Processes for preparing a diazabicyclooctane compound
Inventors
Abe, Takao • Furuuchi, Takeshi • Sakamaki, Yoshiaki
Assignees
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Publication Number
US-11731971-B2
Publication Date
2023-08-22
Expiration Date
Abstract
A process for preparing a diazabicyclooctane compound represented by the following formula (I): wherein A represents RcO—; B represents NH or NC1-6 alkyl; C represents a benzyl group; Rc represents a C1-6 alkyl group; A is substituted with one substituent Fn1, wherein Fn1 represents an azetidine group; the process including: (a) silylating the compound represented by the following formula (IV-c): wherein in the formula (IV-c), OBn represents benzyloxy, and (b) carrying out an intramolecular urea formation reaction.
Core Innovation
The invention relates to diazabicyclooctane derivatives defined by a formula selected from a group of chemical formulae, with OMe representing a methoxy group and OBn representing a benzyloxy group. The disclosure provides compounds defined by chemical formulae and includes structural examples and embodiments within the bicyclic diamide scaffold framework, together with salts, protected intermediates, and variable substituent and protection patterns.
The disclosed subject matter includes sulfooxy diazabicyclooctane carboxamide derivatives and related sulfooxy or sulfonated forms, including stereochemically defined embodiments such as (2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide and related oxy-linked side-chain variants. The material also describes hydrazide, carbohydrazide, carboxamide, piperidine-2-carboxamide, and piperidine-2-carboxylic acid derivatives, including benzyloxyamino-bearing compounds and related intermediates and formula members within the disclosed families.
The document further includes biological assay sections for beta-lactamase inhibitory activity and synergistic activity of the synthesized compounds. The compounds are evaluated against beta-lactamases and in combination contexts described by the document, including nitrocefin and named enzyme targets such as AmpC, TEM-1, KPC-2, and OXA-2, alongside tazobactam and other comparison agents.
Claims Coverage
The consolidated claim coverage centers on compounds selected from a group of chemical formulae, with explicit meanings assigned to OMe as a methoxy group and OBn as a benzyloxy group. Across the provided claims, the inventive features repeatedly refine the same formula-defined scope by specifying particular depicted structures and by reiterating the OMe/OBn meanings.
Formula-defined compounds with methoxy and benzyloxy group meanings
A compound selected from a group consisting of chemical formulae, wherein OMe represents a methoxy group and OBn represents a benzyloxy group.
Specific structural formula depiction for the claimed compound
The compound is defined by a particular chemical formula or structure depiction within the group of formulae, with OBn denoting a benzyloxy group and, where specified, OMe denoting a methoxy group.
Overall, the claims are directed to formula-selected compounds whose scope is controlled by explicit definitions of OMe and OBn as methoxy and benzyloxy groups, with dependent claims narrowing the invention to specific depicted structures within that same framework.
Stated Advantages
The document states that the compounds are effective against beta-lactamase producing bacteria, including ESBL and KPC2 carbapenemase producers.
Diazabicyclooctane derivatives act as potent β-lactamase inhibitors.
Inhibition is stated to include class A/C/D β-lactamases, particularly class C.
The document states activity against ESBL and KPC-2.
β-lactam antibiotic activity is restored when used with these β-lactamase inhibitors.
Documented Applications
Administration of the compound in combination with beta-lactam antibiotics for targeting beta-lactamase producing bacteria.
Use against Class A/Class C beta-lactamase producers, ESBL, and KPC2 carbapenemase producers.
Evaluation in beta-lactamase inhibitory activity and synergistic activity assays.
Use as a β-lactamase inhibitor in bacterial infection treatment.
Pharmaceutical compositions together with β-lactam antibiotics.
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