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Medicine for treating depression

A technology of pharmacy and compound, applied in the field of chemical medicine, can solve the problems of sexual dysfunction, low efficacy, suicidal tendency and so on

Inactive Publication Date: 2018-09-25
郝惠敏
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Clinically commonly used antidepressants such as serotonin reuptake inhibitors (Selective serotonin reuptake inhibitors, SSRIs) antidepressant fluoxetine and other first-line drugs generally have low effective rate, slow onset, sexual dysfunction, and suicide tendencies and many other defects

Method used

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  • Medicine for treating depression
  • Medicine for treating depression
  • Medicine for treating depression

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of (E)-2-((3-(4-(trifluoromethyl)styryl)phenyl)thio)pyridine

[0028] 1-1. Synthesis of 1-iodo-3-nitrobenzene:

[0029]

[0030] Add 70mL of DMF to a 500mL reaction flask, then add nitrobenzene (30.12g, 0.245mol) and potassium carbonate (25.2g, 0.182mol), cool in an ice bath below 10°C, and after stirring, add iodine (0.250mol) Dissolve in 30mL DMF and add dropwise to the reaction system. The dropping time is 1 hour. The reaction mixture is stirred at 25°C for 16 hours until the reaction is complete. Sodium thiosulfate (22.3g, 0.141mol) and potassium carbonate (0.150g) are added. ) Aqueous solution (150mL), while maintaining the internal temperature below 30℃, stirring for 30 minutes, adding 200mL of water while stirring, the solid precipitated, suction filtration, the filter cake was washed with water, and vacuum dried at 60℃ for 12 hours to obtain a pale yellow solid 1-iodine -3-nitrobenzene, 43.84g, yield 72%. 1 H-NMR (400MHz, CDCl3) δ: 7.35 (t, 1H),...

Embodiment 2

[0043] Example 2: Synthesis of (E)-2-((3-(4-(trifluoromethyl)styryl)phenyl)thio)-6-fluoropyridine:

[0044]

[0045] Add 175mL DMF and (E)-1-iodo-3-(4-(trifluoromethyl)styryl)benzene (35.77g, 0.096mol) into a 500mL reaction flask, and add [1,1'- Bis(diphenylphosphine)ferrocene]dichloropalladium dichloromethane complex (1.49g, 0.0018mol), cesium carbonate (19.8g, 0.061mol) and dichloromethane 2mL, add 6-fluoro-pyridine -2-mercaptan (0.102mol), heated to 80℃, reacted for 16 hours until the reaction is complete, rotary evaporation to remove DMF, cooled to room temperature, add ethyl acetate 100mL, water 150mL, stir for 40 minutes, separate the organic phase, brine Wash, separate into layers, dry the organic phase with sodium sulfate, filter, evaporate to dryness, flash column chromatography to obtain pale yellow (E)-2-((3-(4-(trifluoromethyl)styryl)benzene (Yl)thio)-6-fluoropyridine, 29.16g, yield 81%. LC-MS (ESI, pos, ion) m / z: 376 [M+H].

Embodiment 3

[0046] Example 3: Synthesis of (E)-2-((3-(4-(trifluoromethyl)styryl)phenyl)sulfanyl)-6-methyl-pyridine:

[0047]

[0048] Add 175mL DMF and (E)-1-iodo-3-(4-(trifluoromethyl)styryl)benzene (35.77g, 0.096mol) into a 500mL reaction flask, and add [1,1'- Bis(diphenylphosphine)ferrocene]dichloropalladium dichloromethane complex (1.49g, 0.0018mol), cesium carbonate (19.8g, 0.061mol) and dichloromethane 2mL, add 6-methyl- Pyridine-2-thiol (0.102mol), heated to 80°C, reacted for 16 hours until the reaction was complete, rotary evaporated to remove DMF, cooled to room temperature, added ethyl acetate 100mL, water 150mL, stirred for 40 minutes, separated the organic phase, Wash with brine, separate the layers, dry the organic phase with sodium sulfate, filter, evaporate to dryness, flash column chromatography to obtain pale yellow (E)-2-((3-(4-(trifluoromethyl)styryl) Phenyl)sulfanyl)-6-methyl-pyridine, 31.70 g, yield 89%. LC-MS (ESI, pos, ion) m / z: 372 [M+H].

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Abstract

The invention discloses a medicine for treating depression. A formula is shown in the description, wherein R1, R2, R3 and R4 are independently selected from H, F or CH3 respectively. In recent years,an anti-depression medicine with 5-hydroxytryptamine 1A receptor partial agonistic action and selective 5-hydroxytryptamine re-uptake inhibition dual effects becomes a hotspot direction for researching the novel anti-depression medicine. In a rat synaptosome, a [3H]5-HT uptake inhibition action experiment and an h5-HT1A binding affinity experiment prove that the compound disclosed by the inventionhas a 5-HT re-uptake inhibition action and has the agonistic action on a 5-HT1A receptor; the compound disclosed by the invention can be used as the medicine for treating human central nervous systemdysfunctions including the depression and anxiety disorder.

Description

Technical field [0001] The invention belongs to the field of chemical medicine and relates to a medicine for treating depression. Background technique [0002] Depressive disorder is a mental and psychological disorder with high morbidity, disability and suicide rate. It has become a serious social and public health problem. Clinically commonly used antidepressants such as serotonin reuptake inhibitors (Selective serotonin reuptake inhibitors, SSRIs) antidepressant fluoxetine and other first-line drugs generally have low efficiency, slow onset, sexual dysfunction, and suicide Tendency and many other defects. In recent years, antidepressants (serotoninpartial agonist and reuptake inhibitors, SPARIs), which are dual-acting antidepressants (serotoninpartial agonist and reuptake inhibitors, SPARIs), which are partially stimulated by the serotonin 1A receptor and selective serotonin reuptake inhibitors, have potential features such as stronger efficacy and rapid onset of action. , A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/70A61P25/22A61P25/24A61P25/18A61P25/20A61P25/14A61P25/16A61P25/28A61P25/30A61P15/00
CPCC07D213/70A61P15/00A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30
Inventor 郝惠敏
Owner 郝惠敏