ChemicalBook--->CAS DataBase List--->869113-09-7

869113-09-7

869113-09-7 Structure

869113-09-7 Structure
IdentificationBack Directory
[Name]

Umeclidinium bromide
[CAS]

869113-09-7
[Synonyms]

CS-1562
UMeclidiuM
GSK573719A
Umeclidiniu
umeclidinium
UMeclidiniuM broMide
Umeclinidium bromide
Jmechlidinium bromide
Umeclidinium(GSK573719A)
UMeclidiniuM BroMide (API)
Umeclidinium bromide, >=98%
1-Azoniabicyclo[2.2.2]octane
Umeclidinium bromide fandachem
Jmechlidinium bromide fandachem
Umeclidinium bromide(GSK573719A)
GSK573719A;GSK-573719A;GSK 573719A
1-(2-(benzyloxy)ethyl)-4-(hydroxydiphenylmethyl)quinuclidin-1-ium bromide
1-[2-(Benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-quinuclidinium Bromide
diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol
DIPHENYL-[1-(2-PHENYLMETHOXYETHYL)-1-AZONIABICYCLO[2.2.2]OCTAN-4-YL]METHANOL;BROMIDE
4-[Hydroxy(diphenyl)methyl]-1-[2-[(phenylmethyl)oxy]ethyl]-1-azoniabicyclo[2.2.2]octane bromide
1-Azoniabicyclo[2.2.2]octane, 4-(hydroxydiphenylMethyl)-1-[2-(phenylMethoxy)ethyl]-, broMide (1:1)
[EINECS(EC#)]

638-761-1
[Molecular Formula]

C29H34BrNO2
[MDL Number]

MFCD27976798
[MOL File]

869113-09-7.mol
[Molecular Weight]

508.49
Chemical PropertiesBack Directory
[Melting point ]

>231°C (dec.)
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

DMSO (Slightly), Methanol (Slightly), Water (Slightly)
[form ]

Solid
[color ]

White to Off-White
[Stability:]

Hygroscopic
Hazard InformationBack Directory
[Description]

Umeclidinium bromide is a long-acting muscarinic acetylcholine antagonist developed by GlaxoSmithKline and approved by the US FDA at the end of 2013 for use in combination with vilanterol, a b2 agonist, for the treatment of chronic obstructive pulmonary disease. Due to umeclidinium’s poor oral bioavailability, the drug is administrated by inhalation as dry powder.
[Uses]

Umeclidinium Bromide is considered as a potentially long-acting antimuscarinic agent.
[Definition]

ChEBI: A quaternary ammonium salt that is the bromide salt of umeclidinium. Used in combination with vilanterol for long-term maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease.
[Synthesis]

Commercially available ethyl isonipecotate (278) was alkylated with 1-bromo-2-chloroethane in the presence of K2CO3 in acetone to give ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (279). This material was then treated with lithium diisopropylamine (LDA) in THF to affect a transannular substitution reaction resulting in the cyclized quinuclidine 280 in 96% yield. Excess of phenyllithium was added to ester 280 in THF starting at low temperature then gradually warming to room temperature to give tertiary alcohol 281 in 61% yield. Amine 281 was finally alkylated with benzyl 2- bromoethyl ether (282) in MeCN/CHCl3 at elevated temperatures to afford umeclidinium bromide (XXXV) in 69% yield.

Synthesis_869113-09-7

[References]

[1] salmon m, luttmann m a, foley j j, et al. pharmacological characterization of gsk573719 (umeclidinium): a novel, long-acting, inhaled antagonist of the muscarinic cholinergic receptors for treatment of pulmonary diseases. journal of pharmacology and experimental therapeutics, 2013, 345(2): 260-270.
Spectrum DetailBack Directory
[Spectrum Detail]

Umeclidinium bromide(869113-09-7)MS
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