1176326-76-3

Upstream product

• 1176327-35-7 methyl (4,4-dimethoxy-3,4-dihydro-2H-chromen-6-yl)acetate 
• 145760-37-8 methyl (4-oxo-3,4-dihydro-2H-chromen-6-yl)acetate 
• 1176327-34-6 Methyl [4-(3-chloro-3-oxopropoxy)phenyl]acetate 
• 1176327-36-8 6-(2-hydroxyethyl)-2,3-dihydro-4H-chromen-4-one 
• 145760-36-7 3-[4-(2-methoxy-2-oxoethyl)phenoxy]propanoic acid 
• 145760-35-6 methyl [4-(3-hydroxypropoxy)phenyl]acetate 
• 1176327-19-7 tert-butyl 4-(4-bromo-3-(2-methoxyethoxy)benzyl)piperidine-1-carboxylate 
• 1176327-18-6 tert-butyl 4-(4-bromo-3-(2-methoxyethoxy)benzylidene)piperidine-1-carboxylate 
• 1176327-17-5 [4-bromo-3-(2-methoxyethoxy)benzyl](triphenyl)phosphonium bromide 
• 1176327-16-4 4-Bromo-3-(2-methoxyethoxy)benzyl methanesulfonate 
• 1176327-15-3 4-bromo-3-(2-methoxyethoxy)benzoic acid 
• 1176327-20-0 4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidine hydrochloride 
• 1176327-37-9 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate 
• 1147886-95-0 (4-bromo-3-(2-methoxyethoxy)phenyl)methanol 

Downstream Products

• 1265463-49-7 6-(2-{4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-3,4-dihydro-2H-chromen-4-ol benzenesulfonate (salt) 
• 1176326-99-0 6-(2-{4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one hydrobromide 
• 1176326-77-4 6-(2-{4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one hydrochloride 
• 1176326-78-5 6-(2-{4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one benzenesulfonate 
• 1176327-01-7 6-(2-{4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one butanedioate 
• 1176326-95-6 6-(2-{4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one fumarate 

Relevant academic research and scientific papers

Discovery of DSP-1053, a novel benzylpiperidine derivative with potent serotonin transporter inhibitory activity and partial 5-HT1A receptor agonistic activity

We have previously shown that SMP-304, a serotonin uptake inhibitor with weak 5-HT1A partial agonistic activity, may act under high serotonin levels as a 5-HT1A antagonist that improves the onset of paroxetine in the rat swimming test. However, SMP-304 is mostly metabolized by CYP2D6, indicating limited efficacy among individuals and increased side effects. To reduce CYP2D6 metabolic contribution and enhance SERT/5-HT1A binding affinity, we carried out a series of substitutions at the bromine atom in the left part of the benzene ring of SMP-304 and replaced the right part of SMP-304 with a chroman-4-one. This optimization work led to the identification of the antidepressant candidate DSP-1053 as a potent SERT inhibitor with partial 5-HT1A receptor agonistic activity. DSP-1053 showed low CYP2D6 metabolic contribution and a robust increase in serotonin levels in the rat frontal cortex.

BENZYL PIPERIDINE COMPOUND

Provided is a new serotonin-reuptake inhibitor that exhibits affinity for serotonin-1A receptors. Said serotonin-reuptake inhibitor is a compound represented by formula (1) or a pharmacologically acceptable salt thereof. In the formula, R1 represents a hydrogen atom, a 2-hydroxyethyl group, or a 2-methoxyethyl group. R2 represents one of the following bonded to a methylene group which is bonded to a piperidine ring: a chlorine atom bonded in a p-position; a bromine atom bonded in a p-position; a methyl group bonded in a p-position; a chlorine atom bonded in an m-position; or a bromine atom bonded in an m-position. Either Y1 represents a hydrogen atom and Y2 represents a hydrogen atom or a hydroxyl group, or Y1 and Y2 together represent an oxo group. Z represents a group represented by one of the following formulas: formula (3-1-1), formula (3-1-2), formula (3-2-1), formula (3-2-2), formula (3-3-1), formula (3-3-2), formula (3-4-1), or formula (3-4-2). However, if R1 represents a 2-hydroxyethyl group or a 2-methoxyethyl group and Y1 and Y2 both simultaneously represent hydrogen atoms, then Z represents a group represented by one of the following formulas: formula (3-1-2), formula (3-2-1), formula (3-2-2), formula (3-3-1), formula (3-3-2), formula (3-4-1), or formula (3-4-2).

BENZYLPIPERIZINE COMPOUND

Disclosed is a benzylpiperizine compound represented by formula (1) or a pharmaceutically acceptable salt thereof, which is useful as a medicinal agent such as an antidepressant agent. (In the formula (1), R1 represents a hydrogen atom or a met