| abstract |
The present invention relates to a method of preparing an alkylated salicylamide from a protected and activated salicylamide via a dicarboxylated salicylamide intermediate. The present invention also relates to dicarboxylic salicylamide delivery agent compounds for the delivery of active agents. Methods of administration are provided as well. A non limitative example of a particularly preferred dicarboxylated salicylamide may be represented by the formula: (see above formula) where R1, R2, R3, and R4 are independently hydrogen; halogen; C1-C4 alkoxy, optionally substituted with -OH or F; -OH; C1-C4 alkyl, optionally substituted with -OH or F; -COOH; -OC(O)CH3; -SO3H; nitrile; or -NR9R1O; R9 and R10 are independently hydrogen, C1-C4 alkyl, or oxygen; R5 is a protecting group; R6 is an activating group; or R5 and R6 are combined to form a substituted or unsubstituted cyclic group; R7 is a linear C1-C20 alkylene, a linear C2-C20 alkenylene, a linear C2-C20 alkynylene, a branched C3-C20 alkylene, a branched C3-C20 alkenylene, or a branched C3-C20 alkynylene, and comprises a CH unit that is substituted by said -COOR8 and COOR11 groups; R7 is optionally substituted with C1-C4 alkyl, C1-C4 alkenyl, oxygen, nitrogen, sulfur, halogen, -OH, C1-C4 alkoxy, aryl, heteraryl, or vinyl; R7 is optionally interrupted with aryl, heteroaryl, vinyl, oxygen, nitrogen, or sulfur; R8 and R11 are independently C1-C4 alkyl or C1-C4 haloalkyl; and R9 and R10 are independently hydrogen, C1-C4 alkyl, or oxygen. |