Pazufloxacin mesilate

Pazufloxacin mesilate Basic information
Product Name:Pazufloxacin mesilate
Synonyms:(3S)-10-(1-AMinocyclopropyl)-9-fluror-2,3-dihydro-3-Methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Methanesulfonate;Mesylate pazufloxacin;T 3762;PASIL;PAZUCROSS;PAZUFLOXACIN MESILATE;PAZUFLOXACIN MESYLATE;PAZUFLOXACIN METHANESULFONATE
CAS:163680-77-1
MF:C17H19FN2O7S
MW:414.4053632
EINECS:634-946-6
Product Categories:PAZUCROSS;Aromatics;API;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents;Amines
Mol File:163680-77-1.mol
Pazufloxacin mesilate Structure
Pazufloxacin mesilate Chemical Properties
Melting point >255°C (dec.)
alpha D20 -64.2° (c = 1 in 1.0N NaOH)
storage temp. -20°C Freezer
solubility Aqueous Base (Slightly), DMSO (Slightly)
form Solid
color Off-White to Pale Yellow
CAS DataBase Reference163680-77-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,C,F
Risk Statements 36/37/38-34-11
Safety Statements 26-45-36/37/39-16
RTECS UU8815400
HS Code 29349990
MSDS Information
Pazufloxacin mesilate Usage And Synthesis
DescriptionThis fluoroquinolone was co-developed by Toyama and Mitsubishi Pharm and was launched for the intravenous therapy of respiratory, urinary, surgical, gynecological and systemic infections.
DescriptionPazufloxacin is a broad-spectrum synthetic fluoroquinolone antibiotic. It is active against Gram-negative and Gram-positive bacteria, including clinical isolates of E. coli, K. pneumoniae, methicillin-susceptible and -resistant S. aureus, and methicillin-susceptible and -resistant S. epidermidis (MIC90s = 0.05, 0.1, 0.39, 12.5, 0.39, and 6.25 μg/ml, respectively). It inhibits E. coli, P. aeruginosa, and S. aureus DNA gyrase (IC50s = 0.88, 1.9, and 10.2 μg/ml, respectively) and S. aureus topoisomerase IV (IC50 = 24.2 μg/ml) in cell-free assays. In vivo, pazufloxacin is active against systemic E. coli, K. pneumoniae, and methicillin-resistant S. aureus infections in mice (ED50s = 0.15, 5.5, and 4.5 mg/kg, respectively).
Chemical PropertiesCrystalline Solid
UsesA fluorinated quinolone antibiotic. Antibacterial.
SynthesisPazufloxacin Mesilate is elegantly synthesized from commercially available 2,3,4,5-tetrafluorobenzoic acid (168) by an 11-step process with an overall yield 48% [68]. Starting material 168 was first treated with ethyl bromide and then with t-butyl cyanoacetate in the presence of potassium carbonate in DMSO in one flask to give acylated cyanoacetate 169. Intermediate 169 thus obtained without purification was refluxed in toluene with p-TSA to yield 4- cyanomethylbenzoate 170 in 90% yield from 168. Cyclopropanation at the benzylic position of 170 was performed by |á,|á-dialkylation with two equiv. of 1,2- dibromoethane under phase-transfer conditions to give cyanocyclopropyl compound 171. Cyano compound 171 was subjected to hydration with alkaline H2O2 to afford carboxamide 172 in 81% yield from 170. Subsequently, carboxamide 172 was treated with NaOCl for Hofmann rearrangement to give primary amine 173, which was protected as its N-acetyl derivative 174 for the next reaction. Treatment of 174 with imidazole in the presence of thionyl chloride and TEA generated an imidazolide intermediate, which was converted to |?-keto ester 175 by reacting with potassium ethyl malonate and MgCl2. Enamine 176 was obtained without purification by successive treatment of 175 with DMF-dimethylacetal and (S)-(+)-2-aminopropanol. Crude 176 was heated in DMSO in the presence of potassium carbonate to efficiently give tricycle product 177 in 80% yield from 174. Finally, the ethyl ester and acetamide in 177 were hydrolyzed under basic and acidic conditions, respectively, to give the free amine. Pazufloxacin mesilate (20) was obtained in 94% yield by treatment of its corresponding free amine with methanesulfonic acid in ethanol.

Synthesis_163680-77-1

Pazufloxacin mesilate Preparation Products And Raw materials
Methyl Fluorine PAZUFLOXACIN (PREPARATION FOR PAZUFLOXACIN MESILATE) Bensulfuron methyl Methanesulfonic acid 3-Aminopyridine Pefloxacin mesylate Phentolamine mesilate Kresoxim-methyl 5-Amino-2-methylpyridine Thiophanate-methyl methanesulfonate PAZUFLOXACIN Methyl salicylate Methyl bromide METSULFURON METHYL 4-Dimethylaminopyridine 4-Aminopyridine

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