Antimicrobial organosilanes

Abstract

Organosilicon quaternary ammonium compounds, their formulations, including powdered and solid formulations, and methods of use to treat infections in humans and animals. 20 24 21 93 43 2 1 Ju l 2 02 5 ABSTRACT2025 2024219343 21 Jul

Claims

We Claim1. A quaternary ammonium compound of Formula:wherein(I) ora is 1, 2, 3, 4, 5, 6, 7, or 8;R1 is selected from the group consisting of Ce-C22alkyl and C6-C22alkanoyl;R2, R3, R4, R22, R23, and R24 are independently at each occurrence selected from the group consisting of:each R21 is independently selected from the group consisting of Ci-C22alkyl and C2-C22alkanoyl;R7 is independently at each occurrence selected from the group consisting of hydrogen, Ci-Cs alkyl, C2-C8 hydroxyalkyl, and Ci-Cs alkanoyl;R8 and R9 are independently at each occurrence selected from the group consisting of hydrogen, halogen, hydroxyl, N(R7)2, CH2OR7, CON(R7)2, COOR7, C(O)R7, Ci-Csalkyl, Ci-Cshydroxyalkyl, and Ci-Csalkanoyl;X1 is selected from the group consisting of NR17, CH2, CHOH, and C(O);X2 is selected from the group consisting of Ci-Csalkyl and Ci-Cshydroxyalkyl;R16 is Ci-C4alkyl;R17 is hydrogen, C2-C8 hydroxyalkyl, or Ci-Cs alkanoyl;X" is an anion or is absent if the quaternary amine is balanced with an internal anion; and2024219343   03 Sep 2024B+ is a cation.

2. The quaternary ammonium compound of claim 1, wherein the anion is selected from the group consisting of methane sulfonate, chloride, fluoride, iodide, bromide, hydroxide, chlorite, chlorate, hydroxide, formate, acetate, lactate, benzoate, and salicylate anion.

3. The quaternary ammonium compound of claim 1 or 2, wherein the cation B+ is selected from a potassium, sodium, lithium, magnesium, and calcium cation.

4. The quaternary ammonium compound of claim 1, wherein the compound is a zwitterion and X" is absent.

5. The quaternary ammonium compound of any one of claims 1-4, wherein X1 is NH.

6. The quaternary ammonium compound of any one of claims 1-4, wherein X1 is NR17; and wherein R17 is C2-C8 hydroxyalkyl.

7. The quaternary ammonium compound of any one of claims 1-4, wherein X1 is N(CH2CH2OH).

8. The quaternary ammonium compound of any one of claims 1-7, wherein X2 is Ci-C3 alkyl.

9. The quaternary ammonium compound of claim 8, wherein X2 is CH2CH2.

10. The quaternary ammonium compound of any one of claims 1-7, wherein X2 is C1 -C3hydroxyalkyl.

11. The quaternary ammonium compound of claim 10, wherein X2 is CH2CH(OH)CH2.

12. The quaternary ammonium compound of any one of claims 1-11, wherein R8 is CH2OH.

13. The quaternary ammonium compound of any one of claims 1-12, wherein R9 is CH2OH.

14. The quaternary ammonium compound of any one of claims 1-13, wherein R1 is octadecyl.

15. The quaternary ammonium compound of any one of claims 1-14, wherein R16 is CH3.

16. The quaternary ammonium compound of any one of claims 1-15, wherein a is 3.

17. The quaternary ammonium compound of claim 1 selected from the group consisting of:o Ui2024219343   03 Sep 20242024219343   03 Sep 202418. The quaternary ammonium compound of claim 1 selected from the group consisting of:2024219343   03 Sep 202419. The quaternary ammonium compound of claim 1 of structure:2024219343   03 Sep 202421. The quaternary ammonium compound of claim 1 of structure:

22. The quaternary ammonium compound of claim 1 of structure:OH2024219343   03 Sep 202424. The quaternary ammonium compound of claim 1 of structure:

25. The quaternary ammonium compound of claim 1 of structure:2024219343   03 Sep 202427. The quaternary ammonium compound of claim 1 of structure:2024219343   03 Sep 202429. The quaternary ammonium compound of claim 1 of structure:

30. The quaternary ammonium compound of claim 1 of structure:2024219343   03 Sep 202432. An antimicrobial composition comprising a quaternary ammonium compound of any one of claims 1-31 in combination with a pharmaceutically acceptable carrier.

33. The antimicrobial composition of claim 32, wherein the compound is:

34. The antimicrobial composition of claim 32, wherein the compound is:2024219343   03 Sep 202435. The antimicrobial composition of claim 32, wherein the compound is:

36. The antimicrobial composition of claim 32, wherein the compound is:

37. The antimicrobial composition of any one of claims 32-36, wherein the pharmaceutically acceptable carrier is selected from the group consisting of alcohol, aqueous solution, and glycerin solution.

38. The antimicrobial composition of any one of claims 32-37, wherein the composition is suitable for topical delivery.

39. The antimicrobial composition of any one of claims 32-38, wherein the pharmaceutically acceptable carrier is an aqueous solution.2024219343   03 Sep 202440. A method for the treatment of a topical infection in a host, wherein the treatment comprises administering an effective amount of a compound of any one of claims 1-31 or an antimicrobial composition of any one of claims 32-39 to a host in need thereof.

41. The method of claim 40, wherein the infection is selected from the group consisting of an eye infection, ear infection, skin infection, and nail infection.

42. The method of claim 40 or 41, wherein the infection is caused by a bacterium, fungus, amoeba, or virus, or a combination thereof.

43. The method of any one of claims 40-42, wherein the infection is due to biofilm formation.

44. The method of any one of claims 40-43, wherein the host is a human.

45. The method of any one of claims 40-43, wherein the host is a mammal.

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