Cationic steroidal antimicrobial compounds and methods of manufacturing such compounds

摘要

Cationic steroidal antimicrobial (CSA) compounds having amide functionality and methods of manufacturing such CSA compounds. The CSA compound can be a compound of Formula (I), Formula (II), Formula (III), or a salt thereof:;where R18 has the following structure:
—R20—(C═O)—N—R21R22 R20 is omitted or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl, andR21 and R22 are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, or substituted or unsubstituted aryl, provided that at least one of R21 and R22 is not hydrogen.

主权项

1. A cationic steroidal antimicrobial (CSA) compound of Formula (III), or salt thereof:wherein,
R3, R7, and R12 are independently selected from the group consisting of aminoalkyloxy, aminoalkylcarboxy, alkylaminoalkyl, alkoxycarbonylalkyl, alkylcarbonylalkyl, di(alkyl)aminoalkyl, alkylcarboxyalkyl, aminoalkylaminocarbonyl, aminoalkylcarboxamido, guanidinoalkyloxy, guanidinoalkylcarboxy, quaternary ammonium alkylcarboxy, and hydroxyalkyl, R18 has the following structure:
—R20—(C═O)—N—R21R22 R20 is a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, or a substituted or unsubstituted C6 or C10 aryl, and R21 and R22 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C6 or C10 aryl, substituted or unsubstituted 5 to 10 membered heteroaryl, substituted or unsubstituted 5 to 10 membered heterocyclyl, substituted or unsubstituted C7-C13 aralkyl, substituted or unsubstituted (5 to 10 membered heteroaryl)-C1-C6 alkyl, substituted or unsubstituted C3-C10 carbocyclyl, substituted or unsubstituted C4-C10 (carbocyclyl)alkyl, substituted or unsubstituted (5 to 10 membered heterocyclyl)-C1-C6 alkyl, substituted or unsubstituted substituted amido, and amine protecting group, provided that at least one of R21 and R22 is not hydrogen.