Zenarestat
- CAS No.
- 112733-06-9
- Chemical Name:
- Zenarestat
- Synonyms
- CI1014;FK-366;CI-1014;FR 74366;Zenarestat;3-(2-Fluoro-4-bromobenzyl)-7-chloro-2,4(1H,3H)-dioxoquinazoline-1-acetic acid;2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxoquinazolin-1-yl]acetic acid;[3-(4-Bromo-2-fluorobenzyl)-7-chloro-2,4-dioxo-3,4-dihydro-1(2H)- quinazolinyl]acetic acid;3-[(4-Bromo-2-fluorophenyl)methyl]-7-chloro-3,4-dihydro-2,4-dioxo-1(2H)-quinazolineacetic acid;1(2H)-Quinazolineacetic acid, 3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-3,4-dihydro-2,4-dioxo-
- CBNumber:
- CB01180093
- Molecular Formula:
- C17H11BrClFN2O4
- Molecular Weight:
- 441.639
- MDL Number:
- MFCD00865809
- MOL File:
- 112733-06-9.mol
| 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) |
| FDA UNII | 180C9PJ8JT |
Zenarestat Chemical Properties,Uses,Production
Originator
FK 366 ,Fujisawa Pharmaceutical
Uses
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
Zenarestat Preparation Products And Raw materials
Raw materials
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28180 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49391 | 58 |
| Hangzhou MolCore BioPharmatech Co.,Ltd. | +86-057181025280; +8617767106207 | sales@molcore.com | China | 49739 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 | support@targetmol.com | United States | 19973 | 58 |
| TargetMol Chemicals Inc. | 4008200310 | marketing@tsbiochem.com | China | 24018 | 58 |
| Shanghai?Medlife?Pharm-Tech?Co.,?Ltd | 021-59167510 18117107507 | vip@med-life.cn | China | 5019 | 58 |
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