1174020-25-7

Basic information

• Product Name: trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid
• Synonyms: (5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid;(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid;(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid;trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid
• CAS NO: 1174020-25-7
• Molecular Formula: C₁₄H₁₆N₂O₄
• Molecular Weight: 276.28784
• EINECS: -0
• Mol File: 1174020-25-7.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 509.9±39.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• PKA: 5.31±0.20(Predicted)
• CAS DataBase Reference: trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid(1174020-25-7)
• EPA Substance Registry System: trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid(1174020-25-7)

Safety Data

• Hazardous Substances Data: 1174020-25-7(Hazardous Substances Data)

Usage

General Description

Trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid is a compound that belongs to the class of carboxylic acids and bicyclic compounds. It has a trans-configuration and contains a benzyl ether and a ketone functional group, as well as a carboxylic acid moiety. trans-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid has potential pharmaceutical relevance, as it may have biological activity related to its structure and functionality.

Upstream product

• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 
• 1133931-68-6 (2S)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester 
• 1133931-74-4 (2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl ester 
• 1133931-73-3 benzyl (2S)-5-[(benzyloxy)imino]-2-{[(tert-butoxy)carbonyl]amino}-6-chlorohexanoate 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 1416134-47-8 ethyl (2R,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate 
• 1416134-47-8 ethyl (2R)-5-((benzyloxy)amino)piperidine-2-carboxylate 
• 144978-12-1 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 1463501-46-3 (2S,5S)-1-(tert-butyl) 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate 
• 1192650-82-0 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid benzyl ester 
• 1171080-45-7 (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt 
• 695183-75-6 (2S,5S)-5-hydroxypiperidin-2-carboxylic acid methyl ester 
• 63088-78-8 (2S,5R)-5-hydroxypiperidine-2-carboxylic acid 

Downstream Products

• 1383814-59-2 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester 
• 1192651-49-2 (1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1383814-64-9 (2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1192650-82-0 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid benzyl ester 
• 1383814-58-1 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester 
• 1383814-60-5 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester 
• 1471298-01-7 (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471298-12-0 tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate 
• 1471298-14-2 (2S,5R)-6-(benzyloxy)-2-(3-(piperidin-4-yl)-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471298-16-4 (9H-fluoren-9-yl)methyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate 
• 1174020-89-3 (2S,5R)-6-(benzyloxy)-N-[2-(dimethylamino)pyridin-4-yl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1174021-13-6 tert-butyl-(3R,4S)-4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)-3-fluoropiperidine-1-carboxylate 
• 1174020-87-1 (2S,5R)-6-(benzyloxy)-N-(2-methoxypyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1174020-69-9 tert-butyl (4S)-4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylate 

Relevant articles and documents

Discovery of ANT3310, a Novel Broad-Spectrum Serine β-Lactamase Inhibitor of the Diazabicyclooctane Class, Which Strongly Potentiates Meropenem Activity against Carbapenem-Resistant Enterobacterales and Acinetobacter baumannii

The diazabicyclooctanes (DBOs) are a class of serine β-lactamase (SBL) inhibitors that use a strained urea moiety as the warhead to react with the active serine residue in the active site of SBLs. The first in-class drug, avibactam, as well as several other recently approved DBOs (e.g., relebactam) or those in clinical development (e.g., nacubactam and zidebactam) potentiate activity of β-lactam antibiotics, to various extents, against carbapenem-resistant Enterobacterales (CRE) carrying class A, C, and D SBLs; however, none of these are able to rescue the activity of β-lactam antibiotics against carbapenem-resistant Acinetobacter baumannii (CRAB), a WHO "critical priority pathogen"producing class D OXA-type SBLs. Herein, we describe the chemical optimization and resulting structure-activity relationship, leading to the discovery of a novel DBO, ANT3310, which uniquely has a fluorine atom replacing the carboxamide and stands apart from the current DBOs in restoring carbapenem activity against OXA-CRAB as well as SBL-carrying CRE pathogens.

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 FORMS OF DIAZABICYCLOOCTANE DERIVATIVE AND PRODUCTION PROCESS THEREOF

A crystalline form of a diazabicyclooctane derivative represented by the following Formula (VII), and processes for producing the same: