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:
wherein
a is 1, 2, 3, 4, 5, 6, 7 or 8;
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 , R 4 , R 22 , R 23 , and R 24 are independently at each occurrence selected from the group consisting of:
each R 21 is independently selected from the group consisting of C 1 -C 22 alkyl and C 2 -C 22 alkanoyl;
R 7 is independently at each occurrence selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 1 -C 8 hydroxyalkyl, and C 1 -C 8 alkanoyl;
R 8 and R 9 are independently at each occurrence selected from the group consisting of hydrogen, halogen, hydroxyl, N(R 7 ) 2 , 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;
X 1 is NR 17 , CH 2 , CHOH, or C(O);
X 2 is C 1 -C 3 alkyl or C 1 -C 3 hydroxyalkyl;
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 or is absent if the quaternary amine is balanced with an internal anion; and
B + is a cation.
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 B + is selected from the group consisting of Na + , K + , Li + , Mg 2+ , and Ca 2+ .
4. The quaternary ammonium compound of claim 1 , wherein the compound is a zwitterion and X is absent.
5. The quaternary ammonium compound of claim 1 , wherein X 1 is NH or N(CH 2 CH 2 OH).
6. The quaternary ammonium compound of claim 1 , wherein X 2 is CH 2 CH 2 or CH 2 CH(OH)CH 2 .
7. The quaternary ammonium compound of claim 6 , wherein R 16 is CH 3 .
8. The quaternary ammonium compound of claim 7 , wherein R 1 is octadecyl.
9. The quaternary ammonium compound of claim 8 , wherein R 8 and R 9 are each CH 2 OH.
10. The quaternary ammonium compound of claim 9 , wherein a is 3.
11. The quaternary ammonium compound of claim 10 , wherein X 1 is NH or N(CH 2 CH 2 OH).
12. The quaternary ammonium compound of claim 1 selected from the group consisting of:
13. The quaternary ammonium compound of claim 1 of structure:
14. The quaternary ammonium compound of claim 1 of structure:
15. The quaternary ammonium compound of claim 1 of structure:
16. The quaternary ammonium compound of claim 1 of structure:
17. The quaternary ammonium compound of claim 1 of structure:
18. The quaternary ammonium compound of claim 1 of structure:
19. The quaternary ammonium compound of claim 1 of structure:
20. The quaternary ammonium compound of claim 1 of structure:
21. The quaternary ammonium compound of claim 1 of structure:
22. The quaternary ammonium compound of claim 1 of structure:
23. The quaternary ammonium compound of claim 1 of structure:
24. The quaternary ammonium compound of claim 1 of structure:
25. An antimicrobial composition comprising a quaternary ammonium compound of claim 1 and a pharmaceutically acceptable carrier.
26. The antimicrobial according to claim 25 , wherein the pharmaceutically acceptable carrier is selected from the group consisting of alcohol, aqueous solution, and glycerin solution.
27. The antimicrobial composition of claim 26 , wherein the composition is suitable for topical delivery.
28. The antimicrobial composition of claim 25 , wherein the quaternary ammonium compound is
29. The antimicrobial composition of claim 25 , wherein the quaternary ammonium compound is
30. The antimicrobial composition of claim 25 , wherein the quaternary ammonium compound is