160738-57-8

Basic information

• Product Name: Gatifloxacin hydrochloride
• Synonyms: 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-piperazin-1-yl)- 4-oxo-1,4-dihydro-quinoline-3-carboxylic acid hydrochloride;gatifloxacin hydrochloride;GATIFLOXACIN LACTATE;Gatifloxacin acid ester;Gatifloxacin base;4-dihydroquinoline-3-carboxylic acid;GatifloxacineHCL;1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylicac
• CAS NO: 160738-57-8
• Molecular Formula: C₁₉H₂₂FN₃O₄
• Molecular Weight: 465.47
• EINECS: 1308068-626-2
• Product Categories: API
• Mol File: 160738-57-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 162 C
• Boiling Point: 625.1°C at 760 mmHg
• Flash Point: 331.8°C
• Appearance: /
• Vapor Pressure: 1.73E-16mmHg at 25°C
• CAS DataBase Reference: Gatifloxacin hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Gatifloxacin hydrochloride(160738-57-8)
• EPA Substance Registry System: Gatifloxacin hydrochloride(160738-57-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39
• Hazardous Substances Data: 160738-57-8(Hazardous Substances Data)

Usage

Description

Gatifloxacin is a novel orally-active fluoroquinolone antibiotic with a potent and broad spectrum of activity against gram-positive (S.pneumonia, S.aureus) and gram-negative bacteria. It shows good activity against strains resistant to established antituberculosis agents. Gatifloxacin was marketed for the treatment of respiratory tract and urinary infections, particularly the treatment of certain community-acquired infections (such as bronchitis, pneumonia and common sexually-transmitted diseases). Comparative studies with ciprofloxacin, ofloxacin and sparfloxacin against fluoroquinolone-resistant organisms indicated a better or equivalent effectiveness with less phototoxic adverse effects.

Chemical Properties

pale yellow prisms

Originator

Kyori (Japan)

Brand name

Tequin

InChI:InChI=1/C19H22FN3O4.ClH/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26;/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26);1H

Upstream product

• 109-07-9 (RS)-2-methylpiperazine 
• 112811-71-9 ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate 
• 122375-85-3 ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate 
• 112811-68-4 ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate 
• 112811-66-2 2,4,5-trifluoro-3-methoxybenzoyl chloride 
• 112811-65-1 3-methoxy-2,4,5-trifluorobenzoic acid 
• 13332-24-6 1-bromo-3-methoxy-2,4,5-trifluorobenzene 
• 112811-70-8 ethyl 3-(cyclopropylamino)-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate 
• 112811-67-3 diethyl 3-methoxy-2,4,5-trifluorobenzoylmalonate 
• 112811-63-9 3-methoxy-2,4,5-trifluorobenzonitrile 
• 112811-64-0 2,4,5-trifluoro-3-methoxy-benzamide 
• 124-41-4 sodium methylate 
• 103460-89-5 1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid 
• 112811-72-0 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid 

Downstream Products

• 925684-97-5 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(4-(3-(4-(4,4-bis(diethylphosphono)butoxy)phenyl)-3-oxopropyl)-3-methylpiperazin-1-yl)-8-methoxy-4-oxoquinoline-3-carboxylic acid 
• 925685-01-4 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-4-((2-oxo-5-(4-(O-ethyl(diethylphosphonomethyl)phosphonoyl)phenyl)-1,3-dioxol-4-yl)methyl)piperazin-1-yl)-4-oxoquinoline-3-carboxylic acid 
• 925685-11-6 7-(4-(3-(2-acetoxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 
• 925685-14-9 7-(4-(3-(2-(2,2-dimethylacetoxy)-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 
• 925685-17-2 7-(4-(3-(2-butyroxy-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 
• 925685-20-7 7-(4-(3-(2-(diethylphosphoryloxy)-5-(ethoxy(diethylphosphonomethyl)phosphinoyl)phenyl)-3-methylbutanoyl)-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid 
• 1279894-66-4 (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazinyl)-4-oxo-3-quinolinecarboxylic acid hemihydrate 
• 180200-66-2 (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazinyl)-4-oxo-3-quinolinecarboxylic acid dihydrate 
• 180200-66-2 (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazinyl)-4-oxo-3-quinolinecarboxylic acid hemiihydrate 
• 180200-66-2 (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-8-methoxy-4-oxo-3-quinoline carboxylic acid sesquihydrate 

Relevant articles and documents

Gatifloxacin and synthesis method thereof

The invention relates to a gatifloxacin and a synthesis method thereof. The synthesis method comprises the following steps: uniformly mixing N,N-dimethylaminoethyl acrylate, 2,4,5-trifluoro-3-methoxybenzoylchloride, ethyl acetate and triethylamine, and carrying out a complete reaction so as to obtain a first intermediate; uniformly mixing the first intermediate with acetic acid and cyclopropylamine, and carrying out a complete reaction to obtain a second intermediate; uniformly mixing the second intermediate with a strong base, and carrying out a complete reaction to obtain gatifloxacin cyclization ester; carrying out an ester exchange reaction on the gatifloxacin cycliztion ester to so as to obtain a third intermediate; uniformly mixing the third intermediate with 2-methylpiperazine, carrying out a complete reaction, and hydrolyzing and acidifying the obtained reaction product to obtain the gatifloxacin, wherein the strong base is selected from at least one of sodium hydroxide and potassium hydroxide. The synthesis method of gatifloxacin adopts the sodium hydroxide and potassium hydroxide to carry out the cyclization reaction, so that the cyclization reaction time is greatly shortened, and the time cost for synthesizing gatifloxacin is reduced.

METHOD FOR PRODUCING QUINOLONE CARBOXYLIC ACID DERIVATIVE

The present invention relates to a method for producing a quinolone compound having high antibacterial activity and high safety, at high yield and in a simple manner. A quinolonecarboxylic acid derivative (1) of interest is produced through a one-pot manner by reacting a compound (2) with a salt of a cyclic amine (3) and with a boron derivative in a solvent in the presence of a base.

PROCESS FOR THE PREPARATION OF GATIFLOXACIN AND REGENERATION OF DEGRADATION PRODUCTS

The subject of the present invention are an improved synthesis process comprising a process for regeneration of a side product of gatifloxacin and an analysis method for process control in the synthesis of gatifloxacin (Formula I).