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Piperazine derivative

A kind of technology of compound, alkyl group, be applied in the field of piperazine derivative or its salt

Active Publication Date: 2019-04-02
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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

Method used

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Examples

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Embodiment

[0262] 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 methods of the raw material compounds are shown in the production examples, respectively. 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 produced by a combination of these production methods or a method obvious to those skilled in the art.

[0263] In addition, in the following tables, the following abbreviations may be used.

[0264] PEx: production example number, Ex: example number, PSyn: production method of the production example compound (the number in the PSyn column indicates that the compound is produced by the same method as the compound having its number as the pr...

manufacture example 1

[0271] Under argon atmosphere under ice cooling, in (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid (4g), (2R,5S) N,N-diisopropyl Ethylamine (5mL) and O-(7-aza-1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (5.5g) in Stir overnight at room temperature. The reaction mixture was ice-cooled, and saturated aqueous sodium bicarbonate solution was added and stirred. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 80:20) to obtain (2R,5S)-4-{[(3S,4R)-1-tert-butyl - tert-butyl 4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-2,5-dimethylpi...

manufacture example 10

[0273] Under ice cooling, in (2R,5S)-4-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-2 , Add hydrogen chloride (4M di alkane solution, 30mL). Thereafter it was stirred at room temperature for 14 hours. The solvent was distilled off under reduced pressure to obtain [(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl][(2S,5R) -2,5-Dimethylpiperazin-1-yl]methanone dihydrochloride (5.28 g).

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Abstract

To provide a compound useful as an MC4 receptor agonist. The present inventors have made studies on MC4 receptor agonists. As a result, it is confirmed that a piperazine derivative has an MC4 receptoragonist activity, which leads to the accomplishment of the present invention. The piperazine derivative according to the present invention has an MC4 receptor agonist activity, and therefore can be used as a prophylactic or therapeutic agent for disturbance of urination in bladder and urinary tract diseases, particularly underactive bladder, hypotonic bladder, acontractile bladder, detrusor underactivity, neurogenic bladder, urethral relaxation failure, detrusor-sphincter dyssynergia and prostatic hyperplasia.

Description

technical field [0001] The present invention relates to have melanocortin 4 receptor (hereinafter referred to as MC 4 A piperazine derivative or a salt thereof that acts as an agonist and can be used as an active ingredient of a pharmaceutical composition such as a pharmaceutical composition for the prevention or treatment of bladder or urinary system diseases. Background technique [0002] The important functions of the lower urinary tract are urine storage and urination, but these functions are regulated by the coordinated action of the bladder and urethra. That is, when storing urine, the smooth muscle of the bladder relaxes, and the smooth muscle of the urethra and the external urethral sphincter contract, whereby the state of high urethral resistance is maintained and continence is maintained. On the other hand, the smooth muscle of the bladder contracts during urination, and the smooth muscle of the urethra relaxes, and the contraction of the external urethral sphinct...

Claims

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Application Information

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IPC IPC(8): C07D401/14A61K31/496A61P13/02A61P13/10A61P43/00C07D403/06C07D405/14
CPCA61K31/496A61P13/02A61P13/10A61P43/00C07D207/12C07D241/04C07D307/20C07D309/14C07D405/14C07D401/14C07D403/06
Inventor 菅根隆史朝井范夫森友博幸山下大辅细贝直美
Owner ASTELLAS PHARMA INC
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