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A kind of amide arylpiperazine derivative and its preparation method and application

An arylpiperazine and derivative technology, applied in the field of medicinal chemistry, can solve the problems of cardiovascular side effects, difficulty in distinguishing blood vessels and urinary tract α-adrenergic receptors, etc., and achieve strong inhibitory activity, good inhibitory selectivity, and guarantee drug therapeutic effect

Active Publication Date: 2022-05-17
袁牧
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the currently used α1-AR antagonists are generally antagonistic to the three subtypes of α1-AR (Eur.J.Pharmacol.1999,374,495–502), and it is difficult to distinguish vascular and urinary tract α-adrenergic receptors , often lead to a series of cardiovascular side effects in patients while treating BPH

Method used

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  • A kind of amide arylpiperazine derivative and its preparation method and application
  • A kind of amide arylpiperazine derivative and its preparation method and application
  • A kind of amide arylpiperazine derivative and its preparation method and application

Examples

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Effect test

preparation example 1

[0038] Preparation Example 1 Preparation of Intermediate II

[0039]

[0040] Dissolve 5g of 4-bromobutane-1-ammonia hydrobromide and 4.686g (1.5eq) of di-tert-butyl dicarbonate in dichloromethane solution, stir to dissolve, slowly dropwise add 193mg (0.1eq) 4-Dimethylaminopyridine and 8.688g (4eq) of triethylamine in dichloromethane were reacted at room temperature for 1.5h. Finally, the reaction solution was washed with 0.5N hydrochloric acid aqueous solution and saturated brine in a separating funnel, dried over anhydrous sodium sulfate, filtered, and the organic solvent was distilled off under reduced pressure to obtain 5.387 g of Intermediate II.

preparation example 2

[0041] Preparation Example 2 Preparation of Intermediate III

[0042]

[0043] Intermediate II (5.387g) (1.5eq) was dissolved in acetonitrile, and 5.923g (3eq) of potassium carbonate solid and 3.150g of 2-isopropoxyphenylpiperazine were added, and refluxed at 80°C overnight. After the reaction solution was filtered, the mixed sample was applied to a silica gel column, and gradient elution was performed with petroleum ether and ethyl acetate to obtain 4.502 g of intermediate III.

preparation example 3

[0044] Preparation Example 3 Preparation of Intermediate IV

[0045]

[0046]Dissolve 4.502g of intermediate III in 120ml of dichloromethane, slowly dropwise add 30ml of trifluoroacetic acid and stir at room temperature, spot the plate to monitor the end of the reaction. After the reaction was complete, add 20% aqueous sodium hydroxide solution to adjust the reaction solution to be alkaline, then extract 3 times with dichloromethane, dry over anhydrous sodium sulfate, remove the organic solvent by distillation under reduced pressure to obtain 3.203g of intermediate IV, without further purified and used directly in the next reaction.

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Abstract

The invention belongs to the technical field of medicinal chemistry, and specifically relates to an amide-type arylpiperazine derivative, and further discloses a preparation method thereof and an application for preparing a medicine for treating benign prostatic hyperplasia. The amides arylpiperazine derivatives of the present invention and pharmaceutically acceptable salts thereof, through preliminary pharmacological studies, passed the biological function test of rat isolated tissues (spleen, thoracic aorta, vas deferens), the derivatives object pair α 1A -AR,α 1D ‑AR showed strong antagonistic activity and good selectivity, while for α 1B The subtype has weak antagonistic ability, which can effectively reduce the side effects of the drug while ensuring the curative effect of the drug, and can provide a more efficient and safer choice for the research and development of new anti-benign prostatic hyperplasia drugs.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to an amide-type arylpiperazine derivative, and further discloses a preparation method thereof and an application for preparing a medicine for treating benign prostatic hyperplasia. Background technique [0002] Benign prostatic hyperplasia (BPH) is a common urinary disorder in elderly men. The main clinical manifestations of BPH are lower urinary tract symptoms (LUTS), including frequent urination, urgency, waiting for urination, increased nocturia, and urination. Weakness and other symptoms; severe cases can lead to complications, such as acute urinary retention, urinary incontinence, recurrent urinary tract infections, hematuria, kidney failure, bladder stones, etc. In recent years, with the improvement of national living standards, the prolongation of the average life expectancy of the population and the acceleration of population aging, its incidence has ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/13C07D213/56C07D307/79C07D319/20C07D233/26C07D223/10C07D209/18C07D295/15C07D277/30C07D213/80C07D213/803C07D495/04A61P13/08
CPCA61P13/08C07D209/18C07D213/56C07D213/80C07D213/803C07D223/10C07D233/26C07D277/30C07D295/13C07D295/15C07D307/79C07D319/20C07D495/04
Inventor 袁牧陈洪叶碧波邵斌豪黄珺珺刘夏雯
Owner 袁牧
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