1463501-45-2

Upstream product

• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 77925-80-5 N-(2-Nitrophenylsulfonyl)-O-(phenylmethyl)hydroxylamine 
• 208519-98-6 (S)-ethyl 2-(((tert-butoxy)carbonyl)amino)-6-diazo-5-oxohexanoate 
• 1416134-58-1 ethyl (S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ⁶-sulfanylidene)-5-oxohexanoate 

Downstream Products

• 1192651-49-2 (1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1471297-86-5 (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1471297-88-7 (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1174020-25-7 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 
• 1463501-48-5 (2S,5R)-6-(benzyloxy)-2-(hydroxymethyl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1463501-50-9 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde 
• 1471297-34-3 (2S,5R)-5-(N-(benzyloxy)-(2-nitrophenyl)sulfonamido)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acid 
• 1471297-48-9 (3R,6S)-6-(1,2,4-oxadiazol-3-yl)piperidin-3-yl(benzyloxy)carbamic chloride 
• 1471297-50-3 (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471297-60-5 (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1416134-63-8 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester 
• 1471297-71-8 (2S,5R)-tert-butyl 2-(5-(1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidin-4-yl)-1,2,4-oxadiazol-3-yl)-5-(benzyloxyamino)piperidine-1-carboxylate 
• 1471297-75-2 (9H-fluoren-9-yl)methyl 4-(3-((2S,5R)-5-(benzyloxy(chlorocarbonyl)amino)piperidin-2-yl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate 
• 1471297-77-4 (9H-fluoren-9-yl)methyl 4-(3-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate 

Relevant academic research and scientific papers

B-LACTAMASE INHIBITOR AND APPLICATION THEREOF

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.

CRYSTALLINE FORM OF A BETA-LACTAMASE INHIBITOR

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

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.

1,3,4-OXADIAZOLE AND 1,3,4-THIADIAZOLE BETA-LACTAMASE INHIBITORS

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.

ISOXAZOLE β-LACTAMASE INHIBITORS

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

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.