IP Library Granted Patent US 9,730,928
Granted Patent B2
US 9,730,928 · App. 14/896,906 · Granted Aug 15, 2017

Trizol-1-OL analogs anti-retroviral latency drugs

Inventors: Vincente Planelles (Salt Lake City, UT); Alberto Bosque-Pardos (Salt Lake City, UT); Chris M. Ireland (Salt Lake City, UT); Ryan Van Wagoner (Salt Lake City, UT); Mary Kay Harper-Ireland (Salt Lake City, UT); John Alan Maschek (Salt Lake City, UT)
Assignee: Univeristy of Utah Research Foundation
A61K31/501A61K31/416A61K31/4192A61K31/437A61K31/53A61K45/06C07D231/54C07D249/04C07D249/18C07D253/08C07D403/04C07D471/04
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Quick Facts
Patent No.
US 9,730,928
App. No.
14/896,906
Granted
Aug 15, 2017
Kind
B2
Abstract

In one aspect, the invention relates to triazol-1-ol compounds, analogs thereof, compositions comprising same, and methods of using same, alone or in combination with other agents, to reactivate latent retroviruses, and more particularly to reactivate latent HIV-1. Such compounds, compositions, and methods can be used, for example, in connection with diagnosing and/or treating a retrovirus, and more specifically HIV-1. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Claims (28)

1. A method of activating a latent retrovirus in a subject, the method comprising the step of administering to the subject an effective amount of a compound represented by a formula:

wherein n is 0 or 1;

wherein R 1 is selected from H, C1-C4 alkyl, C1-C6 aryl, C(O)Ar, C(O)N(CH 3 ) 2 , SO 2 N(CH 3 ) 2 , fluorenylmethyloxycarbonyl, N-((dimethylamino)methylene)-N-methylmethanaminium tetrafluoroborate, N-((dimethylamino)methylene)-N-methylmethanaminium hexafluorophosphate (V), tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate (V), tris(dimethylamino)phosphonium hexafluorophosphate (V), 1-(pyrrolidine-1-ylmethylene)pyrrolidin-1-ium hexafluorophosphate (V), and 1-(piperidin-1-ylmethylene)piperidin-1-ium hexafluorophosphate (V);

wherein R 2 is selected from H and C1-C4 alkyl; and

wherein R 3 is selected from H and C1-C4 alkyl;

or wherein R 2 and R 3 are covalently bonded and, together with the intermediate atoms, comprise phenyl substituted with 0, 1, 2, or 3 groups independently selected from Cl, CH 3 , and NO 2 or unsubstituted pyridinyl.

2. The method of claim 1 , wherein the retrovirus is selected from HIV-1, HIV-2, SIV, XMRV, HTLV-1, HTLV-2, HTLV-3, and HTLV-4.

3. The method of claim 1 , wherein the retrovirus is HIV-1.

4. A method of activating a latent retrovirus in a subject, the method comprising the step of administering to the subject an effective amount of a compound represented by a formula selected from:

wherein R 1 is selected from H, C1-C4 alkyl, C1-C6 aryl, C(O)Ar, C(O)N(CH 3 ) 2 , SO 2 N(CH 3 ) 2 , fluorenylmethyloxycarbonyl, N-((dimethylamino)methylene)-N-methylmethanaminium tetrafluoroborate, N-((dimethylamino)methylene)-N-methylmethanaminium hexafluorophosphate (V), tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate (V), tris(dimethylamino)phosphonium hexafluorophosphate (V), 1-(pyrrolidine-1-ylmethylene)pyrrolidin-1-ium hexafluorophosphate (V), and 1-(piperidin-1-ylmethylene)piperidin-1-ium hexafluorophosphate (V);

wherein each of R 4 , R 5 , and R 6 is independently selected from H, Cl, CH 3 , and NO 2 ,

wherein each of R 7 , R 8 , and R 9 is independently selected from H, Cl, CH 3 , and NO 2 .

5. The method of claim 4 , wherein the retrovirus is selected from HIV-1, HIV-2, SIV, XMRV, HTLV-1, HTLV-2, HTLV-3, and HTLV-4.

6. The method of claim 4 , wherein the retrovirus is HIV-1.

7. The method of claim 4 , wherein R 1 is selected from H and N-((dimethylamino)methylene) -N-methylmethanaminium hexafluorophosphate (V).

8. The method of claim 4 , wherein R 1 is H.

9. The method of claim 4 , wherein the compound is represented by a formula:

10. The method of claim 4 , wherein the compound is represented by a formula:

11. The method of claim 4 , wherein the compound is represented by a formula:

12. The method of claim 4 , wherein the compound is represented by a formula:

13. A method of activating a latent retrovirus in a subject, the method comprising the step of administering to the subject an effective amount of a compound selected from:

14. The method of claim 13 , wherein the retrovirus is selected from HIV-1, HIV-2, SIV, XMRV, HTLV-1, HTLV-2, HTLV-3, and HTLV-4.

15. The method of claim 13 , wherein the retrovirus is HIV-1.

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

17. The method of claim 16 , wherein the retrovirus is selected from HIV-1, HIV-2, SIV, XMRV, HTLV-1, HTLV-2, HTLV-3, and HTLV-4.

18. The method of claim 16 , wherein the retrovirus is HIV-1.

19. The method of claim 13 , wherein the subject is a population of cells.

20. The method of claim 13 , wherein the subject is a mammal.

Assignments (3)
CONFIRMATORY LICENSE Recorded May 15, 2017
From: UNIVERSITY OF UTAH
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 042462/0183 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2017
From: PLANELLES, VICENTE; BOSQUE-PARDOS, ALBERTO; IRELAND, CHRIS M.; WAGONER, RYAN VAN; HARPER-IRELAND, MARY KAY; MASCHEK, JOHN ALAN
To: UNIVERSITY OF UTAH
Reel/Frame 041388/0285 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2017
From: UNIVERSITY OF UTAH
To: UNIVERSITY OF UTAH RESEARCH FOUNDATION
Reel/Frame 041388/0294 →
Continuity (2)
Provisional Application 61835297 · Jun 14, 2013
Related Publication 20160151365A1 · Jun 2, 2016