COMPLEXING AGENT SALT FORMULATIONS OF PHARMACEUTICAL COMPOUNDS
Provided herein are pharmaceutical formulations and pharmaceutical compound salts which utilize complexing agents as counterions. Such formulations and salts are useful for treating a variety of disease and disorders.
1 . A solid salt comprising the formula:
wherein
each R 1 is independently H, alkyl, or substituted alkyl, wherein when R 1 is a substituted alkyl, the substituted alkyl is deprotonated;
each R 2 is independently H, alkyl, or substituted alkyl;
m is at least 1; and
n is at least 1.
2 . The solid salt of claim 1 , wherein R 1 is a substituted alkyl, and wherein the substituted alkyl is substituted with an anionic functional group.
3 . The solid salt of claim 2 , wherein the substituted alkyl is a C 1 -C 6 alkyl substituted with at least one anionic functional group.
4 . The solid salt of claim 2 , wherein the anionic functional group comprises a conjugate base of a carboxylic acid, a sulfonic acid, a sulfinic acid, a phosphonic acid, or a phosphinic acid.
5 . The solid salt of claim 1 , wherein R 1 is a conjugate base of
6 . The solid salt of claim 1 , wherein R 1 is H.
7 . The solid salt of claim 1 , wherein at least one R 2 is a substituted alkyl, wherein the substituted alkyl is substituted with an anionic functional group.
8 . The solid salt of claim 1 , wherein R 2 is H.
9 . The solid salt of claim 1 , wherein m is a number from 1-7.
10 . The solid salt of claim 1 , wherein n is 6, 7, or 8 and m is a number from 1-8.
11 . The solid salt of claim 1 , wherein the pharmaceutical compound comprises at least one basic nitrogen atom.
12 . The solid salt of claim 11 , wherein the pKa of the at least one basic nitrogen atom is from about 4 to about 12.
13 . The solid salt of claim 12 , wherein the at least one basic nitrogen atom is comprised in a heterocycle.
14 . The solid salt of claim 1 , wherein the solid salt is substantially pure.
15 . The solid salt of claim 1 , wherein the solid salt is at least 98% free of impurities.
16 . A method of dissolving a solid salt, comprising:
dissolving a solid salt in a solution,
the solid salt comprising the formula:
wherein
each R 1 is independently H, alkyl, or substituted alkyl, wherein
when R 1 is a substituted alkyl, the substituted alkyl is deprotonated;
each R 2 is independently H, alkyl, or substituted alkyl;
m is at least 1; and
n is at least 1; and
wherein the solution has a pH of about 4 to about 10.
17 . The method of claim 16 , wherein the solution has a pH of about 4 to about 7.
18 . A method of administering a solid salt to a human subject, comprising:
administering a solid salt to a human subject,
the solid salt comprising the formula:
wherein
each R 1 is independently H, alkyl, or substituted alkyl, wherein
when R 1 is a substituted alkyl, the substituted alkyl is deprotonated;
each R 2 is independently H, alkyl, or substituted alkyl;
m is at least 1; and
n is at least 1; and
wherein the solid salt is formulated for oral administration.
19 . The method of claim 18 , wherein the solid salt is formulated as a powder, tablet, pill, dragee, capsule, lozenge, gel, troche, film, suppository, or a cachet.
20 . The method of claim 18 , wherein the solid salt is formulated as a liquid, syrup, slurry, emulsion, suspension, or a gel.