IP Library Granted Patent US 9,908,851
Granted Patent B2
US 9,908,851 · App. 14/912,137 · Granted Mar 6, 2018

2-piperidinyl substituted N,3-dihydroxybutanamides

Inventors: Pei Zhou (Durham, NC); Eric J. Toone (Durham, NC); Robert A. Nicholas (Chapel Hill, NC)
Assignees: Duke University; University of North Carolina Chapel Hill
C07D211/06C07D211/14A61K31/455
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Quick Facts
Patent No.
US 9,908,851
App. No.
14/912,137
Granted
Mar 6, 2018
Kind
B2
Abstract

Disclosed are compounds of formulae: (I) and pharmaceutically acceptable salts thereof, wherein the variables, R 1 , R 2 , Y, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.

Claims (29)

1. A compound that is:

or pharmaceutically acceptable salts thereof.

2. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier, solvent, adjuvant or diluent.

3. A method of treating Gram-negative bacterial infections, the method comprising administering to a subject in need of such treatment an effective amount of one or more compounds according to claim 1 .

4. A method of inhibiting a deacetylase enzyme in Gram-negative bacteria, the method comprising administering to a subject in need of such treatment an effective amount of one or more compounds according to claim 1 .

5. A compound of formula:

or a pharmaceutically acceptable salt thereof, wherein

R 1 is hydrogen; and

R 2 is

6. A compound according to claim 5 , wherein the compound is of formula:

7. A compound according to claim 5 , wherein R 2 represents

8. A compound according to claim 5 , wherein R 2 represents

9. A compound according to claim 5 that is:

or pharmaceutically acceptable salts thereof.

10. A pharmaceutical composition comprising a compound according to claim 5 and a pharmaceutically acceptable carrier, solvent, adjuvant or diluent.

11. A method of treating Gram-negative bacterial infections, the method comprising administering to a subject in need of such treatment an effective amount of one or more compounds according to claim 5 .

12. A method of inhibiting a deacetylase enzyme in Gram-negative bacteria, the method comprising administering to a subject in need of such treatment an effective amount of one or more compounds according to claim 5 .

13. A compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein

Y represents phenyl optionally substituted with R 4 ;

Z represents phenyl optionally substituted with R 5 ;

R 1 is hydrogen;

R 2 is

each R 4 is independently selected from the group consisting of halogen, —NO 2 , —CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —OH, C 1 -C 6 alkoxy, and C 1 -C 6 haloalkoxy; and

each R 5 is independently selected from the group consisting of halogen, —NO 2 , —CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —OH, C 1 -C 6 alkoxy, and C 1 -C 6 haloalkoxy.

14. A compound according to claim 13 , wherein R 2 represents

15. A pharmaceutical composition comprising a compound according to claim 13 and a pharmaceutically acceptable carrier, solvent, adjuvant or diluent.

16. A method of treating Gram-negative bacterial infections, the method comprising administering to a subject in need of such treatment an effective amount of one or more compounds according to claim 13 .

17. A method of inhibiting a deacetylase enzyme in Gram-negative bacteria, the method comprising administering to a subject in need of such treatment an effective amount of one or more compounds according to claim 13 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2017
From: NICHOLAS, ROBERT A.
To: UNIVERSITY OF NORTH CAROLINA CHAPEL HILL
Reel/Frame 043097/0108 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2017
From: ZHOU, PEI; TOONE, ERIC J.
To: DUKE UNIVERSITY
Reel/Frame 043097/0129 →
CONFIRMATORY LICENSE Recorded Apr 27, 2017
From: UNIV OF NORTH CAROLINA CHAPEL HILL
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 042352/0565 →
Continuity (2)
Provisional Application 61866857 · Aug 16, 2013
Related Publication 20160200682A1 · Jul 14, 2016