Antimicrobial organosilanes
Organosilicon quaternary ammonium compounds, their formulations, including powdered and solid formulations, and methods of use to treat infections in humans and animals.
1. A quaternary ammonium compound of Formula:
or pharmaceutically acceptable salt thereof,
wherein
a is 3;
R 1 is independently at each occurrence selected from the group consisting of C 6 -C 22 alkyl and C 6 -C 22 alkanoyl;
R 2 , R 3 , and R 4 are independently at each occurrence selected from the group consisting of:
R 8 is H or CH 2 OH;
R 9 is H or C 1 -C 8 alkyl,
X 3 is OH or CH 2 OR 7 ;
R 10 , R 11 , and R 12 are independently at each occurrence selected from the group consisting of hydrogen, —CH 2 OR 7 , CON(R 7 ) 2 , COOR 7 , C(O)R 7 , C 1 -C 8 alkyl, C 1 -C 8 hydroxyalkyl, and C 1 -C 8 alkanoyl;
R 13 is selected from the group consisting of CH 2 OR 7 , CON(R 7 ) 2 , COOR 7 , C(O)R 7 , C 1 -C 8 alkyl, C 1 -C 8 hydroxyalkyl, and C 1 -C 8 alkanoyl;
R 7 is independently at each occurrence selected from hydrogen, C 1 -C 8 alkyl, C 1 -C 8 hydroxyalkyl, and C 1 -C 8 alkanoyl;
X 1 is NR 17 , CH 2 , or C(O);
X 4 is selected from the group consisting of hydroxyl, CH 2 OR 7 , CON(R 7 ) 2 , COOR 7 , C(O)R 7 , C 1 -C 8 hydroxyalkyl, and C 1 -C 8 alkanoyl;
R 16 is C 1 -C 4 alkyl;
R 17 is hydrogen, C 1 -C 8 hydroxyalkyl, or C 1 -C 8 alkanoyl;
X − is an anion.
2. The quaternary ammonium compound of claim 1 , wherein X − is selected from the group consisting of chloride, fluoride, iodide, bromide, hydroxide, chlorite, chlorate, hydroxide, formate, acetate, lactate, benzoate, methane sulfonate and salicylate anion.
3. The quaternary ammonium compound of claim 1 , wherein R 2 , R 3 , and R 4 are
and X 3 is OH.
4. The quaternary ammonium compound of claim 1 , wherein R 2 , R 3 , and R 4 are
and R 8 is CH 2 OH and R 9 is C 1 -C 8 alkyl.
5. The quaternary ammonium compound of claim 4 , wherein X 4 is OH and X 1 is C(O).
6. The quaternary ammonium compound of claim 4 , wherein R 1 is octadecyl and R 16 is CH 3 .
7. The quaternary ammonium compound of claim 4 , wherein X 4 is OH and X 1 is CH 2 .
8. The quaternary ammonium compound of claim 1 selected from the group consisting of:
9. The quaternary ammonium compound of claim 8 of structure:
10. The quaternary ammonium compound of claim 8 of structure:
11. The quaternary ammonium compound of claim 8 of structure:
12. The quaternary ammonium compound of claim 8 of structure:
13. An antimicrobial composition comprising a quaternary ammonium compound selected from the group consisting of:
and a pharmaceutically acceptable carrier.
14. The antimicrobial composition according to claim 13 , wherein the pharmaceutically acceptable carrier is selected from the group consisting of alcohol, aqueous solution, and glycerin solution.
15. The antimicrobial composition of claim 13 , wherein the composition is suitable for topical delivery.
16. The antimicrobial composition of claim 13 , wherein the quaternary ammonium compound is
17. The antimicrobial composition of claim 13 , wherein the quaternary ammonium compound is
18. The antimicrobial composition of claim 13 , wherein the quaternary ammonium compound is
19. The antimicrobial composition of claim 13 , wherein the quaternary ammonium compound is
20. The antimicrobial composition of claim 13 , wherein the quaternary ammonium compound is
21. The antimicrobial composition of claim 13 , wherein the quaternary ammonium compound is
22. The quaternary ammonium compound of claim 1 selected from the group consisting of:
wherein anion X − is a methane sulfonate anion.
23. The antimicrobial composition according to claim 13 , wherein the pharmaceutically acceptable carrier is an aqueous solution.
24. An antimicrobial composition comprising a quaternary ammonium compound selected from the group consisting of:
and a pharmaceutically acceptable carrier;
wherein anion X − is a methane sulfonate anion.
25. The antimicrobial composition of claim 24 , wherein the quaternary ammonium compound is
wherein anion X − is a methane sulfonate anion.
26. The antimicrobial composition according to claim 24 , wherein the pharmaceutically acceptable carrier is selected from the group consisting of alcohol, aqueous solution, and glycerin solution.
27. The antimicrobial composition of claim 24 , wherein the composition is suitable for topical delivery.
28. The antimicrobial composition according to claim 24 , wherein the pharmaceutically acceptable carrier is an aqueous solution.