'One kettle process' of preparing cefozopran and its intermediate

A technology of compound and amino group, which is applied in the field of preparation of cefozopran and its intermediates, can solve the problems that the product cannot be prepared economically and the starting materials are not easy to obtain, etc.

Inactive Publication Date: 2006-10-18
BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the above two methods, the starting materials are not easy to get, and the product cannot be prepared more economically, so it is necessary to find a more economical preparation method

Method used

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  • 'One kettle process' of preparing cefozopran and its intermediate
  • 'One kettle process' of preparing cefozopran and its intermediate
  • 'One kettle process' of preparing cefozopran and its intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Under nitrogen flow, add 100 g (0.37 mol) of 7-aminocephalosporanic acid (7-ACA) to 500 ml of Freon F113a, stir and cool to -10°C, add 1.1 mol of triethylamine dropwise under stirring, and control the temperature at -10°C At ~-5°C, 88.9 g (0.44 mol) of iodotrimethylsilane and 52.9 g (0.44 mol) of imidazo[1,2-b]pyridazine were added, and stirred at room temperature for 4 hours. After the reaction was completed, 200 ml of 2N hydrochloric acid aqueous solution was added, and 2000 ml of isopropanol was added to precipitate crystals. Suction filtration, the filter cake was washed with ice-cold isopropanol, and vacuum-dried to obtain 3-(imidazo[1,2-b]pyridazin-1-yl)methyl-3-cephem hydrochloride as a yellow-white solid 75 grams, yield: 75%.

Embodiment 2

[0043] 50 g (0.14 mol) of 3-(imidazo[1,2-b]pyridazin-1-yl)methyl-3-cephem hydrochloride prepared according to Example Method 1 was added to 100 ml of N, -N-diformyl formamide (DMF) and 100 ml of water mixed solution, add (5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetic acid mercapto 59 g (0.168 mol) of benzothiazole active ester, adjust the pH of the reaction system to 8-10 with 1N aqueous sodium hydroxide solution, and stir for about 2 hours. Add hydrochloric acid to adjust the pH to 2-3, and add isopropanol dropwise to precipitate crystals. Suction filtration and vacuum drying gave 54.1 g of cefozopran hydrochloride, yield: 70%.

Embodiment 3

[0045] Under nitrogen flow, 150 grams (0.29mol) of 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]-cephalosporin Add alkanoic acid to 600ml Freon F113a, stir and cool to -10°C, add 0.87mol triethylamine dropwise under stirring, control temperature -10~-5°C, add 88.9g (0.35mol) iodotrimethylsilane. Stir for 3 hours, add 52.9 g (0.44 mol) of imidazo[1,2-b]pyridazine, and stir at room temperature for 5 hours. Add 400 ml of 2N hydrochloric acid aqueous solution, add 4000 ml of isopropanol, and precipitate crystals. After suction filtration, the filter cake was washed with ice-cold isopropanol, and dried in vacuum to obtain 96 g of cefozopram hydrochloride, yield: 60%.

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Abstract

The present invention relates to the process of compound I or its salt. The preparation process includes the reaction between the compound II or its salt with compound A or its alt in the presence of trimethyl silane iodine (TMSI). The compound I may be used in preparing cefozopran as the fourth generation of cephalosporin.

Description

field of invention [0001] The invention relates to a preparation method of cefozopran and its intermediate. Background of the invention [0002] Cephem antibacterial agents have been widely used in the treatment of various diseases caused by pathogenic bacteria in humans and animals. These compounds are especially useful in the treatment of various diseases caused by bacteria resistant to penicillin-type antibacterial agents and in the treatment of patients allergic to penicillin. In these cases, it is desirable to use a cephem-type antibacterial agent that is active against both Gram-positive and Gram-negative bacteria. Therefore, much research has been conducted on cephem-type antibacterial agents having a broad antibacterial spectrum. As a result of long-term research, a variety of effective cephem-type antibacterial agents have been developed. Generally, the cephem-type antibacterial agents that have been researched and marketed are divided into four generations accor...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D487/04C07D501/18
Inventor 川真田博康吴澜李建
Owner BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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