864825-23-0

Basic information

• Product Name: (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE
• Synonyms: (S)-1-(4-phenyl-1H-imidazol-2-yl)ethanamine;1-(4-phenyl-1H-imidazol-2-yl)-ethylamine;1H-Imidazole-2-methanamine, α-methyl-4-phenyl-, (αS)-;1H-Imidazole-2-methanamine, α-methyl-5-phenyl-, (αS)-;(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethanamine;(S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE;(alphaS)-alpha-Methyl-4-phenyl-1H-imidazole-2-methanamine;(S)-alpha-Methyl-4-phenyl-1H -imidazole-2-methanamine
• CAS NO: 864825-23-0
• Molecular Formula: C₁₁H₁₃N₃
• Molecular Weight: 187.245
• EINECS: 1592732-453-0
• Mol File: 864825-23-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 422.1±28.0 °C(Predicted)
• Appearance: /
• Density: 1.145±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.16±0.10(Predicted)
• CAS DataBase Reference: (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE(864825-23-0)
• EPA Substance Registry System: (S)-1-(5-PHENYL-1H-IMIDAZOL-2-YL)ETHANAMINE(864825-23-0)

Safety Data

• Hazardous Substances Data: 864825-23-0(Hazardous Substances Data)

Usage

Uses

(S)-1-(4-Phenyl-1H-imidazol-2-yl)ethanamine is an intermediate used to prepare a δ-opioid antagonists/μ-opioid agonists used in potential therapy for diarrhea-predominant irritable bowel syndrome (IBS-d).

InChI:InChI=1S/C11H13N3/c1-8(12)11-13-7-10(14-11)9-5-3-2-4-6-9/h2-8H,12H2,1H3,(H,13,14)/t8-/m0/s1

Upstream product

• 5468-37-1 2-aminoacetophenone hydrochloride 
• 864825-21-8 benzyl [(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]carbamate 

Downstream Products

• 864825-27-4 (2-(4-hydroxy-2,6-dimethyl-phenyl)-1-{isopropyl-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-carbamoyl}-ethyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

PROCESSES FOR THE PREPARATION OF ELUXADOLINE

The present invention relates to processes for the preparation of eluxadoline. The present invention also provides a compound of Formula V, a process for its preparation, and its use for the preparation of eluxadoline.

Identification of a dual δ or antagonist/μ or agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d)

A small set of acyclic analogs 5 were prepared to explore their structure-activity relationships (SARs) relative to heterocyclic core, opioid receptor (OR) agonists 4. Compound 5l was found to have very favorable OR binding affinities at the δ and μ ORs (r Ki δ = 1.3 nM; r Ki μ = 0.9 nM; h Ki μ = 1.7 nM), with less affinity for the κ OR (gp Ki κ = 55 nM). The OR functional profile for 5l varied from the previously described dual δ/μ OR agonists 4, with 5l being a potent, mixed dual δ OR antagonist/μ OR agonist [δ IC50 = 89 nM (HVD); μ EC50 = 1 nM (GPI); κ EC50 = 1.6 μM (GPC)]. Compound 5l has progressed through a clinical Phase II Proof of Concept study on 800 patients suffering from diarrhea-predominant Irritable Bowel Syndrome (IBS-d). This Phase II study was recently completed successfully, with 5l demonstrating statistically significant efficacy over placebo.

NOVEL COMPOUNDS AS OPIOID RECEPTOR MODULATORS

The present invention is directed to novel opioid receptor modulators of Formula (I). The invention further relates to methods for preparing such compounds, pharmaceutical compositions containing them, and their use in the treatment of disorders that may