US 12,460,050 B2
Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto
Mark H. Schoenfisch, Chapel Hill, NC (US); Lei Yang, Carrboro, NC (US); and Haibao Jin, Carrboro, NC (US)
Assigned to The University of North Carolina at Chapel Hill, Chapel Hill, NC (US)
Appl. No. 16/763,414
Filed by The University of North Carolina at Chapel Hill, Chapel Hill, NC (US)
PCT Filed Nov. 14, 2018, PCT No. PCT/US2018/061061
§ 371(c)(1), (2) Date May 12, 2020,
PCT Pub. No. WO2019/099525, PCT Pub. Date May 23, 2019.
Claims priority of provisional application 62/737,603, filed on Sep. 27, 2018.
Claims priority of provisional application 62/586,404, filed on Nov. 15, 2017.
Prior Publication US 2020/0332061 A1, Oct. 22, 2020
Int. Cl. C08G 73/02 (2006.01); A61K 31/785 (2006.01); A61L 2/16 (2006.01); C08G 83/00 (2006.01)
CPC C08G 73/028 (2013.01) [A61K 31/785 (2013.01); A61L 2/16 (2013.01); C08G 83/006 (2013.01); A61L 2202/24 (2013.01)] 13 Claims
OG exemplary drawing
 
1. A hyperbranched nitric oxide (NO) donating compound, comprising:
a linking group comprising any one or more of Formulas A, B, C, or D:

OG Complex Work Unit Chemistry
wherein,
custom character indicates an attachment to another portion of the hyperbranched NO donating compound;
X1, X2, X3, and X4 are independently selected from the group consisting of —NH—, —N(Ra)—, —O—, and —S—; wherein, at least one instance of X1, X2, X3, and X4 is —N(Ra)—;
wherein each instance of Ra is selected from a NO donating moiety, —H, an optionally substituted C1-C6 alkyl group, or an optionally substituted polyether having 1 to 6 to repeat units; wherein, in at least one instance of Formula A, the secondary amine of Formula A is directly bound to a NO donating moiety or at least one instance of Ra is a NO donating moiety, wherein the NO donating moiety is selected from the group consisting of:

OG Complex Work Unit Chemistry
R1, R2, and R3 are independently selected from the group consisting of —RbN(Rc)Rd—(N(Rc))n—Rb—, —Rb(ORd—)nO—Rb—, and C1-C6 alkyl;
wherein each instance of Rc is independently selected from a NO donating moiety, —H, an optionally substituted C1-C6 alkyl group, or an optionally substituted poly ether having 1 to 6 repeat units;
wherein Rb is a single bond or an optionally substituted C1-C6 alkylene group;
wherein Ra is an optionally substituted C1-C6 alkylene group;
wherein n is an integer selected from 0, 1, 2, 3, 4, 5, or 6;
wherein, where R2 is present, at least one instance of Rd comprises the —C(O)—(CH2)2—X3— group;
wherein, where R3 is present, at least one instance of Rd comprises the —C(O)—(CH2)2—X3— group and at least one instance of Rd comprises the —C(O)—(CH2)2—X4— group;
and,
wherein the hyperbranched compound does not comprise an aminoglycoside or glycoside unit.