119410-05-8

Basic information

• Product Name: 6-Hydroxy Desloratadine
• Synonyms: 6-Hydroxy Desloratadine;8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-
• CAS NO: 119410-05-8
• Molecular Formula: C19H19ClN2O
• Molecular Weight: 326.81996
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 119410-05-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 520.3°C at 760 mmHg
• Flash Point: 268.5°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.19E-11mmHg at 25°C
• Refractive Index: 1.649
• PKA: 13.41±0.20(Predicted)
• CAS DataBase Reference: 6-Hydroxy Desloratadine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy Desloratadine(119410-05-8)
• EPA Substance Registry System: 6-Hydroxy Desloratadine(119410-05-8)

Safety Data

• Hazardous Substances Data: 119410-05-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H19ClN2O/c20-14-3-4-15-16(11-14)17(23)10-13-2-1-7-22-19(13)18(15)12-5-8-21-9-6-12/h1-4,7,11,17,21,23H,5-6,8-10H2

Upstream product

• 119410-04-7 8-Chloro-5,11-dihydro-11-(4-piperidinylidene)-6H-benzo<5,6>cyclohepta<1,2-b>pyridin-6-one 
• 79794-75-5 loratadine 
• 119410-09-2 8-Chloro-6-methoxy-11-(1-methyl-4-piperidinyl)-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-ol 
• 126063-19-2 Ethyl 4-<8-Chloro-6-<(ethoxycarbonyl)oxy>-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-ylidene>-1-piperidinecarboxylate 
• 126063-20-5 Ethyl 4-(8-Chloro-5,6-dihydro-6-oxo-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-ylidene)-1-piperidinecarboxylate 
• 119410-11-6 8-Chloro-5,11-dihydro-11-(1-methyl-4-piperidinylidene)-6H-benzo<5,6>cyclohepta<1,2-b>pyridin-6-one 
• 117811-22-0 8-Chloro-6-methoxy-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one 
• 117811-16-2 8-chloro-11H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-one 
• 31251-41-9 8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one 

Relevant articles and documents

Late-Stage Lead Diversification Coupled with Quantitative Nuclear Magnetic Resonance Spectroscopy to Identify New Structure-Activity Relationship Vectors at Nanomole-Scale Synthesis: Application to Loratadine, a Human Histamine H1Receptor Inverse Agonist

An experimental approach is described for late-stage lead diversification of frontrunner drug candidates using nanomole-scale amounts of lead compounds for structure-activity relationship development. The process utilizes C-H bond activation methods to explore chemical space by transforming candidates into newly functionalized leads. A key to success is the utilization of microcryoprobe nuclear magnetic resonance (NMR) spectroscopy, which permits the use of low amounts of lead compounds (1-5 μmol). The approach delivers multiple analogues from a single lead at nanomole-scale amounts as DMSO-d6 stock solutions with a known structure and concentration for in vitro pharmacology and absorption, distribution, metabolism, and excretion testing. To demonstrate the feasibility of this approach, we have used the antihistamine agent loratadine (1). Twenty-six analogues of loratadine were isolated and fully characterized by NMR. Informative SAR analogues were identified, which display potent affinity for the human histamine H1 receptor and improved metabolic stability.

Hydroxylated Metabolites of Loratadine: An Example of Conformational Diastereomers Due to Atropisomerism

The structures of two metabolites of the nonsedating antihistamine loratadine (1) were confirmed by synthesis.The metabolites 3a and 3b, which are hydroxylated in the bridgehead, were each prepared from tricyclic ketone 8 in seven steps.Each of these compounds was found to exist as a pair of conformational diastereomers which interconvert slowly at room temperature.These conformers arise due to restricted conformational mobility inherent to the diarylcycloheptane ring system.