- Preparation method of cefpodoxime acid
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The invention discloses a preparation method of cefpodoxime acid. The method comprises the following steps: adding a proper amount of solvent, 7-amino-3-chloromethyl cephalosporanic acid as shown in a formula (III), sodium methoxide, a quaternary ammonium salt catalyst and potassium iodide into a reaction container, performing stirring reaction at 0-80 DEG C for 2-8 hours, then adding 2-(2-amino-4-thiazolyl)-2-(Z)-methoxy imino acetyl chloride as shown in a formula (IV), performing stirring reaction at 0-30 DEG C for 2-5 hours, and after the reaction is finished, performing post-treatment to obtain cefpodoxime acid as shown in a formula (II). The method is simple and easy to operate, high in reaction yield, green and environmentally friendly, avoids the use of inflammable and explosive raw materials with high toxicity, improves the purity of the product by the post-treatment process, and is suitable for industrial production.
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- Synthesis and characterization of novel analogues of cefpodoxime proxetil
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The present work describes the origin, identification, synthesis, characterization and control of four novel analogues of cefpodoxime proxetil, which are ethyl, methyl, propyl and N-propyl analogues of cefpodoxime proxetil.
- Reddy, Peketi Rajesh,Musunuri, Sivanadh,Reddy, D. Ramasekhara,Chittala, V. Subrahmanyam,Murthy,Krishnamohan
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p. 1751 - 1755
(2020/07/30)
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- General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent
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In this contribution we demonstrate the feasibility of a recently developed amidation method for a general synthesis of industrially important semi-synthetic cephalosporin antibiotics starting from readily available 7-aminocephalosporanic acid and derivatives thereof. The amidation process is based on the use of 4-toluene-sulfonyl chloride as an economically attractive coupling reagent in combination with methanol or ethyl acetate as one of the solvent components. A broad reaction scope was shown by the successful synthesis of three further cephalosporin antibiotics with different functionalities, which were obtained in high yields of 82–95 % in the reactions even under non-optimized conditions. It is noteworthy that also different oxime functionalities in the side chain of the 7′-position are tolerated as well as an ester moiety in 4′-position and a cationic functionality in 3′-position. Thus, this amidation process through an activated anhydride formed by means of 4-toluenesulfonyl chloride is a broadly applicable methodology for the synthesis of industrial semi-synthetic cephalosporin antibiotics.
- Pieper, Matthias,Schleich, Herbert,Gr?ger, Harald
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p. 3259 - 3263
(2019/06/04)
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- Method for preparing high-purity cefpodoxime proxetil
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The invention discloses a method for preparing high-purity cefpodoxime proxetil. The method comprises the following steps: reacting cefpodoxime proxetil with iodo ester in an organic solvent in the presence of carbonate and basic ionic liquid; and performing post-treatment to obtain the cefpodoxime proxetil after reaction is completed. The cefpodoxime proxetil product prepared by the method has total impurities of less than 3 percent, and delta 3 isomer of 1.5 percent or less (EP7.0 specified total impurities are less than 4 percent, and USP35 specified total impurities are less than 6 percent), has good stability, molar ratio of 78.3-83.7 percent and high yield, is simple and convenient to operate, and is suitable for industrial production.
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Paragraph 0028-0048
(2019/02/04)
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- Preparation method of cefpodoxime proxetil
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The invention discloses a preparation method of cefpodoxime proxetil. In the method, a compound of formula II is used as an initial raw material, the intermediate compound of formula III is not separated during the process, and a crude product of cefpodoxime proxetil is synthesized by one step; and after that, a simple and easy recrystallization method is adopted for purifying the crude product of cefpodoxime proxetil to obtain cefpodoxime proxetil. In the preparation method disclosed by the invention, the yield is increased without reducing the quality, the obtained product has high purity, the synthesis path is simple, and the preparation method is suitable for industrial production.
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- AN IMPROVED PROCESS FOR CEFPODOXIME ACID
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The present invention relates to an improved process for the preparation of cefpodoxime acid from 7-Amino cephalosporanic acid. Further the preparation of cefpodoxime proxetil from cefpodoxime acid is also described.
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Page/Page column 8; 9
(2013/04/10)
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- PROCESS FOR THE PREPARATION OF CEPHEM ESTERS
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The present invention relates to a process for the preparation of cephem esters.
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- AN IMPROVED PROCESS FOR THE PREPARATION OF CEFPODOXIME PROXETIL
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An improved process for the preparation of cefpodoxime proxetil of the formula (I) the said process comprises reacting cefpodoxime acid with 1-haloethyl isopropyl carbonate of the formula (VI) where X represents halogen atom such as chlorine, bromine or iodine using a base such as tetramethylguanidine, di-isopropylethyl amine, 1,5-diazabicyclo(4.3.0)non-5-ene (DBN), 1,4-diazabicyclo[2.2.2]octane (DABCO) in the presence of a solvent at a temperature in the range of -30 °C to 30 °C to produce cefpodoxime proxetil of the formula (I) and isolating the pure cefpodoxime proxetil of the formula (I).
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- An improved method for preparation of cefpodoxime proxetil
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Cefpodoxime proxetil, a third-generation cephalosporin for oral administration, was synthesized by a method based on the following sequence of reactions: acylation of 7-aminocephalosporanic acid (7-ACA) with S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate (MAEM), chloroacetylation of the cefotaxime formed with chloroacetyl chloride, esterification of the acid function with 1-iodoethyl isopropyl carbonate and final cleavage of chloroacetamide protective group by treatment with thiourea in N,N-dimethylacetamide. The developed procedure allows us to obtain better yields of cefpodoxime proxetil and to eliminate the final purification step by column chromatography, necessary during the synthesis of this antibiotic by the previously reported methods.
- Rodriguez, Juan C.,Hernandez, Ricardo,Gonzalez, Maritza,Rodriguez, Zalua,Tolon, Blanca,Velez, Herman,Valdes, Barbara,Lopez, Miguel A.,Fini, Adamo
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p. 363 - 369
(2007/10/03)
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- Crystalline beta-lactam intermediate
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Crystalline 7-[2-(2-formylaminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid-1-(isopropoxycarbonyloxy)ethyl ester and its use.
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