- 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 0095-0097; 0179
(2021/10/27)
-
- ANTIBIOTIC RESISTANCE BREAKERS
-
The invention relates to antibiotic compounds of formula (A1) and pharmaceutically acceptable salts, solvates, tautomers and combinations thereof, wherein X and L are optional linkers and one of RA or R1 comprises Ar1, wherein Ar1 is an antibiotic resistance breaker moiety which comprises an optionally substituted C6-10 aryl, C7-13 aralkyl, C5-10 heteroaryl, C6-13 heteroaralkyl, C5-10 heterocyclyl, C6-13 heterocyclalkyl, C3-10 carbocyclyl, C4-13 carbocyclalkyl, -C(=NR')-NR'R'' or –CH2- CH=CH2 group; wherein after administration of the compound to a bacterial infection this moiety reduces or prevents efflux. The invention also discloses pharmaceutical compositions comprising compounds of formula (A1) and the use of such compounds as medicaments, in particular, to treat bacterial infections, such as drug-resistant bacterial infections.
- -
-
Page/Page column 97
(2019/01/05)
-
- Advanced Continuous Flow Platform for On-Demand Pharmaceutical Manufacturing
-
As a demonstration of an alternative to the challenges faced with batch pharmaceutical manufacturing including the large production footprint and lengthy time-scale, we previously reported a refrigerator-sized continuous flow system for the on-demand production of essential medicines. Building on this technology, herein we report a second-generation, reconfigurable and 25 % smaller (by volume) continuous flow pharmaceutical manufacturing platform featuring advances in reaction and purification equipment. Consisting of two compact [0.7 (L)×0.5 (D)×1.3 m (H)] stand-alone units for synthesis and purification/formulation processes, the capabilities of this automated system are demonstrated with the synthesis of nicardipine hydrochloride and the production of concentrated liquid doses of ciprofloxacin hydrochloride, neostigmine methylsulfate and rufinamide that meet US Pharmacopeia standards.
- Zhang, Ping,Weeranoppanant, Nopphon,Thomas, Dale A.,Tahara, Kohei,Stelzer, Torsten,Russell, Mary Grace,O'Mahony, Marcus,Myerson, Allan S.,Lin, Hongkun,Kelly, Liam P.,Jensen, Klavs F.,Jamison, Timothy F.,Dai, Chunhui,Cui, Yuqing,Briggs, Naomi,Beingessner, Rachel L.,Adamo, Andrea
-
p. 2776 - 2784
(2018/02/06)
-
- A Rapid Total Synthesis of Ciprofloxacin Hydrochloride in Continuous Flow
-
Within a total residence time of 9 min, the sodium salt of ciprofloxacin was prepared from simple building blocks via a linear sequence of six chemical reactions in five flow reactors. Sequential offline acidifications and filtrations afforded ciprofloxacin and ciprofloxacin hydrochloride. The overall yield of the eight-step sequence was 60 %. No separation of intermediates was required throughout the synthesis when a single acylation reaction was applied to remove the main byproduct, dimethylamine.
- Lin, Hongkun,Dai, Chunhui,Jamison, Timothy F.,Jensen, Klavs F.
-
p. 8870 - 8873
(2017/07/17)
-
- IMPROVED PROCESS FOR THE PREPARATION OF CIPROFLOXACIN AND ITS ACID ADDITION SALTS
-
An improved process for the synthesis of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid (Ciprofloxacin) or and its acid addition salts preferablyhydrochloride salt with high yield and high purity, the process comprising of reacting 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid with piperazine in presence of a catalyst in an organic solvent.
- -
-
Page/Page column 7
(2012/10/08)
-
- ANHYDROUS CIPROFLOXACIN HYDROCHLORIDE
-
The present invention provides a new anhydrous crystalline form of ciprofloxacin hydrochloride that is substantially free from solvent molecules, and processes of preparation thereof.
- -
-
Page/Page column 2
(2009/01/20)
-
- An expeditious synthesis of quinolone antibacterials
-
A facile and rapid synthesis of ciprofloxacin under microwave irradiation is described. The product ciprofloxacin was isolated and the impurity was characterized as the product of substitution of fluorine instead of chlorine in acid 1. Similarly norfloxacin was synthesized.
- Heravi, Majid M.,Oskooie, Hossein A.,Motamedi, Radineh,Ghassemzadeh, Mitra
-
p. 423 - 426
(2007/10/03)
-
- Methods for the manufacture of quinolone carboxylic acids derivatives and intermediates thereof
-
Novel process for the preparation of quinolone carboxylic acid derivatives of general formula I, and intermediates thereof as illustrated in Scheme 1 wherein the key intermediate is a compound of formula IX. STR1
- -
-
-
- 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
-
-
- 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
-
The invention relates to 7-amino-1-cyclo-propyl-4-oxo-1,4-dihydro-naphthyridine (or quinoline)-3-carboxylic acids of Formula I as defined in the specifications. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.
- -
-
-
