Solid-phase synthesizing method of ceftriaxone sodium

A technology of ceftriaxone sodium and solid-phase synthesis, which is applied in the field of chemical pharmacy, can solve the problems of low total yield, cumbersome operation, and poor purity, and achieve the effects of improving production efficiency, simplifying reaction procedures, and reducing losses

Active Publication Date: 2017-01-11
SHANGHAI NEW ASIA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention aims to overcome the above-mentioned defects, aiming at the technical problems of low total yield, poor purity and cumbersome operation in the process of preparation of ceftriaxone sodium, a preparation method and convenient post-treatment are provided, and the operation is simple, and A method for solid-phase synthesis of ceftriaxone sodium with higher yield and a purity of not less than 99.5%

Method used

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  • Solid-phase synthesizing method of ceftriaxone sodium
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  • Solid-phase synthesizing method of ceftriaxone sodium

Examples

Experimental program
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Effect test

Embodiment 1

[0065] Example 1: Bridging of 7-ACA and solid phase carrier

[0066]

[0067] In the glazed glass column, react 25g 7-ACA and 100g chloromethyl resin in 100ml DMF, TLC detects that there is no raw material residue, so that it is fully bridged with the solid phase carrier, and after the reaction is completed, use N 2 (Gas such as argon, air, helium) stream to remove solvent, then wash the resin successively with 100ml of dichloromethane and pyridine (or chloroform, toluene and other solvents) respectively, and directly carry out the next step reaction.

[0068] In Embodiment 1, the chloromethyl resin can also be replaced by polystyrene-styrene divinyl cross-linked resin, polyacrylamide, polyethylene-glycol resin, carboxyl resin, amino resin, hydrazide resin, and the like.

[0069] According to the functional group difference of the resin, the dosage ratio of 7-ACA and resin was adjusted. For example: when polystyrene and polyethylene resins are used, the dosage of 7-ACA is ...

Embodiment 2

[0072] Embodiment two: prepare the ceftriaxone of solid phase bridging

[0073]

[0074] A. In the glazed glass column, add 30g of 6-hydroxy-3-mercapto-2-methyl-1,2,4-triazin-5-one in acetonitrile (just completely dissolved state) solution, and heat under nitrogen protection To 50°C, add 56g of catalyst boron trifluoride and react for 2h under stirring. After the reaction is completed, use N 2 (Gas such as argon, air, helium) stream to remove solvent, then wash the resin successively with 100ml of dichloromethane and pyridine (or chloroform, toluene and other solvents) respectively, and directly carry out the next step reaction.

[0075] In this step, 6-hydroxy-3-mercapto-2-methyl-1,2,4-triazin-5-one can also be replaced by a triazine compound with other sulfur-containing leaving groups at the 3-position ,like:

[0076] X: It is a leaving group with structures such as chlorine, iodine, bromine, ester group, and acid halide group.

[0077] The amount of the triazine com...

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Abstract

The invention provides a solid-phase synthesizing method of ceftriaxone sodium. The solid-phase synthesizing method is characterized by including: bridging raw material A to a solid-phase carrier, performing substitution and acylation reactions, and separating from the solid-phase carrier to obtain the ceftriaxone sodium. By using the solid-phase synthesizing method of the ceftriaxone sodium, the post-processing process after the reactions can be omitted, the reaction procedures are simplified greatly, product loss during the post-processing is lowered, the total yield of the reactions is increased to 90% and above, the purity of the ceftriaxone sodium is increased to 99.5% and above, and production benefits are increased.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a solid-phase synthesis method of ceftriaxone sodium. [0002] Background technique: [0003] Ceftriaxone sodium, chemical name [6R[6α,7β(Z)]]-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1 ,2,4-triazin-3-yl)thio]methyl]-7-[[(2-amino-4-thiazolyl](methoxyimino)acetyl]amino]-8-oxo- 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid disodium salt triple hemihydrate, the structural formula is: [0004] [0005] Ceftriaxone sodium is a long-acting antibiotic drug among the third-generation cephalosporins. It has bactericidal effects on many Gram-positive bacteria, negative bacteria and anaerobic bacteria, and it is effective on most β-lactams produced by bacteria The enzyme is highly stable, which enhances its antibacterial effect. Clinically, it is widely used in respiratory tract infection, urinary system infection (including pyelonephritis and gonorrhea), meningit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36
CPCC07D501/36
Inventor 胡国栋崔万胜管海英郝惠庆商鼎
Owner SHANGHAI NEW ASIA PHARMA
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