Fluorinated derivatives of 3-hydroxypyridin-4-ones
Provided are compounds of Formula I which are derivatives of 3-Hydroxypyridin-4-ones. The compounds may be used in treatment of a medical condition related to a toxic concentration of iron. The compounds may be used for preparation of a medicament for treatment of a medical condition related to a toxic concentration of iron. The medical condition related to a toxic concentration of iron may be selected from the group consisting of: cancer, pulmonary disease, progressive kidney disease and Friedreich's ataxia.
1. A morpholinyl-containing fluorinated 3-hydroxy pyridine-4(1H)-one compound of Formula I:
or a pharmaceutically acceptable salt thereof,
wherein:
G 1 is CH 2 NR 1 R 2 , where NR 1 R 2 is morpholinyl;
G 2 is CH 2 CF 2 R 3 ; wherein R 3 is F or H;
G 3 is H or C 1 -C 4 alkyl; and
G 4 is H or C 1 -C 4 alkyl.
2. A morpholinyl-containing fluorinated 3-hydroxy pyridine-4(1H)-one compound of Formula I:
or a pharmaceutically acceptable salt thereof,
wherein
G 1 is C 1 -C 4 alkyl;
G 2 is H, C 1 -C 4 alkyl or cyclopropyl;
G 3 is H or C 1 -C 4 alkyl; and
G 4 is CH(R 8 )CF 3 , wherein R 8 is morpholinyl.
3. A morpholinyl-containing fluorinated 3-hydroxy pyridine-4(1H)-one compound of Formula I:
or a pharmaceutically acceptable salt thereof,
wherein
G 1 is CH(R 4 )CF 3 , wherein R 4 is morpholinyl;
G 2 is H, C 1 -C 4 alkyl or cyclopropyl;
G 3 is H or C 1 -C 4 alkyl; and
G 4 is H or C 1 -C 4 alkyl.
4. A morpholinyl-containing fluorinated 3-hydroxy pyridine-4(1H)-one compound of Formula I:
or a pharmaceutically acceptable salt thereof,
wherein
G 1 is CH(R 7 )CF 2 H, wherein R 7 is morpholinyl;
G 2 is H, C 1 -C 4 alkyl or cyclopropyl;
G 3 is H or C 1 -C 4 alkyl; and
G 4 is H or C 1 -C 4 alkyl.
5. The compound of claim 2 , wherein G 1 is methyl, G 2 is H, and G 3 is H.
6. The compound of claim 2 , wherein G 1 is methyl, G 2 is methyl, and G 3 is H.
7. The compound of claim 1 , wherein R 3 is F, G 3 is methyl and G 4 is H.
8. The compound of claim 1 , wherein R 3 is F, G 3 is H and G 4 is H.
9. The compound of claim 3 , wherein G 2 is methyl, G 3 is methyl, and G 4 is H.
10. The compound of claim 3 , wherein G 2 is methyl, G 3 is H, and G 4 is H.
11. The compound of claim 4 , wherein G 2 is methyl, G 3 is H, and G 4 is H.