528587-71-5

Upstream product

• 67843-74-7 (S)-epichlorohydrin 
• 459-22-3 4-fluorophenylacetonitrile 
• 51594-55-9 (R)-(-)-epichlorohydrin 

Downstream Products

• 528587-79-3 (1S,2R)-1-(4-fluorophenyl)-2-(hydroxymethyl)-N,N-diethylcyclopropanecarboxamide 
• 1369764-07-7 (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(4-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide 
• 1369767-33-8 (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(4-fluorophenyl)cyclopropanecarboxylic acid 
• 528588-03-6 (1S,2R)-1-(4-fluorophenyl)-2-[(S)-1-azidopropyl]-N,N-diethylcyclopropanecarboxamide 
• 528587-95-3 (1S,2R)-1-(4-fluorophenyl)-2-[(S)-1-hydroxypropyl]-N,N-diethylcyclopropanecarboxamide 
• 528587-87-3 (1S,2R)-1-(4-fluorophenyl)-2-formyl-N,N-diethylcyclopropanecarboxamide 
• 528588-19-4 (1S,4S,5R)-2-oxo-4-ethyl-1-(4-fluorophenyl)-3-oxabicyclo[3.1.0]hexane 
• 942493-75-6 (1S,2R)-2-(azidomethyl)-N,N-diethyl-1-(4-fluorophenyl)cyclopropanecarboxamide 

Relevant academic research and scientific papers

Discovery of (1R,2S)-2-{[(2,4-Dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006): A Potent and Efficacious Oral Orexin Receptor Antagonist

The orexin/hypocretin receptors are a family of G protein-coupled receptors and consist of orexin-1 (OX1) and orexin-2 (OX2) receptor subtypes. Orexin receptors are expressed throughout the central nervous system and are involved in the regulation of the sleep/wake cycle. Because modulation of these receptors constitutes a promising target for novel treatments of disorders associated with the control of sleep and wakefulness, such as insomnia, the development of orexin receptor antagonists has emerged as an important focus in drug discovery research. Here, we report the design, synthesis, characterization, and structure-activity relationships (SARs) of novel orexin receptor antagonists. Various modifications made to the core structure of a previously developed compound (-)-5, the lead molecule, resulted in compounds with improved chemical and pharmacological profiles. The investigation afforded a potential therapeutic agent, (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006), an orally active, potent orexin antagonist. The efficacy was demonstrated in mice in an in vivo study by using sleep parameter measurements. (Chemical Equation Presented).

Synthesis of enantiomerically pure milnacipran analogs and inhibition of dopamine, serotonin, and norepinephrine transporters

A series of Milnacipran analogs with variation in the aromatic moiety were prepared in high enantiomeric excess. Structure-activity relationships for two parallel enantiomeric series are described. The (-)-(1R,2S)-naphthyl analog (8h) showed the highest potency in the two series and is a triple reuptake inhibitor of the SERT, NET, and DAT.

CYCLOPROPYL DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS

The present invention relates to cyclopropyl derivatives of formula (I) and salt thereof. These compounds are NK3 receptor antagonists and may therefore be useful for treatment of diseases where the NK3 receptor is implicated, e.g. psychotic disorders.

Synthesis of derivatives of (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC) modified at the 1-aromatic moiety as novel NMDA receptor antagonists: The aromatic group is essential for the activity

(1S,2R)-1-Phenyl-2-[(S)-1-aminopropyl]-N,N-diethylcyclopropanecarboxamide (PPDC, 4a), which is a conformationally restricted analogue of antidepressant milnacipran [(±)-1], is a new class of potent noncompetitive NMDA receptor antagonists. A series of PPD