| Identification | Back Directory | [Name]
2-ethoxyethyl N-(4-(3-methyl-5-isoxazolyl)-2-thiazolyl)oxamate | [CAS]
104777-03-9 | [Synonyms]
2-ethoxyethyl N-(4-(3-methyl-5-isoxazolyl)-2-thiazolyl)oxamate
Acetic acid, 2-[[4-(3-methyl-5-isoxazolyl)-2-thiazolyl]amino]-2-oxo-, 2-ethoxyethyl ester | [Molecular Formula]
C13H15N3O5S | [MDL Number]
MFCD00864627 | [MOL File]
104777-03-9.mol | [Molecular Weight]
325.34 |
| Hazard Information | Back Directory | [Originator]
Asobamast,Onbio Inc. | [Uses]
Asobamast is a potent, orally active antiallergic agent that inhibits ige mediated passive pulmonary allergic responses in rats (ED50=4.7 mg/kg) and inhibits antigen-induced mediator release from sensitized guinea pig lung fragments[1]. | [Manufacturing Process]
1). 179 mmol of bromine in 20 ml of chloroform were added dropwise in 10
minutes to a solution of 172 mmol of 3-methyl-5-acetylisoxazole, (Gass.
Chim. Ital. 72, 242, 194) containing 4.9 ml of glacial acetic acid while the
reaction mixture was maintained under stirring at 48°-50°C. After 5 minutes
the mixture was poured into 300 g of water and crushed ice. The organic
layer was separated, washed with water, dried and evaporated to residual 3-
methyl-5-bromoacetylisoxazole. Yield 87%, white crystalline compound, MP:
44°-46°C (isopropyl ether).
2). A mixture of 50 mmol of 3-methyl-5-bromoacetylisoxazole and 100 mmol
of thiourea in 164 ml of ethyl alcohol was refluxed for 90 minutes and then
cooled for 1 hour with an ice bath. The precipitate was collected by filtration
and added to a mixture of 25 ml of a 10% aqueous solution of sodium
hydroxide and 100 ml of ethyl acetate under vigorous stirring. The organic
layer was separated, washed, dried and evaporated to dryness after
recrystallization from acetonitrile the 2-amino-4-(3-methyl-5-
isoxazolyl)thiazole melts at 208°-210°C. Yield, 57%.
3). To a mixture of 20.5 mmol of 2-amino-4-(3-methyl-5-isoxazolyl)thiazole in
37.4 ml of pyridine maintained under stirring at 5°C were added dropwise
23.6 mmol of 2-ethoxyethyloxalyl chloride. The reaction mixture was
maintained under stirring overnight, then poured into 100 g of crushed ice,
made acid with concentrate hydrochloric acid and extracted with chloroform.
The chloroform extracts were washed with water, dried and evaporated to
dryness. The residual 2-ethoxyethyl-4-(3-methyl-5-isoxazolyl)thiazole-2-
oxamate was re-crystallized from 65 ml of acetonitrile. Yield, 91%, MP: 155°-
156°C. | [Therapeutic Function]
Antiallergic, Anti-asthmatic | [References]
[1] D Chiarino, et al. N-(4-Isoxazolylthiazol-2-yl)oxamic acid derivatives as potent orally active antianaphylactic agents. J Med Chem. 1991 Feb;34(2):600-5. DOI:10.1021/jm00106a020 |
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