160492-56-8

Basic information

• Product Name: Osanetant
• Synonyms: Osanetant;AcetaMide, N-[1-[3-[(3R)-1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-N-Methyl-;N-[1-[3-[(3R)-1-Benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-N-methylacetamide;(R)-N-{{3-[1-Benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]prop-1-yl}-4-phenylpiperidin-4-yl}-N-methylacetamine;SR142801;SR-142801;Osanetant AcetaMide, N-[1-[3-[(3R)-1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-N-Methyl-;N-[1-[3-[(3R)-1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl]-4-phenylpiperidin-4-yl]-N-methylacetamide
• CAS NO: 160492-56-8
• Molecular Formula: C35H41Cl2N3O2
• Molecular Weight: 606.634
• Mol File: 160492-56-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 727.9°Cat760mmHg
• Flash Point: 394°C
• Appearance: white to beige/
• Density: 1.25
• Vapor Pressure: 4.79E-21mmHg at 25°C
• Refractive Index: 1.633
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble15mg/mL, clear
• PKA: 8.33±0.10(Predicted)
• CAS DataBase Reference: Osanetant(CAS DataBase Reference)
• NIST Chemistry Reference: Osanetant(160492-56-8)
• EPA Substance Registry System: Osanetant(160492-56-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 160492-56-8(Hazardous Substances Data)

Usage

Biochem/physiol Actions

Osanetant is a selective antagonist of neurokinin 3 receptor NK3. Neurokinins (tachykinins) are members of a family of at least three neuropeptides, substance P, neurokinin A, and neurokinin B (NKB), with each mediating their biological effects through binding to a preferred G-protein-coupled receptor termed NK1, NK2, or NK3, respectively. All three NK receptors are expressed in regions of the central nervous system that are related to emotion and cognition (i.e., amygdala and hippocampus) and have been linked to various degrees in psychiatric disorders. Neurokinin receptors, including NK3 receptors, are also expressed in the motor and sensory systems of the digestive tract. Osanetant was in clinical trials for both irritable bowel syndrome and schizophrenia.

InChI:InChI=1/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1

Upstream product

• 258337-99-4 osanetant benzenesulfonate 
• 146396-03-4 1-benzoyl-3-(3,4-dichlorophenyl)-3-(3-methane-sulphonyloxypropyl)piperidine 
• 172734-75-7 [3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanone 
• 146395-96-2 2-(3,4-dichloro-phenyl)-5-(tetrahydro-pyran-2-yl-oxy)-pentanenitrile 
• 182621-51-8 (+)-3-(3,4-dichlorophenyl)-3-(3-hydroxypropyl)-piperidine 
• 146396-04-5 N-(4-phenylpiperidin-4-yl)acetamide 
• 182621-49-4 4-Cyano-4-(3,4-dichloro-phenyl)-7-(tetrahydro-pyran-2-yloxy)-heptanoic acid 
• 182621-50-7 Acetic acid 3-[3-(3,4-dichloro-phenyl)-2,6-dioxo-piperidin-3-yl]-propyl ester 
• 182621-52-9 4-Acetylamino-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 172733-78-7 N-(1-benzyl-4-phenylpiperidin-4-yl)acetamide 
• 181641-49-6 1-benzyl-4-phenylpiperidin-4-ylamine 
• 182621-56-3 4-methylamino-4-phenylpiperidine 
• 3218-49-3 3,4-dichloro-benzeneacetonitrile 
• 591-51-5 phenyllithium 

Relevant articles and documents

Crystalline forms of osanetant

The invention relates to crystalline forms of (R)-(+)-N-[[3-[1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]prop-1-yl]-4-phenylpiperidin-4-yl]-N-methylacetamide and to processes for preparing them.

A practical and scalable synthesis of SR 142801, a tachykinin NK3 antagonist

A practical and scalable total synthesis of tachykinin NK3 receptor antagonist SR 142801, (R)-N-[1-[3-[1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4 -piperidinyl]-N-methyl acetamide 1 is described. The absolute configuration of the key intermediate 7 was determined by single crystal X-ray crystallography, on the basis of which, the absolute configuration of SR 142801 should be (R)-(+), instead of the recently reported (S)-(+).