Synthesis of pyrrole acid derivatives
Inventors
Wilkinson, Andrew • Cooper, Ian • Orr, David • FINLAYSON, JONATHAN • BUNT, ADAM • Kirkham, James • Lyth, David • Blades, Kevin
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Assignees
MemberInfex TherapeuticsInfex TherapeuticsInfex Therapeutics is a UK-based specialist engaged in the acquisition, development, and licensing of drugs targeting pandemic and critical-priority infectious diseases, including both bacterial and viral threats. The company has a focus on combating antimicrobial resistance (AMR) by progressing new therapies for life-threatening infections into clinical trials. Infex Therapeutics works collaboratively with global partners, leveraging a robust R&D infrastructure at Alderley Park, and is involved in industry partnerships, public-private initiatives, and clinical-stage development.
Infex Therapeutics is a UK-based specialist engaged in the acquisition, development, and licensing of drugs targeting pandemic and critical-priority infectious diseases, including both bacterial and viral threats. The company has a focus on combating antimicrobial resistance (AMR) by progressing new therapies for life-threatening infections into clinical trials. Infex Therapeutics works collaboratively with global partners, leveraging a robust R&D infrastructure at Alderley Park, and is involved in industry partnerships, public-private initiatives, and clinical-stage development.
Publication Number
US-12606524-B2
Publication Date
2026-04-21
Expiration Date
Abstract
This invention relates to the synthesis of compounds that can be used to treat bacterial infections in combination with other antibacterial agents, and more specifically in combination with a class of antibacterial agents known as carbapenems. The compounds resulting from the novel methods of the present invention are enzyme inhibitors and more particularly are metallo-β-lactamase inhibitors.
Core Innovation
The document describes a method of forming a compound of formula (IV) or a pharmaceutically acceptable salt thereof. The method includes reacting a compound of formula (I) with a compound of formula (II) in the presence of Pd/C to form a compound of formula (III), then forming the compound of formula (IV) or a pharmaceutically acceptable salt thereof from the compound of formula (III).
The document further defines the compound scope by substituent variables X, R1, R2, R3, each R4, and R8a, with R9a options and the corresponding structural combinations for the two R9a substituents. In particular, R8a is BF3K or B(OR9a)2, and the two R9a substituents are defined as either H or C1-4 alkyl, or as together forming (CRaRb)n or together forming —C(O)—(CRaRb)—N(Rc)(—(CRaRb)—C(O)—).
The document also describes conversion of compound (III) to compound (IV) through an intermediate of formula (VI). In that refinement, reacting compound (III) with a compound of formula (V) forms compound (VI), and cleaving substituents R2, R3, and R5 from compound (VI) forms compound (IV) or a pharmaceutically acceptable salt thereof, where R5 is a protecting group.
Claims Coverage
The document provides one independent claim directed to forming a compound of formula (IV) or a pharmaceutically acceptable salt via a Pd/C-promoted step to form compound (III) from compounds (I) and (II), followed by conversion to compound (IV). Dependent claims further refine the conversion through an intermediate of formula (VI) and specify a precursor route to form compound (I).
Pd/C-mediated conversion from compound (I) and compound (II) to compound (III)
Reacting the compound of formula (I) with the compound of formula (II) in the presence of Pd/C to form the compound of formula (III), with defined substituent variables including X, R1, R2, R3, each R4, R8a, and R9a.
Conversion of compound (III) into compound (IV) or pharmaceutically acceptable salt
Forming a compound of formula (IV) or a pharmaceutically acceptable salt thereof from the compound of formula (III), under the defined structural-variable scope.
Intermediate (VI) formation and cleavage of R2, R3, and R5 to yield compound (IV)
Reacting the compound of formula (III) with a compound of formula (V) to form the compound of formula (VI), then cleaving the R2, R3, and R5 substituents from the compound of formula (VI) to form the compound of formula (IV) or a pharmaceutically acceptable salt thereof, where R5 is a protecting group.
Precursor route to form compound (I) from compounds (VII) and (VIII) with restricted R6
Forming the compound of formula (I) by reacting the compound of formula (VII) with a compound of formula (VIII) to generate the compound of formula (I), wherein R6 is independently selected from F, Cl, Br, and I.
The claims cover a Pd/C-mediated workflow that proceeds from compounds (I) and (II) through compound (III) to compound (IV) or a pharmaceutically acceptable salt thereof. Dependent claims add an optional route through compound (VI) with cleavage of specified substituents, and a precursor route for generating compound (I) from compounds (VII) and (VIII).
Stated Advantages
Not explicitly described in patent.
Documented Applications
Not explicitly described in patent.
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