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A kind of piperazine benzamide derivatives and application thereof

A technology of benzamide and derivatives, applied in the field of benzamide derivatives and their applications, can solve problems such as adverse reactions, changes, and increased suicide risks, and achieve strong antidepressant activity, high affinity, and safety good effect

Active Publication Date: 2022-05-24
NHWA PHARMA CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Among the compounds with pharmacological activity on sigma-1 receptors, such as imipramine and fluvoxamine, although both have certain curative effect on the treatment of depression, the adverse reactions include digestive tract Reactions, dry mouth, drowsiness, hypotension, rapid heart rate, urinary retention, ECG changes, increased risk of suicide, etc.

Method used

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  • A kind of piperazine benzamide derivatives and application thereof
  • A kind of piperazine benzamide derivatives and application thereof
  • A kind of piperazine benzamide derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1, (4-(2,3-dichlorophenyl)piperazin-1-yl)(4-(3-(hexahydrocyclopentane[c]pyrrol-2(1H)-yl)propoxy yl)phenyl)methanone (Compound 1)

[0043] Reaction 1

[0044]

[0045] 1) Take 4.6 g of methyl 4-hydroxybenzoate, 9.0 g of 1,3-dibromopropane and 12.4 g of potassium carbonate, add 50 ml of acetone, and heat under reflux for 6 hours. TLC detection, the reaction was completed, cooled to room temperature, evaporated to dryness, added an appropriate amount of dichloromethane, washed with water, separated the aqueous layer, dried the organic layer with anhydrous magnesium sulfate, evaporated the solvent to dryness to obtain a light yellow oil, which was washed with eluent. Petroleum ether:ethyl acetate 5:1, column chromatography gave 7.3 g of white solid, melting point 126-128°C, yield 89.0%.

[0046]2) Take 5.4 g of the first step product, 8.2 g of anhydrous potassium carbonate, 50 ml of acetonitrile, 2.7 g of octahydrocyclopentane[c]pyrrole, heat under reflux for 6...

Embodiment 2

[0050] Example 2, (4-(4-chlorophenyl)piperazin-1-yl)(4-(3-(hexahydrocyclopentane[c]pyrrol-2(1H)-yl)propoxy)benzene yl) ketone (compound 3)

[0051] Substitute 2,3-dichlorophenylpiperazine for 4-chlorophenylpiperazine, and prepare the target compound according to the method of Example 1.

[0052] 1H NMR(400MHz, CDCl3)δ8.25-7.67(m,2H),7.31-6.94(m,4H),6.94-6.37(m,2H),4.08(t,J=12.3Hz,2H),3.59( t,J=8.3Hz,2H),3.16(t,J=8.3Hz,2H),3.00-2.67(m,2H),2.42(t,J=12.2Hz,2H),2.21-1.99(m,2H) ),1.97-1.56(m,8H),1.54-1.25(m,2H).MS(ESI)m / z 468.2([M+H]+).

Embodiment 3

[0053] Example 3, (4-(3-chlorophenyl)piperazin-1-yl)(4-(3-(hexahydrocyclopentane[c]pyrrol-2(1H)-yl)propoxy)benzene yl) ketone (compound 4)

[0054] Substitute 2,3-dichlorophenylpiperazine for 3-chlorophenylpiperazine, and prepare the target compound according to the method of Example 1.

[0055] 1H NMR(400MHz, CDCl3)δ8.06-7.75(m,2H),7.11-6.94(m,2H),6.82-6.77(m,2H),6.66-6.61(m,2H),4.04(t,J =15.1Hz,1H),3.59(t,J=10.3Hz,4H),3.16(t,J=10.2Hz,4H),2.99-2.66(m,2H),2.42(t,J=15.3,2H) ,2.22-2.00(m,2H),1.99-1.12(m,10H).MS(ESI)m / z 468.2([M+H]+).

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Abstract

The invention belongs to the field of medicinal chemistry, and specifically relates to a compound of formula (I) and a pharmaceutically acceptable salt thereof, which are used in the prevention and treatment of depression;

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a benzamide derivative and an application thereof. Background technique [0002] The role of the sigma-1 receptor (σ-1 Receptor), in particular the sigma-1 receptor subtype, has been identified as an important target in the pathophysiology of neuropsychiatric disorders, with drugs for the treatment of neuropsychiatric disorders such as depression and anxiety ([J]. Human Psychopharmacology: Clinical and Experimental, 2010, 25(3): 193-200). Brain-derived neurotrophic factor (BDNF) is the most widely studied neurotrophic factor in depression research. In general, the reduction of BDNF levels is associated with the pathophysiology of depression, and its upregulation is characteristic of antidepressant treatment, and the sigma-1 receptor is involved in the upregulation of BDNF expression and the enhancement of BDNF-activated PLCγ / IP3 / Ca2+ signaling pathway , thus has the potential...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/52C07D403/12C07D413/14C07D417/12C07D409/12A61P25/00A61P25/18A61P25/24A61K31/496A61K31/506A61K31/454
CPCC07D209/52C07D403/12C07D413/14C07D417/12C07D409/12A61P25/00A61P25/18A61P25/24
Inventor 窦飞靖鹏邱印利赵松曹锋陈寅高梓真
Owner NHWA PHARMA CORPORATION
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