160738-57-8

Usage

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 
• 847233-56-1 1-cyclopropyl-1,4-dihydro-6,7-difluoro-8-methoxy-4-oxo-quinoline-3-carboxylic acid difluoroborate ester 
• 835920-87-1 1-cyclopropyl-7-(3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid boron difluoride chelate 
• 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 

Downstream Products

• 180200-66-2 (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-8-methoxy-4-oxo-3-quinoline carboxylic acid sesquihydrate 
• 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-8-methoxy-7-(3-methylpiperazinyl)-4-oxo-3-quinolinecarboxylic acid dihydrate 
• 1279894-66-4 (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazinyl)-4-oxo-3-quinolinecarboxylic acid hemihydrate 
• 1146978-15-5 1-cyclopropyl-6-fluoro-7-[4-[5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid 
• 1146978-14-4 1-cyclopropyl-6-fluoro-7-[4-[5-(3-nitrophenyl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid 
• 1146978-13-3 1-cyclopropyl-6-fluoro-7-[4-[5-(2-nitrophenyl)-1,3,4-thiadiazol-2-yl]-3-methylpiperazin-1-yl]-8-methoxy-4-oxo-quinoline-3-carboxylic acid 
• 1198425-72-7 7-(4-benzoyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1335198-38-3 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-4-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1335198-44-1 C₂₇H₂₅FN₆O₇ 
• 1335198-53-2 1-cyclopropyl-7-(4-(5-(3,4-dinitrophenyl)-1,3,4-oxadiazol-2-yl)-3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1335198-47-4 C₂₈H₂₈FN₅O₆ 
• 1335198-41-8 C₂₉H₃₀FN₅O₇ 
• 1335198-50-9 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 

Relevant academic research and scientific papers

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.

STREAMLINED SYNTHESES OF FLUOROQUINOLONES

Methods of synthesizing fluoroquinolones such as ciprofloxacin are provided. The methods utilize affordable materials, reduce the number of synthesis steps and provide high yields.

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.

A high-throughput impurity-free process for gatifloxacin

An improved process to obtain gatifloxacin (1) through use of boron chelate intermediates has been developed. The methodology involves an initial activation step which accelerates the formation of the first chelate under low-temperature conditions and prevents demethylation of the starting material. To increase the overall yield and to avoid the isolation and manipulation of the resulting intermediates, the process has been designed to be carried out in one pot. As a result, we present here an easy, scaleable and substantially impurity-free process to obtain gatifloxacin (1) in high yield.

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).

AN IMPROVED PROCESS FOR THE PREPARATION OF GATIFLOXACIN

The present invention relates to a process for the preparation of Gatifloxacin by reacting ethvl 1-cyclopropyl-6,7-difluoro-8- methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylate with aqueous hydrofluoroboric acid followed by condensation with 2-methyl piperazine in polar organic solvent resulting in an intermediate Cyclopropyl-7-(3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo- 1,4-dihydro-3-quinoline carboxylic acid boron difluoride chelate which upon hydrolysis yields Gatifloxacin.

PROCESS FOR PREPARING GATIFLOXACIN

This invention relates to a simplified process for preparing gatifloxacin. In said process the compound (II) is used as the starting compund, which is then made to react with 2-methylpiperazine after being silyated and activated in the form of boron chelate.Finally, the boron chelate is eliminated by treatment with a C1-C4 alkyl chain alcohol. One characteristic of the process described is that all the reactions are carried out without isolating the intermediate compounds formed ("one pot" process).

CRYSTALLINE FORM OF GATIFLOXACIN

The present invention relates to a crystalline form of gatifoxacin (formula I) obtainable by process that comprises recrystallisation of the crude gatifloxacin in methanol and which is stable with a water content ranging between 2.5 and 4.5% by weight, to a process for preparing it and to the use thereof as an active substance in the preparation of pharmaceutical formulations.

Antimicrobial drug reduced in effect on heart

An antimicrobial drug containing a compound represented by the following formula (I): a salt of the compound, or a hydrate of the compound or the salt.

Novel crystalline forms of gatifloxacin

Provided are novel crystalline forms of gatifloxacin denominated forms A, B, C, D, E1, F, G, H, I, and J, and methods for their preparation. Also provided are methods for making known crystalline forms of gatifloxacin, in particular forms omega and T2RP.