100276-37-7

Basic information

• Product Name: 6,8-Difluoro-1,4-dihydro-1-(MethylaMino)-7-(4-Methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Sulfate
• Synonyms: 6,8-Difluoro-1,4-dihydro-1-(MethylaMino)-7-(4-Methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Sulfate;6,8-Difluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;Marbofloxacin EP Impurity C
• CAS NO: 100276-37-7
• Molecular Formula: C16H20F2N4O7S
• Molecular Weight: 450.4144064
• Mol File: 100276-37-7.mol

Chemical Properties

• Boiling Point: 522.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.49±0.1 g/cm3(Predicted)
• PKA: 6.14±0.50(Predicted)
• CAS DataBase Reference: 6,8-Difluoro-1,4-dihydro-1-(MethylaMino)-7-(4-Methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: 6,8-Difluoro-1,4-dihydro-1-(MethylaMino)-7-(4-Methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Sulfate(100276-37-7)
• EPA Substance Registry System: 6,8-Difluoro-1,4-dihydro-1-(MethylaMino)-7-(4-Methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Sulfate(100276-37-7)

Safety Data

• Hazardous Substances Data: 100276-37-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6,8-Difluoro-1,4-dihydro-1-(MethylaMino)-7-(4-Methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid Sulfate is used as an intermediate in the synthesis of Marbofloxacin (M197000), a fluorinated quinolone antibacterial agent. It contributes to the development of this antibiotic by providing the necessary structural framework for the final product. Marbofloxacin is effective against a wide range of bacterial infections, making it a valuable addition to the arsenal of antibiotics used in both human and veterinary medicine.
The compound's role in the synthesis of Marbofloxacin highlights its importance in the pharmaceutical industry, as it enables the production of a potent and widely used antibiotic. The fluorination of the quinolone structure enhances the drug's activity against bacterial pathogens, making it a preferred choice for treating various infections. Furthermore, the presence of the methylamino and piperazinyl groups in the molecule contributes to its overall effectiveness and pharmacological properties.

Upstream product

• 109-01-3 1-methyl-piperazine 
• 100276-67-3 6,7,8-Trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid 
• 94714-58-6 ethyl 2-(ethoxymethylene)-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate 
• 100276-64-0 2-(2,3,4,5-Tetrafluorbenzoyl)-3-(2-formyl-2-methylhydrazino)acrylsaeure-ethylester 
• 100276-65-1 6,7,8-Trifluor-1-(formylmethylamino)-1,4-dihydro-4-oxo-3-chinolincarbonsaeure-ethylester 
• 158585-86-5 ethyl 6,8-difluoro-1,4-dihydro-1-(N-methylformamido)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylate 

Relevant articles and documents

A PROCESS FOR A PREPARATION OF MARBOFLOXACIN AND INTERMEDIATE THEREOF

The present invention describes a novel process for the preparation of marbof loxacin and intermediate thereof comprising reaction of ammonium hydroxide of formula (III), NR1R2R3R4, wherein R1, R2, R3 and R4 are independently selected from the group of H, alkyl, alkylaryl, aryl and/or heteroaryl, with compound of formula (II), wherein R is selected from H, alkyl, arylalkyl, alkali metal cation,, NH4 cation, NR1R2R3R4cation; X is halogen, such as chloro, bromo, fluoro, piperazinyl, which may be substituted or unsubstituted, and R' is selected from H, formyl or COOAlkyl.

A process for a preparation of marbofloxacin and intermediate thereof

The present invention describes a novel process for the preparation of marbofloxacin and intermediate thereof comprising reaction of ammonium hydroxide of formula III, NR1R2R3R4 wherein R1, R2, R3 and R4 are independently selected from the group of H, alkyl, alkylaryl, aryl and/or heteroaryl, with compound of formula II, wherein R is selected from H, alkyl, arylalkyl, alkali metal cation, , NH4 cation, NR1R2R3R4cation; X is halogen, such as chloro, bromo, fluoro, piperazinyl, which may be substituted or unsubstituted, and R' is selected from H, formyl or COOAlkyl.

Cycloaracylation of Enamines,II. - Synthesis of 1-Amino-4-quinolone-3-carboxylic Acids

The 2-benzoyl-3-hydrazinoacrylic esters 3, 11, 17, and 23 are obtained by the reactions of 2-chloro-5-nitrobenzoyl chloride (1) with the enehydrazinocarboxylic esters 2 and 2-benzoyl-3-ethoxyacrylic esters 9 with hydrazine derivatives 10, 16, and 22.After cyclocondensation, the above esters afford 1-aminoquinolonecarboxylic esters 4, 12, 18, and 24, which are hydrolyzed to give the corresponding 1-aminoquinolonecarboxylic acids 5, 13, 19, and 26.The 1-amino-7-haloquinolonecarboxylic acids 13a-f, 19a-f, and 26b react with aliphatic amines to afford 1,7-diaminoquinolonecarboxylic acids 30c-m, which possess a high level of bactericidal activity.