Contact us: +91 9550333722 040 - 40102781
Structured search
India
Choose your country
Different countries will display different contents
Try our best to find the right business for you.
My chemicalbook

Welcome back!

HomeProduct name listZenarestat

Zenarestat

Zenarestat Structural

What is Zenarestat?

Originator

FK 366 ,Fujisawa Pharmaceutical

The Uses of Zenarestat

Treatment of diabetic neuropathy (aldose reductase inhibitor).

Manufacturing Process

To a solution of 4-bromo-2-fluorobenzylamine and triethylamine in chloroform was added dropwise a solution of 4-chloro-2-nitrobenzoyl chloride in chloroform at 0°C with stirring and the mixture was stirred at the same temperature for 1 h. The reaction mixture was washed in turn with diluted aqueous hydrochloric acid and water, and then dried. Evaporation of the solvent followed by recrystallization from diethyl ether gave N-(4-bromo-2- fluorobenzyl)-4-chloro-2-nitrobenzamide.
A mixture of N-(4-bromo-2-fluorobenzyl)-4-chloro-2-nitrobenzamide and iron (1.45 g) in acetic acid (66 ml) was stirred at 100°C for 30 min. After cooling, iron was filtered off. The filtrate was evaporated to give a residue, which was made alkaline with aqueous 1 N sodium hydroxide and extracted with ethyl acetate. The extract was washed with water and dried. Removal of the solvent gave 2-amino-N-(4-bromo-2-fluorobenzyl)-4-chlorobenzamide.
2-Amino-N-(4-bromo-2-fluorobenzyl)-4-chlorobenzamide and N,N'- carbonyldiimidazole were dissolved in dioxane (50 ml). The solution was evaporated to give a residue, which was stirred at 150°C for 30 min. After cooling, the precipitates were collected by filtration and washed with ethanol to give 3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4- dioxoquinazoline; melting point >280°C.
To a suspension of 3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro- 2,4-dioxoquinazoline in N,N-dimethylformamide was added sodium hydride (60% in mineral oil) with stirring at 0°C and the mixture was stirred for 15 min at the same temperature. To this mixture was added ethyl bromoacetate and the mixture was stirred for 1 h at room temperature. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried and evaporated to give a residue. Thus obtained product was purified by recrystallization from isopropyl ether to give 2-[3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4- dioxoquinazolin-1-yl]acetic acid melting point 223°-224°C.

Therapeutic Function

Aldose reductase inhibitor

Properties of Zenarestat

Melting point: 223-224°
Boiling point: 624.4±65.0 °C(Predicted)
Density  1.737
solubility  DMSO : 100 mg/mL (226.43 mM; Need ultrasonic)
pka 3.76±0.10(Predicted)
form  Solid
color  White to off-white

Safety information for Zenarestat

Computed Descriptors for Zenarestat

Related products of tetrahydrofuran

You may like

Statement: All products displayed on this website are only used for non medical purposes such as industrial applications or scientific research, and cannot be used for clinical diagnosis or treatment of humans or animals. They are not medicinal or edible.