| Identification | Back Directory | [Name]
Zoliprofen | [CAS]
56355-17-0 | [Synonyms]
480156-S
Zoliprofen
Zoliprofen, 10 mM in DMSO
Benzeneacetic acid, α-methyl-4-(2-thiazolyloxy)- | [Molecular Formula]
C12H11NO3S | [MOL File]
56355-17-0.mol | [Molecular Weight]
249.29 |
| Hazard Information | Back Directory | [Originator]
Zoliprofen,ZYF Pharm Chemical | [Uses]
Zoliprofen (480156-S), a new non-steroidal anti-inflammatory agent, has potent pain suppressing effect. Zoliprofen has strong antagonistic action against bradykinin, markedly inhibiting all bradykinin-induced edema and pain reactions. Zoliprofen weakly inhibits Arachidonic acid (HY-109590)-induced edema and pain reactions but also inhibits PGE2 synthesis of bovine vesicular gland microsomes[1]. | [Manufacturing Process]
A mixture of 2-chlorothiazole (5.0 g), ethyl 2-(4-hydroxyphenyl)propionate
(8.1 g), potassium carbonate powder (8.65 g) and dimethylformamide (80 ml)
is stirred at 150°-155°C for 2.5 hours. The solvent is distilled out under
reduced pressure. To the residue is added water and extracted with ether. The
extract is washed with a 10% aqueous solution of sodium hydroxide and
water and dried. The ether is evaporated. The residue is subjected to
chromatography using silica gel and eluted with 50% benzene-hexane,
benzene and 10% ether-benzene to yield ethyl 2-[4-(2-thiazolyloxy)-
phenyl]propionate (5.8 g).
The product is dissolved in a mixture of a 20% aqueous solution of potassium
hydroxide (30 ml) and 95% ethanol (30 ml). The solution is kept at room
temperature for 30 minutes. The solvent is evaporated. The residue is
acidified with hydrochloric acid after addition of water, and extracted with
ether. The extract is washed with water and dried over magnesium sulfate.
The solvent is distilled out. The residue is recrystallized from ether-hexane to
give 2-[4-(2-thiazolyloxy)phenyl]propionic acid (4.8 g).
The product (5.0 g) is dissolved in an aqueous solution (30 ml) of sodium
hydroxide (0.82 g). To the solution washed with ether is added an aqueous
solution (5 ml) of calcium chloride 2 hydrate (1.6 g) to form a precipitate. The
precipitate washed with water gives calcium 2-[4-(2-thiazolyloxy)phenyl]propionate (5.5 g) melting at 143°-145°C. | [Therapeutic Function]
Antiinflammatory, Analgesic | [References]
[1] K Hirose, et al. Pharmacological properties of 2-[4-(2-thiazolyloxy)-phenyl]-propionic acid (480156-S), a new non-steroidal antiinflammatory agent. Arzneimittelforschung. 1984;34(3):280-6. PMID:6610429 |
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