N-(2-HYDROXY-5-(1-HYDROXY-2-(2-METHYL-1-PHENYLPROPAN-2-YLAMINO)ETHYL)PHENYL)METHANE Property

Boiling point:

574.3±60.0 °C(Predicted)

Density 

1.282±0.06 g/cm3(Predicted)

storage temp. 

Store at +4°C

solubility 

Soluble to 5 mM in water and to 100 mM in DMSO

form 

Powder

pka

8.57±0.50(Predicted)

color 

White to off-white

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

N-(2-HYDROXY-5-(1-HYDROXY-2-(2-METHYL-1-PHENYLPROPAN-2-YLAMINO)ETHYL)PHENYL)METHANE Chemical Properties,Usage,Production

Originator

Zinterol Hydrochloride,ZYF Pharm Chemical

Uses

Bronchodilator.

Uses

Zinterol is a β2-adrenergic agonist. It can be used to induce smooth muscle relaxation in the lungs, gastrointestinal tract, uterus, and various blood vessels.

Manufacturing Process

A). 2'-Hydroxy-5'-([N-(2-methyl-1-phenyl-2-propyl)glycyl]methane- sulfonanilide hydrobromide:
To a solution of α,α-dimethylphenthylamine (120 g, 0.8 mole) in 1.1 liter of acetonitrile is added 5'-bromoacetyl-2'-hydroxymethanesulfonanilide (108 g, 0.35 mole) in a period of 5 minutes. The resulting solution is refluxed for 5 minutes on a steam bath and then permitted to stand for 25 minutes at room temperature after which it is chilled and acidified with 5 N ethanolic hydrogen bromide. The acidified mixture is concentrated in vacuum until a thick slurry is obtained. After standing overnight at room temperature, the slurry is filtered and the crude product triturated with 2-butanone, filtered, washed with 2- butanone and dried to 86.3 g, (54%), MP: 217.5-221°C (dec.).
B). 2'-Hydroxy-5'-(1-hydroxy-2-(2-methyl-1-phenyl-2-propylamino)ethyl) methanesulfonanilide hydrobromide:
2'-Hydroxy-5'-([N-(2-methyl-1-phenyl-2-propyl)glycyl]methanesulfonanilide hydrobromide (132 g, 0.29 mole is dissolved in 2 liters of hot methanol, the methanolic solution is allowed to cool to room temperature and 13 g 10% palladium on carbon catalyst suspended in 50 ml of water is added. Hydrogenation of the stirred mixture is carried out under 1-3 atm. of pressure for 17 hours during which time 0.31 mole of hydrogen is absorbed. The catalyst is filtered and the filtrate concentrated under reduced pressure until a thick slurry is obtained. Isoptopanpl is added tothed slurry and the mixture is again concentrated in vacuum to remove water by azeotropic distillation. Trituration of residual solid with 2-propanol and collection on a filter affords 100.5 g (76% yield) of desired product, MP: 194.5-195.5°C (dec.).
2'-Hydroxy-5'-(1-hydroxy-2-(2-methyl-1-phenyl-2-propylamino)ethyl) methanesulfonanilide base:
2'-Hydroxy-5'-(1-hydroxy-2-(2-methyl-1-phenyl-2-propylamino)ethyl)
methanesulfonanilide hydrobromide (47.7 g) is refluxed with 100 ml of methanol. The material only partly dissolves. A solution of 6.5 g of potassium hydroxide in 25 ml of methanol is then added to the suspension followed by 1 L of water. The mixture is thoroughly stirred and cooled to 5-10°C. The precipitate is collected on a filter and washed with water until a negative test for bromide using silver nitrate is obtained. The product is dried in an oven at 65°C, yield 36 g.

Therapeutic Function

Bronchodilator

Biological Activity

Potent and selective β 2 -adrenoceptor agonist (pK B values are 8.3 and < 5.7 for β 2 and β 1 receptors respectively, as measured in human artery).