Disodium salts, monohydrates, and ethanol solvates for delivering active agents

A method for preparing an anhydrous disodium salt of a delivery agent comprising drying the ethanol solvate of the disodium salt of the delivery agent, wherein the delivery agent has the formula

• 7
• wherein
• R1, R2, R3, and R4 are independently hydrogen, —OH, —NR6R7, halogen, C1-C4 alkyl, or C1-C4 alkoxy;
• R5 is a substitued or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene);
• and
• R6 and R7 are independently hydrogen, oxygen, or C1-C4 alkyl.

A method of preparing an ethanol solvate of the disodium salt of a delivery agent comprising:

• (a) dissolving the delivery agent in ethanol to form a delivery agent/ethanol solution;
• and
• (b) reacting the delivery agent/ethanol solution with a molar excess of a sodium containing salt to form the ethanol solvate,
• wherein the delivery agent has the formula
• 8
• wherein
• R1, R2, R3, and R4 are independently hydrogen, —OH, —NR6R7, halogen, C1-C4 alkyl, or C1-C4 alkoxy;
• R5 is a substitued or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene);
• and
• R6 and R7 are independently hydrogen, oxygen, or C1-C4 alkyl.

A method of preparing a monohlydrate of a disodium salt of a delivery agent, the method comprising

• (a) obtaining an ethanol solvate of the disodium salt of the delivery agent;
• (b) drying the solvate to form an anhydrous disodium salt;
• and
• (c) hydrating the anhydrous disodium salt to form the hydrate,
• wherein the delivery agent has the formula
• 9
• wherein
• R1, R2, R3, and R4 are independently hydrogen, —OH, —NR6R7, halogen, C1-C4 alkyl, or C1-C4 alkoxy;
• R5 is a substitued or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene);
• and
• R6 and R7 are independently hydrogen, oxygen, or C1-C4 alkyl.