914927-40-5

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-5-carbonitrile, 3-(4-hydroxybutyl)is used as an impurity in the development and production of Vilazodone (V265000), a drug being evaluated for its efficacy in treating major depression. Its presence is significant for quality control and safety assessments during the clinical evaluation process.

Upstream product

• 276863-95-7 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile 
• 34067-76-0 6-hydroxyhexanal 
• 2863-98-1 4-hydrazinobenzonitrile hydrochloride 
• 873-74-5 4-Aminobenzonitrile 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 15861-24-2 1H-indole-5-carbonitrile 

Downstream Products

• 163521-12-8 vilazodone 

Relevant academic research and scientific papers

Practical and Scalable Manufacturing Process for a Novel Dual-Acting Serotonergic Antidepressant Vilazodone

Vilazodone combines the effects of a selective serotonin reuptake inhibitor with the 5-HT1A receptor partial agonist activity. Here, we report the development of a viable and scalable process for manufacturing vilazodone that features a convergent synthetic approach, with low cost and high purity. The key indole synthesis was improved to first make up the hydrazone intermediate and then modify a pendant hydroxy group to realize a much increased overall yield. This process was successfully used to prepare >2 kg of vilazodone hydrochloride with a total yield of 56.2% and purity of 99.93%.

Substituted indole compounds, as well as using method and application thereof

The invention relates to substituted indole compounds, a using method and application of the substituted indole compounds, as well as a medicine composition including the compounds and application thereof. The compounds or medicine composition can be used for inhibiting reuptake of 5-hydroxytryptamine. The invention further relates to a method for preparing the compounds and the medicine composition, as well as application of the compounds and medicine composition in treatment of central nervous system dysfunction.

Substituted indole compound and method and use thereof

The invention provides a new indole compound, pharmaceutically acceptable salts and medicinal preparations thereof, and a use of the new indole compound in selective inhibition of 5-hydroxytryptamine reuptake and /or excitation of a 5-HT1A receptor. The invention also relates to medicinal compositions comprising the compounds, and a method for treating the central nervous system dysfunction of mammals, especially humans by using the medicinal compositions.

SUBSTITUTED PIPERAZINE COMPOUNDS AND METHODS OF USE AND USE THEREOF

The invention relates to substituted piperazine compounds and methods of use and uses thereof, and further to the pharmaceutical compositions comprising the compounds and uses thereof, wherein the compound has Formula (I) or a stereoisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof. The substituted piperazine compounds and pharmaceutical compositions comprising the compounds disclosed herein can be used for inhibiting 5-hydroxytryptamine reuptake and/or stimulating 5-HT1A receptors. The invention also relates to processes for preparing these compounds and pharmaceutical compositions, and their uses in the treatment of a central nervous system dysfunction.

SUBSTITUTED HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are novel heteroaryl compounds, pharmaceutically acceptable salts and pharmaceutical formulations thereof for selectively inhibiting serotonin reuptake and/or acting as 5-HT1A receptor agonists. Also provided herein are pharmaceutical compositions comprising the heteroaryl compounds and methods of using the pharmaceutical compositions in treating central nervous system (CNS) dysfunction in a mammal, especially a human being.

SUBSTITUTED PIPERAZINE COMPOUNDS AND METHODS AND USE THEREOF

Provided herein are novel piperazine compounds acting as selective serotonin reuptake inhibitors and/or the 5-HT1A receptor agonists. The invention also relates to the methods of preparing the compound and pharmaceutical composition, and the use of treating central nervous system dysfunction in mammals especially in humans.

IMPROVED PROCESS FOR PREPARING BENZOFURAN-2-CARBOXAMIDE DERIVATIVES

Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of benzofuran-2-carboxamide derivatives and their intermediates, or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided particularly herein are novel, commercially viable and industrially advantageous processes for the preparation of vilazodone or a pharmaceutically acceptable salt thereof in high yield and purity. Provided also herein is an improved and commercially viable process for the preparation of 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile, in high yield and purity, using novel intermediate compound 3-(4-hydroxybutyryl)-1H-indole-5-carbonitrile.

Alternative approach to synthesis of 3-(4-Chloro butyl)- 1H -indole-5-carbonitrile: A key intermediate of vilazodone hydrochloride, an antidepressant drug

An alternative and efficient telescopic approach to the synthesis of 3-(4-chloro butyl)-1H-indole -5-carbonitrile (2), a key intermediate in the synthesis of vilazodone hydrochloride (1), is described.