Antimicrobial compounds, compositions, and uses thereof

• US 10,752,651 B2
• Filed: 07/08/2019
• Issued: 08/25/2020
• Est. Priority Date: 03/10/2017
• Status: Active Grant

• Current Assignee: Lakewood Amedex Inc.
• Original Assignee: Lakewood Amedex Inc.
• Inventors: Sleet, Randolph B., Kates, Steven A., Parkinson, Steven
• Primary Examiner(s): Lau, Jonathan S
• Application Number:
  US16/505,497
• Publication Number:
  US 20190330255A1
• Time in Patent Office: 414 Days
• CPC Class Codes: A61P 13/02 of urine or of the urinary tract, e.g. urine acidifiers
• CPC Class Codes: A61P 15/02 for disorders of the vagina
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 27/16 Otologicals
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: C07F 9/65586 at least one of the hetero rings does not contain nitrogen as ring hetero atom
• CPC Class Codes: C07H 19/02 sharing nitrogen
• CPC Class Codes: C07H 19/04 Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 19/23 Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22

Abstract

Antimicrobial compounds and compositions of Formula (I) and methods of use are disclosed.

Claims

1. A compound having the formula:

2. The pharmaceutically acceptable salt of the compound according to claim 1 selected from the group consisting of an ammonium salt, a calcium salt, a sodium salt, a potassium salt, a magnesium salt, and a cobalt salt.

3. The pharmaceutically acceptable salt according to claim 2, wherein the ammonium salt is ammonium ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((butoxyoxidophosphor-yl)oxy)tetrahydrofuran-2-yl)methyl butyl phosphate.

4. The pharmaceutically acceptable salt according to claim 2, wherein the calcium salt is calcium ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((butoxyoxidophosphor-yl)oxy)tetrahydrofuran-2-yl)methyl butyl phosphate.

5. The pharmaceutically acceptable salt according to claim 2, wherein the sodium salt is sodium ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((butoxyoxidophosphor-yl)oxy)tetrahydrofuran-2-yl)methyl butyl phosphate.

6. The pharmaceutically acceptable salt according to claim 2, wherein the potassium salt is potassium ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((butoxyoxidophosphor-yl)oxy)tetrahydrofuran-2-yl)methyl butyl phosphate.

7. The pharmaceutically acceptable salt according to claim 2, wherein the magnesium salt is magnesium ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((butoxyoxidophosphor-yl)oxy) tetrahydrofuran-2-yl)methyl butyl phosphate.

8. The pharmaceutically acceptable salt according to claim 2, wherein the cobalt salt is cobalt ((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((butoxyoxidophosphor-yl)oxy)tetrahydrofuran-2-yl)methyl butyl phosphate.

9. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound, or a pharmaceutically acceptable salt thereof, is a protonated compound having a pH when dissolved in water of about pH 3 to about pH 5.

10. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound, or a pharmaceutically acceptable salt thereof, is a protonated compound having a pH when dissolved in water of about pH 3 to about pH 4.

11. A pharmaceutical composition comprising a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers, excipients, or diluents.

12. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition includes at least one additional active ingredient.

13. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition is adapted for topical administration.

14. The pharmaceutical composition of claim 13, wherein the pharmaceutical composition is in the form of a lotion, gel, cream, ointment, oil, solution, suspension, emulsion or other viscous composition.

15. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition is adapted for oral administration.

16. The pharmaceutical composition of claim 15, wherein the pharmaceutical composition is in the form of a capsule, tablet, powder, liquid suspension, solution, elixir, syrup or concentrated drop.

17. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition is adapted for inhalation administration.

18. The pharmaceutical composition of claim 17, wherein the pharmaceutical composition is in the form of a dry powder, solution, suspension or aerosol.

19. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition is adapted for intravesical administration.

20. The pharmaceutical composition of claim 19, wherein the pharmaceutical composition is adapted for administration via a catheter.

21. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition is adapted for parenteral administration.

22. The pharmaceutical composition of claim 21, wherein the pharmaceutical composition is adapted for administration via a needle.