IP Library › Granted Patent US 8,119,680
Granted Patent B2
US 8,119,680 · App. 12/875,935 · Granted Feb 21, 2012

α-Haloketone derivatives of imidazolyl-substituted aromatic compounds and compounds prepared therefrom

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Quick Facts
Patent No.
US 8,119,680
App. No.
12/875,935
Granted
Feb 21, 2012
Kind
B2
Abstract

Novel compounds, compositions, and kits are provided. Methods of modulating Aβ levels, and methods of treating a disease associated with aberrant Aβ levels are also provided.

Claims (40)

1. A compound having a structure corresponding to Formula (I):

A-B—C(O)—CR 2 —X  (I)

wherein A is:

wherein each E is independently CR 1 ; and

each R 1 is independently hydrogen, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylamido, substituted or unsubstituted alkylamino, substituted or unsubstituted amino, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl;

B is

wherein each G is independently CR 2 ; and

wherein each R 2 is independently selected from hydrogen, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylamido, substituted or unsubstituted alkylamino, substituted or unsubstituted amino, provided that at least one R 2 is halogen or substituted or unsubstituted alkoxy;

each R is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkylamido, substituted or unsubstituted alkylamino, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl; and

X is halogen.

2. A compound according to claim 1 having the structure:

3. A compound according to claim 1 having the structure:

4. A compound according to claim 1 wherein A is unsubstituted imidazolyl.

5. A compound according to claim 1 wherein A is a substituted imidazolyl.

6. A compound according to claim 5 wherein A is a 4-substituted imidazolyl.

7. A compound according to claim 5 wherein said imidazolyl is alkyl substituted.

8. A compound according to claim 5 wherein said imidazolyl is C 1 -C 5 alkyl substituted.

9. A compound according to claim 8 wherein said imidazolyl is methyl substituted.

10. A compound according to claim 8 wherein said imidazolyl is ethyl substituted.

11. A compound according to claim 5 wherein said imidazolyl is halogen substituted.

12. A compound according to claim 11 wherein said imidazolyl is chloro-substituted.

13. A compound according to claim 11 wherein said imidazolyl is bromo-substituted.

14. A compound according to claim 1 wherein at least one R 2 is a halogen.

15. A compound according to claim 14 wherein said halogen is fluorine.

16. A compound according to claim 1 wherein at least one R 2 is optionally substituted alkoxy.

17. A compound according to claim 1 wherein at least one R is hydrogen.

18. A compound according to claim 1 wherein each R is hydrogen.

19. A compound according to claim 1 wherein X is chlorine.

20. A compound according to claim 1 wherein X is bromine.

21. A compound according to claim 1 wherein X is iodine.

22. A compound according to claim 1 having a structure selected from the group consisting of:

23. A method of making a compound according to claim 1 , said method comprising:

contacting an acetylphenyl-boronic acid with an optionally substituted imidazole in a suitable solvent under conditions suitable to form an imidazolyl phenyl ketone, and thereafter

contacting said imidazolyl phenyl ketone with bromine under conditions suitable to form a compound of Formula (I).

24. A method of making a compound according to claim 1 , said method comprising:

contacting a 4-fluorophenyl-alkanone with an optionally substituted imidazole in a suitable solvent under conditions suitable to form an imidazolyl phenyl ketone, and thereafter

contacting said imidazolyl phenyl ketone with bromine under conditions suitable to form a compound of Formula (I).

25. A method of making a compound according to claim 1 , said method comprising:

contacting a 3,4-difluorophenyl-alkanone with an optionally substituted imidazole in a suitable solvent under conditions suitable to form an imidazolyl fluorophenyl ketone, and thereafter

contacting said imidazolyl fluorophenyl ketone with bromine under conditions suitable to form a compound of Formula (I).