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US 2011/0257199 A1Published application
Novel teraryl compounds as antiparasitic agents
AssigneesThe University of North Carolina at Chapel Hill, Georgia State University Research Foundation, Inc.
InventorsRichard R. Tidwell, David W. Boykin, W. David Wilson, Reto Brun, Karl Werbovetz, Mohamed A. Ismail, Reem K. Arafa, Laixing Hu
Life of this patent
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Abstract
Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues.
Claims24
An aza teraryl compound comprising a structure of Formula (III):
- wherein:
- p and q are each independently an integer from 0 to 8;
- A1, Y1, and Z1 are independently selected from the group consisting of N and CR7, wherein R7 is selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl, wherein at least one of A1, Y1, and Z1 is N;
- R6 is selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl;
- Ar1 is:
- wherein m is an integer from 0 to 4 and each R1 is independently selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl;
- Ar3 is:
- wherein:
- A, D, E, G, Y, and Z are independently selected from the group consisting of N and CR4, wherein R4 is selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl, wherein at least one of A, D, E, G, Y, and Z is nitrogen;
- R2 and R21 are selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl;
- and
- L1 and L2 are independently selected from the group consisting of:
- wherein:
- R11, R12, R13, R14, R15, and R20 are each independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, hydroxyalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aminoalkyl, acyloxyl, alkylaminoalkyl, and alkoxycarbonyl;
- or
- R11 and R12 together represent a C2 to C10 alkyl, C2 to C10 hydroxyalkyl, or a C2 to C10 alkylene;
- or
- R11 and R12 together are:
- wherein u is an integer from 1 to 4, and R16 is H or —CONHR17NR18R19, wherein R17 is alkyl, and R18 and R19 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof.
17 more elements
3-10. (canceled)
15-18. (canceled)
21-22. (canceled)
A method of treating a microbial infection in a subject in need of treatment thereof, the method comprising administering to the subject an effective amount of an aza teraryl compound of Formula (III):
- wherein:
- p and q are each independently an integer from 0 to 8;
- A1, Y1, and Z1 are independently selected from the group consisting of N and CR7, wherein R7 is selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl, wherein at least one of A1, Y1, and Z1 is N;
- R6 is selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl;
- Ar1 is:
- wherein:
- m is an integer from 0 to 4;
- each R1 is independently selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl;
- Ar3 is:
- wherein:
- A, D, E, G, Y, and Z are independently selected from the group consisting of N and CR4, wherein R4 is selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl, wherein at least one A, D, E, G, Y, and Z is nitrogen;
- R2, and R21 are selected from the group consisting of H, hydroxyl, halo, nitro, alkyl, substituted alkyl, alkoxyl, aryl, substituted aryl, and aryloxyl;
- and
- L1 and L2 are independently selected from the group consisting of:
- wherein:
- R11, R12, R13, R14, R15, and R20 are each independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, hydroxyalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aminoalkyl, acyloxyl, alkylaminoalkyl, and alkoxycarbonyl;
- or
- R11 and R12 together represent a C2 to C10 alkyl, C2 to C10 hydroxyalkyl, or a C2 to C10 alkylene;
- or
- R11 and R12 together are:
- wherein u is an integer from 1 to 4, and R16 is H or —CONHR17NR18R19, wherein R17 is alkyl, and R18 and R19 are each independently selected from the group consisting of H and alkyl;
- or a pharmaceutically acceptable salt thereof.
19 more elements
27-34. (canceled)
39-42. (canceled)
45-50. (canceled)
Dependencies are inferred from the claim text.