179756-58-2

Usage

Uses

Used in Pharmaceutical Industry:
Eptapirone is used as an anxiolytic agent for its potential to alleviate anxiety symptoms by selectively targeting the 5-HT1A receptor, which is implicated in the regulation of mood and anxiety.
Eptapirone is also used as an antidepressant agent for its demonstrated ability to exhibit antidepressant-like effects in preclinical models, suggesting its potential to treat depressive disorders by modulating the serotonin system.
Additionally, Eptapirone is used in the development of drug candidates for the treatment of anxiety and depression, given its high selectivity and potency as a 5-HT1A receptor agonist, which may lead to improved therapeutic outcomes with fewer side effects compared to existing treatments.

Upstream product

• 179756-87-7 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione 
• 20980-22-7 N-(2-pyridinyl)piperazine 
• 78069-54-2 1-(2-pyrimidinyl)piperazine hydrochloride 

Relevant academic research and scientific papers

An improved synthesis of the 5-HT1A receptor agonist Eptapirone free base

Eptapirone free base, F11440,4-methyl-2-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-1,2,4-triazine-3,5(2H,4H)-dione, represents a potent and selective 5-HT1A receptor agonist with high efficacy and the potential to regulate anxiety disorders. Herein, we report a method to retro-synthesize eptapirone free base. The compound consists of heterocyclic aromatic portion and aliphatic portion, and the synthetic route consisted of a total of nine steps with an overall yield of 8.8% starting from the commercially available materials. The key steps in the synthetic method involved: (1) using sodium hydroxide and ethylene glycol as solvent resulted in a better cyclization and yield (61.6%) of 1,2,4-triazine-3,5(2H,4H)-dione; (2) an acceptable yield (63.1%) of 4-tert-butyl(pyrimidin-2-yl)piperazine-1-carboxylate was obtained under an optimized conditions of using triethylamine as a base, ethanol as a solvent, and a reaction temperature of 50?°C for 16?h with non-metal catalysis and less byproducts; (3) the reaction step of eptapirone could get a better yield (49.6%) with an optimized condition of potassium carbonate as a base, acetonitrile as a solvent, NaI as a catalyst, and a reaction temperature of 50?°C for 12?h by nucleophilic substitution reaction. The main advantages of this route were an acceptable product purity, the commercial availability of all starting materials and the absence of high temperature, high pressure and noble metal catalysts, which could result in more feasible commercial applications.

Full synthesis method of eptapirone

The invention discloses a full synthesis method of eptapirone. The full synthesis method comprises the following steps: (1) taking aminourea hydrochloride and trichloracetic aldehyde as raw materialsand carrying out a series of reaction to obtain 2-[2-(aminocarbonyl)hydrazono](CD-1); (2) synthesizing 6-azauracil(CD-2) by the 2-[2-(aminocarbonyl)hydrazono] under the action of sodium hydroxide; (3)taking the 6-azauracil and acetic anhydride to react to obtain 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone(CD3); (4) taking the 2-acetyl-2H-[1,2,4]triazine-3,5(2H,4H)-diketone to react to obtain3-methyl-6-azauracil(CD-4); (5) taking the 3-methyl-6-azauracil to react to obtain 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone(CD-5); (6) taking 2-bromopyrimidine, 1-Boc-piperazine and triethylamine to react to obtain 4-(pyrimidine-2-yl)piperazine-1-tert-butyl formate(CD-6); furthermore, reacting to obtain 2-(1-piperazinyl)pyrimidine hydrochloride (1 to 1)(CD-7); (7) taking the 2-(4-chlorobutyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-diketone in step (5) to react with the 2-(1-piperazinyl)pyrimidine hydrochloride in step (6) to obtain the eptapirone(CD-8). The product disclosed by the invention is high in purity and yield and is suitable for industrialized production.

Synthesis and evaluation of arylpiperazines derivatives of 3,5-dioxo-(2H,4H)-1,2,4-triazine as 5-HT1AR ligands

5-HT1AR agonist or partial agonists are established drug candidates for psychiatric and neurological disorders. We have reported the synthesis and evaluation of a series of high affinity 5-HT1AR partial agonist PET imaging agents with greater selectivity over α-1AR. The characteristic of these molecules are 3,5-dioxo-(2H,4H)-1,2,4-triazine skeleton tethered to an arylpiperazine unit through an alkyl side chain. The most potent 5-HT1AR agonistic properties were found to be associated with the molecules bearing C-4 alkyl group as the linker. Therefore development of 3,5-dioxo-(2H,4H)-1,2,4-triazine bearing arylpiperazine derivatives may provide high affinity selective 5-HT1AR ligands. Herein we describe the synthesis and evaluation of the binding properties of a series of arylpiperazine analogues of 3,5-dioxo-(2H,4H)-1,2,4-triazine.

RADIOLABELED COMPOUNDS AND METHODS THEREOF

The present invention relates to radiodiagnostic compounds, methods of making those compounds, and methods of use thereof as imaging agents for preferably a HA serotonin 5-HT1A receptor for use in PET or SPECT, preferably PET. Compositions comprising an imaging-effective amount of radiolabeled compounds are also disclosed. The present invention also relates to non-radiolabeled compounds, methods of making those compounds, and methods of use thereof to treat various neurological and/or psychiatric disorders.

3,5-dioxo-(2H,4H)-1,2,4-triazine derivatives

Novel 3,5-dioxo-(2H,4H-triazine derivatives of general formula (I): wherein R1 is hydrogen, a C1 -C4 alkyl radical, phenyl C1 -C4 alkyl or phenyl, the phenyl ring being optionally substituted by one o