894351-87-2

Usage

Type of compound

Potent 5-HT3 receptor antagonist

Potential use

Treatment of various neurological disorders, including cognitive impairments and psychiatric conditions (e.g. Alzheimer's disease, schizophrenia)

Mechanism of action

Selectively blocking the activity of 5-HT3 receptors, which regulate neurotransmission and synaptic plasticity in the brain

Preclinical results

Promising

Further research

Needed to understand the efficacy and safety of the compound for potential medical uses.

Upstream product

• 894351-85-0 2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide 
• 894351-84-9 2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide 
• 1200070-42-3 2-(4-amino-3-iodo-phenyl)ethanesulfonic acid methylamide 
• 1268266-01-8 2-(4-benzylamino-3-ethynylphenyl)ethanesulfonic acid methylamide 
• 1268265-97-9 2-(4-benzylamino-3-trimethylsilanylethynyl-phenyl)ethanesulfonic acid methylamide 
• 1268265-93-5 2-(4-benzylamino-3-iodophenyl)ethanesulfonic acid methylamide 
• 98623-16-6 2-(4-amino-phenyl)ethanesulfonic acid methylamide 
• 63263-88-7 1-benzyl-1H-indole-5-carbaldehyde 
• 63263-84-3 N-benzylindoline-5-carboxaldehyde 
• 894351-86-1 2-[1-benzyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide 

Downstream Products

• 121679-13-8 naratriptan 
• 143388-64-1 naratriptan hydrochloride 

Relevant academic research and scientific papers

A PROCESS FOR THE SYNTHESIS OF NARATRIPTAN

The present invention relates to a process for preparing naratriptan or a salt thereof, the process comprising: (a) reacting a compound of formula (3) with a compound of the formula HCCR wherein Z is a protecting group, Y is a leaving group and R is a trialkyl silyl group, a trialkylstannyl group or a zinc (II) halide, to obtain the compound of formula (4); (b) converting the compound of formula (4) to a compound of formula (5) wherein Z'' is hydrogen or a benzyl group; (c) converting the compound of formula (5) to naratriptan; and (d) optionally converting naratriptan to a salt thereof. The present invention also provides novel compounds (3) and (4) and processes for their preparation.

New synthesis of naratriptan

A new synthesis of N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide (naratriptan, 1a) has been elaborated starting from 1-benzyl-1H-indole-5-carbaldehyde (14b). The 1-benzyl group proved to be an advantageous protecting group in the course of the construction of the ethanesulfonamide and methylpipieridinyl side-chains and it was removed in the last step of the synthesis.{A figure is presented}.