- Novel crystal form of compound for treating bacterial infection and preparation method thereof
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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.
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Paragraph 0038
(2021/04/14)
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- Toward Orally Absorbed Prodrugs of the Antibiotic Aztreonam. Design of Novel Prodrugs of Sulfate Containing Drugs. Part 2
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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.
- Ding, Pingyu,Duncton, Matthew A. J.,Fan, Dazhong,Gordon, Eric M.,Grygorash, Ruslan,Li, Xianfeng,Low, Eddy,Ni, Zhi-Jie,Qi, Longwu,Sun, Jiawei,Wang, Brian J.,Yu, Guijun
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supporting information
p. 162 - 165
(2020/01/31)
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- An improved method for the synthesis of Aztreonam
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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.
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Paragraph 0029
(2017/01/05)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF MONOBACTAM ANTIBIOTIC
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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).
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Page/Page column 8-9
(2008/06/13)
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- PROCESS FOR MAKING AZTREONAM
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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.
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Page/Page column 7
(2008/06/13)
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- AZTREONAM β POLYMORPH WITH VERY LOW RESIDUAL SOLVENT CONTENT
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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.
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- PREPARATION OF AZTREONAM
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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.
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- Regioselective activation of aminothiazole(iminoxyacetic acid)acetic acid: An efficient synthesis of the monobactam aztreonam
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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.
- Singh, Janak,Denzel, Theodor W.,Fox, Rita,Kissick, Thomas P.,Herter, Rolf,Wurdinger, Joseph,Schierling, Peter,Papaioannou, Chris G.,Moniot, Jerome L.,Mueller, Richard H.,Cimarusti, Christopher M.
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p. 863 - 868
(2013/09/06)
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- Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains
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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.
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- Crystalline anhydrous aztreonam
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The crystalline anhydrous form of [3S-[3α(Z), 4β]]-3-[[(2-amino-4-thiazolyl) [(1-carboxy-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid is prepared.
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- Heteroaroylhydrazide derivatives of monocyclic beta-lactam antibiotics
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Compounds having the formula STR1 and pharmaceutically acceptable salts thereof and possessing antibacterial activity, and intermediates to compounds of formula I having the formula
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- Delta form of aztreonam and preparation thereof
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The crystalline delta(δ)-form of [3S-[3α(Z),-4β]]-3-[[(2-amino-4-thiazolyl) [(1-carboxy-1-methylethoxy)imino]acetyl]amino]-4-methyl-2-oxo-1-azetidinesulfonic acid is prepared.
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- 2-OXO-1-AZETIDINESULFONIC ACID SALTS
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Antibacterial activity is exhibited by beta-lactams having a sulfonic acid salt substituent in the 1-position and an amino or acylamino substituent in the 3-position.
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- Copper-mediated oximation reaction
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The presence of a copper salt during the oximation of a β-lactam containing compound having glyoxylamino substituents of the formula STR1 by reaction with an aminooxy compound having the formula or a salt or ester thereof, results in a product wherein the ratio of syn isomer to anti isomer is increased.
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- MONOBACTAMS: RING ACTIVATING N-1-SUBSTITUENTS IN MONOCYCLIC &β-LACTAM ANTIBIOTICS
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Several alternatives to the sulfonate residue in the naturally-occurring monobactams, 3-acylamino-2-oxoazetidine-1-sulfonates, provide new monobactams having potent activity against aerobic gram-negative bacteria.The monobactams compared here include: (a) those where the anionic activating group (sulfonate or phosphonate(-inate)) is attached to the β-lactam nitrogen, and (b) those where an oxygen atom is interposed between the acidic group and the β-lactam nitrogen, i.e. sulfate and phosphate(-onate) groups.Chemical and biological relationships between these classesof monobactams are presented.
- Slusarchyk, William A.,Dejneka, Tamara,Gordon, Eric M.,Weaver, Eugene R.,Koster, William H.
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p. 191 - 210
(2007/10/02)
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