US 11,718,585 B2
Bis-cyclic guanidines as antibacterial agents
Jianfeng Cai, Tampa, FL (US); Peng Teng, Tampa, FL (US); and Alekhya Nimmagadda, Tampa, FL (US)
Assigned to University of South Florida, Tampa, FL (US)
Filed by University of South Florida, Tampa, FL (US)
Filed on Nov. 1, 2021, as Appl. No. 17/516,546.
Application 17/516,546 is a continuation of application No. 16/629,805, granted, now 11,214,550, previously published as PCT/US2018/038716, filed on Jun. 21, 2018.
Claims priority of provisional application 62/536,295, filed on Jul. 24, 2017.
Prior Publication US 2022/0119352 A1, Apr. 21, 2022
Int. Cl. C07D 233/46 (2006.01); A61K 45/06 (2006.01); A61P 31/04 (2006.01); A61K 31/4178 (2006.01); C07D 403/12 (2006.01); A61K 38/12 (2006.01)
CPC C07D 233/46 (2013.01) [A61K 31/4178 (2013.01); A61K 45/06 (2013.01); A61P 31/04 (2018.01); C07D 403/12 (2013.01); A61K 38/12 (2013.01)] 17 Claims
 
1. A method of preparing a compound of Formula (I)

OG Complex Work Unit Chemistry
wherein
R1 at each occurrence is independently hydrogen, C1-C10 alkyl, alkenyl, alkynyl, aryl, aryl-C1-C6 alkyl, cycloalkyl, or cycloalkyl-C1-C6 alkyl;
R2 at each occurrence is independently hydrogen, C1-C10 alkyl, alkenyl, alkynyl, aryl, aryl-C1-C6 alkyl, cycloalkyl, or cycloalkyl-C1-C6 alkyl;
X is O or NH
L1 is —(CRxRy)n1;
L2 is —(CRxRy)n2;
L is —(CRxRy)n3—(CH2CH2O)m1-G-(CH2CH2O)m2—(CRxRy)n4—
Rx and Ry at each occurrence is independently hydrogen or C1-C4 alkyl;
G is a bond or -(G1)t-, wherein G1 at each occurrence is independently aryl, cycloakyl, heteroaryl, or heterocycle;
n1 and n2 are each independently 1-4;
m1, m2, n3, and n4 are each independently 0-10;
t is 1, 2, 3, or 4; and
wherein R1, R2, Rx, Ry, and G1 optionally are each independently substituted with one or more substituents selected from the group consisting of halogen, cyano, —OH, C1-C6 alkoxy, —COOH, C1-C6 alkoxycarbonyl, oxo, and amino;
comprising:
reacting an intermediate of Formula (I-i)

OG Complex Work Unit Chemistry
 to form the compound of Formula (I).