An improved method for preparation of cefpodoxime proxetil.
Cefpodoxime proxetil, a third-generation cephalosporin for oral administration, was synthesized by a method based on the following sequence of reactions: acylation of 7-aminocephalosporanic acid (7-ACA) with S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate (MAEM), chloroacetylation of the cefotaxime formed with chloroacetyl chloride, esterification of the acid function with 1-iodoethyl isopropyl carbonate and final cleavage of chloroacetamide protective group by treatment with thiourea in N,N-dimethylacetamide. The developed procedure allows us to obtain better yields of cefpodoxime proxetil and to eliminate the final purification step by column chromatography, necessary during the synthesis of this antibiotic by the previously reported methods.
Department of Chemical Synthesis, Center of Pharmaceutical Chemistry, Ave. 200 y 21, Atabey, Playa, Havana City, Cuba.
Juan C
JC
Rodríguez
Ricardo
R
Hernández
Maritza
M
González
Zalua
Z
Rodríguez
Blanca
B
Tolón
Hermán
H
Velez
Bárbara
B
Valdés
Miguel A
MA
López
Adamo
A
Fini
D000085:Acetates / Q000138:chemical synthesis*; D000215:Acylation; D000284:Administration, Oral; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D052160:Benzothiazoles; D015296:Ceftizoxime / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002511:Cephalosporins / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D004339:Drug Compounding; D013844:Thiazoles / Q000138:chemical synthesis*; D000097627:Cefpodoxime Proxetil
D000085:Acetates; D000900:Anti-Bacterial Agents; D052160:Benzothiazoles; D015296:Ceftizoxime; D002511:Cephalosporins; D013844:Thiazoles; D000097627:Cefpodoxime Proxetil; C480878:(Z)-2-(2-chloroacetamido-4-thiazolyl)-2-(methoxyimino)acetic acid; C480879:S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate; C030735:7-aminocephalosporanic acid