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Medicine comprising dicyanopyridine derivative

A kind of technology of dicyanopyridine and alkyl, applied in the field of medicines containing dicyanopyridine derivatives, can solve the problem of no reporting relationship and the like

Inactive Publication Date: 2003-09-10
YAMANOUCHI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, the relationship between these compounds and "highly conductive calcium-sensitive potassium channel openers", "bladder smooth muscle relaxants" and "drugs for urinary frequency and urinary incontinence" were not reported

Method used

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  • Medicine comprising dicyanopyridine derivative
  • Medicine comprising dicyanopyridine derivative
  • Medicine comprising dicyanopyridine derivative

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0193] To 10 ml of benzaldehyde in ethanol-water (7:3) 100 ml solution, 6.5 g of malononitrile and 0.1 g of glycine were added, and the mixture was stirred at room temperature for 6 hours. The precipitated crystals were collected by filtration, and the obtained crystals were washed with ethanol-water (7:3) and dried under reduced pressure to obtain 13.1 g of benzylmalononitrile.

[0194] As in Reference Example 1, the compounds of Reference Examples 2-7 were obtained.

reference example 8

[0196] At room temperature, add 6.0 g of sodium bicarbonate and 7.6 g of di-tert-butyl dicarbonate to a solution of 5.0 g of 4-aminomethyl benzoic acid in 40 ml of dioxane-water (1:1). The solution was 20 ml and stirred at room temperature for 4 days. The solvent was distilled off under reduced pressure, neutralized with dilute hydrochloric acid, the precipitated solid was filtered, and dried under reduced pressure to obtain 8.0 g of carboxylic acid. 0.60 g of 1,1'-carbonylbis-1H-imidazole was added to 10 ml of THF solution containing 0.85 g of carboxylic acid under ice cooling, and the mixture was stirred at 50°C for 40 minutes. In the resulting solution, add 0.43 g of N, O-dimethylhydroxylamine hydrochloride, triethylamine (Et 3 N) 0.7 mL, and stir overnight at room temperature. Water was added to the reaction solution, and extraction was performed with ethyl acetate (EtOAc). The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was distil...

reference example 9

[0198] At room temperature, in 20 ml of dioxane-water (1:1) solution of 2.0 g of 3-bromobenzylamine hydrochloride, add 1.5 g of sodium bicarbonate and 2.2 g of di-tert-butyl dicarbonate in turn. 10 ml solution of alkane was stirred at room temperature for 1 day. Water was added to the reaction solution and extracted with ethyl acetate. After the organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 3.0 g of bromide. To a 30 ml THF solution of 3.0 g bromide, 14 ml of a 1.5M butyl lithium-hexane solution was added at -78°C, and stirred at the same temperature for 30 minutes. At -78°C, 10 ml of THF solution containing 1.7 ml of DMF was added to the resulting solution, and the temperature was raised to -15°C in 1.5 hours. An aqueous ammonium chloride solution was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, an...

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PUM

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Abstract

Compounds having a high conductance-type of calcium-activated K channel opening effect and a smooth muscle relaxant effect for bladder based on the K-channel opening effect, which can be used in treating pollakiuria and urinary incontinence, are provided. 3,5-Dicyanopyridine derivatives or their salts.

Description

Technical field [0001] The present invention relates to a pharmaceutical composition containing a 3,5-dicyanopyridine derivative or a pharmaceutically acceptable salt thereof as an effective component, a highly conductive calcium-sensitive K channel opener, a bladder smooth muscle relaxant, and frequent urination and urine Incontinence treatment drugs and new 3,5-dicyanopyridine derivatives or pharmaceutically acceptable salts thereof. Background technique [0002] It is known that potassium channels play an important role in the occurrence of cell resting membrane potential and action potential. The opening of potassium channels inhibits cell excitability through excessive polarization of the cell membrane, and plays a role in relaxing smooth muscle (J. Urol., 154, 1914-20, 1995). [0003] High-conductivity calcium-sensitive potassium channels (also called maxi-K channels or BK channels) are one of the calcium-sensitive potassium channels that open when the intracellular calcium...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/44A61K31/4409A61K31/4412A61K31/443A61K31/4436A61K31/4439A61K31/506A61K31/5377A61P13/06A61P13/10C07D213/85C07D213/89C07D401/04C07D401/10C07D401/12C07D405/04C07D405/12C07D409/04C07D417/04C07D521/00
CPCC07D417/04A61K31/506A61K31/4409C07D213/85C07D405/12C07D405/04A61K31/5377C07D401/10A61K31/44C07D401/12C07D409/04C07D213/89A61K31/4439A61K31/4436C07D231/12C07D249/08A61K31/4412C07D233/56A61K31/443C07D401/04A61P13/06A61P13/10
Inventor 原田博规四月朔日晋宅和知文川口贤一冈崎利夫平野雄介齐藤亲
Owner YAMANOUCHI PHARMA CO LTD
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