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Cephaene onium salt compound and its preparation, and synthesis of cephapyrazde sulfate therefrom

A compound, cephem technology, applied in chemical instruments and methods, preparation of lactams, organic chemistry, etc., can solve the problem of expensive reagents and other problems, and achieve the effects of easy disposal of three wastes, easy recovery, and mild reaction conditions

Inactive Publication Date: 2005-05-11
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sodium iodide and silane amide reagents used in this method are more expensive, and the halide reagents (such as phosphorus pentachloride, phosgene, etc.) that are irritating and corrosive are used when the seven substituents are used

Method used

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  • Cephaene onium salt compound and its preparation, and synthesis of cephapyrazde sulfate therefrom
  • Cephaene onium salt compound and its preparation, and synthesis of cephapyrazde sulfate therefrom
  • Cephaene onium salt compound and its preparation, and synthesis of cephapyrazde sulfate therefrom

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 7β-formylamino-3-[3-formylamino-2-(2-formyloxyethyl)-1-pyrazolium]methyl-3-cephem-4-carboxylate (I-a) Preparation of:

[0047] In a 250ml reaction flask, add compound 7β-formamido-3-chloromethyl-3-cephem-4-carboxylic acid (IV-a) 50g, dimethylformamide 200ml, sodium bicarbonate 30g, and 5-Formylamino-1-(2-formyloxyethyl)pyrazole (VIII) 99g, stirred at room temperature for 5 hours, filtered, poured the filtrate into 2000ml of ethyl acetate, filtered, collected the resulting precipitate, 75 g of light yellow solid compound (I-a) was obtained.

[0048] IR (KBr, Max): 3423, 1770, 1632, 1574cm -1

[0049] m / e: 424 [M-H] +

Embodiment 2

[0051] 7β-acetylamino-3-[3-formylamino-2-(2-formyloxyethyl)-1-pyrazolium]methyl-3-cephem-4-carboxylate (I-b) preparation:

[0052] Add 20g of 7β-acetylamino-3-chloromethyl-3-cephem-4-carboxylic acid, 40ml of sulfolane, 7.2g of sodium carbonate, and 5-formylamino-1-(2-methyl Acyloxyethyl) pyrazole (VII) 15.5g, stirred at room temperature for 2 hours, filtered, the filtrate was poured into 800ml acetone, filtered, and the resulting precipitate was collected to obtain 29g of light yellow solid compound (I-b).

[0053] IR (KBr, cm -1 ):

Embodiment 3

[0055] Preparation of 7β-amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolium]methyl-3-cephem-4-carboxylic acid chloride hydrochloride (V) :

[0056] At room temperature, add 23ml of concentrated hydrochloric acid to compound 7β-formylamino-3-[3-formylamino-2-(2-formyloxyethyl)-1-pyrazolium]methyl-3-cephalosporin In the mixture of ene-4-carboxylate (I-a) 20g and methanol 100ml, at the same temperature, after stirring for 2 hours, the mixture was added dropwise into 200ml of ethyl acetate, and a nearly white solid was precipitated, filtered, and an appropriate amount of ethyl acetate After ester washing, 17 g of white solid compound (V) was obtained.

[0057] 1 H-NMR (D 2 O) δ: 3.16-3.31 (6H, m), 3.57-3.60 (2H, t), 4.09-4.37 (2H, m),

[0058] 4.85(1H, d), 5.01(1H, d). 5.06-5.28(2H, g), 5.87(1H, d),

[0059] 7.38(2H, s), 8.00(1H, d)

[0060] IR (KBr, cm -1 ): 3413, 1786, 1636, 1592

[0061] m / e: 340 [M-H] +

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Abstract

This invention relates to cephalene onium salt compound and its preparation and synthesis of cephapyrazole sulfate therefrom. It is produced from 7beta-alkyl amido-3-[3-alkyl amido-2-(2-alkyl acyl oxethyl)-1-pyrazole onium group]methyl-3-cephalene- 4-carboxylic salt as intermediate by hydrolyzing it and reacting with alpha-(2-amino thiazole-4-radicle)-alpha-(Z)-methoxy imino acetic acid(benzo thiazole-2-radicle)hydrosulfate. The reacting condition is moderate, its raw materials can be obtained easily, and no expensive and strong irritant reagent is needed.

Description

technical field [0001] The invention belongs to the field of synthesis of cephalosporin antibiotics, and more specifically relates to a cephem onium salt compound and a preparation method thereof, and the compound is used as a raw material to prepare cephalosporin (-)-5-amino -2-[[(6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido]-2-carboxy-8-oxo Substituent-5-thia-1-azabicyclo[4.2.0]oct-2-enyl-3-yl]methyl]-1-(2-hydroxyethyl)-1H-pyrazolium inner salt, Monosulfate, i.e. the synthetic method of cefpirazole sulfate. Background technique [0002] The preparation of cefpirazole sulfate was once seen in the Chinese patent (88106644.3) and Japanese patent JP Ping 4-173792 reported by Sakane Kazuo and Kawazui Koji of Fujisawa Pharmaceutical Co., Ltd. in Japan. [0003] Chinese patent 88106644.3 uses 7-tert-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylic acid benzhydryl ester as the starting material, and is combined with 5-formylamino-1-(2 -Formyloxyethyl)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D201/04C07D501/48
Inventor 孟红赵平刘志友王学知齐斌
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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