100361-18-0

Basic information

• Product Name: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• Synonyms: 7-Chloro-1-Cyclopropyl-6-Fluoro-4-Oxo-1,4-Dihydro-1,8-Naphthyridin-3-Carboxylic Acid;1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyl ridine carbox.acid;7-Chloro-1-Cyclopropyl-6-Fluoro-1,4-Dihydro-4-Qxoquinoline-3-CarboxylicAcid98%;7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylicacid;7-Chloro-1-cyclopropyl-6-fluor;7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-Ox;7-Chloro-1-cyclopropyl-1,4-dihydro-3-oxo-1,8-naphthyridine-3-carboxylic aci;1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-1,8-NAPHTHYLRIDINE CARBOXYLIC ACID 99%
• CAS NO: 100361-18-0
• Molecular Formula: C₁₂H₈ClFN₂O₃
• Molecular Weight: 282.65
• EINECS: 1312995-182-4
• Product Categories: Heterocycles;Intermediate;Intermediates & Fine Chemicals;Pharmaceuticals;Fluorine series
• Mol File: 100361-18-0.mol

Chemical Properties

• Melting Point: 209-212 °C
• Boiling Point: 485.919 °C at 760 mmHg
• Flash Point: 247.675 °C
• Appearance: White powder
• Density: 1.727 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 5.96±0.70(Predicted)
• CAS DataBase Reference: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid(100361-18-0)
• EPA Substance Registry System: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid(100361-18-0)

Safety Data

• Hazardous Substances Data: 100361-18-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid is used as an intermediate for the synthesis of Gemifloxacin, a fluoroquinolone antibiotic. It serves as a key component in the development of this potent antibacterial agent, which is effective against a wide range of bacterial infections, including respiratory and skin infections.
As a Gemifloxacin intermediate, 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid plays a crucial role in the pharmaceutical industry, contributing to the production of an essential antibiotic that helps combat bacterial infections and improve public health.

InChI:InChI=1/C12H8ClFN2O3/c13-10-8(14)3-6-9(17)7(12(18)19)4-16(5-1-2-5)11(6)15-10/h3-5H,1-2H2,(H,18,19)

Upstream product

• 96568-04-6 ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate 
• 122-51-0 orthoformic acid triethyl ester 
• 765-30-0 Cyclopropylamine 
• 96568-07-9 ethyl-7-chloro-6-fluoro-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 96568-06-8 3-cyclopropylamino-2-(2,6-dichloro-5-fluoropyridine-3-carbonyl) acrylate 
• 99735-42-9 1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-1,8-naphthyridine-3-carboxylic acid 
• 99735-36-1 4-[6-(acetylcyclopropylamino)-3-fluoro-2-pyridinyl]-1-piperazine-carboxylic acid,ethyl ester 

Downstream Products

• 122536-87-2 7-[3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid 
• 99735-41-8 ciprofloxacin 
• 113533-65-6 1-cyclopropyl-6-fluoro-1,4-dihydro-7-<3-<(methylamino)methyl>-1-pyrrolidinyl>-4-oxo-1,8-naphthyridine-3-carboxylic acid 
• 175463-14-6 gemifloxacin 

Relevant articles and documents

Quinolone Antibacterials Containing the New 7- Side Chain: The Effects of the 1-Aminoethyl Moiety and Its Stereochemical Configurations on Potency and in Vivo Efficacy

A series of stereochemically pure 7--1,4-dihydro-4-oxoquinoline and 1,8-naphthyridine-3-carboxylic acids, with varied substituents at the 1-, 5-, and 8-positions, were synthesized to study the effects of the 7-3-(1-aminoe

Novel lead generation of an anti-tuberculosis agent active against non-replicating mycobacteria: Exploring hybridization of pyrazinamide with multiple fragments

The key to shortening tuberculosis (TB) drug regimen lies in eliminating the reservoir of non-replicating persistent (NRP) Mycobacterium tuberculosis (Mtb). Pyrazinamide (PZA) is the only known drug used as part of a combination therapy that is believed to kill NRP Mtb and achieve sterilization. PZA is active only under low pH screening conditions. Screening and identification of NRP-active anti-TB compounds are severely limited because compounds are usually inactive under regular assay conditions. In an effort to design novel NRP-active anti-TB compounds, we used pyrazinamide as a core and hybridized it with the fragments derived from marketed drugs. One of these designs, compound 8, was a hybrid with fluoroquinolone. This compound exhibited >10 fold improvement in NRP activity under low pH condition as compared to pyrazinamide and a modest activity (0.8 log10 kill) under nutritionally starved NRP condition. Furthermore, compound 8 was active against fluoroquinolone-resistant strains and did not show any activity in a DNA supercoiling assay (gyrase inhibition), suggesting that its mechanism of action is not that of the parent fluoroquinolone. These results provide a novel avenue in the exploration of new chemotypes that are active against non-replicating Mtb.

Structure aided design of chimeric antibiotics

The rise of antibiotic resistance is of great clinical concern. One approach to reducing the development of resistance is to co-administer two or more antibiotics with different modes of action. However, it can be difficult to control the distribution and

PROCESS FOR PREPARING 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID

Starting from ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propanoate (1), the present invention provides highly pure 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (5) inone-potfour stepsusing a single solvent.

Synthesis and structure-activity relationships of novel 7-substituted 1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acids as antitumor agents. Part 1

In an attempt to search for clinically useful antitumor agents, we have discovered that a series of 1,7-disubstituted-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids possessed moderate cytotoxic activity. We investigated the structure-acti

Naphthyridine antibacterial agents

Novel naphthyridine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.

4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivative as antibacterial agents

Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

6,7-disubstituted 1-cycloproply-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

New 6,7-disubstituted-1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxy lic acids of the formula (I) STR1 in which X represents halogen or nitro and A represents STR2 wherein R1, R2, R3 and R4 are defined hereinbelow are disclosed as well as their usefulness as antibacterial agents.

1,8-naphthyridine derivatives useful as anti-bacterial agents

The present invention relates to a 1,8-naphthyridine derivative of the formula STR1 wherein X is a fluorine or chlorine atom, and R is a hydrogen atom, or a methyl or ethyl group; and esters thereof and salts thereof are processes for preparation thereof.