65052-63-3 Usage
Synthesis
Suspend 2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetic acid in tetrahydrofuran, add half amount of phosphorus oxychloride dropwise at 0 °C, keep the temperature not more than 5 lookchem °C, dropwise The reaction was completed for 30 minutes. Dimethylformamide and the other half of phosphorus oxychloride were added, and the reaction was carried out at 0 °C for 1 h to obtain a solution of active ester (I) at -5 °C.7-ADCA, bis-trimethylsilyl urea and ethyl acetate were refluxed at 75-77 °C for 2 h to obtain a solution of 7-ADCA silicon ester, which was cooled to -5 °C. It was combined with the solution of active ester and stirred at -5～0°C lookchem for 2h. Be raised to 15 ℃, add water, stir for 30min. Separate the water layer, adjust to Ph=2.6～3.0 with sodium hydroxide solution, place to separate out crystallization. Filtration, acetone recrystallization to give Cefetamet, yield 82%.
Description
Ceftazidime hydrochloride is an oral third-generation cephalosporin, which has the same antibacterial activity against gram-positive bacteria as cefixime, and is superior to cefaclor, especially against Streptococcus pneumoniae and Streptococcus pyogenes. It has obvious antibacterial activity against a variety of gram-negative bacteria such as Escherichia coli, Proteus, Klebsiella pneumoniae, Haemophilus influenzae, and Neisseria gonorrhoeae, especially against Serratia, indole-positive Proteus, Enterobacter The antibacterial activity of Citrobacter and Citrobacter was significantly enhanced.
Uses
Cefetamet is a third-generation cephalosporin antibiotic and the active agent of Cefeamet pivoxil (C242780) after hydrolysis.
Antimicrobial activity
A semisynthetic cephalosporin formulated for oral use as the
prodrug ester, cefetamet pivoxyl. It is less active than cefaclor
and cefadroxil against Staph. aureus, but as active against
streptococci and more active against enterobacteria, H. influenzae
and N. gonorrhoeae, including β-lactamase-producing
strains. L. monocytogenes, C. difficile, Sten. maltophilia and Burk.
cepacia are all resistant. It is resistant to hydrolysis by common
plasmid-mediated enzymes.
The absolute bioavailability is about 50%. The plasma peak
is delayed by food. Binding to plasma protein is about 20%.
The volume of distribution approximates to the extracellular
water. It is excreted into urine with a half-life of 2–2.5 h,
principally in the glomerular filtrate. Elimination is linearly
related to creatinine clearance. Side effects and uses are similar
to those of other group 5 cephalosporins.
Check Digit Verification of cas no
The CAS Registry Mumber 65052-63-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,0,5 and 2 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 65052-63:
(7*6)+(6*5)+(5*0)+(4*5)+(3*2)+(2*6)+(1*3)=113
113 % 10 = 3
So 65052-63-3 is a valid CAS Registry Number.
InChI:InChI=1/C14H15N5O5S2/c1-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24-2)6-4-26-14(15)16-6/h4,8,12H,3H2,1-2H3,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
65052-63-3Relevant articles and documents
Cefetamet pivoxil hydrochloride preparation method
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Page/Page column 6-9, (2018/10/19)
The invention relates to a cefetamet pivoxil hydrochloride preparation method, which comprises: generating an intermediate I by using 7-ADCA and ethyl methylaminothiazolyloximate as starting raw materials under the catalysis of AlMe3; and carrying out an esterification reaction on the intermediate I and iodomethyl pivalate under the actions of a phase transfer catalyst and an acid adsorbent, carrying out salt formation on the esterified product, and crystallizing to obtain the target product cefetamet pivoxil hydrochloride. According to the present invention, the method has characteristics ofmild reaction conditions, high product purity, high yield and stable process, and is suitable for industrial production.
IMPROVED PROCESS FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS
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Page/Page column 10-11, (2008/06/13)
Abstract The present invention more particularly relates to a process for the preparation of cephalosporin antibiotics of the Formula (I) wherein R1 represents hydrogen, trityl, alkyl like CH3, CRaRbCOORc where Ra and Rb independently represent hydrogen or methyl and Rc represents hydrogen or (C1-C6) alkyl; R2 is carboxylate ion or COORd, where Rd represents hydrogen, ester or a counter ion which forms a salt; R3 represents hydrogen, CH3, CH2OCH3, CH2OCOCH3, CH=CH2, Formula (II).
Preparation of new intermediates and their use in manufacturing of cephalosporin compounds
-
, (2008/06/13)
The present invention provides new thioester derivatives of 4-halogeno-2-methoxyimino-3-oxo-butyric acid of the general formula (I), also, the invention provides a method by which the said thioester derivatives can be prepared by reacting 4-halogeno-2-methoxyimino-3-oxo-butyric acid of the general formula (II) with 2-mercapto-5-substituted-1,3,4-oxadiazoles of the general formula (III) in a solvent, in the presence of DMF/POCl3and in presence of an organic base and if desired the so obtained thioester derivatives so obtained are reacted with 7-amino-cephem carboxylic acids of the general formula (V) to produce condensed products which are insitu reacted with thiourea to get cephalosporin antibiotic compounds having the general formula (VI).
