Furanic quaternary ammonium salts
Disclosed herein is a method for making a quaternary ammonium salt according to the formula Also disclosed is a method for making the ammonium salts from an oleofuran compound. The compounds are useful as antibacterial and/or antiviral compounds and methods for administering the compounds also are disclosed.
1 . A compound having a formula
wherein:
R 1 is optionally substituted C 6-20 alkyl;
each of R 2 , R 3 , and R 4 independently is H, C 1-6 alkyl, aldehyde, or OH;
R 5 is H or C 1-3 alkyl;
R 10 is optionally substituted C 2-20 aliphatic;
each of R 11 and R 12 independently is H or C 1-6 alkyl; and
X is halide or OH.
2 . The compound of claim 1 wherein R 1 , R 10 or both are independently substituted with one or more hydroxy, amine, or carbonyl moieties, or a combination thereof.
3 . The compound of claim 1 , wherein R 1 is C 6-18 alkyl.
4 . The compound of claim 1 , wherein R 10 is C 2-4 alkyl.
5 . The compound of claim 1 , wherein each of R 11 and R 12 independently is C 1-6 alkyl.
6 . The compound of claim 1 , wherein one or both of R 11 and R 12 is methyl.
7 . The compound of claim 1 , wherein each of R 2 , R 3 , and R 4 independently is H or C 1-6 alkyl.
8 . The compound of claim 1 , wherein R 2 , R 3 , and R 4 are all H.
9 . The compound of claim 1 , wherein X is Cl, Br, I or OH.
10 . The compound of claim 1 , wherein:
R 1 is C 6 alkyl;
R 10 is C 3 alkyl;
R 2 , R 3 , and R 4 are all H;
R 11 and R 12 are both methyl; and
X is Cl.
11 . A pharmaceutical composition comprising a compound according to claim 1 , and a pharmaceutically acceptable excipient.
12 . A method of making a compound according to claim 1 , the method comprising:
a) forming a mixture comprising a compound having a formula A-1
and a compound having a formula
to form a compound having a formula A-2
b) exposing the compound having formula A-2 to reducing conditions to form a compound having a formula A-3
c) treating the compound having the formula A-3 with a compound of formula R 11 X and a compound of formula R 12 X to form a compound having a formula A-4
wherein
R 1 is optionally substituted C 6-20 alkyl;
each of R 2 , R 3 , and R 4 independently is H, C 1-6 alkyl, aldehyde, or OH;
R 5 is H or C 1-3 alkyl;
R 10 is optionally substituted C 2-20 aliphatic;
each of R 11 and R 12 independently is H, or C 1-6 alkyl; and
each X independently is halide or OH.
13 . The method of claim 12 wherein exposing the compound having formula A-2 to reducing conditions comprises treating the compound with a reducing agent or hydrogen gas in the presence of a catalyst.
14 . The method of claim 13 , wherein:
the reducing agent is a borohydride reagent; or
the catalyst is a palladium-based catalyst.
15 . The method of claim 12 , wherein each X is Cl or Br.
16 . A method of making a compound according to claim 1 , the method comprising:
a) forming a mixture comprising a compound having a formula A-1
and a compound having a formula
and exposing the mixture to reducing conditions to form a compound having a formula A-5
and
b) treating the compound having the formula A-5 with a compound of formula R 12 X to form a compound having a formula A-6
wherein
R 1 is optionally substituted C 6-20 alkyl;
each of R 2 , R 3 , and R 4 independently is H, C 1-6 alkyl, aldehyde, or OH;
R 5 is H or C 1-3 alkyl;
R 10 is optionally substituted C 2-20 aliphatic;
each of R 11 and R 12 independently is H, or C 1-6 alkyl; and
each X independently is halide or OH.
17 . The method of claim 16 wherein exposing the mixture to reducing conditions comprises treating the compound with a reducing agent or hydrogen gas optionally in the presence of a catalyst.
18 . The method of claim 17 , wherein:
the reducing agent is a borohydride reagent; or
the catalyst is a palladium-based catalyst.
19 . The method of claim 16 , wherein each X is Cl or Br.