64485-90-1

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Cephalosporin derivatives.

InChI:InChI=1/C25H21N3O3S/c1-31-28-22(23(29)30)21-17-32-24(26-21)27-25(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3,(H,26,27)(H,29,30)/b28-22-

Upstream product

• 64485-88-7 ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate 
• 65872-41-5 cefotaxime 
• 76-83-5 trityl chloride 
• 64485-89-8 ethyl (Z)-2-(methoxyimino)-2-[2-(triphenylmethyl)-aminothiazol-4-yl]acetate 

Downstream Products

• 65052-63-3 cefetamet 
• 111540-31-9 4-styryl 3-<<(2-trityl-amino 4-thiazolyl)(methoxyimino)acetyl>amino> 2-azetidinone 
• 135587-52-9 (2R,2aR,7aS)-2-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-1-oxo-6-phenyl-2,2a-dihydro-1H,7H-3-thia-7b-aza-cyclobuta[e]indene-7a-carboxylic acid 
• 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 
• 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 
• 104112-35-8 N-((2S,3S)-2-Fluoromethyl-4-oxo-azetidin-3-yl)-2-[(Z)-methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetamide 
• 142466-80-6 trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido>-4-ethoxycarbonylmethyl-2-azetidinone 
• 142466-81-7 trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido>-4-t-butyloxycarbonylmethyl-2-azetidinone 
• 141992-85-0 trans-3-<2-(2-tritylaminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido>-4-(t-butyloxycarbonylmethylcarbamoylmethyl)-2-azetidinone 
• 143677-60-5 <4-bis<2Z-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetyl>amino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl>acetate de tert-butyle 
• 76470-69-4 (6R,7S)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 76470-70-7 (4S,6R,7S)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-4-methyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 117901-29-8 amino-2 N-<(hydroxy-4 phenyl)-1 oxo-2 azetidinyl-3> (methoxyimino)-α thiazolyl-4 acetamide (3-S) (Z) 
• 117901-28-7 amino-2 N-<(hydroxy-3 phenyl)-1 oxo-2 azetidinyl-3> (methoxyimino)-α thiazolyl-4 acetamide (3-S) (Z) 

Relevant academic research and scientific papers

Preparation method of triphenylmethyl aminothiazoly loximic acid

The invention belongs to the field of preparation of organic compounds, and particularly relates to a preparation method of triphenylmethyl aminothiazoly loximic acid, which comprises the following steps: 1, dissolving aminothiazoly loximic acid and diisopropylethylamine in dichloromethane, and dropwisely adding triphenylchloromethane to react to obtain a reaction solution; 2, adding an acidic solution into the reaction solution obtained in the step 1, adjusting to be acidic, separating the solution, and reserving an organic phase; 3, dropwise adding an alkaline solution into the organic phase in the step 2, filtering, and respectively leaching with dichloromethane and water to obtain precipitates; and 4, adding water into the precipitate obtained in the step 3, pulping, dropwise adding an acidic solution into the precipitate in the pulping process, adjusting to acidity, filtering, and drying to obtain the triphenylmethyl aminothiazoly loximic acid. By using the method provided by the invention, DMF is prevented from being used as a solvent, less waste is generated, the subsequent operation steps are simple, the yield of the obtained triphenylmethyl aminothiazoly loximic acid is greater than 94%, and the purity of the obtained triphenylmethyl aminothiazoly loximic acid is higher than 99%.

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.

Cephem compounds

There are provided new cephem compounds (synisomers) represented by the following general formula (I): STR1 wherein R1 means a lower group, R2 denotes an ester-forming group of the carboxyl group, and the 4-methylthiazolyl group and the cephem moiety are cis to each other relative to the carbon-carbon double bond of the substituted vinyl group in the side chain at the 3-position of the cephem nucleus. The cephem compounds exhibit strong antibacterial activities not only against resistant strains of bacteria and gram-negative bacteria but also against gram-positive bacteria and moreover have very low toxicity.

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.

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 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.

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.