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Application of Heterocyclic Substituted Phenylpiperazine or Phenylpiperidine Derivatives in Antidepressants

A technology of phenylpiperazine and phenylpiperidine is applied in the application field of heterocyclic substituted phenylpiperazine or phenylpiperidine derivatives in antidepressant drugs, and can solve the new antidepressant drug with three-target action Less problems, to achieve the effect of outstanding pharmacokinetic characteristics, outstanding targeting novelty, and remarkable novelty

Active Publication Date: 2021-09-24
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, at home and abroad for SSRI / 5-HT 1A / 5-HT 7 There are few research reports on new antidepressants with triple-target effects. Therefore, drug research and development in this direction has great innovation and important scientific significance

Method used

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  • Application of Heterocyclic Substituted Phenylpiperazine or Phenylpiperidine Derivatives in Antidepressants
  • Application of Heterocyclic Substituted Phenylpiperazine or Phenylpiperidine Derivatives in Antidepressants
  • Application of Heterocyclic Substituted Phenylpiperazine or Phenylpiperidine Derivatives in Antidepressants

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] 5-Fluoro-3-(2-(4-(2-(pyridin-4-yl)phenyl)piperazin-1-yl)ethyl)-1H-indole (V-1) and its hydrochloride preparation of

[0124] o-iodobromobenzene compound (I) (0.1mol), N-Boc-piperazine (0.12mol), Pd 2 (dba) 3 (0.01mol) and Me 4 tBuXPhos (0.01 mol) was dissolved in toluene (300 mL), and sodium tert-butoxide (0.2 mol) was added, followed by general method 1 and step 1 to obtain intermediate II (white solid) with a yield of 72%. MS(m / z):341.08[M+1] + .

[0125] Intermediate (II) (0.05mol) was dissolved in methanol (300mL), and methanolic hydrochloride (4N, 0.2mol) was added. According to general method 1 and step 2, intermediate III (colorless liquid) was obtained with a yield of 80%. MS(m / z):241.03[M+1] + .

[0126] 2-(5-fluoro-1H-indol-3-yl)ethyl-4-methylbenzenesulfonate compound (IV) (0.05mol) and intermediate (III) (0.05mol) were dissolved in acetonitrile (200mL ), potassium carbonate (0.1 mol) was added. According to general method 1 and step 3, intermediate ...

Embodiment 2

[0130] 5-Fluoro-3-(2-(4-(2-(pyridin-3-yl)phenyl)piperazin-1-yl)ethyl)-1H-indole (V-2) and its hydrochloride preparation of

[0131] o-iodobromobenzene compound (I) (0.1mol), N-Boc-piperazine (0.12mol), Pd 2 (dba) 3 (0.01mol) and Me 4 tBuXPhos (0.01 mol) was dissolved in toluene (300 mL), and sodium tert-butoxide (0.2 mol) was added, followed by general method 1 and step 1 to obtain intermediate II (white solid) with a yield of 68%. MS(m / z):341.08[M+1] + .

[0132] Intermediate (II) (0.05mol) was dissolved in methanol (300mL), and methanolic hydrochloride (4N, 0.2mol) was added. According to general method 1 and step 2, intermediate III (colorless liquid) was obtained with a yield of 75%. MS(m / z):241.03[M+1] + .

[0133]2-(5-fluoro-1H-indol-3-yl)ethyl-4-methylbenzenesulfonate compound (IV) (0.05mol) and intermediate (III) (0.05mol) were dissolved in acetonitrile (200mL ), potassium carbonate (0.1 mol) was added. According to general method 1 and step 3, intermediate V...

Embodiment 3

[0137] 5-fluoro-3-(3-(4-(4-fluoro-2-(pyridin-3-yl)phenyl)piperazin-1-yl)propyl)-1H-indole (V-3) and Preparation of its hydrochloride

[0138] 2-Bromo-4-fluoro-1-iodobenzene compound (I) (0.1mol), N-Boc-piperazine (0.12mol), Pd 2 (dba) 3 (0.01mol) and Me 4 tBuXPhos (0.01 mol) was dissolved in toluene (300 mL), and sodium tert-butoxide (0.2 mol) was added, followed by general method 1 and step 1 to obtain intermediate II (white solid) with a yield of 70%. MS(m / z):359.10[M+1] + .

[0139] Intermediate (II) (0.05mol) was dissolved in methanol (300mL), and methanolic hydrochloride (4N, 0.2mol) was added. According to general method 1 and step 2, intermediate III (colorless liquid) was obtained with a yield of 78%. MS(m / z):259.12[M+1] + .

[0140] 3-(5-fluoro-1H-indol-3-yl)propyl-4-methylbenzenesulfonate compound (IV) (0.05mol) and intermediate (III) (0.05mol) were dissolved in acetonitrile (200mL ), potassium carbonate (0.1 mol) was added. According to general method 1 an...

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Abstract

The invention discloses the application of a heterocyclic substituted phenylpiperazine (pyridine) derivative in antidepressant drugs. 1A and 5‑HT 7 The two receptors have good inhibitory activity, the compound has good antidepressant activity in vivo, has the effect of improving cognitive function and is well tolerated in animals. The heterocyclic substituted phenylpiperazine (pyridine) derivatives are compounds represented by general structural formula (I) or pharmaceutically acceptable salts thereof:

Description

technical field [0001] The invention relates to a class of heterocyclic substituted phenylpiperazine or phenylpiperidine derivatives and their application in treating depression. Background technique [0002] Depression is the mental illness with the highest incidence rate in the world. It has the characteristics of long duration and easy recurrence, and it can lead to suicide in severe cases. According to the World Health Organization (WHO), depression is currently the fourth leading disease in the world. Depression is projected to become the second-largest medical burden worldwide by 2030. [0003] To date, the mechanism of action of antidepressant drugs has not been fully elucidated. Drugs with clear curative effects basically act on the synaptic site of nerve endings, and exert therapeutic effects by regulating the level of neurotransmitters in the synaptic cleft. Biochemical studies of its etiology have shown that depression is mainly related to the central five-hydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07D409/12C07D209/16C07D209/14C07D403/12C07D405/12C07D409/14C07D401/06A61P25/24A61K31/496A61K31/5377A61K31/415A61K31/454A61K31/506
CPCA61P25/24C07D209/14C07D209/16C07D401/06C07D401/12C07D403/12C07D405/12C07D409/12C07D409/14
Inventor 李建其王文韬周爱南张庆伟钱浩吴建威
Owner SHANGHAI INST OF PHARMA IND CO LTD
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