IP Library Granted Patent US 7,247,648
Granted Patent B2
US 7,247,648 · App. 11/152,002 · Granted Jul 24, 2007

N-alkyl-4-methyleneamino-3-hydroxy-2-pyridones

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Quick Facts
Patent No.
US 7,247,648
App. No.
11/152,002
Filed
Jun 14, 2005
Granted
Jul 24, 2007
Kind
B2
Art Unit
1625
USPC
514/343
Abstract

Compounds of Formula (I) are effective in the treatment of a microbial infection.

Claims (35)

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.