194805-07-7

Basic information

• Product Name: 7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER
• Synonyms: Ethyl-7-bromo-1-cyclopropyl-8-difluoromethoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate;7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER;ETHYL 7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLATE
• CAS NO: 194805-07-7
• Molecular Formula: C₁₆H₁₄BrF₂NO₄
• Molecular Weight: 402.1874664
• Mol File: 194805-07-7.mol

Chemical Properties

• Boiling Point: 477.438 °C at 760 mmHg
• Flash Point: 242.546 °C
• Appearance: /
• Density: 1.624
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: 2-8°C
• PKA: -4.46±0.40(Predicted)
• CAS DataBase Reference: 7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER(194805-07-7)
• EPA Substance Registry System: 7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER(194805-07-7)

Safety Data

• Hazardous Substances Data: 194805-07-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER is used as an antibacterial agent for the treatment of respiratory and urinary tract infections. It works by inhibiting the bacterial DNA gyrase enzyme, which is crucial for the replication and repair of bacterial DNA, thereby preventing bacterial growth and spread.
Used in Antibacterial Applications:
7-BROMO-1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER is employed as a broad-spectrum antibiotic, effective against both gram-positive and gram-negative bacteria. Its ability to target the DNA gyrase enzyme makes it a valuable tool in combating bacterial infections and reducing the risk of antibiotic resistance.

InChI:InChI=1/C16H14BrF2NO4/c1-2-23-15(22)10-7-20(8-3-4-8)12-9(13(10)21)5-6-11(17)14(12)24-16(18)19/h5-8,16H,2-4H2,1H3

Upstream product

• 121-71-1 3-Hydroxyacetophenone 

Downstream Products

• 194804-45-0 ethyl (+)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2-trityliso-indolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 1026744-13-7 7-(2-benzyloxycarbonyl-3-methyl-2,3-dihydro-1H-isoindol-5-yl)-1-cyclopropyl-8-difluoromethoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 194804-56-3 (+)-1-Cyclopropyl-8-difluoromethoxy-7-[2-benzyloxycarbonyl-1-methylisoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 194804-72-3 (+/-)-1-cyclopropyl-8-difluoromethoxy-7-(1-methylisoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 1026081-96-8 7-(2-benzyloxycarbonyl-2,3-dihydro-1H-isoindol-5-yl)-1-cyclopropyl-8-difluoromethoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 194804-41-6 Ethyl (+)-1-cyclopropyl-8-difluoromethoxy-7-[2-benzyloxycarbonyl-1-methylisoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate 

Relevant articles and documents

Synthesizing method of 1-cyclopropyl-4-oxo-7-bromo-8-difluoromethoxy-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

The invention discloses a synthesizing method of 1-cyclopropyl-4-oxo-7-bromo-8-difluoromethoxy-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester, and belongs to the technical field of chemical synthesis. The synthesizing method is characterized by comprising the following steps that 1, 2,4-dibromo-3-difluoromethoxy acetophenone reacts with diethyl carbonate in the presence of strong alkali to obtain 2,4-dibromo-3-difluoromethoxy benzoylacetic acid ethyl ester; 2, the obtained 2,4-dibromo-3-difluoromethoxy benzoylacetic acid ethyl ester reacts with triethyl orthoformate in the presence of acetic anhydride to obtain 3-ethyoxyl-2-(2,4-bromo-3-difluoromethoxy benzoyl)ethyl acrylate; 3, the obtained 3-ethyoxyl-2-(2,4-bromo-3-difluoromethoxy benzoyl)ethyl acrylate reacts with cyclopropylamine to obtain 3-cyclopropylamino-2-(2,4-bromo-3-difluoromethoxy benzoyl)ethyl acrylate; 4, the obtained 3-cyclopropylamino-2-(2,4-bromo-3-difluoromethoxy benzoyl)ethyl acrylate is subjected to cyclization in the presence of alkali to obtain the 1-cyclopropyl-4-oxo-7-bromo-8-difluoromethoxy-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester. The synthesizing method has the advantages of being short in reaction step, easy to operate, little in pollution, high in synthesizing yield, good in product quality and the like and is suitable for industrialized application.

Method for preparing 1-cyclopropyl-4-oxo-7-bromine-8-difluoromethoxy-1,4-dihydro-quinoline-3-nonanoic acid-ethyl ester

The invention discloses a method for synthesizing 1-cyclopropyl-4-oxo-7-bromine-8-difluoromethoxy-1,4-dihydro-quinoline-3-nonanoic acid-ethyl ester, and belongs to the technical field of chemical synthesis. The method is characterized by comprising the following steps that 1, 2,4-dibromo-3-difluoromethoxy ethyl benzoylacetate is prepared; 2, 3-ethyoxyl-2-(2,4-dibromo-3-difluoromethoxy benzoyl)ethyl acrylate is prepared; 3, 3-amino cyclopropyl-2-(2,4-dibromo-3-difluoromethoxy benzoyl)ethyl acrylate is prepared; 4, 1-cyclopropyl-4-oxo-7-bromo-8-difluoromethoxy-1,4-dihydro-quinoline-3-carboxylic ethyl ester is prepared. The method for synthesizing 1-cyclopropyl-4-oxo-7-bromine-8-difluoromethoxy-1,4-dihydro-quinoline-3-nonanoic acid-ethyl ester has the advantages of that the reaction steps are short, operation is easy, pollution is low, the synthesis yield is high, product quality is good, and is suitable for industrialized application.

Processes for producing 7-isoindolinequinolonecarboxylic derivatives and intermediates therefor, salts of 7-isoindolinequinolonecarboxylic acids, hydrates thereof, and composition containing the same as active ingredient

This invention relates to processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: wherein R1represents a hydrogen atom or a carboxyl-protecting group; R2represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R3represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio groups, nitro group, cyano group, acyl groups, protected or unprotected hydroxyl groups and protected or unprotected or substituted or unsubstituted amino groups; R4represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio groups, protected or unprotected hydroxyl or imino groups, protected or unprotected or substituted or unsubstituted amino groups, alkylidene groups, oxo group and groups each forming a cycloalkane group together with the carbon atom to which R4bonds; R5represents a hydrogen atom, an amino-protecting group, a substituted or unsubstituted alkyl, cycloalkyl, alkylsulfonyl, arylsulfonyl, acyl or aryl group; R6represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or amino group or a nitro group; and A represents CH or C—R7in which R7represents a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group or a protected or unprotected hydroxyl group, and to a salt of a 7-isoindoline-quinolonecarboxylic acid represented by the general formula [1], a hydrate thereof and a composition comprising them as an active ingredient.

N-cyclopropyl-2-difluoromethoxy-3-halogenoanilines and intermediates for the preparation thereof

N-Cyclopropyl-2-difluoromethoxy-3-halogenoanilines which serve as important intermediates in the preparation of quinolonecarboxylic acids useful as synthetic antimicrobial agents from industrially inexpensive and easily available raw materials; and intermediates for the preparation thereof. Specifically, compounds represented by the general formula (1), (2) and (3), wherein X is halogeno; and Y is nitro or amino, (2) wherein X is halogeno; and R1is lower alkyl, (3) wherein X is halogeno; and R is hydrogen or —CH═C(CO2R2)2, R2being lower alkyl.

Quinolonecarboxylic acid derivatives or salts thereof

PCT No. PCT/JP97/00317 Sec. 371 Date Aug. 10, 1998 Sec. 102(e) Date Aug. 10, 1998 PCT Filed Feb. 7, 1997 PCT Pub. No. WO97/29102 PCT Pub. Date Aug. 14, 1997The present invention relates to a quinolone-carboxylic acid derivative represented by the general