IP Library Granted Patent US 9,624,187
Granted Patent B2
US 9,624,187 · App. 14/958,225 · Granted Apr 18, 2017

Oxathiazine derivatives as antibacterial and anticancer agents

Inventor: Rolf W. Pfirrmann (Weggis, CH)
Assignee: Geistlich Pharma AG
C07D291/06A61K31/39A61K31/54A61K45/06C07D327/10C07D419/06
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Quick Facts
Patent No.
US 9,624,187
App. No.
14/958,225
Granted
Apr 18, 2017
Kind
B2
Abstract

New oxathiazin-like compounds and their derivatives are useful as antineoplastic and antimicrobial agents. Compositions and methods of using oxathiazin-like compounds and their derivatives are disclosed.

Claims (31)

1. A compound selected from the group consisting of:

2. The compound of claim 1 , comprising compound A3.

3. The compound of claim 1 , comprising compound 2245.

4. A method of treating a subject suffering from cancer comprising administering to said subject a compound selected from the group consisting of:

wherein said cancer is glioblastoma, glioma, neuroblastoma, astrocytoma, carcinomatous meningitis, colon cancer, rectal cancer, colo-rectal cancer, ovarian cancer, breast cancer, prostate cancer, lung cancer, mesothelioma, melanoma, renal cancer, liver cancer, pancreatic cancer, gastric cancer, esophageal cancer, urinary bladder cancer, cervical cancer, cardiac cancer, gall bladder cancer, skin cancer, bone cancer, cancers of the head or neck, leukemia, lymphoma, lymphosarcoma, adenocarcinoma, or fibrosarcoma, or metastases thereof.

5. The method of claim 4 , wherein cancer cells of said cancer are killed, or growth of said cancer cells is inhibited, by at least one of oxidative stress, apoptosis, anti-angiogenesis or antitubulogenesis.

6. The method of claim 4 , wherein said compound is 2245.

7. The method of claim 4 , wherein said compound is 2255.

8. The method of claim 4 , wherein said compound is 2245.

9. The method of claim 4 , wherein said compound is 2255.

10. A method of treating glioblastoma in a subject, comprising administering to said subject the compound of claim 1 .

11. A method of treating glioma in a subject, comprising administering to said subject the compound of claim 1 .

12. A method of treating bacterial infection in a subject comprising administering to said subject a compound selected from the group consisting of:

13. The method of claim 12 wherein said compound is 2245.

14. The method of claim 12 wherein said bacterial infection is S. aureaus, E. coli, H. pylori or MRSA infection.

15. A method of treating tumor stem cells in a subject comprising administering to said subject a compound selected from the group consisting of:

wherein said tumor stem cells are in a subject suffering from glioblastoma, glioma, neuroblastoma, astrocytoma, carcinomatous meningitis, colon cancer, rectal cancer, colo-rectal cancer, ovarian cancer, breast cancer, prostate cancer, lung cancer, mesothelioma, melanoma, renal cancer, liver cancer, pancreatic cancer, gastric cancer, esophageal cancer, urinary bladder cancer, cervical cancer, cardiac cancer, gall bladder cancer, skin cancer, bone cancer, cancers of the head or neck, leukemia, lymphoma, lymphosarcoma, adenocarcinoma, or fibrosarcoma, or metastases thereof.

16. The method of claim 15 wherein said compound is 2255.

17. A method of treating glioblastoma tumor stem cells in a subject comprising administering to said subject a compound selected from the group consisting of:

18. The method of claim 17 wherein said compound is 2245.

19. The method of claim 17 wherein said compound is 2255.

20. A method of killing tumor stem cells comprising administering to a subject in need thereof a compound selected from the group consisting of

in combination with taurolidine and/or taurultam.

21. A pharmaceutical composition comprising compound 2255

and a pharmaceutically acceptable carrier.

22. The pharmaceutical composition of claim 21 , wherein said composition is in the form of an orally administrable composition.

23. The pharmaceutical composition of claim 21 , wherein said composition is in the form of a capsule, a tablet, or a pharmaceutically acceptable solution.

24. The pharmaceutical composition of claim 21 , wherein said composition contains compound 2255 at a concentration of about 0.01 to about 3% w/v.

25. The pharmaceutical composition of claim 21 , wherein said composition contains compound 2255 at a concentration of about 0.01 to about 1000 μg/ml.

26. The pharmaceutical composition of claim 21 , wherein said composition contains one or more solubilizing agents.

27. The pharmaceutical composition of claim 21 , wherein said solubilizing agent is a polyol.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 1, 2026
From: GEISTLICH PHARMA AG
To: PERSEVERE THERAPEUTICS INC.
Reel/Frame 075325/0017 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 31, 2015
From: PFIRRMANN, ROLF W.
To: GEISTLICH PHARMA AG
Reel/Frame 037388/0645 →
Continuity (4)
Division 14409352
Provisional Application 61661092 · Jun 18, 2012
Provisional Application 61694452 · Aug 29, 2012
Related Publication 20160159759A1 · Jun 9, 2016