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Process for prepn. of cefdinir

A technology for cefdinir and a compound is applied in the field of industrial-scale preparation of cefdinir, and can solve problems such as difficulty in large-scale production, cumbersome post-processing operation steps and the like

Inactive Publication Date: 2005-06-15
RANBAXY LAB LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the post-treatment operation steps are cumbersome, and high-boiling point acids often need to be distilled under reduced pressure, which is difficult to produce on a large scale

Method used

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  • Process for prepn. of cefdinir
  • Process for prepn. of cefdinir
  • Process for prepn. of cefdinir

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] 7β-[2-(2-Aminothiazol-4-yl)-2(Z)-trityloximino-3-vinyl-3-cephem-4-carboxylic acid, sulfate, 3N,N- Dimethylacetamide solvate

[0057]7-amino-3-vinyl-3-cephem-4-carboxylic acid (10g) was added to N,N-dimethylacetamide (100ml), and then 2-benzothiazolyl (Z)- 2-(2-Aminothiazol-4-yl)-2-trityloxyiminothioacetate (28.2 g). The reaction mixture was cooled to 10-15°C and tri-n-butylamine (17.2 g) was added at 10-15°C over 20-30 minutes. The reaction mixture was stirred at room temperature for 6-7 hours to complete the reaction. Thereafter, it was cooled to -10°C, and sulfuric acid (13.4 g) was added dropwise within 30 minutes below 0°C. Under cooling, toluene (100 ml) was added to the reaction mixture, followed by hexane (100 ml). The temperature of the reaction mixture was raised to 35-40°C and crystallization proceeded. The temperature was maintained at 35-40°C for 30 minutes. The precipitate thus obtained was filtered and washed with toluene, and then dried to obtain 41...

Embodiment 2

[0065] 7β-[2-(2-aminothiazol-4-yl)-2(Z)-(trityloxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid, methyl Sulfonate, 3N,N-Dimethylacetamide solvate

[0066] 7-amino-3-vinyl-3-cephem-4-carboxylic acid (10g) was added to N,N-dimethylacetamide (150ml), and then 2-benzothiazolyl (Z)- 2-(2-Aminothiazol-4-yl)-2-trityloxyiminothioacetate (26.8 g). At 10-15°C, tri-n-butylamine (16.78 g) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 7-8 hours to complete the reaction. Anhydrous methanesulfonic acid (13 g) was added to the reaction mixture over 15-20 minutes at below 10°C, followed by diisopropyl ether (150 ml). The temperature of the reaction mixture was raised back to 30-35°C, and crystallization proceeded. The precipitate thus obtained was filtered and washed with diisopropyl ether, and then dried to obtain 38.5 g (yield: 96%) of the title compound as off-white crystals.

[0067] HPLC purity: 99.3%, m.p.=125-127°C, N,N-dimethylac...

Embodiment 3

[0072] 7β-[2-(2-aminothiazol-4-yl)-2(Z)-(trityloxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid, methyl Sulfonate, 2N,N-Dimethylacetamide solvate

[0073] 7-amino-3-vinyl-3-cephem-4-carboxylic acid (15g) was added to N,N-dimethylacetamide (225ml), and then 2-benzothiazolyl (Z)- 2-(2-Aminothiazol-4-yl)-2-trityloxyiminothioacetate (45 g). At 10-15°C, tri-n-butylamine (27 g) was added to the reaction mixture. The reaction mixture was stirred at 25-30°C for 7-8 hours to complete the reaction. Anhydrous methanesulfonic acid (210 g) was added to the reaction mixture over 15-20 minutes at below 10°C, followed by diisopropyl ether (450 ml). The temperature of the reaction mixture was raised back to 38-40°C and stirred for 45 minutes for crystallization. The suspension was cooled to 25-30°C and stirred for a further 1 hour. The precipitate thus obtained was filtered and washed with diisopropyl ether, and then dried to obtain 56.7 g (yield: 94.2%) of the title compound as off...

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Abstract

The present invention relates to a process for the preparation of cedinir on an industrial scale.

Description

field of invention [0001] The present invention relates to an improved process for the preparation of cefdinir on an industrial scale. Background of the invention [0002] The chemical name of cefdinir is 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid ( cis isomer), first described in US Patent 4,559,334. It is a third-generation cephalosporin antibiotic for oral use and has a broader antibacterial spectrum than other oral antibiotics. [0003] [0004] Formula I [0005] Several methods for the preparation of cefdinir have been reported. U.S. Patent 4,559,334 describes a process for the preparation of cefdinir comprising 7-amino-3-vinyl-3-cephem-4-carboxylate (7-AVCA ester) of formula P(i) and Coupling of reactive derivatives of open-chain carboxylic acids, [0006] [0007] Formula P(i) [0008] [0009] Formula P(ii) [0010] The resulting 7-acylamino compound is treated with a nitrosatin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/00C07D501/22
CPCC07D501/00C07D501/22
Inventor Y·库马M·普拉萨德A·普拉萨德S·K·辛格N·P·库马
Owner RANBAXY LAB LTD
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