80951-91-3

Upstream product

• 123539-91-3 3-<<(2-amino-4-thiazolyl)-<<1-(diphenylmethoxycarbonyl)-1-methyl ethoxy>-imino>-acetyl>-amino>-4-methyl-2-oxoazetidi-ne-1-sulfonic acid 
• 330944-50-8 [3S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid 
• 80951-91-3 aztreonam 
• 7732-18-5 water 
• 80542-76-3 (Z)-2-Amino-α-[[2-(diphenylmethoxy)-1,1-dimethyl-2-oxoethoxy]-imino]-4-thiazoleacetic acid 
• 139714-26-4 (Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid diphenylmethyl ester methanesulfonate (1:1) salt 
• 139714-28-6 (Z)-2-[[[1-(2-amino-4-thiazolyl)-2-(3-oxido-1H-benzotriazol-1-yl)-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid methanesulfonate (1:1) salt 
• 80082-65-1 (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid 
• 477528-80-6 2-amino-4-[(1-carboxy-1-methyl-ethoxyimino)-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-methyl]-thiazol-3-ium methanesulfonate 
• 102507-85-7 2-amino-α-[(1-carboxy-1-methylethoxy)imino]-4-thiazoleacetic acid 
• 89604-92-2 (Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>-2-methyl propanoic acid 1,1-dimethylethyl ester 
• 86299-47-0 (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid 

Downstream Products

• 80951-91-3 aztreonam 

Relevant academic research and scientific papers

Novel crystal form of compound for treating bacterial infection and preparation method thereof

The invention belongs to the field of medicines, and discloses a new crystal form of a compound for treating bacterial infection and a preparation method thereof. Specifically, the invention discloses a new crystal form of an aztreonam compound and a preparation method thereof. The novel aztreonam crystal form disclosed by the invention is different from the prior art, and an X-ray powder diffraction pattern measured by using Cu-K alpha rays is as shown in Figure 1. According to the invention, the pH value is adjusted in sections after the purified water is added, so that the problem that triethylamine easily exceeds the standard is solved, and meanwhile, the novel aztreonam crystal form with good stability, low solvent residue and low impurity content is prepared and is suitable for industrial mass production.

Toward Orally Absorbed Prodrugs of the Antibiotic Aztreonam. Design of Novel Prodrugs of Sulfate Containing Drugs. Part 2

Aztreonam, first discovered in 1980, is an FDA approved, intravenous, monocyclic beta-lactam antibiotic. Aztreonam is active against Gram-negative bacteria and is still used today. The oral bioavailability of aztreonam in humans is less than 1%. Herein we describe the design and synthesis of potential oral prodrugs of aztreonam.

An improved method for the synthesis of Aztreonam

The invention provides an improved synthetic method of aztreonam. According to the improved synthetic method, alpha-(2-aminothiazole-4-yl)-alpha-[(tert-butoxycarbonyl)-propoxyimino)] acetic acid mercaptobenzothiazole ester, and (2S, 3S) 3-amino-2-methyl-4-oxoazetidine sulfonic acid are taken as reaction intermediates; an organic amine is used as a catalyst; and a mixed acid water solution of formic acid and an organic acid is used for removing tertiary butyl protecting group so as to obtain aztreonam. Separation of the intermediates is not necessary, operation is simple and convenient, deprotection method is mild, yield is high, and product purity is high.

AN IMPROVED PROCESS FOR THE PREPARATION OF MONOBACTAM ANTIBIOTIC

The present invention relates to the process for the preparation of monobactam antibiotic of formula (I). More particularly, the present invention relates to the preparation of Aztreonam of formula (I) from its precursor, tertiary butyl ester of Aztreonam of formula (II).

PROCESS FOR MAKING AZTREONAM

A simplified process for the one-pot preparation of aztreonam, using azetidine and TAEM as starting materials, without the intermediary separation of t-butyl-aztreonam is provided.

Stability of aztreonam in AZACTAM

The influence of temperature and relative humidity on the stability of aztreonam in AZACTAM was investigated. Changes of the concentration of aztreonam were followed using the HPLC method with UV detection. The first-order rate constants of the reversible reaction of isomerization Z-aztreonam ? E-aztreonam and the parallel reaction Z-aztreonam → products were determined at RH = 76.4% and T = 313, 323, 333, 343 and 353 K, and at T = 343 K and RH = 50.9%, 60.5%, 66.5% and 76.4%. The thermodynamic parameters-energy, enthalpy and entropy of these reactions were calculated.

PREPARATION OF AZTREONAM

The invention relates to a process for the synthesis of Aztreonam Specifically, the process entails hydrolyzing [3 S-[3α(Z),4β]]-3-[[(2-amino-4-thiazolyl)[(1-t-butoxycarbonyl-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-l-azetidinesulfonic acid (t-Bu Aztreonam) to form Aztreonam.

AZTREONAM β POLYMORPH WITH VERY LOW RESIDUAL SOLVENT CONTENT

The invention relates to the β polymorph of Aztreonam, which contains less than 2.5 % by weight residual solvent and to a process of making said polymorph.

Regioselective activation of aminothiazole(iminoxyacetic acid)acetic acid: An efficient synthesis of the monobactam aztreonam

An efficient synthesis of the monobactam aztreonam [[2S-[2α,3β(Z)]]-3[[(2-amino-4-thiazolyl)[(1-carboxy-1- methylethoxy)imino]acetyl]amino]-2-methyl-4-oxo-1-azetidinesulfonic acid] (1) by acylation of α-aminoazetidinone 22 with the regioselectively activated aminothiazoleiminoxyacetic diacid 15 or 18 is described. Reaction of benzhydryl ester 10 with N-hydroxy-benzotriazole and dicyclohexylcarbodiimide followed by ester deprotection formed the monoacid amide 15. Alternatively, chemoselective transient silylation of the diacid 9 followed by activation with N-hydroxysuccinimide formed active ester 18. Acylation of α-aminoazetidinone 22 with amide 15 or ester 18 produced aztreonam (1) in 75-85% yield.

Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains

Disclosed herein are processes for preparing a compound of the formula STR1 in which a novel compound of the formula STR2 is reacted with a beta lactam of the formula STR3 by treatment with a base, wherein the symbols are as defined in the specification.