Aralkylpiperidine derivative and application thereof in preparing analgesic and sedative medicament

A technology of aralkylpiperidine and derivatives, which is applied in the field of aralkylpiperidine derivatives, and can solve problems such as reduced gastric motility

Active 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

[0006] One of the technical problems to be solved in the present invention is to disclose a class of aralkylpiperidinol derivative compounds with medical value to overcome the defects of existing drugs with side effects such as addiction, respiratory depression, and gastric motility reduction. Clinical problems to meet people's analgesic needs;

Method used

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  • Aralkylpiperidine derivative and application thereof in preparing analgesic and sedative medicament
  • Aralkylpiperidine derivative and application thereof in preparing analgesic and sedative medicament
  • Aralkylpiperidine derivative and application thereof in preparing analgesic and sedative medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0158] III-1 Preparation of N-benzyl-4-phenacyl-4-piperidinol hydrochloride and N-benzyl-4-phenacyl-4-piperidinol hydrobromide:

[0159] Anhydrous cerium chloride (1.98 g, 8.0 mmol) and sodium iodide (3.6 g, 24.0 mmol) were added to 20 ml of anhydrous tetrahydrofuran solvent to form a suspension. Bromoacetophenone 1.60 (8.0mmol) and N-benzyl-4-piperidone 1.51g (8.0mmol) were dissolved in 10ml of anhydrous tetrahydrofuran, and the solution was added dropwise to the above suspension, according to the general method The operation of the synthesis and post-treatment methods of the third method gave 1.05 g of white crystals with a yield of 36%.

[0160] N-benzyl-4-phenacylmethyl-4-piperidinol was prepared by the above method, acidified with hydrobromic acid / ethanol solution to form a salt during post-treatment, and recrystallized from ethyl acetate / ethanol to obtain white crystals. Yield 32%.

[0161] Elemental analysis: (Theoretical %: C66.01, H7.20, N3.85, Cl9.74 Experimental...

Embodiment 2

[0166] III-2 N-p-chlorobenzyl-4-phenacyl-4-piperidinol hydrochloride

[0167] First prepare 4-phenacyl-4-piperidinol (II) according to the synthesis and post-treatment method of general method one, and then p-chlorobromobenzyl 1.76 (8.8mmol) and 4-phenacyl-4 - piperidinol (II) 1.75g ​​(8.0mmol), potassium iodide 0.03g (0.2mmol) and anhydrous K 2 CO 3 3.53g (25.6mmol) was placed in anhydrous acetone (60ml), and refluxed for 8 hours. According to the post-treatment operation of General Method 2, 2.25g of white crystals were obtained with a yield of 70.5%.

[0168] Elemental analysis: (Theoretical %: C60.31, H6.33, N3.52, Cl17.80 Experimental %: C60.42, H6.15, N3.30, Cl17.96)

[0169] 1 HNMR (DMSO-d 6 ): 1.80-2.10(m, 4H, piperidine-H), 3.00-3.20(m, 4H, piperidine-H), 3.15(s, 2H, CH 2 CO), 4.25-4.40 (m, 2H, PhCH 2 ), 4.98 (s, IH, piperidine-NHCl), 7.20-8.10 (m, 9H, ArH), 10.5-11.5 (2B, 1H, piperidine-OH).

[0170] MS: m / z 344 (M + )

Embodiment 3

[0172] III-3 N-p-fluorobenzyl-4-phenacyl-4-piperidinol hydrochloride

[0173] First prepare 4-phenacyl-4-piperidinol (II) according to the synthesis and post-treatment method of general method one, and then p-fluorobromobenzyl 1.66 (8.8mmol) and 4-phenacyl-4 - piperidinol (II) 1.75g ​​(8.0mmol), potassium iodide 0.03g (0.2mmol) and anhydrous K 2 CO 3 3.53g (25.6mmol) was placed in anhydrous acetone (60ml), and refluxed for 8 hours. According to the post-treatment operation of General Method 2, 2.06g of white crystals were obtained with a yield of 67.5%.

[0174] Elemental analysis: (Theoretical %: C62.90, H6.60, N3.67, Cl9.28 Experimental %: C60.87, H6.45, N3.39, Cl9.56)

[0175] 1 HNMR (DMSO-d 6 ): 1.80-2.10(m, 4H, piperidine-H), 3.00-3.20(m, 4H, piperidine-H), 3.13(s, 2H, CH 2 CO), 4.25-4.40 (m, 2H, PhCH 2 ), 5.02 (s, IH, piperidine-NHCl), 7.20-8.10 (m, 9H, ArH), 10.6-11.2 (2B, 1H, piperidine-OH).

[0176] MS: m / z 328 (M + )

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Abstract

The invention relates to aralkyl piperidine derivatives, a compound thereof and an application in the preparation of a novel analgesic and sedative drug. The derivatives of the invention are free alkali or salt of the general formula compound. The pharmacological test shows that the compound of the invention has good analgesic and sedative activity and extremely small side effect.

Description

technical field [0001] The invention relates to an aralkyl piperidine derivative and its application in preparing analgesic and sedative drugs. 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] The existing opioid analgesics have side effects such as drug addiction, respiratory depression, and decreased gastric motility, which limit their widespread use. Central analgesic drugs are not only the main research target in the field of pain relief, but also an important field of innovative drug research. Despite considerable e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/48C07D401/10C07D401/06C07D413/10A61K31/445A61K31/4523A61P25/20A61P25/04
Inventor 李建其王冠张桂森马彦琴季文华张媛郭琳
Owner NHWA PHARMA CORPORATION
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