106516-07-8

Usage

Uses

Used in Medicinal Chemistry:
5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a potential building block for the development of new drugs due to its complex structure and the presence of the indole ring, which is a common structural motif in many biologically active compounds.
Used in Drug Discovery:
The molecule is of interest for further research and development in drug discovery, as the presence of fluorine and chlorine atoms could impart specific properties that may be beneficial for the design of novel therapeutic agents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-CHLORO-1-(4-FLUORO-PHENYL)-3-(1,2,3,6-TETRAHYDRO-PYRIDIN-4-YL)-1H-INDOLE is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds, potentially leading to the creation of new medications with improved efficacy and selectivity.

Upstream product

• 41979-39-9 4-piperidone hydrochloride 
• 138900-22-8 1-(4-fluorophenyl)-5-chloroindole 
• 40064-34-4 piperidine-4,4-diol hydrochloride 
• 138900-12-6 methyl 5-chloro-1-(4-fluorophenyl)-3-hydroxy-1H-indol-2-carboxylate 
• 948553-95-5 5-Chloro-1-(4-fluoro-phenyl)-2,3-dihydro-1H-indol-3-ol 
• 170232-17-4 5-chloro-2,3-dihydro-1-(4-fluorophenyl)-1H-indol-3-one 

Downstream Products

• 106516-54-5 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1,2,3,6-tetrahydro-1-pyridyl]ethyl]-2-imidazolidinone 
• 138900-50-2 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-cyclopentyl-imidazolidin-2-one 
• 138900-48-8 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-isopropyl-imidazolidin-2-one 
• 138900-44-4 1-(6-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-hexyl)-imidazolidin-2-one 
• 138900-42-2 1-(5-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-pentyl)-imidazolidin-2-one 
• 138900-40-0 1-(4-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-butyl)-imidazolidin-2-one 
• 138900-38-6 1-(3-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-propyl)-imidazolidin-2-one 
• 138900-46-6 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-methyl-imidazolidin-2-one 
• 138900-52-4 1-(2-{4-[5-Chloro-1-(4-fluoro-phenyl)-1H-indol-3-yl]-piperidin-1-yl}-ethyl)-3-phenyl-imidazolidin-2-one 
• 106516-24-9 Sertindole 
• 138900-27-3 5-chloro-1-(4-fluorophenyl)-3-(4-piperidinyl)-1H-indole 

Relevant academic research and scientific papers

Method of manufacturing sertindole

The present invention relates to a new method of manufacturing the compound 1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1-H-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone having the recommended INN name sertindole and a new method of manufacturing the intermediates, N-(4-fluorophenyl)-N-(2-carboxy-4-chlorophenyl)glycine and 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole used in the method.

Process for the preparation of 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole and method of manufacturing sertindole

A process of manufacturing sertindole comprising reacting 5-chloro-1-(4-fluorophenyl)indole with 4-piperidone in a mixture of an acetic acid and concentrated HCl; reduction of the resulting 5-chloro-1-(4-fluorophenyl)-3-(1,2,3,6-tetrahydropyridin-4-yl)indole and reaction of this compound with 1-(2-chloroethyl)-2-imidazolidinon in order to obtain sertindole.

Noncataleptogenic, centrally acting dopamine D-2 and serotonin 5-HT2 antagonists within a series of 3-substituted 1-(4-fluorophenyl)-1H-indoles

A series of 1-(4-fluorophenyl)-1H-indoles substituted at the 3-position with 1-piperazinyl, 1,2,3,6-tetrahydro-4-pyridinyl, and 4-piperidinyl was synthesized. Within all three subseries potent dopamine D-2 and serotonin 5- HT2 receptor affinity was found in ligand binding studies. Quipazine-induced head twitches in rats were inhibited by most derivatives as a measure of central 5-HT2 receptor antagonism. Piperazinyl and tetrahydropyridyl indoles were cataleptogenic, while piperidyl substituted indoles surprisingly were found to be noncataleptogenic or only weakly cataleptogenic. Noncataleptogenic piperidyl derivatives also failed to block dopaminergic- mediated stereotypies, that is methyl phenidate-induced gnawing behavior in mice. These profiles resemble that of the atypical neuroleptic clozapine. 1- Ethyl-2-imidazolidinone was found to be the optimal substituent of the basic nitrogen atom in order to avoid catalepsy. The atypical neuroleptic 1-[2-[4- [5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1-piperidinyl]ethyl]-2- imidazolidinone (sertindole, compound 14c) was selected for further development as a result of these structure/activity studies.