The inventors have discovered that the disodium salt of certain delivery
agents has surprisingly greater efficacy for delivering active agents
than the corresponding monosodium salt. Furthermore, the inventors have
discovered that the disodium salts of these delivery agents form solvates
with ethanol and hydrates with water. The delivery agents have the
formula
##STR00001##
wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently
hydrogen, halogen, C.sub.1-C.sub.4 alkyl, or C.sub.1-C.sub.4 alkoxy; and
R.sup.5 is a substituted or unsubstituted C.sub.2-C.sub.16 alkylene,
substituted or unsubstituted C.sub.2-C.sub.16 alkenylene, substituted or
unsubstituted C.sub.1-C.sub.12 alkyl(arylene), or substituted or
unsubstituted aryl(C.sub.1-C.sub.12 alkylene). The hydrates and solvates
of present invention also have surprisingly greater efficacy for
delivering active agents, such as heparin and calcitonin, than their
corresponding monosodium salts and free acids. The present invention
provides an alcohol solvate, such as ethanol solvate, of a disodium salt
of a delivery agent of the formula above. The invention also provides a
hydrate of a disodium salt of a delivery agent of the formula above.
Preferred delivery agents include, but are not limited to,
N-(5-chlorosalicyloyl)-8-aminocaprylic acid (5-CNAC),
N-(10-[2-hydroxybenzoyl]amino)decanoic acid (SNAD), and sodium
N-(8-[2-hydroxybenzoyl]amino)caprylate (SNAC). The invention also
provides methods of preparing the disodium salt, ethanol solvate, and
hydrate and compositions containing the disodium salt, ethanol solvate,
and/or hydrate.