Quinolone-3-diarylethers
Disclosed are derivative compounds of ELQ-300 that include an ester at position 4. These compounds have enhanced properties relative to ELQ-300. Also disclosed are pharmaceutical compositions comprising the compounds and methods of treating and preventing malaria infections involving administering the pharmaceutical compositions to the subject.
1. A compound of the structure:
wherein X is halogen and R is a carbonate ester, or a pharmaceutically acceptable salt thereof.
2. The compound of claim 1 wherein X is selected from fluoro and chloro, or a pharmaceutically acceptable salt thereof.
3. The compound of claim 1 wherein R is selected from methyl carbonate; ethyl carbonate; 2-methoxyethylcarbonate; 2-(2-methoxyethoxy)ethyl carbonate; (2-(2-(2-methoxyethoxy)ethoxy)ethyl) carbonate; allyl carbonate; tert-butyl carbonate; ((2,2-dimethyl-1,3-dioxolan-4-yl)methyl) carbonate; ((2-oxo-1,3-dioxolan-4-yl)methyl) carbonate; 2,3-dihydroxypropyl carbonate; and 1,1-dioxidotetrahydrothiophen-3-yl carbonate, or a pharmaceutically acceptable salt thereof.
4. The compound of claim 3 wherein X is chloro, or a pharmaceutically acceptable salt thereof.
5. A compound selected from the group consisting of:
or a pharmaceutically acceptable salt thereof.
6. The compound of claim 3 wherein X is fluoro, or a pharmaceutically acceptable salt thereof.
7. The compound of claim 2 wherein X is fluoro, or a pharmaceutically acceptable salt thereof.
8. The compound of claim 2 wherein X is chloro, or a pharmaceutically acceptable salt thereof.