Umeclidinium bromide Struktur

Umeclidinium bromide

Bezeichnung:Umeclidinium bromide

CAS-Nr869113-09-7

Englisch Name:Umeclidinium bromide

CBNumberCB92625301

SummenformelC29H34BrNO2

Molgewicht508.48976

MOL-Datei869113-09-7.mol

Umeclidinium bromide physikalisch-chemischer Eigenschaften

Schmelzpunkt	>231°C (dec.)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Aggregatzustand	Solid
Farbe	White to Off-White
Stabilität	Hygroscopic

Gefahreninformationscode (GHS)

Umeclidinium bromide Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Verwenden
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.
Synthese
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.
Einzelnachweise
[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.

Umeclidinium bromide Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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