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Morpholine benzamide compound and application thereof

A technology of compounds and drugs, applied in the field of medicine, can solve problems such as increased suicide risk, changes, adverse reactions, etc.

Active Publication Date: 2020-07-07
NHWA PHARMA CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 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, increased heart rate, urinary retention, ECG changes, increased risk of suicide, etc.

Method used

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  • Morpholine benzamide compound and application thereof
  • Morpholine benzamide compound and application thereof
  • Morpholine benzamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1, (2,6-dimethylmorpholino) (4-(3-(hexahydrocyclopentane [c] pyrrol-2 (1H)-yl) propoxy) phenyl) ketone ( Compound 4)

[0066]

[0067] ① Take 7.6g of methyl 4-hydroxybenzoate, 15.0g of 1,3-dibromopropane, 20.7g of potassium carbonate, add 50mL of acetone, and heat to 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 to remove the water layer, added anhydrous magnesium sulfate to the organic layer, dried, evaporated to dryness, and obtained a light yellow oil, which was analyzed by column chromatography (eluent petroleum ether: ethyl acetate = 5:1) to obtain 10.1 g of white solid with a melting point of 126-128°C and a yield of 74.3%.

[0068] ② Take 9.5g of the first step product, 14.5g of anhydrous potassium carbonate, 50mL of acetonitrile, 4.7g of octahydrocyclopentane[c]pyrrole, heat and reflux for 6 hours, cool t...

Embodiment 2

[0072] Example 2, (3,5-dimethylmorpholino) (4-(3-(hexahydrocyclopentane [c] pyrrol-2 (1H)-yl) propoxy) phenyl) ketone ( Compound 5)

[0073] The target compound 5 was prepared according to the method of Example 1, in step ④, 3,5-dimethylmorpholine was used instead of 2,6-dimethylmorpholine.

[0074] 1 H NMR (400MHz, CDCl 3 )δ8.19-7.73(m,2H),7.38-6.86(m,2H),4.32-3.89(m,4H),3.76-3.68(m,2H),3.43-3.35(m,2H),3.02- 2.68(m,2H),2.43(t,J=12.3Hz,1H),2.20-1.98(m,2H),1.96-1.54(m,8H),1.55-1.30(m,2H),1.26(d, J=9.8Hz,6H).MS(ESI)m / z387.3([M+H] + ).

Embodiment 3

[0075] Example 3, (2,3-dimethylmorpholino) (4-(3-(hexahydrocyclopentane [c] pyrrol-2 (1H)-yl) propoxy) phenyl) ketone ( Compound 6)

[0076] The target compound 6 was prepared according to the method of Example 1, and 2,6-dimethylmorpholine was replaced by 2,3-dimethylmorpholine in step ④.

[0077] 1 H NMR (400MHz, CDCl 3 )δ8.10-7.58(m,2H),7.47-6.76(m,2H),4.04(t,J=11.8Hz,2H),3.97-3.86(m,1H),3.77-3.30(m,5H) ,3.01-2.70(m,2H),2.46-2.39(m,2H),2.23-2.00(m,2H),1.99-1.55(m,8H),1.58-1.31(m,2H),1.26(d, J=9.9Hz, 3H), 1.13(d, J=9.3Hz, 3H).MS(ESI) m / z 387.3([M+H] + ).

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Abstract

The invention belongs to the field of medical treatment, and particularly relates to a morpholine benzamide compound and application thereof, the morpholine benzamide compound has a compound structureshown as a formula (A), and the compound can be applied to antidepressant drug treatment.

Description

technical field [0001] The invention belongs to the field of medicine, and specifically relates to a novel morpholine benzamide compound, a preparation method thereof, a composition containing the compound, and an application. [0002] technical background [0003] The role of the sigma-1 receptor (σ-1 Receptor), especially the sigma-1 receptor subtype, has been identified as an important target in the pathophysiology of neuropsychiatric diseases, and drugs for the treatment of neuropsychiatric diseases, 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, decreased BDNF levels are associated with the pathophysiology of depression, while their upregulation is characteristic of antidepressant treatment, and sigma-1 receptors are involved in the upregulation of BDNF expression and BDNF-activated...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D209/52A61K31/5377A61K31/538A61P25/00A61P25/18A61P25/20A61P25/22A61P25/24
CPCC07D413/12C07D209/52A61P25/00A61P25/18A61P25/20A61P25/22A61P25/24
Inventor 窦飞靖鹏高梓真邱印利赵松李颀楠殷辉陈寅
Owner NHWA PHARMA CORPORATION
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