Patent ID: 6433001
Filing Date: 2002-08-13
Classification: A61P,C07D

Abstract:
An (acyloxy) alkyl ester prodrug derivative of a 1H-indole-3-glyoxylamide of the invention represented by the formula (I); wherein;both X are oxygen; R1 is selected from the group consisting of where R10 is a radical independently selected from halo, C1-C10 alkyl, C1-C10 alkoxy, â€”Sâ€”(C1-C10 alkyl), and C1-C10 haloalkyl and t is a number from 0 to 5; R2 is selected from the group; halo, cyclopropyl, methyl, ethyl, and propyl; R4 and R5 are independently selected from hydrogen, a non-interfering substituent, or the group, â€”(La)-(acidic group); wherein â€”(La)â€” is an acid linker; provided, the acid linker group, â€”(LaLâ€”, R4 is selected from the group consisting of; â€ƒand provided, the acid linker, â€”(La)â€”, for R5 is selected from group consisting of; wherein R84 and R85 are each independently selected from hydrogen, C1-C10 alkyl, aryl, C1-C10 alkaryl, C1-C10 aralkyl, carboxy, carbalkoxy, and halo; and provided, that at least one of R4 and R5 must be the group, â€”(La)-(acidic group) and wherein the (acidic group) on the group â€”(La)-(acidic group) of R4 or R5 is selected from â€”CO2H, â€”SO3H, or â€”P(O) (OH)2; R6 and R7 are each independently selected form hydrogen and non-interfering substituents, with the non-interfering substituents being selected from the group consisting of the following: C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C7-C12 aralkyl, C7-C12 alkaryl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, tolulyl, xylenyl, biphenyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C12 alkoxyalkyl, C2-C12 alkoxyalkyloxy, C2-C12 alkylcarbonyl, C2-C12 alkylcarbonylamino, C2-C12 alkoxyamino, C2-C12 alkoxyaminocarbonyl, C2-C12 alkylamino, C1-C6 alkylthio, C2-C2 alkylthiocarbonyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C2-C6 haloalkoxy, C1-C6 haloalkylsulfonyl, C2-C6 haloalkyl, C1-C6 hydroxyalkyl, â€”C(O)O(C1-C6 alkyl), â€”(CH2)nâ€”Oâ€”(C1-C6 alkyl), benzyloxy, phenoxy, phenylthio, â€”(CONHSO2R), â€”CHO), amino, amidino, bromo, carbamyl, carboxyl, carbalkoxy, â€”(CH2)nâ€”CO2H, chloro, cyano, cyanoguanidinyl, fluoro, guanidino, hydrazide, hydrazino, hydrazido, hydroxy, hydroxyamino, iodo, nitro, phosphono, â€”SO3H, thioacetal, thiocarbonyl, and C1-C6 carbonyl; where n is from 1 to 8.