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2-acylaminothiazole derivative or salt thereof

A kind of technology of alkyl group and group, applied in the field of pharmaceutical composition

Active Publication Date: 2017-02-15
ASAHI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these drugs, cholinergic side effects such as diarrhea, abdominal pain, and sweating are known

Method used

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  • 2-acylaminothiazole derivative or salt thereof
  • 2-acylaminothiazole derivative or salt thereof
  • 2-acylaminothiazole derivative or salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0370] 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. In addition, the production method of the compound of formula (I) is not limited to the production method of the specific examples shown below, and the compound of formula (I) can also be obtained by a combination of these production methods, or those skilled in the art method manufacturing.

[0371] In this specification, naming software such as ACD / Name (registered trademark, Advanced Chemistry Development, Inc.) may be used for naming compounds.

[0372] In the measurement of powder X-ray diffraction, RINT-TTRII is used, and the measurement is carried out under the following conditions: the tube ball is Cu, the tube current is 300mA, the ...

manufacture example 1

[0378] 4-[3-fluoro-5-(trifluoromethyl)phenyl]-5-{[(2R)-2-methylpyrrolidin-1-yl]methyl}-1,3-thiazole-2 - A mixture of amine (1.0g), 5-chloropyrazine-2-carboxylic acid (685mg), COMU (1.9g), dioxane (10mL) and N,N-diisopropylethylamine (1.5mL) Stir at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5-chloro-N-(4-[3-fluoro-5-(trifluoromethyl)phenyl]-5-{[ (2R)-2-Methylpyrrolidin-1-yl]methyl}-1,3-thiazol-2-yl)pyrazine-2-carboxamide (800 mg).

manufacture example 2

[0380] 5-chloropyrazine-2-carboxylic acid (1.7g), N,N-dimethyl-4-aminopyridine (340mg) and WSCD.HCl (2.1g) were added to 5-{[(2R)-2 -Methylpyrrolidin-1-yl]methyl}-4-[4-(trifluoromethyl)thiophen-2-yl]-1,3-thiazol-2-amine (2.9g) and dichloromethane ( 60 mL) and stirred at 40°C for 15 minutes. The reaction mixture was cooled to room temperature, diluted with chloroform, and washed with saturated aqueous sodium bicarbonate. The aqueous layer was extracted with chloroform / methanol, and the organic layers were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-ethyl acetate) to obtain 5-chloro-N-(5-{[(2R)-2-methylpyrrolidin-1-yl]methyl}-4 -[4-(Trifluoromethyl)thiophen-2-yl]-1,3-thiazol-2-yl)pyrazine-2-carboxamide (2.4 g).

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Abstract

To provide a compound useful as an active ingredient of a pharmacological composition for the treatment of urinary storage symptoms, dysuria, lower urinary tract diseases, and the like. The inventors perfected the present invention after discovering that thiazole derivatives substituted at position 2 by pyrazinylcarbonylamino are exceptional muscarinic M3 receptor positive allosteric modulators and can be expected to serve as agents for the prevention or treatment of urinary bladder and urinary tract diseases involving bladder contraction mediated by muscarinic M3 receptors. The 2-acylaminothiazole derivatives or salts thereof of the present invention can be expected to serve as agents for the prevention or treatment of urinary bladder and urinary tract diseases involving bladder contraction mediated by muscarinic M3 receptors, e.g., underactive bladder and the like.

Description

technical field [0001] The present invention relates to a kind of pharmaceutical composition, especially can be used as and muscarine M 3 A 2-acylaminothiazole derivative or a salt thereof, which is an active ingredient of a pharmaceutical composition for treating bladder / urological diseases related to receptor-mediated bladder contraction. Background technique [0002] The important functions of the lower urinary tract are urine storage and voiding, which are regulated by the synergistic action of the bladder and urethra. In other words, the smooth muscle of the bladder relaxes during the storage of urine, and the urethral resistance is maintained at a high state through the contraction of the urethral sphincter, thereby maintaining urinary continence. On the other hand, the bladder smooth muscle contracts during urination, and at the same time the urethral smooth muscle relaxes, and the contraction of the external urethral sphincter is also inhibited. Disorders of the lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14A61K31/497A61P13/02A61P13/10A61P43/00
CPCC07D417/14A61K31/497A61P13/00A61P13/02A61P13/10A61P43/00A61K31/427
Inventor 高桥泰辅小池贵德根来贤二田中宏明前田纯横山和宏高松肇
Owner ASAHI PHARMA CO LTD
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