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Amide-type phenylpiperazine derivative, and salt and application thereof in preparing medicine for treating benign prostatic hyperplasia

A kind of phenylpiperazine-like and derivative technology, which is applied in the application field of preparing medicine for treating benign prostatic hyperplasia, and achieves the effect of high urinary tract selectivity

Inactive Publication Date: 2014-08-13
GUANGZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large number of experiments confirmed that the traditional α 1 Receptor antagonists such as prazosin, terazosin, alfuzosin do not have alpha 1 Isotype selectivity, for α 1B Subtypes produce the same degree of antagonism and are the main cause of side effects such as orthostatic hypotension, fatigue, and drowsiness of this class of drugs

Method used

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  • Amide-type phenylpiperazine derivative, and salt and application thereof in preparing medicine for treating benign prostatic hyperplasia
  • Amide-type phenylpiperazine derivative, and salt and application thereof in preparing medicine for treating benign prostatic hyperplasia
  • Amide-type phenylpiperazine derivative, and salt and application thereof in preparing medicine for treating benign prostatic hyperplasia

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of N-(3-bromopropyl) tert-butyl carbamate

[0035]

[0036] 3-Bromopropylamine hydrobromide (5g, 22.84mmol) and di-tert-butyl dicarbonate (5.98g, 27.40mmol) were dissolved in an appropriate amount of dichloromethane and stirred at room temperature, and triethylamine (9.5ml, 68.16 mmol) and 4-dimethylaminopyridine (0.28g, 2.28mmol) in dichloromethane mixed solution. The titration time was controlled to be 1 h, and stirring was continued at room temperature for 30 min after the titration was completed. After the reaction was complete, the reaction solution was washed once with 0.5N HCl and saturated brine, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the organic solvent to obtain 4.17 g of a light yellow oil, and the obtained crude product was not further purified. used directly for the next reaction.

Embodiment 2

[0037] Example 2: Preparation of N-tert-butoxycarbonyl-3-[4-(2-methoxyphenyl)-1-piperazinyl]propylamine

[0038]

[0039] Dissolve 4.17 g of crude tert-butyl N-(3-bromopropyl)carbamate and 1-(2-methoxyphenyl)piperazine (3.70 g, 19.24 mmol) obtained in the previous step in an appropriate amount of CH 2 Cl 2 , add anhydrous potassium carbonate (2.66g, 19.24mmol) and sodium iodide (0.26g, 1.73mmol), stir at room temperature for 1d. After the reaction was completed, the reaction solution was washed once with water, anhydrous NaSO 4 Dry and concentrate under reduced pressure to obtain 7.28 g of crude milk product. The crude product was purified by 300-400 mesh silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4:1, adding 5‰ triethylamine) to obtain 5.69 g of light yellow oil, Example 1 and Example 2 The total yield of the two-step reaction was 71.3%. ESI-MS(m / z): 350.3[M+H] + .

Embodiment 3

[0040] Example 3: 3-[4-(2-methoxyphenyl)-1-piperazinyl]propylamine

[0041]

[0042] Dissolve 500mg of N-tert-butoxycarbonyl-3-[4-(2-methoxyphenyl)-1-piperazinyl]propylamine in 40ml of dichloromethane, slowly add 10ml of trifluoroacetic acid dropwise, and stir at room temperature for 3h. After the reaction was complete, 20% NaOH solution was added to the reaction solution to adjust the pH to 13. Dichloromethane was extracted twice, and the organic layers were combined. After the organic layer was dried with anhydrous sodium sulfate, it was concentrated under reduced pressure to remove the organic solvent and a light yellow oil was obtained. The obtained product was directly used in the next reaction without further purification. ESI-MS(m / z): 2502[M+H] + .

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Abstract

The invention discloses an amide-type phenylpiperazine derivative, salt and anapplication thereof in preparing medicines for treating benign prostatic hyperplasia. The phenylpiperazine type compounds can selectively antagonize <1A>- or <1D>- adrenergic receptors. Researches indicate that an <1A> / <1D> selective antagonist has high urinary tract selectivity, and at the same time, is not liable to cause side effects of postural hypotension, exhaustion, drowsiness and the like are not . When being used as an antagonist of the <1A>- or <1D>- adrenergic receptors, the compounds, provided by the invention, can be used for treating benign prostatic hyperplasia.

Description

technical field [0001] The invention relates to amides phenylpiperazine derivatives, a preparation method thereof and an application in preparation of medicines for treating benign prostatic hyperplasia. Background technique [0002] Benign prostatic hyperplasia (benign prostate hyperplasia, BPH) is a common multiple disease in middle-aged and elderly men. It usually begins to occur after the age of 40, and the incidence rate increases with age. According to relevant data, the incidence rate of BPH in 50-year-old men is over 50%, and the incidence rate of 80-year-old men is as high as 90%. Progressive enlargement of the glands can cause lower urinary tract symptoms (LUTS), clinically manifested as obstructive symptoms such as frequent urination, urgency, and urinary retention, which has brought great pain to many patients. Seriously affect the quality of life of middle-aged and elderly people. At present, the treatment methods for benign prostatic hyperplasia are mainly di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/26C07D215/48C07D241/44C07D241/42C07D319/20C07D231/56C07D471/04C07D295/13C07D333/68C07D213/82C07D213/81C07D209/48C07D317/68C07D319/18C07D311/84C07D311/24C07D209/42C07D307/68A61K31/496A61K31/495A61K31/498A61P13/08
CPCC07D217/26C07D209/42C07D209/48C07D213/81C07D213/82C07D215/48C07D231/56C07D241/42C07D241/44C07D295/13C07D307/68C07D311/24C07D311/84C07D317/68C07D319/18C07D319/20C07D333/68C07D471/04
Inventor 袁牧黄亚建黄珺珺叶碧波许芳何雪兰黄敏怡黄莉陈洪朱柳朱着徐静仪
Owner GUANGZHOU MEDICAL UNIV
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