Cefdinir compound and preparation method thereof

A technology for cefdinir and compounds, which is applied in the field of refining cefdinir compounds, can solve the problems of poor stability, low purity and low cefdinir purity, and achieves the effects of low cost, simple process and convenient operation

Inactive Publication Date: 2009-10-07
HAINAN MEIDA PHARMA
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

U.S. Patent No. 4935507 discloses a process for the preparation of crystalline cefdinir by reacting amorphous cefdinir with an acid in a solvent and adding a non-polar solvent thereto to precipitate an acid addition salt of cefdinir, such as cefdinir Ni HCl, Cefdinir H 2 SO 4 and Cefdinir CH 3 SO 3 H, however, the acid addition salt formed as an intermediate in this process is an amorphous loose material with poor stability and low purity
[0006] The cefdinir synthesized by the above-mentioned patent has always had the disadvantage of low purity, and the general refining method of dissolution and crystallization cannot fundamentally improve its purity.

Method used

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  • Cefdinir compound and preparation method thereof
  • Cefdinir compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Take 100 g of cefdinir crude product, add 2 mol / L sodium hydroxide solution, fully stir until clarified to obtain cefdinir sodium solution, add 5 g of activated carbon to absorb at room temperature for 30 minutes, filter for decarburization, add 10% sodium dihydrogen phosphate solution to the filtrate , stirred and reacted, crystals were precipitated, filtered, washed with water, and dried under reduced pressure at 50° C. to obtain 92.2 g of cefdinir refined product, with a yield of 92.2%, and a purity of 99.7% by HPLC.

[0017] Structural confirmation: Elemental analysis theoretical value C: 42.5%, H: 3.3%, N: 17.7%, O: 20.2%, S: 16.2%; experimental value C: 42.4%, H: 3.4%, N: 17.5%, O : 20.3%, S: 16.3%.

[0018] H-NMR (δ, DMSO-d 6 ): 3.56, 3.87 (2H, Abq, C-2), 5.21 (1H, d, C-6), 5.32 (1H, d, -CH=CH 2 ), 5.63 (1H, d, -CH=CH 2 ), 5.79-5.84 (1H, m, C-7), 6.68 (1H, s, aminothiazole ring-H), 6.89-6.98 (1H, m, -CH=CH 2 ), 7.15 (2H, brds, -NH 2 ), 9.79 (1H, d, -NH-).

Embodiment 2

[0020] Take 100 g of cefdinir crude product, dissolve it in 500 ml of acetonitrile, add 5 mol / L of sodium acetate solution, stir well until clarification, to obtain cefdinir sodium solution, add 8 g of activated carbon to absorb at room temperature for 20 minutes, filter for decarburization, add 1 mol / L of filtrate L hydrochloric acid solution, stirred and reacted, precipitated crystals, filtered, washed with water, and dried under reduced pressure at 40°C to obtain 90.8g of cefdinir refined product, with a yield of 90.8%, and a purity of 99.6% by HPLC.

[0021] Structural confirmation: Elemental analysis theoretical value C: 42.5%, H: 3.3%, N: 17.7%, O: 20.2%, S: 16.2%; experimental value C: 42.6%, H: 3.3%, N: 17.6%, O : 20.4%, S: 16.1%.

[0022] H-NMR (δ, DMSO-d 6 ): 3.57, 3.87 (2H, Abq, C-2), 5.22 (1H, d, C-6), 5.33 (1H, d, -CH=CH 2 ), 5.63 (1H, d, -CH=CH 2 ), 5.79-5.85 (1H, m, C-7), 6.68 (1H, s, aminothiazole ring-H), 6.89-6.97 (1H, m, -CH=CH 2 ), 7.15 (2H, brds, -NH ...

Embodiment 3

[0024] Get cefdinir crude product 100g, add 10% potassium bicarbonate solution, fully stir until clarification, obtain cefdinir potassium solution, add 6g gac to absorb at room temperature for 20 minutes, filter for decarburization, add 2% acetic acid solution to the filtrate, stir to react, Crystals were precipitated, filtered, washed with water, and dried under reduced pressure at 45°C to obtain 93.1 g of cefdinir refined product with a yield of 93.1% and a purity of 99.8% by HPLC.

[0025] Structural confirmation: Elemental analysis theoretical value C: 42.5%, H: 3.3%, N: 17.7%, O: 20.2%, S: 16.2%; experimental value C: 42.4%, H: 3.5%, N: 17.6%, O : 20.1%, S: 16.3%.

[0026] H-NMR (δ, DMSO-d 6 ): 3.55, 3.86 (2H, Abq, C-2), 5.23 (1H, d, C-6), 5.31 (1H, d, -CH=CH 2 ), 5.64 (1H, d, -CH=CH 2 ), 5.78-5.84 (1H, m, C-7), 6.69 (1H, s, aminothiazole ring-H), 6.89-6.98 (1H, m, -CH=CH 2 ), 7.16 (2H, brds, -NH 2 ), 9.78 (1H, d, -NH-).

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Abstract

The invention relates to a cefdinir compound and a preparation method thereof. In the method, the crude product of cefdinir prepared by the prior art is processed by the following steps to obtain a relatively pure cefdinir compound: aqueous alkali is added into the crude product of the cefdinir and full reaction is conducted till a clear solution is obtained, and then a cefdinir solution is obtained, and the cefdinir solution is absorbed with added active carbon and filtered; or the crude product of cefdinir is dissolved in an organic solvent and reacts with the added aqueous alkali to obtain a cefdinir solution, and the cefdinir solution is absorbed with added active carbon and filtered; and then the two filter liquors are added with acid or solid acid salt respectively; and crystal is separated out, filtered, washed and dried to obtain a cefdinir refined product.

Description

technical field [0001] The invention relates to a method for refining cefdinir compounds, belonging to the technical field of medicine. Background technique [0002] Cefdinir, its chemical name is: (6R, 7R) 7-[(2-amino-4-thiazolyl)-(oximino)acetoxy]amino]-3-vinyl-8-oxo-5- Thia-1-azabicyclo[4.2.0]oct-2-ene-2-hydroxy acid, molecular formula: C 14 h 13 N 5 o 5 S 2 , molecular weight: 395.42, structural formula: [0003] [0004] It is an oral third-generation cephalosporin with a broad antibacterial spectrum, and has a wide range of antibacterial spectrum against Gram-positive bacteria and Gram-negative bacteria, especially Staphylococcus aureus and Streptococcus among Gram-positive bacteria etc. Compared with conventional oral cephalosporins, it has stronger antibacterial activity, is stable against β-lactamase produced by various bacteria, and has excellent antibacterial activity against β-lactamase-producing bacteria. Clinically, it can be used to treat tonsillitis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/12A61P31/04
Inventor 郑仙锋
Owner HAINAN MEIDA PHARMA
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