923932-15-4

Usage

Uses

Used in Pharmaceutical Industry:
(3S,4R)-3-((benzo[d][1,3]dioxol-(2,2-d2)-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine hydrochloride is used as a chemical intermediate for the synthesis of various medications for the treatment of psychiatric disorders. Its potential antidepressant and anxiolytic properties make it a valuable compound in the development of new therapies for mental health conditions.

Upstream product

• 1131450-88-8 (3S,4R)-4-phenyl 3-((2,2-d2-benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate 
• 153257-53-5 (3S,4R)-trans-4-(4-fluorophenyl)-1-methyl-3-phenylsulphonyloxymethylpiperidine 
• 923924-69-0 benzo[d][1,3]dioxole-2,2-d₂-5-carbaldehyde 
• 710336-81-5 dideuterocatechol 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 1005412-34-9 (3S,4R)-4-nitrophenyl 3-((benzo[d][1,3]dioxol-(2,2-d2)-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate 
• 936838-88-9 (3S,4R)-3-((benzo[d][1,3]dioxol-(2,2-d2)-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine 
• 923932-05-2 benzo[d][1,3]dioxol-(2,2-d2)-5-ol 
• 1131450-87-7 ((3S,4R)-4-(4-fluorophenyl)-1-methylpiperidin-3-yl)methylmethanesulfonate hydrochloride 
• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 
• 923932-43-8 (3S,4R)-3-((2,2-d2-benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine 
• 936838-89-0 trans-(4R,3S)-d2-3-(benzo[1,3]dioxol-5-yloxymethyl)-4-(4-fluorophenyl)-piperidine-1-carboxylic acid 2-chloroethyl ester 

Relevant academic research and scientific papers

Altering metabolic profiles of drugs by precision deuteration: Reducing mechanism-based inhibition of CYP2D6 by Paroxetine

Selective deuterium substitution as a means of ameliorating clinically relevant pharmacokinetic drug interactions is demonstrated in this study. Carbon-deuterium bonds are more stable than corresponding carbon-hydrogen bonds. Using a precision deuteration platform, the two hydrogen atoms at the methylenedioxy carbon of paroxetine were substituted with deuterium. The new chemical entity, CTP-347 [(3S,4R)-3-((2,2-dideuterobenzo[d][1,3]dioxol-5-yloxy)me thyl)-4-(4-fluorophenyl)piperidine], demonstrated similar selectivity for the serotonin receptor, as well as similar neurotransmitter uptake inhibition in an in vitro rat synaptosome model, as unmodified paroxetine. However, human liver microsomes cleared CTP-347 faster than paroxetine as a result of decreased inactivation of CYP2D6. In phase 1 studies, CTP-347 was metabolized more rapidly in humans and exhibited a lower pharmacokinetic accumulation index than paroxetine. These alterations in the metabolism profile resulted in significantly reduced drug-drug interactions between CTP-347 and two other CYP2D6-metabolized drugs: tamoxifen (in vitro) and dextromethorphan (in humans). Our results show that precision deuteration can improve the metabolism profiles of existing pharmacotherapies without affecting their intrinsic pharmacologies.

SYNTHESIS OF DEUTERATED CATECHOLS AND BENZO[D][1,3] DIOXOLES AND DERIVATIVES THEREOF

The present invention provides a convenient and efficient process for the synthesis of d2-benzo[d][l,3]dioxoles.

Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties

Chemical syntheses and medical uses of novel inhibitors of the uptake of monoamine neurotransmitters and pharmaceutically acceptable salts and prodrugs thereof, for the treatment and/or management of psychotropic disorders, anxiety disorder, generalized anxiety disorder, depression, post-traumatic stress disorder, obsessive-compulsive disorder, panic disorder, hot flashes, senile dementia, migraine, hepatopulmonary syndrome, chronic pain, nociceptive pain, neuropathic pain, painful diabetic retinopathy, bipolar depression, obstructive sleep apnea, psychiatric disorders, premenstrual dysphoric disorder, social phobia, social anxiety disorder, urinary incontinence, anorexia, bulimia nervosa, obesity, ischemia, head injury, calcium overload in brain cells, drug dependence, and/or premature ejaculation are described. [image]

NOVEL BENZO [D] [1,3]-DIOXOL DERIVATIVES

The present invention relates to an isotopologue of Compound 1 substituted with deuterium at the methylene carbon of the benzodioxol ring. The isotopologues of this invention selective serotonin reuptake inhibitors (SSRIs) and possess unique biopharmaceutical and metabolic properties compared to Compound 1. They may also be used to accurately determine the concentration of Compound 1 in biological fluids and to determine metabolic patterns of Compound 1 and its isotopologues. The invention further provides compositions comprising these deuterated isotopologues and methods of treating diseases and conditions that are responsive to increased neuronal serotonin transmission, alone and in combination with additional agents.