US 12,459,898 B2
Polycationic amphiphiles as antimicrobial agents and methods using same
William M. Wuest, Wallingford, PA (US); and Kevin P. C. Minbiole, Media, PA (US)
Assigned to Temple University-Of The Commonwealth System of Higher Education, Philadelphia, PA (US); and Villanova University, Villanova, PA (US)
Filed by Temple University-Of The Commonwealth System of Higher Education, Philadelphia, PA (US); and Villanova University, Villanova, PA (US)
Filed on Sep. 7, 2021, as Appl. No. 17/468,349.
Application 17/468,349 is a continuation of application No. 16/343,418, granted, now 11,111,216, previously published as PCT/US2017/058409, filed on Oct. 26, 2017.
Claims priority of provisional application 62/413,129, filed on Oct. 26, 2016.
Prior Publication US 2021/0403430 A1, Dec. 30, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 213/90 (2006.01); A01N 33/12 (2006.01); A01N 43/40 (2006.01); C07C 211/63 (2006.01); C07D 401/06 (2006.01); C07D 401/14 (2006.01)
CPC C07D 213/90 (2013.01) [A01N 33/12 (2013.01); A01N 43/40 (2013.01); C07C 211/63 (2013.01); C07D 401/06 (2013.01); C07D 401/14 (2013.01)] 32 Claims
 
1. A composition comprising
(i) at least one compound selected from the group consisting of formula I-IV:

OG Complex Work Unit Chemistry
wherein in formula I-III:
R1, R2, and R3 are each independently selected from the group consisting of H and C1-C25 alkyl, wherein the alkyl group may be optionally substituted with —OR′, —NR′2, —NR′—C(O)R′, —C(O)NR′2, —NR′—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, halogen, benzyl, o-vinylbenzyl, m-vinylbenzyl, p-vinylbenzyl, phenyl, allyl, and substituted allyl, further wherein the alkyl group may optionally be interrupted with a —O—C(O)— group or a —C(O)O— group;
each occurrence of Ra, Rb, Rc, Rd, and Re is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
each occurrence of R′ is independently selected from the group consisting of H and C1-4 alkyl;
Y is N or CR″;
R″ is H or C1-C6 alkyl, wherein the alkyl group may be optionally substituted and may combine with any of Ra, Rb, and Rc to form a ring;
each occurrence of Z is independently a counterion;
m is an integer from 0 to 4;
n is an integer from 0 to 4; and
p is an integer from 0 to 4; and
wherein in formula IV: R1 and R2 are each independently selected from the group consisting of H and C10-C13 alkyl, wherein the alkyl group may be optionally substituted with —OR′, —NR′2, —NR′—C(O)R′, —C(O)NR′2, —NR′—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, halogen, benzyl, o-vinylbenzyl, m-vinylbenzyl, p-vinylbenzyl, allyl, and substituted allyl, further wherein the alkyl group may optionally be interrupted with a-O—C(O)-group or a-C(O)O— group;
each occurrence of Ra, Rb, Rc, Rd, and Re is independently selected from the group consisting of H, C1-C6 alkyl, —OR′, —CN, —NO2, —NR′2, —N—C(O)R′, —C(O)NR′2, —N—C(O)CR′═CR′, —SR′, —O—C(O)R′, —C(O)OR′, —C(O)R′, —CF3, —OCF3, and halogen;
each occurrence of R′ is independently selected from the group consisting of H and C1-4 alkyl;
Y is N or CR″;
R″ is H or C1-C6 alkyl, wherein the alkyl group may be optionally substituted and may combine with any of Ra, Rb, and Rc to form a ring;
each occurrence of Z is independently a counterion;
m is an integer from 0 to 4;
n is an integer from 0 to 4; and
p is an integer from 0 to 4; and
(ii) at least one selected from the group consisting of a pharmaceutically acceptable carrier, base material, antimicrobial agent, a second compound or a moiety, and any combination thereof.