urination, and they are regulated by the coordination of the bladder and the urethra. That is, during urine storage, the smooth muscle of the bladder relaxes and the urethral sphincter contracts, thereby maintaining the high resistance state of the urethra and maintaining urinary incontinence. On the other hand, during urination, the smooth muscle of the urethra relaxes while the smooth muscle of the bladder contracts, and the contraction of the external urethral sphincter is also inhibited. Lower urinary tract disorders include urinary storage...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14A61K31/497A61K31/5377A61P13/10A61P43/00C07D491/107
CPCA61K31/497A61K31/5377C07D417/14C07D491/107C07D491/08A61P13/10A61P43/00
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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