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Substituted phenyl piperazinyl aralkylone derivatives and application thereof to preparation of analgesics

A technology of phenylpiperazine and aralkylone, which is applied in the field of substituted phenylpiperazine aralkylone derivatives, can solve problems such as the reduction of addictive gastric motility, and achieve the effect of strong anti-pain writhing response.

Inactive Publication Date: 2011-03-16
NHWA PHARMA CORPORATION +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] One of the technical problems to be solved in the present invention is to disclose a class of substituted phenylpiperazine aryl alkanone derivatives, to overcome the defects of existing analgesics that have side effects such as addiction and respiratory depression, gastric motility reduction and sedation, to solve clinical problems

Method used

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  • Substituted phenyl piperazinyl aralkylone derivatives and application thereof to preparation of analgesics
  • Substituted phenyl piperazinyl aralkylone derivatives and application thereof to preparation of analgesics
  • Substituted phenyl piperazinyl aralkylone derivatives and application thereof to preparation of analgesics

Examples

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preparation example Construction

[0087] 1) Preparation of α-bromophenone

[0088] 0.1 mol of aryl alkanone was dissolved in 200 ml of a mixed solvent of chloroform and ethyl acetate (volume ratio 1:1), and 0.2 mol of solid copper bromide was added under stirring at room temperature, and the reaction was refluxed for 12 hours. Cool the reaction solution to room temperature, filter, and concentrate the filtrate to dryness. The remaining oil is extracted with petroleum ether (2x100ml) to remove insoluble matter. The petroleum ether phases are combined and evaporated to dryness to obtain an oil. Yield: 40-94%.

[0089] 2) Preparation of 1-substituted phenyl-4-aroylalkylpiperazine hydrochloride

[0090] Substituted phenylpiperazine (0.01mol) and a-bromoaryl alkanone (0.012mol) were dissolved in 50ml of acetone solvent, anhydrous potassium carbonate (4.15g, 0.03mol) was added, and the temperature was raised to reflux for 5 hours. Cool the reaction solution, filter, evaporate the filtrate to dryness, add 150ml of e...

Embodiment 1

[0092] Preparation of 1-(4-methoxyphenyl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone hydrochloride (I-1)

[0093] Using p-methoxyacetophenone as raw material, prepare a-bromo-p-methoxyacetophenone according to the synthesis and post-treatment methods in the general method. Take a-bromo-p-methoxyacetophenone (0.66g, 2.86mmol) and 3-trifluoromethylphenylpiperazine (0.60g, 2.6mmol), dissolve them in 50ml of acetone solvent, add anhydrous potassium carbonate (1.08g, 7.8mmol), heated and refluxed for 5 hours. According to the post-treatment operation in the general method, 1-(4-methoxyphenyl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone hydrochloride was obtained Salt 0.86g, yield 79.26%. Melting point: 216.7-218.7℃, MS(m / s): 379.0[M+1] + .

[0094] 1 HNMR (DMSO-d6): δ3.33-3.96 (m, 8H, piperazine-H), 3.87 (s, 3H, -OCH 3 ), 5.12 (s, 2H, -CH2-), 7.12-7.98 (m, 8H, Ar-H).

Embodiment 2

[0096] Preparation of 1-(3-methoxyphenyl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone hydrochloride (I-2)

[0097] Using 3-methoxyacetophenone as a raw material, prepare a-bromo-3-methoxyacetophenone according to the synthesis and post-treatment methods in the general method. Take a-bromo-3-methoxyacetophenone (0.66g, 2.86mmol) and 3-trifluoromethylphenylpiperazine (0.60g, 2.6mmol), dissolve in 50ml of acetone solvent, add anhydrous Potassium carbonate (1.08g, 7.8mmol) was heated and refluxed for 5 hours. According to the post-treatment operation in the general method, 1-(3-methoxyphenyl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone hydrochloride was obtained Salt 0.82g, yield 75.93%. Melting point: 219.9-222.3℃, MS(m / s): 379.1[M+1] + .

[0098] 1 HNMR (DMSO-d6): δ3.36-3.96 (m, 8H, piperazine-H), 3.84 (s, 3H, -OCH 3 ), 5.22(s, 2H, -CH 2 -), 7.14-7.59 (m, 8H, Ar-H).

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Abstract

The invention discloses substituted phenyl piperazinyl aralkylone derivatives and application thereof to the preparation of analgesics. The derivatives of the invention may be free alkali or salts of compounds with a general structural formula. Pharmacological experiments show that the compounds of the invention are nonopioid analgesics and have high analgesic activity, relatively poorer toxic or side effect and the general structural formula.

Description

technical field [0001] The invention relates to a substituted phenylpiperazine aryl alkanone derivative and its application in the preparation of analgesics. Background technique [0002] Severe acute and chronic pain refers to the excitation of nociceptors caused by various injurious stimuli, and the impulse of the messenger is transmitted through nociceptive information, which is transmitted to the central nervous system to cause nociception and pain. Severe acute and chronic pain, including tumor pain, postoperative pain, and various recurrent acute and chronic pains, plagues tens of millions of patients and is a major clinical problem at present. [0003] Clinically used analgesics can be roughly divided into the following three categories: 1) non-steroidal anti-inflammatory analgesics 2) opioid analgesics 3) auxiliary analgesics, including: local anesthetics, antidepressants, antiepileptics Wait. [0004] Currently, opioid analgesics are mainly used clinically for acu...

Claims

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Application Information

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IPC IPC(8): C07D295/108C07D333/22A61K31/495A61K31/496A61P29/00A61P25/00
CPCA61K31/496A61K31/495C07D295/10C07D333/22C07D295/108A61P25/00A61P25/04A61P29/00
Inventor 李建其解鹏张桂森王冠王玉梅徐祥清刘世成
Owner NHWA PHARMA CORPORATION
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