N-alkyl-4-methyleneamino-3-hydroxy-2-pyridones
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, phenyl, 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 pyrrolidine ring, optionally substituted with one or more hydrogen, halo, cyano, hydroxy, carboxy, keto, thioketo, amino, acylamino, acyl, amido, alkyl, alkenyl, alkynyl, heteroalkyl, haloalkyl, alkoxy, and combinations thereof; and
d) R 5 and R 6 are each 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; or
optical isomers, diastereomers and enantiomers of the formula above, or a pharmaceutically-acceptable salt thereof.
2. The compound of claim 1 , wherein R 1 is substituted or unsubstituted phenyl.
3. The compound of claim 2 , wherein the phenyl group of R 1 is substituted with an alkoxy.
4. The compound of claim 1 , wherein R 1 is aryl substituted with a heteroalkyl.
5. The compound of claim 1 , wherein R 1 is aryl substituted with an aryl.
6. The compound of claim 1 , wherein R 1 is aryl substituted with an aryloxy.
7. The compound of claim 1 , wherein R 2 is hydrogen.
8. The compound of claim 1 , wherein R 5 and R 6 are hydrogen.
9. The compound of claim 1 , chosen from:
1-Benzyl-3-Hydroxy-4-pyrrolidin-1-ylmethyl-1H-pyridin-2-one;
1-Benzyl-3-Hydroxy-4-(3-hydroxypyrrolidin-1-ylmethyl)-1H-pyridin-2-one;
1-(1-Benzyl-3-hydroxy-2-oxo-1,2-dihydropyridin-4-ylmethyl)pyrrolidine-2-carboxylic acid methyl ester;
1-Benzyl-3-hydroxy-4-(2-methoxymethylpyrrolidin-1-ylmethyl)-1H-Pyridin-2-one;
3-Hydroxy-1-(pyridin-4-ylmethyl)-4-(pyrrolidin-1-ylmethyl)pyridin-2(1H)-one; and
3-Hydroxy-1-(3-methoxybenzyl)-4-pyrrolidin-1-ylmethyl-1H-pyridin-2-one.
10. A method of treating a microbial infection comprising administering a safe and effective of amount of a compound according to claim 1 , in a subject in need thereof.
11. A method of treating a microbial infection comprising administering a safe and effective of amount of a compound according to claim 9 , in a subject in need thereof.
12. A pharmaceutical composition comprising:
a. a safe and effective of amount of a compound according to claim 1 ;
b. a pharmaceutically-acceptable excipient.
13. A pharmaceutical composition comprising:
a. a safe and effective of amount of a compound according to claim 9 ;
b. a pharmaceutically-acceptable excipient.
14. The compound of claim 1 , wherein R 1 , R 2 , R 5 , and R 6 are hydrogen.
15. The compound of claim 9 , which is 1-Benzyl-3-hydroxy-4-(2-methoxymethylpyrrolidin-1-ylmethyl)-1H-Pyridin-2-one.
16. A method of treating a microbial infection comprising administering a safe and effective of amount of a compound according to claim 15 , in a subject in need thereof.
17. A pharmaceutical composition comprising:
c. a safe and effective of amount of a compound according to claim 15 ;
d. a pharmaceutically-acceptable excipient.