- DERIVATIZATION OF BETA-LACTAM ANTIBIOTICS AS CALIBRATORS/ISTD IN MASSSPEC MEASUREMENTS
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The invention relates to a complex comprising an antibiotic substance and a nucleophilic derivatization reagent, compositions comprising the complex, kits comprising complex or composition, as well as uses of the complex or composition.
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Page/Page column 3; 37-38
(2021/05/21)
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- Meropenem side chain intermediate and method for preparing same
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The invention relates to a meropenem side chain intermediate and a method for preparing the same, and belongs to the technical field of medicinal chemistry. The meropenem side chain intermediate and the method have the advantages that the requirements of
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Paragraph 0048-0050; 0055-0057
(2019/01/23)
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- A luer Ertapenem, luer he lateral chain and its preparation method
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The invention discloses ertapenem and ertapenem side chains, as well as preparation methods of ertapenem and ertapenem side chains. L-hydroxyproline is protected by p-nitrobenzyl ester to obtain (2S,4R)-4-hydroxyl-1-(((4-Nitrobenzformyl)-oxyl)caboyl)pyrrolidine-2-carboxylic acid; then 4-nitro(1S,4S)-3-oxo-2-thia-5-azabicyclo[2.2.1]heptan-5-carboxylic anhydride can be obtained, and reacts with m-aminobenzoic acid p-nitrobenzyl ester to obtain ertapenem side chain III; and the ertapenem can be synthesized through two-step chemical reaction of condensation and deprotection to the ertapenem side chain III and a raw material MAP. An ertapenem side chain I (10), an ertapenem side chain II (13) and the ertapenem side chain III (2) which are prevailing in the market can be synthesized through simple steps, without the need of ultralow temperature, industrialization is easy, and the product purity is high, and the operation is simple and convenient.
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Paragraph 0123; 0124; 0125
(2017/07/14)
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- Selective Inhibition of an Apicoplastic Aminoacyl-tRNA Synthetase from Plasmodium falciparum
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The resistance of malaria parasites to available drugs continues to grow, and this makes the need for new antimalarial therapies pressing. Aminoacyl-tRNA synthetases (ARSs) are essential enzymes and well-established antibacterial targets and so constitute
- Hoen, Rob,Novoa, Eva Maria,López, Alba,Camacho, Noelia,Cubells, Laia,Vieira, Pedro,Santos, Manuel,Marin-Garcia, Patricia,Bautista, Jose Maria,Cortés, Alfred,Ribas de Pouplana, Lluís,Royo, Miriam
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p. 499 - 509
(2013/05/09)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF MEROPENEM
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The present invention provides an improved process for the preparation of methyl carbapenem derivative of formula (I) or its pharmaceutically acceptable salts or hydrates thereof in a pure form.
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Page/Page column 7-9
(2011/12/02)
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- A PROCESS FOR THE PREPARATION OF THE INTERMEDIATE OF Β-METHYL CARBAPENEM
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A process of preparation of the intermediate of β-methyl carbapenem is disclosed, in which 4-acetylazacyclobutanone as the raw material is firstly reacted with α-bromopropionamide having a big inductive group. Since this reaction is highly stereoselectivity, most of the product is the required parent nucleus of β-methyl carbapenem, a product of β-configuration. Compared with the prior art, the process of the present invention is highly-yielding, cost-effective and can be used for large scale production.
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Page/Page column 15-16
(2010/11/28)
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- A PROCESS FOR THE PREPARATION OF MEROPENEM
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The invention relates to a process for the preparation of meropenem, a β-methylcarbopenem. The said process comprises the following steps: preparing the compound of Formula (XI) from the compound of Formula (IV) through three steps "one-pot process"; then condensing the compound of Formula (XI) with the compound of Formula (XX) to form the compound of Formula (XXIV); finally preparing meropenam of Formula (I) from the compound of Formula (XXIV) by deprotection reaction by means of catalyst. The process of the invention is easily to carry out, the product is isolated in high content and yield, and the cost is reduced, thereby overcoming the shortage of the prior art.
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Page/Page column 18
(2010/11/28)
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- Practical large-scale synthesis of the 2-aminomethylpyrrolidin-4-ylthio-containing side chain of the novel carbapenem antibiotic doripenem
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The first synthesis using an original procedure and a practical large-scale process using an improved procedure for the synthesis of the N-PNZ-protected 2-aminomethylpyrrolidin-4-ylthio-containing side chain of doripenem hydrate (S-4661), a novel parenteral 1β-methylcarbapenem antibiotic, are described, trans-4-Hydroxy-L-proline (4) was converted in an efficient process to (2S,4S)-4-acetylthio-2-(N-sulfamoyl-tert-butoxycarbonylaminomethyl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3) in 55-56% overall yield via a six-step sequence, which includes the two alternative routes to intermediate 13. This process requires no chromatographic purifications, no cryogenic temperatures, no haloalkane solvents, and short operating times and is amenable to a multikilogram-scale preparation. Several kilograms of the side chain 3 were successfully prepared by this process.
- Nishino, Yutaka,Komurasaki, Tadafumi,Yuasa, Tetsuya,Kakinuma, Makoto,Izumi, Kenji,Kobayashi, Makoto,Fujiie, Shinichiro,Gotoh, Teruhiro,Masui, Yoshiyuki,Hajima, Makoto,Takahira, Masayuki,Okuyama, Akira,Kataoka, Takahiro
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p. 649 - 654
(2013/09/05)
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- Synthesis and antibacterial activity of new carbapenems containing isoxazole moiety
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The synthesis and biological activity of a series of new 1β- methylcarbapenems 1a-g containing 5'-isoxazolopyrrolidin-3'-ylthio derivatives as C-2 side chain are described. Most compounds exhibited potent and well-balanced antibacterial activity as well as high stability to DHP-I comparable to that of meropenem. 1e and 1c showed the best combination of antibacterial activity and stability to DHP-I, respectively.
- Kang, Yong Koo,Shin, Kye Jung,Yoo, Kyung Ho,Seo, Kyung Jae,Hong, Chang Yong,Lee, Chang-Seok,Park, Seung Yong,Kim, Dong Jin,Park, Sang Woo
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- Synthesis and antibacterial activity of 1β-methylcarbapenem having a 1,3-diazabicyclo[3.3.0]octan-4-one moiety, Part II
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The synthesis of a new series of 1β-methylcarbapenems having a 1,3- diazabicyclo[3.3.0]octan-4-one moiety is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria are tested and the effect of substituent on the bicyclic ring was investigated. A particular compound (11h) having aminoethyl group showed the most potent antibacterial activity.
- Oh, Chang-Hyun,Lee, Seung Chan,Park, Sung-Jin,Lee, In-Kyu,Nam, Ki Hong,Lee, Ki-Soo,Chung, Bong-Young,Cho, Jung-Hyuck
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p. 111 - 114
(2007/10/03)
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- An unexpected Mitsunobu reaction. A direct route to the 2,5-diazabicyclo[2.2.1]heptan-3-one skeleton as a γ-lactam mimic of β-lactam antibiotics
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Treatment of anilides of N-protected (2S,4R)-4-hydroxyproline, e.g. 1, with thioacetic acid under Mitsunobu conditions gives, unexpectedly, 2,5-diazabicyclo[2.2.1]heptan-3-ones, e.g. 2, the products of intramolecular cyclisation. However, the less acidic N-benzylamides of these proline derivatives, e.g. 7, are not sufficiently acidic and the hydrazido anion generated in the Mitsunobu reaction displaces the activated hydroxy group in an intermolecular reaction to give 8. The bicyclic γ-lactams are potential analogues of the β-lactam antibiotics and suitable derivatives 9, 10,11 and 12 are found to be competitive inhibitors of class A and C β-lactamases, with Ki as low as 70 μM.
- Hadfield, Peter S.,Galt, Ron H. B.,Sawyer, Yvonne,Layland, Nicola J.,Page, Michael I.
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p. 503 - 509
(2007/10/03)
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- Aminothiazole substituted penicillins and antibacterial compositions thereof
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The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof: STR1 wherein R1 is hydrogen or an amino protecting group and R is substituted methyl; optionally substituted C2-12 alkyl, alkenyl or alkynyl; carbocyclyl; aryl or heterocyclyl. These compounds have antibacterial properties, and therefore are of use in the treatment of bacterial infections in humans and animals caused by a wide range of organisms.
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