Antibiotics effective for gram-negative pathogens
AssigneeThe Board of Trustees of the University of Illinois
InventorsPaul J. Hergenrother, Emily Jane Geddes, Bryon Shane Drown, Stephen E. Motika, Erica Nicole Parker
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Abstract
Disclosed herein are antibacterial compounds that accumulate in Gram-negative bacteria, methods of preparing the compounds, and methods of using the compounds to inhibit or kill microbes, and methods of treating microbial infections, such as Gram-negative bacterial infections. Compounds selected for conversion to potential Gram-negative antibacterial compounds were identified based on compounds having low globularity and low flexibility. Amine substituents were then strategically added to the selected compounds to provide compounds having antibacterial activity against Gram-negative bacteria.
Claims15
A compound of Formula Ia or Formula Ib:
- or a pharmaceutically acceptable salt thereof;
- wherein
- X3 is selected from the group consisting of C(R8a)(R8b) and N(R9);
- each R1 is independently selected from the group consisting of halogen, hydroxyl, —O(C1-C6)alkyl, nitro, cyano, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, and heteroaralkyl;
- R5a and R5b are each independently selected from the group consisting of hydrogen, and —(C1-C6)alkyl;
- or together R5a and R5b form an oxo;
- R8a is hydrogen;
- R8b is selected from the group consisting of N(R12a)(R12b), and —((C1-C6)alkylene)N(R12a)(R12b);
- R9 is —((C1-C6)alkylene)N(R12a)(R12b);
- R12a and R12b are each independently selected from the group consisting of hydrogen, —(C1-C6)alkyl, —C(O)(C1-C6)alkyl, and C(O)O(C1-C6)alkyl;
- p is an integer from 0-5;
- and
- q is an integer from 1-4.
Dependencies are inferred from the claim text.