64485-89-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (Z)-alpha-(methoxyimino)-2-(tritylamino)thiazol-4-acetate is used as a pharmaceutical intermediate for its potential role in the development of new drugs. Its unique structural features may offer novel therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, ethyl (Z)-alpha-(methoxyimino)-2-(tritylamino)thiazol-4-acetate serves as a key building block or reagent in the synthesis of more complex organic molecules. Its distinct functional groups can participate in various chemical reactions, facilitating the creation of new compounds with specific applications.

Upstream product

• 584-08-7 potassium carbonate 
• 66338-99-6 ethyl (Z)-2-hydroxyimino-2-(2-triphenylmethylaminothiazol-4-yl)acetate 
• 76-83-5 trityl chloride 
• 67-68-5 dimethyl sulfoxide 
• 74-88-4 methyl iodide 
• 65872-39-1 (Z)-γ-bromo-β-oxo-α-methoxyiminobutyric acid ethyl ester 
• 64485-88-7 ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate 

Downstream Products

• 63527-52-6 cefotaxime 
• 65052-63-3 cefetamet 
• 64485-90-1 2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid 
• 104146-53-4 7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt 
• 104146-13-6 p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3(E)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 138450-73-4 p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 138514-32-6 Pivaloyloxymethyl 7-<(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(E)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate 
• 117467-28-4 cefditoren pivoxil 

Relevant academic research and scientific papers

Synthesis and oral activity of pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)-(4-methylt hiazol-5-yl)vinyl-3-cephem-4 carboxylate (ME1207) and its related compound

7-[2-(2-Aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3(Z)-(4-methylth iazol-5-yl)vinyl-3-cephem-4-carboxylic acid (11, ME1206) and its 3-trans isomer (13) were prepared to test antibacterial activity. These compounds exhibited excellent antibacterial activity against both gram-positive and gram-negative bacteria, including β-lactamase producing strains. The pivaloyloxymethyl esters (12 and 14) of the compounds (11 and 13) were prepared by esterification with pivaloyloxymethyl iodide. Among them, pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)-(4-methylt hiazol-5-yl)vinyl-3-cephem-4-carboxylate (12, ME1207) showed good urinary recovery after oral administration in mice.

Cephalosporins

Compounds of the formula STR1 wherein R1 is hydrogen or a conventional amino-protecting group, and R2 is a straight or branched chain alkyl group containing from 1 to 4 carbon atoms, allyl, 2-butenyl or 3-butenyl, and nontoxic pharmaceutically acceptable salts and solvates thereof, as well as processes for their preparation, are disclosed. The compounds in which R1 is hydrogen are potent antibacterial agents.

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.