IP Library › Granted Patent US 7,973,065

Granted Patent B2

US 7,973,065 · App. 12/898,806 · Granted Jul 5, 2011

Antimicrobial compounds

Assignee: Shaw Intellectual Properties Holding, Inc.

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Quick Facts

Patent No.: US 7,973,065
App. No.: 12/898,806
Granted: Jul 5, 2011
Kind: B2

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Abstract

The compounds disclosed herein are isoxazole derivatives that are useful as antimicrobial compounds, particularly as anti-bacterial compounds. The disclosed methods comprise incubating at least two different substrates in the presence of at least one oxygenase to provide the disclosed compounds, or to prepare and identify compounds that have antimicrobial activity.

Claims (66)

1. A compound of the formula:

wherein:

X 1 -X 3 are independently selected from N, NH, O, S, CH, and CH 2 ;

R 1 is selected from hydrogen, hydroxy, and C 1 -C 4 alkyl;

R 2a -R 2d are independently selected from hydrogen, hydroxy, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, cyano, and nitro; and

each ------ is independently an optional bond; or

a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , of the formula:

3. The compound of claim 1 , of the formula:

4. The compound of claim 1 , wherein R 1 is hydrogen.

5. The compound of claim 1 , wherein R 2a -R 2d are independently selected from hydrogen, hydroxy, and halogen.

6. The compound of claim 1 , selected from:

4-(3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one;

4-(4-fluoro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one;

4-(4-chloro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one;

4-(5-fluoro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one;

4-(5-chloro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one;

4-(6-fluoro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one;

4-(6-chloro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one;

4-(7-fluoro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one; and

4-(7-chloro-3-oxoindolin-2-ylidene)benzo[c]isoxazol-5(4H)-one.

7. The compound of claim 1 , selected from:

7-(3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one;

7-(4-fluoro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one;

7-(4-chloro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one;

7-(5-fluoro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one;

7-(5-chloro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one;

7-(6-fluoro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one;

7-(6-chloro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one;

7-(7-fluoro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one; and

7-(7-chloro-3-oxoindolin-2-ylidene)-7,7a-dihydrobenzo[d]isoxazol-6(3aH)-one.

8. A method of treating a bacterial infection in a subject in need thereof, comprising:

administering to the subject a therapeutically effective amount of a compound of the formula:

wherein:

X 1 -X 3 are independently selected from N, NH, O, S, CH, and CH 2 ;

R 1 is selected from hydrogen, hydroxy, and C 1 -C 4 alkyl;

R 2a -R 2d are independently selected from hydrogen, hydroxy, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, cyano, and nitro; and

each ------ is independently an optional bond; or

a pharmaceutically acceptable salt thereof.

9. The method of claim 8 , wherein the compound is of the formula:

10. The method of claim 8 , wherein the compound is of the formula:

11. The method of claim 8 , wherein R 1 is hydrogen.

12. The method of claim 8 , wherein R 2a -R 2d are independently selected from hydrogen, hydroxy, and halogen.

13. The method of claim 8 , wherein the compound is selected from: