103772-14-1

Basic information

• Product Name: 5-Amino-l-Cyclopropyl-6,7, 8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid
• Synonyms: 5-Amino-1-cyclopropyl-1,4-dihydro-4-oxo-6,7,8-trifluoro-3-quinolinecarboxyl;5-Amino-l-Cyclopropyl-6,7, 8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid;5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;Sparfloxacin Impurity 2
• CAS NO: 103772-14-1
• Molecular Formula: C₁₃H₉F₃N₂O₃
• Molecular Weight: 298.2173696
• Mol File: 103772-14-1.mol

Chemical Properties

• Boiling Point: 512.4°Cat760mmHg
• Flash Point: 263.7°C
• Appearance: /
• Density: 1.762g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: 5-Amino-l-Cyclopropyl-6,7, 8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-l-Cyclopropyl-6,7, 8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid(103772-14-1)
• EPA Substance Registry System: 5-Amino-l-Cyclopropyl-6,7, 8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid(103772-14-1)

Safety Data

• Hazardous Substances Data: 103772-14-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Amino-1-Cyclopropyl-6,7,8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid is used as an impurity in the production of Sparfloxacin (S679250), a fluorinated quinolone antibacterial agent. The presence of 5-Amino-l-Cyclopropyl-6,7, 8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid in the manufacturing process of Sparfloxacin is significant as it can impact the overall quality, safety, and efficacy of the final product. As a result, monitoring and controlling the levels of this impurity are crucial for ensuring the therapeutic benefits and minimizing potential side effects of the antibacterial drug.
In the context of pharmaceutical development, understanding the properties and effects of impurities like 5-Amino-1-Cyclopropyl-6,7,8-Trifluoro-1,4-Dihydro-4-Oxo-3-Quinolinearboxylic Acid is essential for optimizing the manufacturing process and ensuring the safety and efficacy of the final drug product. This knowledge can also be applied to the development of new drugs or the improvement of existing ones, potentially leading to more effective treatments for various bacterial infections.

InChI:InChI=1/C13H9F3N2O3/c14-7-8(15)10(17)6-11(9(7)16)18(4-1-2-4)3-5(12(6)19)13(20)21/h3-4H,1-2,17H2,(H,20,21)

Upstream product

• 110872-04-3 ethyl 5-(benzylamino)-1-cyclopropyl-6,7,8-trifluoro-4(1H)-oxoquinoline-3-carboxylate 
• 1201-31-6 2,3,4,5-tetrafluorobenzoic acid 
• 107564-01-2 ethyl 3-cyclopropylamino-2-pentafluorobenzoyl acrylate 
• 114226-95-8 ethyl-2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate 
• 3516-87-8 ethyl 2,3,4,5,6-pentafluorobenzoylacetate 
• 2251-50-5 pentafluorobenzoylchloride 
• 602-94-8 Pentafluorobenzoic acid 
• 107564-02-3 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester 
• 104885-01-0 ethyl α-(ethoxymethylene)-2,3,4,5-tetrafluoro-6-nitro-β-oxobenzenepropanoate 
• 103772-11-8 2-nitro-3,4,5,6-tetrafluoro-β-oxobenzenepropanoic acid,ethyl ester 
• 103772-10-7 2,3,4,5-tetrafluoro-6-nitro-benzoyl chloride 
• 16583-08-7 2,3,4,5-tetrafluoro-6-nitrobenzoic acid 
• 103772-12-9 ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-5-nitro-4-oxo-3-quinolinecarboxylate 
• 103772-13-0 ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 

Downstream Products

• 110236-78-7 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid 
• 112654-98-5 5-amino-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 120379-32-0 5-Amino-1-cyclopropyl-6,8-difluoro-7-((R)-3-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 110871-85-7 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 124256-02-6 5-amino-7-(2-aminoethyl)thio-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 111542-93-9 5-amino-1-cyclopropyl-7-(3,5-dimethyl-piperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 110871-86-8 sparfloxacin 
• 150281-54-2 5-amino-7-[3-[2-(aminomethyl)phenyl]-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 150281-62-2 5-amino-7-[3-[4-(aminomethyl)phenyl]-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 150281-66-6 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-[3-[4-[(methylamino)methyl]phenyl]-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid 
• 143699-74-5 5-Amino-1-cyclopropyl-6,8-difluoro-7-[3-(4-Phenyl-1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 

Relevant articles and documents

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Quinoline derivatives and processes for preparation thereof

The present invention relates to a quinoline derivative of the formula wherein Z is an amino group or a halogen atom, R1 is a hydrogen atom or a methyl or ethyl group, R2 is a hydrogen atom or a methyl or fluoromethyl group, R3 and R4 are the same or different and each represents a hydrogen atom or a methyl group, and n is 1 or 2; and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents

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A series of 5,7-disubstituted 1-cyclopropyl-6,8-difluoro-4(1H)-oxoquinoline-3-carboxylic acids (10-36) were prepared; the C-5 substituent in these compounds comprised halo, hydroxy, mercapto, and amino groups and the C-7 functional group included variously substituted piperazines.In vitro antibacterial screening results indicated that the amino group was optimal among the C-5 substituents.A combination of the C-5 amino group and the C-7 3,5-dimethylpiperazinyl appendage in this series conferred the best overall antibacterial property with lack of adverse drug interactions.Compound 36k was superior to ciprofloxacin in both in vitro and in vivo potency and hence was selected as a promising candidate for an improved therapeutic agent.