Alatrofloxacin Mesylate

Chemical properties

White Solid

Originator

Alatrofloxacin mesylate,Pfizer

The Uses of Alatrofloxacin Mesylate

Alatrofloxacin Mesylate is the parental prodrug of Trovafloxacin (T893000), on phagocytic, anti-inflammatory and immunomodulation events of human THP-1 monocytes.

What are the applications of Application

Alatrofloxacin mesylate is the prodrug of the antibiotic Trovafloxacin

Manufacturing Process

The dipolar cycloaddition of ethyldiazoacetate to the protected dihydropyrrole (with carbobenzyloxy (CBZ) protecting group) gives the fused pyrrazolidine- (CBZ-3-ethylperoxy-1,3a,4,5,6,6a-hexahydro-pyrrolo{3,4-c}pyrazole). Pyrolysis results in loss of nitrogen and formation of the cyclopyrrolidine ring. The ester is then saponified to the corresponding carboxylic acid (CBZ-6-azabicyclo[ 3.1.0]hexene-3-carboxylic acid).This acid undergoes a version of the Curtius rearrangement when treated with diphenylphosphinous azide to afford transient isocyanate. That reactive function adds tert-butanol from the reaction medium to afford the product as its butoxycarbonyl (BOC) derivative. CBZ-protecting group is removed by catalytic hydrogenation on Pd to afford the BOC-protected secondary amine - BOC-6-aza-bicyclo[3.1.0]hex-3-ylamine. In a standard quinolone reaction, this amine is then used to displace the more reactive fluorine at 7-position in the quinolone - 1-(2,4 difluoro-phenyl)-6,7- difluoro-4-oxo-1,4-dihydro[1,8]naphthylridine-3-carboxylic acid ethyl ester. Treatment of the displacement product with hydrogen chloride cleaves the BOC protecting group to afford the antibiotic trovafloxacin. The peptide-like alanylalanylamide derivative, alatrofloxacin can in principle be prepared by reaction of the ester precursor of trovafloxacin with alanylalanine followed by saponification and treatment by methane sulphonic acid (mesylate).

brand name

Trovan (Pfizer).

Therapeutic Function

Antibacterial