1463501-46-3Relevant academic research and scientific papers
MODULATORS OF THE INTEGRATED STRESS RESPONSE PATHWAY
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Page/Page column 57; 58, (2020/12/30)
The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts, solvates, hydrates, tautomers or stereoisomers thereof, wherein R1, R2, R2a, R3, Ra2, Ra4, R
Use of Lipase Catalytic Resolution in the Preparation of Ethyl (2 S,5 R)-5-((Benzyloxy)amino)piperidine-2-carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam
Wang, Tao,Du, Liang-Dong,Wan, Ding-Jian,Li, Xiang,Chen, Xin-Zhi,Wu, Guo-Feng
, p. 1738 - 1744 (2018/12/11)
Here we describe an efficient and cost-effective chemoenzymatic synthesis of the β-lactamase inhibitor avibactam starting from commercially available ethyl 5-hydroxypicolinate hydrochloride. Avibactam was synthesized in 10 steps with an overall yield of 23.9%. The synthetic route features a novel lipase-catalyzed resolution step during the preparation of (2S,5S)-ethyl 5-hydroxypiperidine-2-carboxylate, a valuable precursor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. Our synthetic route was used to produce 400 g of avibactam sodium salt.
B-LACTAMASE INHIBITOR AND APPLICATION THEREOF
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Paragraph 0097; 0098, (2018/03/07)
The present invention relates to a compound of Formula (I)-(IV) useful as β-lactamase inhibitor, a pharmaceutically acceptable salt, ester, solvate or stereoisomer thereof, wherein R1, R2, M and ring A have definitions as those in the specification. The present invention further relates to methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and uses of these compounds. For example, the compounds of the present invention can be used as β-lactamase inhibitors, for treatment and/or prophylaxis of diseases caused by bacterial infections, solving drug-resistance problems caused by β-lactamases, especially bacterial drug-resistant diseases caused by type B metallo-β-lactamases.
A synthesis method of avey batanbatan sodium (by machine translation)
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, (2018/07/30)
The invention discloses a method for synthesizing avey batanbatan sodium. The current method for synthesizing method, the production cost is higher; intermediate reduction of low selectivity, leading to reduced yield; at the same time the reaction by-products created in toxicity is relatively large, not friendly to the environment and other factors also limits the large-scale production. The invention relates to 5 - hydroxy - 2 - pyridine carboxylic acid ethyl ester as the starting material, reduction and hydrogenation, biological lipase split, electrophilic addition, nucleophilic substitution, de-Boc, aminolysis, intramolecular immortal, debenzylation, sulfonic ester, salt and cation exchange a total of 11 obtain avey batanbatan sodium. Synthesis method of the invention has high yield, route is brief, mild reaction conditions, small pollution to the environment, it is easy to large-scale preparation and the like. (by machine translation)
RETRACTED ARTICLE: A New Synthetic Route to Avibactam: Lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation
Wang, Tao,Du, Liang-Dong,Wan, Ding-Jian,Li, Xiang,Chen, Xin-Zhi,Wu, Guo-Feng
, p. 267 - 272 (2018/03/22)
An efficient synthesis of avibactam starting from commercially available ethyl-5-hydroxypicolinate was completed in 10 steps and 23.9% overall yield. The synthesis features a novel lipase-catalyzed resolution, in the preparation of (2S,5S)-5-hydroxypiperidine-2-carboxylate acid, which is a valuable precusor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. An optimized one-pot debenzylation/sulfation reaction, followed by cation exchange, gave the avibactam sodium salt on a 400.0 g scale.
Preparation method of Avibactam intermediate
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Paragraph 0068; 0069; 0070, (2017/07/19)
The invention relates to a preparation method of an Avibactam intermediate. The intermediate is (1R, 2S, 5R)-6-benzyloxy-7-oxo-1,6-diazacyclo[3.2.1]octane-2-methanamide. The method is easy to implement; total yield is high; purity of the product obtained is high; and the product is easy to purify.
Production method for diazabicyclooctane derivative and intermediary body thereof
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, (2016/10/08)
The present invention provides a production method for a diazabicyclooctane derivative expressed by formula (IV), and an intermediary body thereof (in the formula: P is an acid-removable NH protective group; R1 represents a 2, 5-dioxopyrrolidine-1-yl, a 1, 3-dioxo-3a, a 4, 7, 7a-tetrahydro-1H-isoindole-2(3H)-yl, a 1, 3-dioxohexahydro-1H-isoindole-2(3H)-yl, or a 3, 5-dioxo-4-azatricyclo[5.2.1.02, 6]deca-8-en-4-yl; R2 represents hydrogen, C1CO-, or C13COCO-, R3 represents a C1-6 alkyl or a heterocyclyl, or joins with a bonded -O-NH- to form a 3-7 member heterocyclyl ring; and OBn represents a benzyloxy).
CRYSTALLINE FORM OF A BETA-LACTAMASE INHIBITOR
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, (2014/09/29)
This disclosure provides compositions containing solid forms of sodium (2S,5R)-2-(1,3,4-oxadiazol-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate, and methods of manufacturing and using these compositions.
1,2,4-OXADIAZOLE AND 1,2,4-THIADIAZOLE BETA-LACTAMASE INHIBITORS
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, (2013/11/06)
β-Lactamase inhibitor compounds (BLIs) are disclosed, including compounds that have activity against class A, class C or class D β-lactamases. Methods of manufacturing the BLIs, and uses of the compounds in the preparation of pharmaceutical compositions and antibacterial applications are also disclosed.
BETA-LACTAMASE INHIBITORS
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, (2013/11/19)
Aryl substituted diazabicyclooctanes (DBO) compounds that inhibit β-lactamases of class A, class C or class D and potentiate β-lactam antibiotics are disclosed. In particular, this disclosure provides DBO compounds that, when used in the disclosed Synergy MIC Assay with a β-lactam antibiotic at a fixed concentration have an MIC of 8 μg/mL or less against one or more isogenic β-lactamase expressing bacterial strains.
