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Substituted aryl piperazine aralkyl ketone derivative and application of derivative in preparing analgesic

A technology of arylpiperazine and aralkanone, which is applied in the field of arylpiperazine and aralkanone compounds, can solve problems such as the reduction of gastric motility, and achieve strong analgesic effect and strong anti-pain writhing reaction effect

Active Publication Date: 2013-10-23
NHWA PHARMA CORPORATION +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] One of the technical problems to be solved in the present invention is to disclose a class of substituted arylpiperazine aryl alkanone derivatives to overcome the defects of existing drugs that have side effects such as addiction, respiratory depression, and gastric motility reduction, so as to solve clinical problems

Method used

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  • Substituted aryl piperazine aralkyl ketone derivative and application of derivative in preparing analgesic
  • Substituted aryl piperazine aralkyl ketone derivative and application of derivative in preparing analgesic
  • Substituted aryl piperazine aralkyl ketone derivative and application of derivative in preparing analgesic

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] 1-(Pyridin-2-yl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone (I-1) hydrochloride, hydrobromide and Preparation of sulfate

[0082] 1) Intermediate: Synthesis of 2-bromo-1-(pyridin-2-yl)ethanone hydrobromide

[0083] Add 1-(pyridin-2-yl)ethanone (6.00g, 0.05mol) to 55ml of glacial acetic acid, then add bromine (8.80g, 0.055mol) and 40% hydrobromic acid (10.20g, 0.05mol), heated to 75℃ and reacted for 3.0h, stopped heating, cooled in an ice-water bath, filtered, recrystallized with a mixed solvent of ethyl acetate and methanol (weight ratio 5:1) to obtain a white solid 2-bromo-1-( (Pyridin-2-yl)ethanone hydrobromide 12.4g, yield 88.2%.

[0084] ESI-MS[M+H]+: m / z 199.96

[0085] 2) Synthesis of 1-(pyridin-2-yl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone (I-1) hydrochloride

[0086] Combine m-trifluoromethylphenylpiperazine hydrochloride (2.67g, 0.01mol), 2-bromo-1-(pyridin-2-yl)ethanone hydrobromide (2.81g, 0.011mol) and anhydrous Potassium carbonate (5....

Embodiment 2

[0098] Preparation of 1-(pyridin-3-yl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone (I-2) hydrochloride 1) intermediate :Synthesis of 2-bromo-1-(pyridin-3-yl)ethanone hydrobromide

[0099] Add 1-(pyridin-3-yl) ethyl ketone (6.00g, 0.05mol) to 55ml of glacial acetic acid, then add bromine (8.80g, 0.055mol) and a weight content of 40% hydrobromic acid (10.20g, 0.05mol), heated to 75°C and reacted for 3.0h, stopped heating, cooled in an ice-water bath, filtered, recrystallized with a mixed solvent of ethyl acetate and methanol (weight ratio 5:1) to obtain an off-white solid 2-bromo-1- (Pyridin-3-yl)ethanone hydrobromide 13.1g, yield 93.2%.

[0100] ESI-MS[M+H]+: m / z 199.96

[0101] 2) Synthesis of 1-(pyridin-3-yl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone (I-2) hydrochloride

[0102] Combine m-trifluoromethylphenylpiperazine hydrochloride (2.67g, 0.01mol), 2-bromo-1-(pyridin-3-yl)ethanone hydrobromide (2.81g, 0.011mol) and anhydrous Potassium carbonate (5.52g,...

Embodiment 3

[0107] Preparation of 1-(pyridin-4-yl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone (I-3) hydrochloride

[0108] 1) Intermediate: Synthesis of 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide

[0109] Add 1-(pyridin-3-yl)ethanone (2.42g, 0.02mol) to 25ml of glacial acetic acid, then add bromine (3.52g, 0.022mol) and 40% hydrobromic acid (4.08g, 0.02mol), heated to 75°C and reacted for 3.0h, stopped heating, cooled in an ice-water bath, filtered, and recrystallized with a mixed solvent of ethyl acetate and methanol (weight ratio 5:1) to obtain an off-white solid 2-bromo-1- (Pyridin-4-yl)ethanone hydrobromide 4.04g, yield 71.9%.

[0110] ESI-MS[M+H] + : M / z 199.98

[0111] 2) Synthesis of 1-(pyridin-4-yl)-2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethanone (I-3) hydrochloride

[0112] Combine m-trifluoromethylphenylpiperazine hydrochloride (2.67g, 0.01mol), 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (2.81g, 0.011mol) and anhydrous Potassium carbonate (5.52g, 0.04mol) was...

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Abstract

The invention discloses a substituted aryl piperazine aralkyl ketone derivative and an application of the derivative in preparing an analgesic. The substituted aryl piperazine aralkyl ketone derivative as well as physiologically acceptable salt thereof have quite a useful pharmaceutical property and excellent tolerance, particularly applied as a novel analgesic. The compound is a non-addictive central analgesic and free from remarkable sedation through animal experiments, and the compound is quite low in toxic and side effects and relatively high in a safety index. The substituted aryl piperazine aralkyl ketone derivative is free alkali or salt of a compound expressed as the structural general formula in the specification.

Description

Technical field [0001] The invention relates to an aryl piperazine aryl alkanone compound and its application in preparing analgesic drugs. Background technique [0002] Severe acute and chronic pain refers to the excitement of nociceptors caused by various damaging stimuli, and the impulse of the messenger through nociceptive information is transmitted to the central nervous system to cause nociception and pain. Severe acute and chronic pain, including tumor pain, postoperative pain, various recurrent acute and chronic pain, etc., plagues tens of millions of patients, and is currently a major clinical problem. [0003] Analgesics used clinically can be roughly divided into the following three categories: 1) Non-steroidal anti-inflammatory analgesics 2) Opioid analgesics 3) Other non-opioid analgesics, including: local anesthetics, antidepressants , Anti-epileptic drugs, etc. [0004] Currently, opioid analgesics are mainly used clinically for acute pain and cancer pain. The addic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/50C07D213/74C07D239/26A61K31/496A61K31/506A61P25/04A61P29/02
Inventor 李建其王冠张桂森徐祥清张莉刘世成赵松于民权
Owner NHWA PHARMA CORPORATION
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