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2-Substituted diphenyl sulfide derivatives and uses thereof

A technology of use and medicine, applied in the compound and pharmaceutical composition of affective disorders, in the field of treatment of central nervous system dysfunction, can solve the problems of delay and deterioration of SSRIs treatment effect, and achieve good safety, stable properties and good metabolic stability Effect

Active Publication Date: 2020-11-24
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, clinical studies of depression have highlighted the lack of response to known SSRIs. Another factor that is often overlooked in antidepressant treatment is that the therapeutic effect of SSRIs is often delayed, sometimes during the first few weeks of treatment. will get worse
Additionally, sexual dysfunction is a common side effect of SSRIs

Method used

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  • 2-Substituted diphenyl sulfide derivatives and uses thereof
  • 2-Substituted diphenyl sulfide derivatives and uses thereof
  • 2-Substituted diphenyl sulfide derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] Example 1 Synthesis of 2-(2-((2,4-dimethylphenyl)thio)phenyl)-N-methylethylamine

[0143]

[0144] Step 1) Synthesis of 2-bromophenethylcarbamate tert-butyl ester

[0145] Weigh 2-(2-bromophenyl)ethylamine (1.00g, 5.00mmol) and add triethylamine (0.8mL, 6mmol) and anhydrous tetrahydrofuran (12mL) into a 100mL single-necked bottle, place in an ice bath, add Boc 2 A solution of O (1.4 g, 4.7 mmol) in anhydrous THF (6 mL) was then warmed to room temperature and stirred overnight. The reaction solution was concentrated, ethyl acetate (60 mL) was added, washed successively with sodium bicarbonate solution and brine, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was purified by column chromatography (petroleum ether / ethyl acetate ( v / v)=10 / 1) gave a colorless oil (1.4 g, 93%).

[0146] MS(ESI,pos.ion)m / z:244.15[M-56+H] + .

[0147] 1 H NMR (400MHz, CDCl 3 )δ7.54(d,J=7.8Hz,1H),7.28–7.21(m,2H),7.13–7.00(m,1H),3.54...

Embodiment 2

[0160] Example 2 Synthesis of 2-(2-((3,4-dichlorophenyl)thio)phenyl)-N-methylethylamine

[0161]

[0162] Step 1) Synthesis of tert-butyl 2-((3,4-dichlorophenyl)thio)phenethylcarbamate

[0163] Weigh tert-butyl 2-bromophenethylcarbamate (500mg, 1.67mmol), 3,4-dichlorothiophenol (447mg, 2.50mmol), tris(dibenzylideneacetone) dipalladium (79mg, 0.08 mmol), bis(2-diphenylphosphinephenyl) ether (92mg, 0.17mmol) and potassium tert-butoxide (394mg, 3.34mmol) in a 100mL single-necked bottle, then add toluene (25mL) and vacuum three times for nitrogen, Placed at 100°C and stirred for 3h. The reaction was stopped, the reaction solution was directly concentrated, and the residue was purified by column chromatography (petroleum ether / ethyl acetate (v / v)=10 / 1) to obtain the title compound as a pale yellow oil (300 mg, 45%).

[0164] MS(ESI,pos.ion)m / z:299.05[M-100+H] + .

[0165] Step 2) Synthesis of tert-butyl 2-((3,4-dichlorophenyl)thio)phenethyl(methyl)carbamate

[0166] Add...

Embodiment 3

[0174] Example 3 Synthesis of 3-(2-((2,4-dimethylphenyl)thio)phenyl)-N-methylpropan-1-amine

[0175]

[0176] Step 1) Synthesis of (3-(2-bromophenyl) propyl) tert-butyl carbamate

[0177] Weigh 2-bromoamphetamine (1.00g, 4.67mmol) in a 100mL single-necked bottle, add triethylamine (0.74mL, 5.3mmol) and tetrahydrofuran (12mL), place in an ice bath, add Boc 2 O (1.2g, 3.8mmol) in anhydrous tetrahydrofuran (8mL) was then raised to room temperature and stirred overnight. The reaction solution was concentrated, ethyl acetate (100 mL) was added, washed successively with sodium bicarbonate solution and brine, the organic phase was dried over anhydrous sodium sulfate, concentrated, and the residue was purified by column chromatography (petroleum ether / ethyl acetate (v / v)=10 / 1) gave the title compound as a colorless oil (1.2 g, 82%). MS(ESI,pos.ion)m / z:336.05[M+Na] + .

[0178] 1 H NMR (400MHz, CDCl 3 )δ7.52(d, J=8.0Hz, 1H), 7.21(t, J=5.3Hz, 2H), 7.10–7.00(m, 1H), 3.18(d, J...

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Abstract

The invention discloses a 2-substituted diphenyl sulfide derivative and application thereof, and a drug composition comprising the compound, which can be used for inhibiting re-uptake of serotonin. The invention further relates to methods of preparing the compound and the drug composition, and application thereof in treatment of functional disorder of a central nervous system, particularly affective disorder.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to compounds and pharmaceutical compositions for treating central nervous system dysfunction, especially affective disorders, as well as their application methods and applications. In particular, the present invention describes 2-substituted diphenylsulfide derivatives that are useful as serotonin reuptake inhibitors. Background technique [0002] 5-HT (serotonin), a neurotransmitter that transmits signals in the brain and nervous system, plays a role in central nervous system (CNS) dysfunction, especially anxiety, depression, aggression and impulsive mood. play an important role. The five-serotonin transporter (5-HT transporter, 5-HTT / serotonin transporter, SERT) is a transmembrane transporter with high affinity for 5-HT, which reuptakes five-serotonin from the synaptic cleft into the presynaptic neuron , which directly affects the concentration of serotonin in the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/32C07C323/37A61K31/137A61K31/136A61P25/24A61P25/22A61P25/18A61P25/00A61P25/14A61P25/16A61P25/28A61P25/30A61P25/20A61P15/10
CPCA61P15/10A61P25/00A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30C07C323/32C07C323/37
Inventor 金传飞许腾飞薛亚萍梁海平
Owner SUNSHINE LAKE PHARM CO LTD
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