Zopolrestat Property

Melting point:

197-198℃

Density 

1.58

storage temp. 

2-8°C

solubility 

DMSO: ≥20mg/mL

pka

pKa (dioxane/water): 5.46 (1:1); 6.38 (2:1)

form 

powder

color 

off-white to light brown

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

Zopolrestat Chemical Properties,Usage,Production

Originator

Alond,Pfizer

Uses

Antidiabetic; inhibitor (aldose reductase).

Manufacturing Process

A mixture of 2-methyl-5-trifluoromethylbenzothiazole (1 mole-equivalent), N- bromosuccinimide (1 mole-equivalent), carbon tetrachloride (700 ml) and a catalytic amount of benzoyl peroxide (0.2 g) was refluxed under irradiation by an UV lamp for 14 hours. The reaction mixture was cooled to room temperature, filtered to remove the precipitated succinimide and the filtrate was evaporated to dryness. The resulting solid was chromatographed over silica gel to obtain the 2-bromomethyl-5-trifluoromethyl-benzothiazole. To a mixture of ethyl 4-oxo-3H-phthalazin-1-ylacetate (1 mole-equivalent) and sodium hydride (50% w/w dispersion in mineral oil) in dimethylformamide (150 ml) was added 2-bromomethyl-5-trifluoromethylbenzothiazole (1 mole- equivalent) and the resulting mixture stirred at room temperature for 1 hour. This reaction mixture was poured over ice-water (500 ml); sufficient 10% HCl was added to adjust the pH to about 4.0 and the precipitated crude solid was collected. This was chromatographed over silica gel to obtain the ethyl[4-oxo- 3-(5-trifluoromethylbenzothiazol-2-yl)-3,4-dihydro-phthalazin-1-yl]acetate; MP: 134°-136°C. A solution of methyl or ethyl [4-oxo-3-(5-trifluoromethylbenzothiazol-2-yl)- 3,4-dihydrophthalazin-1-yl]acetate (1 mole-equivalent) in methanol (50 ml)

Therapeutic Function

Aldose reductase inhibitor