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Aralkyl piperidine (piperazidine) derivate and use thereof in mental disease treatment

A technology of aralkylpiperidine and derivatives is applied in the application field of preparing medicines for treating mental and neurological diseases, and can solve the problems of obvious symptoms, elevated prolactin and the like

Inactive Publication Date: 2008-11-12
JIANGSU HENGYI PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] One of the technical problems to be solved in the present invention is to disclose a kind of aralkyl piperidine (azine) derivatives, to overcome the defects of side effects such as obvious extrapyramidal symptoms and elevated prolactin in existing drugs, to solve clinical problems and meet clinical requirements. medication needs;

Method used

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  • Aralkyl piperidine (piperazidine) derivate and use thereof in mental disease treatment
  • Aralkyl piperidine (piperazidine) derivate and use thereof in mental disease treatment
  • Aralkyl piperidine (piperazidine) derivate and use thereof in mental disease treatment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] I-17-[4-(4-(6-chloro-benzoisoxazole)-1-piperazinyl)-n-butoxy]-3,4-dihydro-2(1H)-quinolinone Hydrochloride

[0117] a) Preparation of 4-chloro-methyl salicylate

[0118] Slowly drop 5ml of concentrated sulfuric acid into 100ml of methanol, add 4-chloro-salicylic acid powder (17.20g, 0.1mol) after the solution is cooled, reflux for 24h, cool down, a large amount of precipitate precipitates, filter out, wash with a small amount of methanol, and Recrystallized from absolute ethanol to obtain 15.60 g of methyl 4-chloro-salicylate, with a yield of 83%.

[0119] b) Preparation of 4-chloro-N,2-dihydroxy-benzamide

[0120] Put (5.25g, 75mmol) hydroxylamine chloride solid in an eggplant-shaped bottle, add a small amount of water dropwise under ice bath to dissolve it, then add 15ml of 50% NaOH solution dropwise, stir for 5 minutes, and add 4 - Chloro-methyl salicylate (9.3g, 50mmol) in dioxane solution 50ml, react at room temperature for 24h after the dropwise addition, a redd...

Embodiment 2

[0135] I-27-[4-(4-(5-chloro-benzoisoxazole)-1-piperazinyl)-n-butoxy]-3,4-dihydro-2(1H)-quinolinone Hydrochloride

[0136] With 5-chloro-salicylic acid salicylic acid as the starting material, the target compound was synthesized according to the method of preparation I-1

[0137] Elemental Analysis: C 24 h 27 ClN 4 o 3 • 2HCl (theoretical %: C 63.36, H 5.98, N 12.31; found % C 62.72, H 5.92, N 12.24).

[0138] 1 HNMR (DMSO-d 6 ): δ10.03 (s, 1H, CONH), 7.99-6.46, (6H, aromatic ring-H), 4.10-4.15 (2H, piperazine-H), 3.99 (t, J=6.4HZ, 2H, O -CH2,) 3.50-3.70 (2H, piperazine-H), 3.22-3.57 (m, 6H), 2.75 (t, J=8HZ, 2H), 2.45 (t, J=8HZ, 2H) 1.71-1.98 ( m, 4H)

[0139] MS: m / z 454

Embodiment 3

[0141] I-37-[4-(4-(Benzisoxazole)-1-piperazinyl)-n-butoxy]-3,4-dihydro-2(1H)-quinolinone hydrochloride

[0142] Using salicylic acid as the starting material, the target compound was synthesized according to the method of preparation I-1.

[0143] Elemental Analysis: C 24 h 28 N 4 o 3 • 2HCl (theoretical %: C 68.55, H 6.71, N 13.32; found % C 68.00, H 6.65, N 13.21).

[0144] 1 HNMR (DMSO-d 6 ): δ10.00 (s, 1H, CONH), 7.96-6.48, (7H, aromatic ring-H), 4.05-4.10 (2H, piperazine-H), 3.93 (t, J=6.4HZ, 2H, O -CH2,) 3.59-3.62 (2H, piperazine-H), 3.20-3.50 (m, 6H), 2.78 (t, J=8HZ, 2H) 2.41 (t, J=8HZ, 2H) 1.73-1.93 (m , 4H)

[0145] MS: m / z 420

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Abstract

The invention discloses an aralkyl piperidine (oxazine) derivative and an application of the derivative in treating neurological and mental diseases. Pharmacological tests show that the derivative has a good effect of resisting schizophrenia and little toxicity. The derivative is free alkali or salt of a compound having the following structure general formula.

Description

technical field [0001] The invention relates to aralkyl piperidine (azine) derivatives and their application in the preparation of drugs for treating mental and nervous diseases. Background of the invention [0002] Schizophrenia is a common severe mental illness, the most serious and harmful of all mental illnesses, with a global incidence of about 1%. With the deterioration of the social environment and the increasing pressure of life , the incidence rate showed a clear upward trend. Most schizophrenic patients give up treatment due to the long treatment cycle, high cost, and large side effects, which often lead to more serious social consequences. Schizophrenia is not only a mental health problem that urgently needs to be overcome, but also an arduous social responsibility that medical workers must bear. [0003] The current clinically used drugs are mainly traditional antipsychotics (such as dopamine D2 receptor antagonists) and atypical antipsychotics (such as D2 / 5-HT...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D417/12C07D417/14A61K31/4709A61P25/00
Inventor 李建其彭少平蔡王平高凯
Owner JIANGSU HENGYI PHARMA
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