IP Library › Granted Patent US 10,882,872
Granted Patent B2
US 10,882,872 · App. 16/580,676 · Granted Jan 5, 2021

Oxaborole esters and uses thereof

Inventors: Tsutomu Akama (Sunnyvale, CA); David Scott Carter (Sunnyvale, CA); Jason S. Halladay (Los Gatos, CA); Robert T. Jacobs (Wake Forest, NC); Yang Liu (Foster City, CA); Jacob J. Plattner (Berkeley, CA); Yong-Kang Zhang (San Jose, CA); Michael John Witty (Dover, GB)
Assignee: Anacor Pharmaceuticals, Inc.
C07F5/027A61K31/166A61K31/443A61K31/4525A61K31/69C07F5/025A61K31/4178A61K31/431A61K31/47A61K31/5377Y02A50/30
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Quick Facts
Patent No.
US 10,882,872
App. No.
16/580,676
Granted
Jan 5, 2021
Kind
B2
Abstract

The present invention provides oxaborole ester compounds and compositions thereof which are useful to treat diseases associated with parasites, such as Chagas Disease and African Animal Trypanosomosis.

Claims (39)

1. A compound selected from the group consisting of:

(6-(Trifluoromethyl)pyridin-3-yl)methyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

4-Fluorobenzyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

4,4-Difluorocyclohexyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate; and

Tetrahydro-2H-pyran-4-yl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein the compound is:

(6-(Trifluoromethyl)pyridin-3-yl)methyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein the compound is:

4-Fluorobenzyl(1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 , wherein the compound is:

4,4-Difluorocyclohexyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 , wherein the compound is:

Tetrahydro-2H-pyran-4-yl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

6. A method of treating a Trypanosomatid-mediated disease or disorder in a subject comprising administering to a subject a compound selected from the group consisting of:

(6-(Trifluoromethyl)pyridin-3-yl)methyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

4-Fluorobenzyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

4,4-Difluorocyclohexyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate; and

Tetrahydro-2H-pyran-4-yl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

7. The method of claim 6 , wherein the Trypanosomatid-mediated disease or disorder involves a parasite which is a member selected from the group consisting of Trypanosoma cruzi, Trypanosoma congolense, Trypanosoma vivax , and Trypanosoma evansi.

8. The method of claim 6 , wherein the Trypanosomatid-mediated disease or disorder is trypanosomiasis.

9. The method of claim 6 , wherein the Trypanosomatid-mediated disease or disorder is African Animal Trypanosomosis.

10. The method of claim 6 , wherein the compound is:

(6-(Trifluoromethyl)pyridin-3-yl)methyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

11. The method of claim 6 , wherein the compound is:

4-Fluorobenzyl(1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

12. The method of claim 6 , wherein the compound is:

4,4-Difluorocyclohexyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

13. The method of claim 6 , wherein the compound is:

Tetrahydro-2H-pyran-4-yl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate;

or, a pharmaceutically acceptable salt thereof.

Continuity (3)
Continuation 15590159 · May 9, 2017
Provisional Application 62335565 · May 12, 2016
Related Publication 20200017531A1 · Jan 16, 2020