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Derivant of cephalosporin of amidinothioacetamide, preparation method and application

A cephalosporin, cephalosporanic acid technology, applied in the direction of pharmaceutical formulations, antibacterial drugs, medical preparations containing active ingredients, etc.

Active Publication Date: 2007-05-16
GUANGZHOU BAIYUNSHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention selects commercially feasible N, the N disubstituted thiourea reacts with the cephalosporin nuclei that the C-3 position is a halogen, and the C-3 halogen substituting group used in the compound of the present invention, especially chlorine, is well known in the field of cephems, However, it has not been combined with the C-7 substituent in the present invention before

Method used

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  • Derivant of cephalosporin of amidinothioacetamide, preparation method and application
  • Derivant of cephalosporin of amidinothioacetamide, preparation method and application
  • Derivant of cephalosporin of amidinothioacetamide, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of intermediate 7-bromoacetamido-3-chloro-3-cephem-4-carboxylic acid

[0054] 2.34g7-amino-3-chloro-3-cephem-4-carboxylic acid (7-ACCA) was added to 30mlH 2 O, and then add 30ml of toluene. Stir in an ice-water bath, and when the temperature drops to 0-5°C, slowly add 1.4ml of triethylamine dropwise, and the 7-amino-3-chloro-3-cephem-4-carboxylic acid in the system is completely dissolved. Then add bromoacetyl bromide dropwise in batches, first add 0.8ml bromoacetyl bromide dropwise, stir rapidly, raise the temperature to 25-30°C, and add NaHCO dropwise at the same time 3 solution (5%) until the system is completely clear; after 20 minutes, add 0.3ml bromoacetyl bromide dropwise, and add NaHCO dropwise at the same time 3 solution (5%) until the system is completely clear. After reacting for 2 hours, the water phase was separated, and the pH of the water phase was adjusted to 1.0-1.5 with 6 mol / l hydrochloric acid, and a large amount of precipitation was p...

Embodiment 2

[0059] Preparation of intermediate 7-bromoacetamido-3-chloro-3-cephem-4-carboxylic acid

[0060] First add 2.34g of 7-amino-3-chloro-3-cephem-4-carboxylic acid to 30mlH 2 O, then add 30ml CH 2 Cl 2 . Stir in an ice-water bath, and when the temperature drops to 0-5°C, slowly add 1.15ml of tetramethylguanidine dropwise, and the 7-amino-3-chloro-3-cephem-4-carboxylic acid in the system is completely dissolved. Then add bromoacetyl bromide dropwise in batches, first add 0.8ml bromoacetyl bromide dropwise, stir rapidly, raise the temperature to 25-30°C, and at the same time add triethylamine dropwise until the system is completely clear; after 20 minutes, add 0.3ml bromoacetyl bromide dropwise Bromine, while adding triethylamine dropwise until the system is completely clear. After reacting for 2 hours, the water phase was separated, and the pH of the water phase was adjusted to 1.0-1.5 with 6 mol / l hydrochloric acid, and a large amount of precipitation was precipitated. After ...

Embodiment 3

[0065] Preparation of intermediate 7-bromoacetamido-3-chloro-3-cephem-4-carboxylic acid

[0066] First add 2.34g of 7-amino-3-chloro-3-cephem-4-carboxylic acid to 30mlH 2 O, then add 30ml acetone. Stir in an ice-water bath, and when the temperature drops to 0-5°C, add 0.75ml of ammonia water (25%), and the 7-amino-3-chloro-3-cephem-4-carboxylic acid in the system is completely dissolved. Then add bromoacetyl bromide dropwise in batches, first add 0.8ml bromoacetyl bromide dropwise, stir rapidly, raise the temperature to 25-30°C, and at the same time add diethylamine dropwise until the system is completely clear; after 20 minutes, add 0.3ml bromoacetyl bromide dropwise bromine, while adding diethylamine dropwise until the system is completely clear. After reacting for 2 hours, the water phase was separated, and the pH of the water phase was adjusted to 1.0-1.5 with 6 mol / l hydrochloric acid, and a large amount of precipitation was precipitated. After growing crystals in an i...

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Abstract

A C-3 chloroonium salt type cephalophytanic acid derivative or its pharmacologically acceptable salt is disclosed, which has high antibacterial activity to G+ bacterium and a certain antibacterial activity to enterococcus and G- bacterium. It is prepared by the reaction between 7-amino C-3 chloro 4-carboxyl cephalophytanic acid (7-ACCA) and bromoacetyl bromine or N,N bisubstituted thiourea.

Description

technical field [0001] The present invention relates to new cephalosporins, especially a new therapeutically active 7-amidinethioacetamide cephalosporin, its synthesis method and application. Background technique [0002] Cefaclor, in which methylene acetoxy is replaced by a chlorine atom at the 3-position of 7-ACA carbon, is the only unique structure among cephalosporins. The excellent antibacterial activity of cefaclor: including broad antibacterial spectrum, strong antibacterial activity, relatively stable to β-lactamase, pharmacokinetics, wide tissue distribution in vivo and high blood concentration, etc., making it the second-generation drug. Even the third-generation oral pharmacological efficacy and reference drugs for clinical evaluation. [0003] Cefaclor anti-G+ is the same or stronger than the first-generation cephalosporins such as cephalexin and cefadroxil, anti-G- is stronger than the first-generation cephalosporins, but G- including Serratia spp. aeruginosa a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/20C07D501/06A61K31/545A61P31/04
Inventor 罗春刘学斌黄敏康许淑文李宁张小娜
Owner GUANGZHOU BAIYUNSHAN PHARM CO LTD