IP Library › Granted Patent US 7,989,422
Granted Patent B2
US 7,989,422 · App. 12/096,771 · Granted Aug 2, 2011

Antibacterial agents

Assignee: Alchemia Limited
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Quick Facts
Patent No.
US 7,989,422
App. No.
12/096,771
Granted
Aug 2, 2011
Kind
B2
Abstract

The present invention, in one aspect, provides a method of inhibiting bacterial growth by contacting bacteria with an effective amount of at least one monosaccharide compound of formula (1) as described herein:

Claims (31)

1. A method of inhibiting bacterial growth comprising contacting bacteria with at least one monosaccharide compound, or a pharmaceutically acceptable salt thereof, of formula (1):

wherein,

n is 1; the ring is of the galacto-configuration and the anomeric center may be of either the α or β configuration;

R1 is selected from the group consisting of hydrogen; OZ; SZ; OPO 2 (OZ)Z; SO 2 N(Z)Q; S(═O)N(Z)Q; N-Het wherein N and Het combine to form a heterocycle which may be further substituted with U groups; and —N(Z)Y wherein:

Y is selected from hydrogen, or the following, where G denotes the point of connection to the nitrogen atom in N(Y)Z;

Q is selected from hydrogen or W;

the groups W are independently selected from alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, arylalkyl and heteroarylalkyl, of 1 to 20 carbon atoms, each of which is optionally substituted, branched and/or linear; wherein W is optionally substituted by one or more substituents selected from the group consisting of OH, NO, NO 2 , NH 2 , N 3 , halogen, CF 3 , CHF 2 , CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidiniums, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, aminoalkyl, aminodialkyl, aminotrialkyl, aminoacyl, carbonyl, substituted or unsubstituted imine, sulfate, sulfonamide, phosphate, phosphoramide, hydrazide, hydroxamate, and hydroxamic acid;

each occurrence of Z is independently selected from the group consisting of: hydrogen, alkyl, alkenyl, alkynyl, heteroalkyl, acyl, arylacyl, heteroarylacyl, aryl, heteroaryl, arylalkyl and heteroarylalkyl, of 1 to 20 carbon atoms, each of which is optionally substituted, branched and/or linear; wherein Z is optionally substituted by one or more substituents selected from the group consisting of OH, NO, NO 2 , NH 2 , N 3 , halogen, CF 3 , CHF 2 , CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidiniums, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, aminoalkyl, aminodialkyl, aminotrialkyl, aminoacyl, carbonyl, substituted or unsubstituted imine, sulfate, sulfonamide, phosphate, phosphoramide, hydrazide, hydroxamate, and hydroxamic acid; or

wherein each occurrence of U is independently selected from the group consisting of: OH, NO, NO 2 , NH 2 , N 3 , halogen, CF 3 , CHF 2 , CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidinium, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, aminoalkyl, aminodialkyl, aminotrialkyl, aminoacyl, carbonyl, substituted or unsubstituted imine, sulfate, sulfonamide, phosphate, phosphoramide, hydrazide, hydroxamate, hydroxamic acid; heteroaryloxy, aminoaryl, aminoheteroaryl, thioalkyl, thioaryl, thioheteroaryl, alkyl, alkenyl, alkynyl, acyl, arylacyl, and heteroarylacyl; of 1 to 20 carbon atoms, each of which is optionally substituted, branched and/or linear; and

wherein

the groups R2, R3, and R5 are independently selected from OZ or N-Het, wherein N and Het combine to form a heterocycle which may be further substituted with U groups; or N(Z)Y or OPO 2 (OZ)Z, wherein the groups Z and Y are as defined above; and

wherein R4 is N-Het, wherein N and Het combine to form a heterocycle which may be further substituted with U groups.

2. The method according to claim 1 , wherein R2 is N(Z)Y.

3. The method according to claim 2 wherein the N-het heterocycle is a monocyclic or bicyclic ring of 4 to 10 membered ring structure.

4. The method according to claim 1 , wherein R2 is N-Het, and wherein the N-het heterocycle is a monocyclic or bicyclic ring of 4 to 10 membered ring structure.

5. The method according to claim 1 , wherein the N-het heterocyclic ring is selected from the group consisting of triazoles, benzimidazoles, benzimidazolothione, benzimidazolone, imidazole, hydanthione, thiohydanthione and purine.

6. The method according to claim 1 , wherein the N-het heterocyclic ring is further substituted with U groups selected from the group consisting of substituted alkyl, aryl, carboxyl and amino.

7. The method according to claim 1 , wherein the U group is selected from the group consisting of OH, NO, NO 2 , NH 2 , N 3 , halogen, CF 3 , CHF 2 , CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidinium, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, primary, secondary or tertiary amines, aminoacyl, carbonyl and substituted or unsubstituted imine.

8. The method according to claim 1 , wherein in each occurrence Z is independently selected from the group consisting of: hydrogen, alkyl, alkenyl, alkynyl, heteroalkyl, acyl, arylacyl, heteroarylacyl, aryl, heteroaryl, arylalkyl and heteroarylalkyl, of 1 to 20 carbon atoms which is optionally substituted, branched and/or linear.

9. The method according to claim 1 , wherein the substituents are selected from the group consisting of OH, NO, NO 2 , NH 2 , N 3 , halogen, CF 3 , CHF 2 , CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidiniums, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, aminoalkyl, aminodialkyl, aminotrialkyl, aminoacyl, carbonyl, substituted or unsubstituted imine, sulfate, sulfonamide, phosphate, phosphoramide, hydrazide, hydroxamate, and hydroxamic acid.

10. The method according to claim 1 , wherein the compound of formula I is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

11. A pharmaceutical composition comprising a compound of formula (1) selected from the group consisting of

tautomers, esters, solvates, or pharmaceutically acceptable salts thereof, and a pharmaceutically acceptable carrier.

12. The method of claim 1 , wherein the bacteria is Gram-positive bacteria.

13. The method of claim 1 , wherein the bacteria is selected from the group consisting of an Escherichia bacteria, a Staphylococcus bacteria, Micrococcus bacteria, an Enterococcus bacteria, and a Streptococcus bacteria.

14. The method of claim 1 , wherein said contacting comprises administering an effective amount of a compound of formula (1), or a pharmaceutically acceptable salt thereof, to a subject in need of such treatment.

15. The method of claim 13 , wherein the Staphylococcus bacteria is a methicillin resistant Staphylococci.

16. The method of claim 13 , wherein the Staphylococcus bacteria is selected from the group consisting of Staphylococcus aureus and Staphylococcus aureus MRSA.

17. The method of claim 13 , wherein the Enterococcus bacteria is a Vancomycin resistant Enterococci.

18. The method of claim 2 , wherein R1 is hydrogen.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT SERIAL NUMBER FROM 13722222 TO 13772222 PREVIOUSLY RECORDED AT REEL: 036387 FRAME: 0028. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Nov 23, 2015
From: ALCHEMIA LIMITED
To: VAST BIOSCIENCE PTY LIMITED
Reel/Frame 037155/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 21, 2015
From: ALCHEMIA LIMITED
To: VAST BIOSCIENCE PTY LIMITED
Reel/Frame 036387/0028 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2008
From: MEUTERMANS, WIM; MCKEVENEY, DECLAN; ZUEGG, JOHANNES; PREMRAJ, RAJARATNAM; MULDOON, CRAIG; THANH LE, GIANG
To: ALCHEMIA LIMITED
Reel/Frame 021397/0158 →
Priority Claims (1)
AU 2005907230 · Dec 22, 2005 · national
Continuity (1)
Related Publication 20090023669A1 · Jan 22, 2009