503068-34-6

Basic information

• Product Name: Vilanterol
• Synonyms: Vilanterol;GW 642444X;Vilanterol API;GW 642444;GW642444;GW-642444;4-[(R)-2-[[6-[2-(2,6-Dichlorobenzyloxy)ethoxy]hexyl]amino]-1-hydroxyethyl]-2-hydroxymethylphenol;Vilanterol(GW642444)
• CAS NO: 503068-34-6
• Molecular Formula: C₂₄H₃₃Cl₂NO₅
• Molecular Weight: 486.42852
• EINECS: 690-631-3
• Product Categories: Inhibitors
• Mol File: 503068-34-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 646.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• Solubility: Soluble in DMSO
• PKA: 9.99±0.20(Predicted)
• CAS DataBase Reference: Vilanterol(CAS DataBase Reference)
• NIST Chemistry Reference: Vilanterol(503068-34-6)
• EPA Substance Registry System: Vilanterol(503068-34-6)

Safety Data

• Hazardous Substances Data: 503068-34-6(Hazardous Substances Data)

Usage

Definition

ChEBI: An dichlorobenzene derivative that is used in the form of its trifenate salt for treatment of chronic obstructive pulmonary disease.

Biological Activity

vilanterol is a novel and selective agonist of β2-ar with a pec50 value of 10.37±0.05 [1].vilanterol is a novel long-acting β2-ar agonist (laba) with 24h activity in development for inhaled once daily treatment. in the radioligand binding studies, vilanterol has shown the binding affinity in the one-affinity site model with pkd values of 9.44±0.07 and 10.82±0.12 in the presence gpp(nh)p and absence gpp(nh)p, respectively. in dissociation studies, vilanterol has been reported to bind from the β2-ar with a dissociation t1/2 value of 3.5 min in the presence of gpp(nh)p. vilanterol has been found to have a good selectivity for β2-ar over the other β-ar receptor subtypes(β1and β3) with pec50 values of 10.37±0.05, 6.98±0.03 and 7.36±0.03, respectively. vilanterol has exhibited at least 1000-fold selectivity over both β1-and β3-ar subtypes [1].

references

[1] slack rj1, barrett vj, morrison vs, sturton rg, emmons aj, ford aj, knowles rg.in vitro pharmacological characterization of vilanterol, a novel long-acting β2-adrenoceptor agonist with 24-hour duration of action.j pharmacol exp ther. 2013 jan; 344(1):218-30.

Upstream product

• 54030-34-1 1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanone 
• 102293-80-1 2-bromo-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethanone 
• 452339-70-7 di-(tert-butyl) 2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxoethyliminodicarbonate 
• 452339-71-8 tert-butyl 2-(2,2-dimethyl-4H-1,3-benzodioxane-6-yl)-2-carbonylethylcarbamate 
• 452339-72-9 tert-butyl (2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethylcarbamate 
• 452339-73-0 (5R)-5-(2,2-dimethyl- 4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one 
• 20443-98-5 2,6-Dichlorobenzyl bromide 
• 503070-57-3 2-((2-((6-bromohexyl)oxy)ethoxy)methyl)-1,3-dichlorobenzene 
• 52113-69-6 6-bromo-2,2-dimethyl-4H-benzo[1,3]dioxine 
• 503068-36-8 (5R)-3-{6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one 
• 503068-37-9 (2R)-hydroxy-2-(2,2-dimethyl-4Η-1,3-benzodioxole-6-yl)-N-3-[6-[2-[(2,6-dichlorophenyl)methoxy]ethoxy]hexyl]-ethylamine 
• 2316-64-5 5-bromo-2-hydroxybenzyl alcohol 
• 743460-69-7 (R)-(2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethoxy)(tert-butyl)dimethylsilane 
• 72189-44-7 3-hydroxymethyl-4-hydroxymandelic acid 

Downstream Products

• 503070-59-5 4-[(1R)-2-({6-[(2-{[(2,6-dichlorophenyl)methyl]oxy}ethyl)oxy]-hexyl}-amino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol α-phenylcinnamate 
• 503070-58-4 4‐{(1R)‐2‐[(6‐{2‐[(2,6‐dichlorobenzyl)oxy]ethoxy}hexyl)amino]‐1‐hydroxyethyl}‐2‐(hydroxymethyl)phenol triphenylacetate 

Relevant articles and documents

METHOD FOR THE PURIFICATION OF VILANTEROL TRIFENATATE

Method for the purification of vilanterol trifenatate It is provided a method for the purification of vilanterol trifenatate of formula (I) comprising crystallizing vilanterol trifenatate from a ketone solvent selected from the group consisting of methyl ethyl ketone (MEK), methyl isobutyl ketone (MIK), ethyl isopropyl ketone, methyl isopropyl ketone, 3-methyl-2-pentanone, and a mixture thereof.

Preparation method of vilanterol

The invention provides a preparation method of vilanterol, which comprises the following steps: 1) oxidation reaction: reacting a compound A with an oxidant to obtain a compound B; wherein the oxidantis selenium dioxide; 2) reductive amination reaction: carrying out condensation reaction on the compound B and a compound C to generate an imine intermediate, and carrying out a reaction on the imineintermediate under the action of a reducing agent to obtain a compound D; 3) reduction reaction: carrying out a reaction on the compound D with a chiral catalyst and a reducing agent to obtain a compound E, and 4) ring-opening reaction: performing deprotection ring-opening on the compound E under an acidic condition to obtain vilanterol. The method is advantaged in that the initial raw materialsare easy to obtain, the process is suitable for industrial production, the production yield is high and quality is stable.

Method for preparing Vilanterol

The invention discloses a method for preparing Vilanterol, and belongs to the field of drug synthesis. The method includes the steps: (1) performing addition reaction on salicyloyl and glyoxylic acidto generate an intermediate 1; (2) performing chiral resolution on the intermediate 1 to obtain a chiral intermediate 2; (3) performing acylation reaction on the intermediate 2 and an intermediate 3 to generate an intermediate 4; (4) reducing the intermediate 4 to obtain the Vilanterol. The intermediate 3 is obtained by performing Darebin reaction on an intermediate 5. Raw materials are easily obtained, a synthetic route is short, production cost is reduced, reaction conditions are mild, and the method is simple in operation and suitable for industrial production.