IP Library Granted Patent US 9,492,428
Granted Patent B2
US 9,492,428 · App. 14/358,731 · Granted Nov 15, 2016

Compounds, compositions, pharmaceutical compositions, and methods of use

Inventors: Gerald B. Hammond (Shelbyville, KY); Zhuang Jin (West Palm Beach, FL); Paula J. Bates (Louisville, KY); Elsa Merit Reyes-Reyes (Prospect, KY); Abraham Vaisberg (Lima, PE)
Assignee: University of Louisville Research Foundation, Inc.
A61K31/366A61K36/81
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Quick Facts
Patent No.
US 9,492,428
App. No.
14/358,731
Granted
Nov 15, 2016
Kind
B2
Abstract

Certain embodiments of the invention include compositions comprising a compound of Formula (I), and salts, isomers, and derivatives thereof. Pharmaceutical compositions of some embodiments of the present invention comprise a compound of Formula (I), and salts, isomers, and derivatives thereof. Other embodiments of this invention include methods for treating disease (e.g., cancer) and methods for administering a compound of Formula (I), and salts, isomers, and derivatives thereof.

Claims (31)

1. A composition comprising a compound, wherein the compound is selected from the group consisting of Formula (I), salts of Formula (I), isomers of Formula (I), and derivatives of Formula (I), and the concentration of the compound is at least about 0.20% by weight and Formula (I) is

where R 1 , R 2 , and R 3 can be the same or different, and are selected from the group consisting of H, halogen, hydroxyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl.

2. The composition of claim 1 , wherein the concentration of the compound is at least about 10.0% by weight.

3. The composition of claim 1 , wherein the concentration of the compound is at least about 50.0% by weight.

4. The composition of claim 1 , wherein the concentration of the compound is at least about 90.0% by weight.

5. The composition of claim 1 , wherein R 1 , R 2 , and R 3 can be the same or different and are selected from group consisting of H, hydroxyl, halogen, methyl, ethyl, methoxy, and ethoxy.

6. The composition of claim 1 , wherein the compound is selected from the group consisting of I-1, I-2, and I-3.

7. The composition of claim 1 , wherein the compound causes arrest in the G 2 /M phase of the cell cycle or induces apoptosis.

8. A composition comprising a compound, wherein the composition is a pharmaceutical composition and the compound is selected from the group consisting of Formula (I), salts of Formula (I), isomers of Formula (I), and derivatives of Formula (I), and Formula (I) is

where R 1 , R 2 , and R 3 can be the same or different, and are selected from the group consisting of H, halogen, hydroxyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl.

9. The composition of claim 8 , wherein the concentration of the compound is at least about 10.0% by weight.

10. The composition of claim 8 , wherein the compound is selected from the group consisting of I-1, I-2, and I-3.

11. The composition of claim 8 , wherein the compound causes arrest in the G 2 /M phase of the cell cycle or induces apoptosis.

12. The composition of claim 8 , wherein the compound is present in a therapeutically effective amount to treat a disease.

13. The composition of claim 8 , wherein the compound is present in a therapeutically effective amount to treat a cancer.

14. The composition of claim 8 , wherein the composition further comprises a formulary ingredient or pyrogen-free water.

15. A method for treating a disease in an animal comprising

administering to the animal a composition comprising a compound,

wherein the compound is selected from the group consisting of Formula (I), salts of Formula (I), isomers of Formula (I), and derivatives of Formula (I), and the disease is cancer and Formula (I) is

where R 1 , R 2 , and R 3 can be the same or different, and are selected from the group consisting of H, halogen, hydroxyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl.

16. The method of claim 15 , further comprising identifying an animal with the disease.

17. The method of claim 15 , wherein the the disease comprises a cancerous tumor.

18. The method of claim 15 , wherein the disease is a cancer selected from the group consisting of basal cell carcinoma, thyroid cancer, squamous cell carcinoma, neuroblastoma, ovarian cancer, melanoma, renal cell carcinoma, hepatocellular carcinoma, breast cancer, colon cancer, lung cancer, pancreatic cancer, prostate cancers, chronic lymphocytic leukemia (CLL), acute lymphoblastic leukemia, rhabdomyosarcoma, Glioblastoma multiforme, meningioma, bladder cancer, gastric cancer, Glioma, oral cancer, nasopharyngeal carcinoma, kidney cancer, rectal cancer, stomach cancer, uterine cancer, and leukemias.

19. The method of claim 15 , wherein the compound causes arrest in the G 2 /M phase of the cell cycle or induces apoptosis.

20. The method of claim 15 , wherein the animal is a mammal or a human.

21. The method of claim 15 , wherein the administering is by an oral route or by a parenteral route.

22. The method of claim 15 , wherein the concentration of the compound is at least about 10.0% by weight.

23. The method of claim 15 , wherein the compound is selected from the group consisting of I- 1 , I-2, and I-3.

24. The method of claim 15 , wherein the disease is a cancer selected from the group consisting of breast cancer, colon cancer, lung cancer, ovarian cancer, melanoma, renal cell carcinoma, pancreatic cancer, prostate cancers, chronic lymphocytic leukemia (CLL), acute lymphoblastic leukemia, bladder cancer, gastric cancer, rectal cancer, stomach cancer, uterine cancer, and leukemias.

25. The composition of claim 1 , wherein the composition does not consist of I-1, I-2, I-3, or combinations thereof.

26. The composition of claim 8 , wherein the composition does not consist of I-1, I-2, I-3, or combinations thereof.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2016
From: VAISBERG, ABRAHAM
To: CAYETANO HEREDIA UNIVERSITY
Reel/Frame 038555/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2015
From: HAMMOND, GERALD B; JIN, ZHUANG; BATES, PAULA J; REYES-REYES, ELSA MERIT
To: UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.
Reel/Frame 035903/0259 →
CONFIRMATORY LICENSE Recorded Jul 1, 2014
From: UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION
To: US ARMY, SECRETARY OF THE ARMY
Reel/Frame 033218/0691 →
Continuity (3)
Provisional Application 61560502 · Nov 16, 2011
Provisional Application 61593135 · Jan 31, 2012
Related Publication 20150025129A1 · Jan 22, 2015