US 12,454,550 B2
Compositions and methods for bioorthogonal surface coating
Enver Cagri Izgu, Piscataway, NJ (US); Kern Hast, Jersey City, NJ (US); Zhaojun Jia, Piscataway, NJ (US); and Melih Baci, Piscataway, NJ (US)
Assigned to Rutgers, The State University of New Jersey, New Brunswick, NJ (US)
Filed by Rutgers, The State University of New Jersey, New Brunswick, NJ (US)
Filed on Sep. 30, 2022, as Appl. No. 17/937,041.
Claims priority of provisional application 63/250,552, filed on Sep. 30, 2021.
Prior Publication US 2023/0105381 A1, Apr. 6, 2023
Int. Cl. C07K 5/12 (2006.01); A61K 38/14 (2006.01)
CPC C07K 5/12 (2013.01) [A61K 38/14 (2013.01)] 20 Claims
 
1. A compound of formula (I) or a salt thereof:

OG Complex Work Unit Chemistry
wherein:
L1 is a linker of formula *—X—(Y)m—Z—, wherein * is the bond between X and the carbon marked as **, wherein:
X is a bond (null), —C(═O)—, —C(═O)NH—, —C(═O)NH(C6-C10 arylene)-, —C(═O)NH(substituted C1-C10 arylene)-, —C(═O)NH(C2-C10 alkenylene)-, or —C(═O)NH(C1-C10 alkylene)-, wherein the substituted C6-C10 arylene comprises at least one substituent independently selected from the group consisting of halogen, —R′, —OR′, and —C(═O)OR′;
each occurrence of Y is independently selected from the group consisting of —CH2CH2O—, —CH(CH3)CH2O—, —CH2CH(CH3)O—, —C(CH3)2CH2O—, —CH2C(CH3)2O—, —C(CH3)2C(CH3)2O—, —OCH2CH2—, —OCH(CH3)CH2—, —OCH2CH(CH3)—, —OC(CH3)2CH2—, —OCH2C(CH3)2—, —OC(CH3)2C(CH3)2—, —CH2CH2—, —CH(CH3)CH2—, —CH2CH(CH3)—, —C(CH3)2CH2—, —CH2C(CH3)2—, —C(CH3)2C(CH3)2—, with the proviso that O—O bonds are not present;
Z is selected from the group consisting of optionally substituted C1-C6 alkylene, optionally substituted C6-C10 arylene, and optionally substituted C2-C8 heteroarylene;
each occurrence of R′ is independently selected from the group consisting of H, optionally substituted C1-C6 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C6-C10 aryl, and optionally substituted C2-C8 heteroaryl;
m is selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10;
R1 is selected from the group consisting of H and C1-C6 alkyl;
each of Ra1, Ra2 and Ra3 is H;
Rb1 and Rb2 are each independently selected from the group consisting of H and optionally substituted C1-C6 alkyl, wherein at least one of Rb1 and Rb2 is H;
wherein each optional substituent is independently selected from the group consisting of F, Cl, Br, I, OR, OC(O)N(R)2, CN, NO2, N3, CF3, OCF3, R, N(R)2, SR, S(O)R, SO2R, SO2N(R)2, SO3R, C(O)R, C(O)OR, OC(O)R, C(O)N(R)2, OC(O)N(R)2, N(R)SO2R, N(R)SO2N(R)2, N(R)C(O)OR, N(R)C(O)R, and N(R)C(O)N(R)2; and
each occurrence of R is independently selected from the group consisting of H, C1-C8 alkyl, C3-C8 cycloalkyl, C6-C14 aryl, C1-C8 alkyl(C6-C14 aryl), 5- to 12-membered ring heteroaryl, and C1-C8(5- to 12-membered ring heteroaryl).