Olodaterol Hydrochloride

Base Information

• Chemical Name: Olodaterol Hydrochloride
• CAS No.: 869477-96-3
• Molecular Formula: C₂₁H₂₆N₂O₅*(x)ClH
• Molecular Weight: 422.90248
• European Community (EC) Number: 810-630-5
• UNII: 65R445W3V9
• ChEMBL ID: CHEMBL2105743
• DSSTox Substance ID: DTXSID901027733
• NCI Thesaurus Code: C166904
• RXCUI: 1546396
• Wikidata: Q27156746
• Mol file: 869477-96-3.mol

Synonyms:6-hydroxy-8-(1-hydroxy-2-((2-(4-methoxyphenyl)-1,1-dimethylethyl)amino)ethyl)-2H-1,4-benzoxazin-3(4H)-one;BI 1744 CL;BI-1744 CL;olodaterol;Striverdi Respimat

Chemical Property of Olodaterol Hydrochloride

Chemical Property:

• PSA: 103.54000
• LogP: 3.65400
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 422.1608497
• Heavy Atom Count: 29
• Complexity: 521

Purity/Quality:

98% ^*data from raw suppliers

Olodaterol Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CC1=CC=C(C=C1)OC)NCC(C2=C3C(=CC(=C2)O)NC(=O)CO3)O.Cl
• Isomeric SMILES: CC(C)(CC1=CC=C(C=C1)OC)NC[C@@H](C2=C3C(=CC(=C2)O)NC(=O)CO3)O.Cl
• Recent ClinicalTrials: Pharmacokinetics and Safety of BI 1744 CL Plus Tiotropium Bromide in Chronic Obstructive Pulmonary Disease (COPD)
• Recent EU Clinical Trials: Effects of ultra-long acting bronchodilator therapy assessed by impulse oscillometry in smoking asthmatics taking inhaled corticosteroids
• Recent NIPH Clinical Trials: Safety of LAMA/LABA combination therapy in the COPD patients
• Description: Olodaterol hydrochloride was approved for long-term, oncedaily maintenance treatment of chronic obstructive pulmonary disease (COPD) in 2013 in the following countries: Canada, Russia, United Kingdom, Denmark, and Iceland. The drug has been recommended by a federal advisory panel for approval by the FDA. Developed and marketed by Boehringer Ingelheim, olodaterol is a long-acting b2-adrenergic receptor agonist with high selectivity over the b1- and b3-receptors (219- and 1622-fold, respectively). Upon binding to and activating the b2-adrenergic receptor in the airway, olodaterol stimulates adenyl cyclase to synthesize cAMP, leading to the relaxation of smooth muscle cells in the airway. Administered by inhalation using the Respimat? Soft Mist inhaler, it delivers significant bronchodilator effects within five minutes of the first dose and provides sustained improvement in forced expiratory volume (FEV1) for over 24 h.
• Uses: Olodaterol is a long acting β-adrenoceptor agonist used as an inhalation for treating patients with chronic obstructive pulmonary disease (COPD).

Technology Process of Olodaterol Hydrochloride

There total 21 articles about Olodaterol Hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.27%

6-(phenylmethoxy)-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one hydrochloride (926319-48-4) → 6-hydroxy-8-{(1R)-1-hydroxy-2-{[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino}ethyl}-4H-[1,4]benzoxazin-3-one hydrochloride (869477-96-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 50 ℃; under 2250.23 Torr;

Reference yield: 95.0%

6-benzyloxy-8-{(R)-1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamino]ethyl}-4H-benzo[1,4]oxazin-3-one (869478-13-7) → Olodaterol hydrochloride (869477-96-3)

Guidance literature:

6-benzyloxy-8-{(R)-1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamino]ethyl}-4H-benzo[1,4]oxazin-3-one; With hydrogen; palladium 10% on activated carbon; In methanol; at 50 ℃; under 2250.23 Torr;

With hydrogenchloride; In water; isopropyl alcohol; Product distribution / selectivity;

Reference yield: 90.0%

6-(phenylmethoxy)-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one hydrochloride (926319-48-4) → Olodaterol hydrochloride (869477-96-3)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 40 ℃; for 5h; under 2280.15 Torr;

upstream raw materials:

6-benzyloxy-8-{(R)-1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-4H-benzo[1,4]oxazin-3-one

6-benzyloxy-8-{(R)-1-hydroxy-2-[2-(4-methoxyphenyl)-1,1-dimethylethylamino]ethyl}-4H-benzo[1,4]oxazin-3-one

(R)-6-hydroxy-8-{(1R)-1-hydroxy-2-{[1-(4-methoxyphenyl)-2-methylpropan-2-yl]amino}ethyl}-4H-1,4-benzoxazin-3-one

6-(phenylmethoxy)-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one hydrochloride

Refernces

• 1、 -. "IMPROVED PROCESS FOR THE MANUFACTURE OF R-6-HYDROXY-8-[1-HYDROXY-2-[2-(4-METHOXYPHENYL)-1,1-DIMETHYLETHYLAMINOETHYL]-2H-1,4-BENZOXAZIN-3(4H)-ONE HYDROCHLORIDE". Page/Page column 40; 42. . Retrieved 2018/07/29.
• 2、 -. "Hydrochloric acid [...] B and its preparation method". . . Retrieved 2019/01/08.