- Photoisomerization kinetics of cefuroxime axetil and related compounds
-
The photoisomerization kinetics of aqueous solutions of cefuroxime axetil under irradiation at 254 nm was investigated by HPLC. The overall degradation is the result of a competition between the isomerization of the alkoxyimino group and the photolysis of the β-lactam ring. Cefuroxime axetil exists as a mixture of two diastereomers which are shown to react at different rates. This is true not only for the photoisomerization step but also for ground- state hydrolysis in alkaline conditions. Photoisomerization of the alkoxyimino group is also observed for the anti isomer of cefuroxime axetil and for some of its degradation products. The quantum yields for all these photoisomerizations are always lower than 1%, which explains the relative importance of the photolysis step. A stationary syn to anti ratio of 1 is measured for cefuroxime axetil and of 2.1 for cefuroxime. From this and previous studies, it appears that cefuroxime axetil is the most sensitive under irradiation at 254 nm when compared to other antibiotics bearing the alkoxyimino group. Aztreonam is the most stable followed by cefotaxime, cefuroxime, and cefuroxime axetil.
- Fabre,Ibork,Lerner
-
-
Read Online
- Preparation method of cefuroxime acid
-
The invention relates to a preparation method of cefuroxime acid, wherein the preparation method comprises the following steps: (1) adding D-7ACA into water, and dropwisely adding an alkali solution to dissolve; adding a methoxyimino furan acetyl chloride dichloromethane solution to carry out acylation reaction, layering to obtain a water phase after the reaction is finished, adding activated carbon to decolorize, filtering, then adding dichloromethane, dropwise adding hydrochloric acid to crystallize, filtering and drying to obtain MDCC; and (2) adding MDCC into an organic solvent, adding chlorosulfonyl isocyanate to carry out aminomethyl acylation reaction, and after the reaction is finished, adding pre-cooling water to hydrolyze to obtain a cefuroxime acid suspension; and dropwise adding an alkaline solution for multiple times, growing crystals after dropwise adding is completed each time, finally adjusting the pH value of the system to 1.0-2.0, filtering, and washing to obtain the cefuroxime acid product. The obtained product is good in stability, good in product flowability and easy to subpackage; the crystallization size phase of the product is greatly improved, and the stability is obviously improved.
- -
-
Paragraph 0055; 0058-0059; 0060; 0065-0066; 0067; 0072-0073
(2021/04/21)
-
- Cefuroxime sodium compound prepared through advanced on-line process control technology and preparation thereof
-
The invention discloses a cefuroxime sodium compound prepared through an advanced on-line process control technology and a preparation thereof. The project of high-grade medical product refining crystallization technology research and development and industrialization receives national scientific and technological progress second prize in 2015. The advanced on-line process control technology belongs to the high-grade medical product refining crystallization technology. An X ray powder diffraction test on cefuroxime sodium shows that in the spectrum, main characteristic peaks represented by diffraction angle 2theta are as follows: 9.71 degrees, 14.18 degrees, 16.19 degrees, 21.10 degrees, 22.88 degrees, 25.16 degrees and 30.77 degrees. The compound has the characteristics of high purity, low impurity content, good fluidity and good stability. The preparation is a cefuroxime sodium injection.
- -
-
-
- Method for preparing cefuroxime acid
-
The invention provides a method for preparing cefuroxime acid. The method is characterized by comprising the following steps: (1) mixing deammonized formyl cefuroxime in liquid ester, adding a strong amino carbamylation reagent sulfonylisocynate, and performing a temperature-controlled reaction; (2) adding purified water after the reaction is completed, and performing hydrolysis; (3) adding the liquid ester after hydrolysis is completed, adjusting the pH value to be 1.9-2.0 by using hydrochloric acid, standing for layering, and performing vacuum concentration on an organic layer so as to obtain an organic layer concentrated solution; (4) adding purified water into the organic layer concentrated solution, performing crystallization, and filtering so as to obtain cefuroxime acid, wherein the liquid ester used in the step (1) and the step (3) is selected from methyl acetate, acetic ether, n-butyl acetate, methyl formate, ethyl formate and propyl formate. The method for preparing cefuroxime acid, which is provided by the invention, is green and environmental-friendly, low in cost, high in yield and good in quality.
- -
-
-
- A Cefuroxime lysine and its preparation
-
The invention relates to a cefuroxime lysine compound. The invention is characterized in that the cefuroxime lysine contains 98-99.99 wt% of cefuroxime lysine and 0.01-2 wt% of descarbamoyl cefuroxime, wherein the molecular formula of the descarbamoyl cefuroxime is disclosed as Formula I. The cefuroxime lysine provided by the invention has higher stability than the cefuroxime lysine in the prior art, and lower impurity content and polymer content than the cefuroxime lysine in the prior art, and is very suitable for clinical application.
- -
-
-
- A Cefuroxime lysine and its preparation
-
The invention relates to a cefuroxime lysine compound. The cefuroxime lysine contains 98-99.99% by weight of cefuroxime lysine and 0.01-2% of trans-cefuroxime acid, and the molecular formula of the trans-cefuroxime acid is as shown in formula I. The obtained cefuroxime lysine disclosed by the invention has very strong stability which is higher than that of the prior art; and the impurity content and the polymer content are lower than those of the cefuroxime lysine in the prior art, thus the cefuroxime lysine is very suitable for clinical applications.
- -
-
-
- A adopt the particle process crystal product molecular assembly and shape optimization technique of the new crystalline form of cefuroxime sodium compound and preparation (by machine translation)
-
The invention discloses a new crystalline form of cefuroxime sodium compound and its crystallization preparation method, the new crystalline form of the compound is sodium [...] particle process crystal product molecular assembly and shape optimization technique to prepare. The stability tests prove that the new crystalline form of compound has high purity, low impurity content, guide the low moisture, the good characteristic of stability. At the same time, the invention also discloses the preparation of cefuroxime sodium employing the above described head-injection for the preparation. (by machine translation)
- -
-
-
- AN IMPROVED PROCESS FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTIC
-
The present invention provides a process for the preparation of the compound of formula (I) and its salt and esters. More particularly, this present invention relates to an improved process for the preparation Cefcapene of formula (I) and its salt and esters.
- -
-
Page/Page column 10-12
(2009/01/23)
-
- Process for the preparation of cefuroxime sodium
-
The present invention relates to an improved process for the preparation of the sterile cefuroxime sodium of formula (I). 1
- -
-
-
- Process for the synthesis of beta-lactam derivatives
-
The invention is directed towards a process for the preparation of Cefuroxime acid or for a corresponding pharmaceutically acceptable salt or ester. The process comprises the carbamoylation of a Cefuroxime precursor with an activated isocyanate. Additionally, the process is characterized by the fact that a carbonic C1-C4alkyl ester is used as a solvent for the carbamoylation reaction.
- -
-
Page/Page column 3-4
(2008/06/13)
-
- Process for the preparation of β-lactam derivatives
-
A process for the preparation of Cefuroxime acid (I), which comprises the following steps: (1) Extraction of deacetyl 7-glutaryl ACA (II) aqueous solution at acid pH with organic solvents (for example according to the procedures disclosed in U.S. Pat. No. 5,801,241); (2) drying the resulting solution while preventing lactonization of the intermediate; (3) carbamoylation of the hydroxymethyl group at the 3-position by reaction with chlorosulfonyl isocyanate or similar products; (7) extraction of the carbamoyl derivative from step 3 with water at neutral pH; (8) enzymatic hydrolysis of the amide at the 7-position of the cephalosporanic ring with glutaryl acylase; (6) acylation of the amnino group by condensation with 2-furanyl(sin-methoxyimino)acetic acid chloride or mixed anhydride.
- -
-
-
- 6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
-
6-beta-Halopenicillanic acid 1,1-dioxides, physiologically acceptable salts thereof and esters thereof readily hydrolyzable; pharmaceutical compositions containing a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable; and a method for enhancing the effectiveness of a beta-lactam antibiotic, using a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable.
- -
-
-
- Process for the preparation of cephalosporin compounds
-
A process for the preparation of cephalosporins having a phosphonocarbamoyloxymethyl group at the 3-position by reacting a cephalosporin having at the 3-position a group STR1 (wherein R4 and R5 are independently alkyl, aralkyl, alicyclic or aryl groups or together form a divalent group) with a compound of formula STR2 (wherein R6, R7 and R8 are independently alkyl, aralkyl, alicyclic or aryl groups or any two of R6, R7 and R8 together form a divalent group, and X is halogen) followed by hydrolysis. The 3-phosphonocarbamoyloxymethyl cephalosporin products of the process exhibit antibiotic activity, and if desired may be readily converted to 3-carbamoyloxymethyl cephalosporins which themselves show antibiotic activity.
- -
-
-
- DERIVATIVES OF 6BETA-HYDROXYALKYLPENICILLANIC ACIDS AS BETA-LACTAMASE INHIBITORS
-
6beta-Hydroxyalkylpenicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several beta-lactam antibiotics against many beta-lactamase producing bacteria, and 6beta-substituted penicillanic acid benzyl ester derivatives as useful intermediates leading to said agents which enhance the effectiveness of beta-lactam antibiotics
- -
-
-