IP Library Granted Patent US 10,526,312
Granted Patent B2
US 10,526,312 · App. 16/259,096 · Granted Jan 7, 2020

Metalloenzyme inhibitor compounds

Inventors: William J. Hoekstra (Durham, NC); Robert J. Schotzinger (Raleigh, NC); Stephen W. Rafferty (Lake Worth, FL)
Assignee: Mycovia Pharmaceuticals, Inc.
C07D401/06A61K45/06C07F9/6524C12N9/0073
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Quick Facts
Patent No.
US 10,526,312
App. No.
16/259,096
Granted
Jan 7, 2020
Kind
B2
Abstract

The instant invention describes compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.

Claims (59)

1. A compound of Formula I, or salt thereof, wherein:

MBG is tetrazolyl;

R 1 is halo;

R 2 is halo;

R 3 is independently halo, haloalkoxy, haloalkoxyalkyl, or hydroxyl;

R 4 is aryl, optionally substituted with 0, 1, 2 or 3 independent R 3 ;

R 5 is H or —P(O)(OH) 2 ;

R 6 is H or halo; and

n is 0, 1, 2 or 3.

2. The compound of claim 1 , wherein R 1 and R 2 are fluoro.

3. The compound of claim 1 , wherein R 3 is haloalkoxyalkyl or haloalkoxy, and n is 1.

4. The compound of claim 1 , wherein R 3 is 2,2,2-trifluoroethoxy, and n is 1.

5. The compound of claim 1 , wherein R 4 is phenyl optionally substituted with 0, 1, 2, or 3 independent halo.

6. The compound of claim 1 , wherein R 4 is phenyl optionally substituted with 2 halo.

7. The compound of claim 1 , wherein R 4 is phenyl substituted with 2 fluoro.

8. The compound of claim 1 , wherein R 5 is hydrogen.

9. The compound of claim 1 , wherein

R 1 and R 2 are fluoro;

R 3 is 2,2,2-trifluoroethoxy and n is 1;

R 4 is difluorophenyl; and

R 5 and R 6 are hydrogen.

10. A pharmaceutical composition comprising the compound of claim 1 , or salt, solvate, hydrate or prodrug thereof, and a pharmaceutically acceptable carrier.

11. A method of inhibiting metalloenzyme activity comprising contacting the compound of claim 1 , or a salt, solvate, hydrate, or prodrug thereof, with a metalloenzyme which is lanosterol demethylase (CYP51).

12. A method of treating a subject suffering from or susceptible to a metalloenzyme-related disorder or disease, comprising administering to the subject an effective amount of a compound of claim 1 , or salt, solvate, hydrate or prodrug thereof.

13. A compound of Formula I, or salt thereof, wherein:

MBG is tetrazolyl;

R 1 is halo;

R 2 is halo;

R 3 is independently halo, haloalkoxy, or haloalkoxyalkyl;

R 4 is aryl, optionally substituted with 0, 1, 2 or 3 independent R 3 ;

R 5 is —P(O)(OH) 2 ;

R 6 is hydrogen; and

n is 0, 1, 2 or 3.

14. The compound of claim 13 , wherein R 1 and R 2 are fluoro.

15. The compound of claim 13 , wherein R 3 is haloalkoxyalkyl or haloalkoxy, and n is 1.

16. The compound of claim 13 , wherein R 3 is 2,2,2-trifluoroethoxy, and n is 1.

17. The compound of claim 13 , wherein R 4 is phenyl substituted with 2 fluoro.

18. The compound of claim 13 , wherein R 5 is hydrogen.

19. The compound of claim 13 , wherein:

R 1 and R 2 are fluoro;

R 3 is 2,2,2-trifluoroethoxy, and n is 1;

R 4 is difluorophenyl; and

R 5 and R 6 are hydrogen.

20. A compound of Formula I, or salt, solvate, hydrate or prodrug thereof, wherein:

MBG is tetrazolyl;

R 1 is fluoro;

R 2 is fluoro;

R 3 is haloalkoxy or haloalkoxyalkyl;

R 4 is phenyl substituted with 1, 2, or 3 fluoro;

R 5 is hydrogen;

R 6 is hydrogen; and

n is 1.

21. The compound of claim 20 , wherein R 3 is 2,2,2-trifluoroethoxy.

22. The compound of claim 20 , wherein R 4 is 2,4-difluorophenyl.

23. The compound of claim 20 , wherein:

R 3 is 2,2,2-trifluoroethoxy; and

R 4 is 2,4-difluorophenyl.

24. The compound or the salt, solvate, hydrate, or prodrug of claim 20 , wherein the compound has the formula:

and wherein R 3 is 2,2,2-trifluoroethoxy.

Continuity (3)
Continuation 14373314
Provisional Application 61589076 · Jan 20, 2012
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