N-alkyl-4-methyleneamino-3-hydroxy-2-pyridones
View Patent ↗Compounds of Formula (I): are effective in the treatment of a microbial infection.
1. A compound of formula (I):
wherein:
a) each R 1 is independently chosen from hydrogen, halo, cyano, hydroxy, carboxy, keto, thioketo, amino, acylamino, acyl, amido, aryloxy, alkyl, alkenyl, alkynyl, heteroalkyl, haloalkyl, alkoxy, aryl, and cycloalkyl;
b) each R 2 is independently chosen from hydrogen, halo, cyano, hydroxy, carboxy, keto, thioketo, amino, acylamino, acyl, amido, phenyl, aryloxy, alkyl, alkenyl, alkynyl, heteroalkyl, haloalkyl, alkoxy, aryl, and cycloalkyl;
c) R 3 and R 4 , together with the nitrogen atom to which they are bonded, join to form a piperidin-1-yl unit, optionally substituted with one or more halo, cyano, hydroxy, carboxy, keto, thioketo, amino, acylamino, acyl, amido, alkyl, alkenyl, alkynyl, heteroalkyl, haloalkyl, alkoxy, substituted or unsubstituted aryl, wherein the aryl ring can be substituted with from 1 to 4 halo, cyano, hydroxy, carboxy, keto, thioketo, amino, acylamino, acyl, amido, aryloxy, alkyl, alkenyl, alkynyl, and combinations thereof; and
d) R 5 and R 6 are each independently chosen from of hydrogen, halo, cyano, hydroxy, carboxy, keto, thioketo, amino, acylamino, acyl, amido, aryloxy, alkyl, alkenyl, alkynyl, heteroalkyl, haloalkyl, alkoxy, aryl, and cycloalkyl; or
optical isomers, diastereomers and enantiomers of the formula above, or a pharmaceutically-acceptable salt.
2. The compound of claim 1 , wherein each R 1 is hydrogen.
3. The compound of claim 1 , wherein R 1 is one or more alkoxy.
4. The compound of claim 1 , wherein R 1 is a heteroalkyl.
5. The compound of claim 1 , wherein R 1 is an aryl.
6. The compound of claim 1 , wherein R 1 one or more methyl.
7. The compound of claim 1 , wherein R 1 , R 2 , R 5 and R 6 are hydrogen.
8. The compound of claim 1 , wherein R 2 is hydrogen.
9. The compound of claim 1 , wherein R 5 and R 6 are hydrogen.
10. The compound of claim 1 , chosen from:
1-Benzyl-3-Hydroxy-4-piperidin-1-ylmethyl-1H-pyridin-2-one; and
1-Benzyl-4-(4-benzylpiperidin-1-ylmethyl)-3-hydroxy-1H-pyridin-2-one.
11. A method of treating a microbial infection comprising administering a safe and effective amount of a compound according to claim 1 , to a subject in need thereof.
12. A method of treating a microbial infection comprising administering a safe and effective amount of a compound according to claim 10 , to a subject in need thereof.
13. A pharmaceutical composition comprising:
a) a safe and effective amount of a compound according to claim 1 ; and
b) a pharmaceutically-acceptable excipient.
14. A pharmaceutical composition comprising:
a) a safe and effective amount of a compound according to claim 10 ; and
b) a pharmaceutically-acceptable excipient.