135729-78-1

Basic information

• Product Name: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide
• Synonyms: (S)-N-1-azabicyclo[2.2.0]oct-3-yl-5,6,7,8-tetrahydro-1-naphthalenecarboxamide;(S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide;Palonosetron Intermediate;(S)-N-(Quinuclidin-3-yl)-5,6,7,8-tetrahydronaphthalene-1-carboxaMide;N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-5,6,7,8-tetrahydro-1-naphthalenecarboxaMide;N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl] 5,6,7,8-tetrahydronaphthalene-1-carboxamide;Palonosetron Impurity 3
• CAS NO: 135729-78-1
• Molecular Formula: C₁₈H₂₄N₂O
• Molecular Weight: 284.4
• Product Categories: Intermediate of palonosetron hcl
• Mol File: 135729-78-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 439.2 °C at 760 mmHg
• Flash Point: 219.4 °C
• Appearance: /
• Density: 1.17
• Vapor Pressure: 6.48E-08mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide(135729-78-1)
• EPA Substance Registry System: (S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide(135729-78-1)

Safety Data

• Hazardous Substances Data: 135729-78-1(Hazardous Substances Data)

Usage

Uses

(S)-N-(1-Azabicyclo[2.2.2]oct-3-yl)-5,6,7,8-tetrahydro-1-naphthalenecarboxamide is an impurity in the synthesis of Palonosetron HCl (P165800), a serotonin 5-HT3 receptor antagonist used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). Antiemetic.

InChI:InChI=1/C18H24N2O/c21-18(19-17-12-20-10-8-14(17)9-11-20)16-7-3-5-13-4-1-2-6-15(13)16/h3,5,7,14,17H,1-2,4,6,8-12H2,(H,19,21)/t17-/m1/s1

Upstream product

• 4242-18-6 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid 
• 110808-69-0 5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride 
• 6530-09-2 (S)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride 
• 79-37-8 oxalyl dichloride 
• 120570-05-0 (S)-3-aminoquinuclidine 

Downstream Products

• 135755-51-0 palonosetron hydrochloride 
• 135755-51-0 RS 25233-198 
• 135729-56-5 (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one 
• 135755-51-0 palonosetron hydrochloride 
• 135729-60-1 palonosetron 
• 135729-60-1 palonosetron 

Relevant articles and documents

Synthesis and Pharmacological Evaluation of [11C]Granisetron and [18F]Fluoropalonosetron as PET Probes for 5-HT3 Receptor Imaging

Serotonin-gated ionotropic 5-HT3 receptors are the major pharmacological targets for antiemetic compounds. Furthermore, they have become a focus for the treatment of irritable bowel syndrome (IBS) and there is some evidence that pharmacological modulation of 5-HT3 receptors might alleviate symptoms of other neurological disorders. Highly selective, high-affinity antagonists, such as granisetron (Kytril) and palonosetron (Aloxi), belong to a family of drugs (the "setrons") that are well established for clinical use. To enable us to better understand the actions of these drugs in vivo, we report the synthesis of 8-fluoropalonosetron (15) that has a binding affinity (Ki = 0.26 ± 0.05 nM) similar to the parent drug (Ki = 0.21 ± 0.03 nM). We radiolabeled 15 by nucleophilic 18F-fluorination of an unsymmetrical diaryliodonium palonosetron precursor and achieved the radiosynthesis of 1-(methyl-11C)-N-granisetron ([11C]2) through N-alkylation with [11C]CH3I, respectively. Both compounds [18F]15 (chemical and radiochemical purity >95%, specific activity 41 GBq/μmol) and [11C]2 (chemical and radiochemical purity ≥99%, specific activity 170 GBq/μmol) were evaluated for their utility as positron emission tomography (PET) probes. Using mouse and rat brain slices, in vitro autoradiography with both [18F]15 and [11C]2 revealed a heterogeneous and displaceable binding in cortical and hippocampal regions that are known to express 5-HT3 receptors at significant levels. Subsequent PET experiments suggested that [18F]15 and [11C]2 are of limited utility for the PET imaging of brain 5-HT3 receptors in vivo.

PREPARATION OF CRYSTALLINE PALONOSETRON HYDROCHLORIDE

Processes for the preparation of palonosetron hydrochloride and its crystalline forms.

Tricyclic 5-HT3 receptor antagonists

The present invention is directed to 5-HT 3 receptor antagonist compounds of formula I: STR1 in which the dashed line denotes an optional double bond;n is 1, 2 or 3;p is 0, 1, 2 or 3;q is 0, 1 or 2;each R 1 is independently selected from halogen, hydroxy, lower alkoxy, lower alkyl, nitro, amino, amino carbonyl, (lower alkyl)amino, di(lower alkyl)amino, and (lower alkanoyl)amino;each R 2 is lower alkyl; andR 3 is a group selected from Formulae (a), (b), (c) and (d): STR2 in which u is 0 or 1;z is 1, 2 or 3; andR 4 is C 1-7 alkyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl-C 1-2 alkyl, or a group (CH 2) t R 5 where t is 1 or 2 and R 5 is thienyl, pyrrolyl, or furyl, each optionally further substituted by one or two substituents selected from C 1-6 alkyl, C 1-6 alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C 1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C 1-4 alkyl optionally substituted by hydroxy, C 1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolyzable acyloxy; and the pharmaceutically acceptable salts, individual isomers, mixtures of isomers, processes for preparation, compositions, and methods of use thereof.