64486-18-6

Usage

Chemical Properties

SLIGHTLY BEIGE TO YELLOWISH CRYSTALLINE POWDER

Upstream product

• 65872-41-5 cefotaxime 
• 79-04-9 chloroacetyl chloride 
• 65243-09-6 2-(2-aminothiazol-4-yl)-2-syn-methoxyiminoacetic acid methyl ester 
• 65243-10-9 methyl 2-(2-chloroacetamidothiazol-4-yl)-2-(syn)-methoxyiminoacetate 
• 64486-17-5 ethyl 2-(2-chloroacetamidothiazol-4-yl)-2-(syn)-methoxyiminoacetate 

Downstream Products

• 65872-41-5 cefotaxime 
• 64486-19-7 7β-[2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid 
• 94417-87-5 2-Chloroacetamido-4-<(Z)-1-methoxyimino-1-diphenylmethoxycarbonyl>methylthiazole N-Oxide 
• 72292-38-7 (6R*,7S*)-7-<2-(2-amino-4-thiazolyl)-2-syn-methoxyiminoacetamido>-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid 
• 79656-34-1 2-Choroacetamido-4-<(Z)-1-methoxyimino-1-diphenylmethoxycarbonyl>methylthiazole 

Relevant academic research and scientific papers

Process for the production of cefotaxime sodium

A process for the production of 7-[2-(2-amino-4-thiazolyl)-2-syn-methoxyimino-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (Cefotaxime) in aqueous isopropyl alcohol is provided. The synthesis provides the product in greater than 99 % HPLC purity.

Manufacture of cefalosporins and intermediates

There is described a process for the preparation of 3-disubstituted cepham-4-carboxylic acid derivatives of formula I wherein R″ is 4-methoxybenzyl, X is the residue of a thioether and Z is a residue of a nucleophilic compound and the conversion of these novel intermediates into the corresponding 3-cephem derivatives by oxidative cleavage of the mercaptan X-SH. By suitable deprotection, these 3-cephem derivatives afford cephalosporins such as ceftiofur, cefotaxime and ceftriaxone.

Process for producing chloroacetylaminothiazoleacetic acid derivatives

The present invention relates to a simple process for producing 2-aminothiazoleacetic acid derivatives useful as intermediates for producing cephalosporin-type antibiotics. The process for producing chloroacetylaminothiazoleacetic acid derivatives represented by the following formula (II) ???wherein R1 is a protection group for the hydroxyl group,comprises reacting aminothiazoleacetic acid derivatives represented by the following formula (I) ???wherein R1 is a protection group for the hydroxyl group,with a chloroacetylating agent.

Cephalosporin derivatives

Novel 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]cephalosporanic acid derivatives of the formula: STR1 wherein R1 NH is an amino group which may optionally be protected, R2 is a halogen atom or a hydroxyl, thiol or amino group which may optionally be substituted; COOR is a carboxyl group which may optionally be esterified, and pharmaceutically acceptable salts thereof, have excellent antimicrobial activity against a broad spectrum of microorganisms including Gram-negative bacteria such as Escherichia coli, Serratia marcescens, Proteus rettgeri, Enterobacter cloacae, Citrobacter freundii. Thus, these compounds may be used as antibacterial agents for therapeutic purposes.

7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido] cephalosporins

A 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido] cephalosporin derivative of the formula; STR1 wherein R3 is hydrogen or a residue of a nucleophilic compound; R2 NH is an amino group which may optionally be protected, pharmaceutically acceptable salt or ester thereof, is found to have excellent anti-bacterial activity against a broad spectrum of bacteria inclusive of gram-negative bacteria such as Escherichia coli, Serratia marcescens, Proteus rettgeri, Enterobacter cloacae and Citrobacter freundii. Thus, this compound may be used for an antibacterial agent in therapeutical purposes.

3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives

Compounds of the formula STR1 wherein R is hydrogen, R' is selected from the group consisting of alkenyl and alkynyl of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base and the OR' group is in the syn position having antibiotic activity and process for their preparation.

Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids

Novel alkyloximes of 7-amino-thiazolyl-acetamidocephalosporanic acids of the formula STR1 wherein R is selected from the group consisting of alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms and --CH2 --SR', R' is selected from the group consisting of acyl of an alkanoic acid of 2 to 4 carbon atoms, 1-methyl-tetrazolyl and 2-methyl-1,3,4-thiadiazolyl, R1 is selected from the group consisting of hydrogen and a group easily removeable by acid hydrolysis or hydrogenolysis, R2 is selected from the group consisting of alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen, an alkali metal cation, an equivalent of an alkaline earth metal or magnesium, an organic amine base cation and an ester group easily removeable by acid hydrolysis or hydrogenolysis with the proviso that when R1 is hydrogen, A is not an ester group easily removeable by hydrogenolysis or acid hydrolysis and the wavy line means that OR2 is in one or the other of the two possible syn or anti isomeric positions having a very good antibiotic activity and novel processes and intermediates for their preparation.

3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives

Compounds of the formula STR1 wherein R is selected from the group consisting of hydrogen and groups easily removable by acid hydrolysis or hydrogenolysis, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl and alkynyl of 2 to 4 carbon atoms and groups easily removable by acid hydrolysis or hydrogenolysis, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base with the proviso that when R' is a group easily removable by acid hydrolysis or hydrogenolysis, R is also and when R' is hydrogen, R also is hydrogen and the wavy line means the OR' group may be in either one of the two possible syn or anti positions having antibiotic activity and process for their preparation.