- Pharmacological characterization of 7-(4-(Piperazin-1-yl)) ciprofloxacin derivatives: Antibacterial activity, cellular accumulation, susceptibility to efflux transporters, and intracellular activity
-
Purpose: To evaluate pharmacological properties (antibacterial activity; accumulation in phagocytic cells; activity against intracellular bacteria; susceptibility to fluoroquinolone efflux transporters) of ciprofloxacin derivatives modified at C-7 of the
- Marquez, Beatrice,Pourcelle, Vincent,Vallet, Coralie M.,Mingeot-Leclercq, Marie-Paule,Tulkens, Paul M.,Marchand-Bruynaert, Jacqueline,Van Bambeke, Francoise
-
-
Read Online
- Preparation method of quinolone carboxylic acid derivative or phthalazinone carboxylic acid derivative
-
The invention belongs to the field of pharmaceutical chemicals, relates to a preparation method of a quinolone carboxylic acid derivative or a phthalazinone carboxylic acid derivative, and particularly relates to a preparation method of a 7-substituted-3-quinolone carboxylic acid derivative or a 7-substituted-1,5-phthalazinone carboxylic acid derivative. The preparation method comprises the following steps: (1) in an organic solvent, carrying out coupling reaction on a boron chelate II and organic amine III in the presence of an organosilicon compound to obtain a compound IV; and (2) mixing the compound IV with hydrochloric acid, and then filtering and separating the precipitated compound I. Compared with conventional methods, the preparation method provided by the invention has the advantages that the conditions are milder, the hydrolysis of the substrate quinoline carboxylic acid boric acid ester can be reduced, and meanwhile, the influence of a byproduct HF on the product purity is avoided. The method is high in yield and high in purity; compared with the traditional alkali, the organic silicon is more suitable for industrial preparation of the 7-substituted-3-quinolone carboxylic acid derivative or the 7-substituted-1,5-phthalazinone carboxylic acid derivative.
- -
-
Paragraph 0104-0106; 0179
(2021/10/27)
-
- A norfloxacin, ciprofloxacin and enrofloxacin synthetic method
-
The present invention provides a norfloxacin, ciprofloxacin and enrofloxacin preparation method, which comprises the carboxylic acid and piperazine in the solvent under the catalytic action of the catalyst in the reaction step, the catalyst is AlBr3 , FeBr3 , ZnBr2 , CuBr2 Or SnBr4 , It has high yield, low cost and the advantage of energy saving and emission reduction.
- -
-
Paragraph 0008; 0034-0039; 0044; 0045
(2019/07/10)
-
- Nano-Fe3 O4@ZrO2-SO3 H as highly efficient recyclable catalyst for the green synthesis of fluoroquinolones
-
Nano-Fe3 O4 @ZrO2-SO3 H (n-FZSA), was utilized as a magnetic catalyst for the synthesis of various fluoroquinolone compounds. These compounds were prepared by the direct amination of 7-halo-6-fluoroquinolone-3-carboxylic acids with piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b] pyridine in water. The results showed that n-FZSA exhibited high catalytic activity towards the synthesis of fluoroquinolone derivatives, giving the desired products in high yields. Furthermore, the catalyst was recyclable and could be used at least seven times without any discernible loss in its catalytic activity. Overall, this new catalytic method for the synthesis of fluoroquinolone derivatives provides rapid access to the desired compounds in refluxing water following a simple work-up procedure, and avoids the use of organic solvents.
- Nakhaei, Ahmad,Ramezani, Shirin,Shams-Najafi, Sayyed Jalal,Farsinejad, Sadaf
-
p. 739 - 746
(2018/09/26)
-
- Conventional and microwave-assisted synthesis of quinolone carboxylic acid derivatives
-
Various antibacterial fluoroquinolone compounds are synthesized by the direct amination of 7-halo-6-fluoroquinolone-3-carboxylic acids with a variety of piperazine derivatives and (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b]pyridine using microwave under different reaction conditions. Solvent free high yield microwave synthesis of antibacterial fluoroquinolone compounds is convenient, rapid and environmentally friendly method.
- Mirzaie,Lari,Vahedi,Hakimi
-
p. 2865 - 2869
(2017/03/22)
-
- A norfloxacin, ciprofloxacin and enrofloxacin preparation method
-
The invention discloses a preparation method of norfloxacin, ciprofloxacin and enrofloxacin. The preparation method comprises the following steps: directly reacting 1-ethyl-6-fluoro-7-chlo-4-oxo-1,4-dihydro-quinoline-3-carboxylate or 1-cyclopropyl-6-fluoro-7-chlo-4-oxo-1,4-dihydro-quinoline-3-carboxylate with piperazine (or N-ethyl piperazine); and then, performing after-treatment to prepare a corresponding target product norfloxacin (or ciprofloxacin or enrofloxacin). The preparation method disclosed by the invention is short in reaction step, convenient to operate, less investment and beneficial to industrial production; consumption of piperazine (or N-ethyl piperazine) can be reduced by more than half; under the catalytic action, the reaction temperature is low, the byproducts are less, the yield is high and the cost is low; heavy use of inorganic acid and inorganic alkaline is avoided, so that the pollution is reduced.
- -
-
Paragraph 0125-0126
(2017/04/25)
-
- NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES
-
The invention relates to a method of preparation of fluoroquinolones of formula (I) from compounds of formula (II): in which R1, R2, R3, R4, R5, R6, R7, and X are as defined in Claim 1.
- -
-
Page/Page column 6; 10
(2009/04/24)
-
- Convenient one pot synthesis of some fluoroquinolones in aqueous media
-
A one pot synthetic strategy for the preparation of fluoroquinolones from 1 is introduced. Product 3 was condensed with piperazine in an aqueous media to produce pharmaceutical grade ciprofloxacin in 86% yield. The method was extended to the synthesis of some other fluoroquinolones with pharmaceutical grade quality.
- Abaee, M. Saeed,Sharifi, Ruhollah,Borhani, Shahin,Heravi, Majid M.,Motahari, Hossein
-
p. 415 - 418
(2007/10/03)
-
- Process for the preparation of quinolone derivatives
-
This invention relates to an improved process for the preparation of quinolone drugs of the formula (I), wherein R=C1-C6 alkyl, C3-C6 cycloalklyl, aryl, substituted aryl, NR1R2=diarylamino, arylalkylamino, C1-C6-dialkylamino, piprazinyl, N or C alkyl (C1-C6) substituted piperazinyl, morpholino, pyrrolidinyl, substituted pyrrolidinyl, aralkyl, substituted aralkyl etc. Some of the compounds falling within the formula (I) are ciprofloxacin, enrofloxin, pefloxacin, etc. These compounds are useful as antibacterial drugs. The process of the present invention for preparation of compound of formula (I) comprises in enhancing the reactivity of the displaceable halogen (X) in the compound of the formula (II) towards various amines of formula (III) wherein R=as defined for compound of formula (I), R3=COOR6 (R6=C1-C6 alkyl, aryl, aralkyl), nitrile a carboxamide (—CONR7R8, R7 and R8=C1-C6 alkyl, C3-C6 cycloalkyl, aralkyl), X=Cl, Br, F; NR1R2=as defined above by introducing a nitro group ortho to the displaceable halo group and subsequently removing the nitro group in a conventional manner. The process of the present invention enhances the yield of the compound of the formula (I) and also improves the quality of the prepared compound.
- -
-
-
- Molecular structures of new ciprofloxacin derivatives
-
Two new derivatives from the ciprofloxacin fluoroquinoline family, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo- quinoline-3-methylcarbamate and 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo) [4,3-c]quinoline, were synthesised, tested for antibacterial activity and crystallised. Their molecular and crystal structures were determined. Tests in vitro reveal lower activities than for ciprofloxacin. Characteristic structural features of these compounds are comparable to data for other known fluoroquinolines. The bicyclic quinoline ring is planar in both compounds; the carbamate side chain and five-membered pyrazolo ring are almost coplanar with it. A piperazinyl ring exhibits a chair conformation. In the crystal packing of the carbamate analogue, two C-HO interactions form a dimer. The pyrazolo derivative crystallises as solvate with 1.5 water molecules per quinoline molecule. In its crystal structure donor and acceptor functionalities form dimers, via hydrogen bonds, which are connected into an infinite pattern through hydrogen bonded water molecules.
- Tomi?i?, Zrinka Bani?,Kujund?i?, Nedjeljko,Kraja?i?, Mirjana Bukvi?,Vi?njevac, Aleksandar,Koji?-Prodi?, Biserka
-
-
- Process and device for producing liquid dosage formulations of medicinal compounds on demand from tablets and capsules
-
The present invention provides a process for preparing liquid pharmaceutical formulations on demand from tablets and capsules.
- -
-
-
- A solid phase approach to quinolones using the DIVERSOMER technology
-
The first example of a library of the quinolone antibacterial agents prepared by solid phase organic synthesis is described. Results of these studies and the parallel synthesis, isolation, purification and analysis of eight quinolones are discussed.
- MacDonald, Alasdair A.,DeWitt, Sheila H.,Hogan, Eleonora M.,Ramage, Robert
-
p. 4815 - 4818
(2007/10/03)
-
- Preparation of quinolinecarboxylic acids
-
STR1 is reacted with an amine STR2 to give the compound of the formula STR3 Because the starting material (I) has F in 7-position rather than Cl, the reaction proceeds at relatively low temperature with minimum side reactions.
- -
-
-
- Baron chelates of quinoline carboxylic acids
-
The invention relates to a new process for the preparation of compounds of the general Formula I STR1 /wherein R stands for piperazinyl, 4-methyl-piperazinyl or 4-ethyl-piperazinyl group/ and pharmaceutically acceptable salts thereof which comprises reacting a compound of the general Formula II STR2 /wherein R1 and R2 stand for halogen, for an aliphatic acyloxy group containing 2 to 6 carbon atoms and optionally substituted by halogen, or for an aromatic acyloxy group containing 7 to 11 carbon atoms/ with a piperazine derivative of the general Formula STR3 /wherein R3 stands for hydrogen, methyl or ethyl/ or a salt thereof and subjecting the compound of the general Formula IV STR4 thus obtained /wherein R, R1 and R2 are as stated above/ to hydrolysis after or without isolation and if desired converting the compound of the general Formula I thus obtained into a salt thereof or setting free the same from its salt. The compounds of the general Formula I are known antibacterial agents. The advantage of the present invention is that it makes the desired compounds of the general Formula I available in a simple manner, with high yields and in a short reaction time.
- -
-
-
- A new organosilylpolyphosphoric reagent, its preparation and application to the process of synthesis of 3-carboxyquinolones or azaquinolones and their salts
-
A process for the preparation of new organosilylpoly-phosphates from the reaction of phosphorus pentoxide with a siloxane or alkyloxysilane to obtain, in solution, reagents the composition of which is [P2O5]N[SILANE], where 1 N 10 where N is a function of temperatu-re, reaction time and solvent, being applied to the modulation of cyclization reaction of N-susbtituted aminomethylenemalonates leading to quinolones or azaqui-nolones. The N-substituted aminomethylenemalonates are prepared by the reaction of anilines with dialkyl trimethylsilyloxy-methylene-malonates.
- -
-
-
- Cycloaracylation of Enamines, I. - Synthesis of 4-Quinolone-3-carboxylic Acids
-
Starting with o-halobenzoyl chlorides 4 and open-chain secondary enamines 5, a new synthesis of 4-quinolone-3-carboxylic acids 12 is described.The reaction of 7-haloquinolone-3-carboxylic acids 12a-k with aliphatic amines 14 produces highly active antibacterial 7-aminoquinolone-3-carboxylic acids 15.The main product of the 1-cyclopropyl series, "ciprofloxacin" (15a), is being developed as a broad-spectrum chemotherapeutic agent.
- Grohe, Klaus,Heitzer, Helmut
-
-
- Immunostimulating agents
-
1-Cyclopropylquinolone-3-carboxylic acids of the formula STR1 in which R1 is hydrogen, methyl, ethyl or β-hydroxyethyl, and R2 is hydrogen, chlorine or fluorine or salts thereof stimulate the immune system, especially in conjunction with an antigen.
- -
-
-