US 11,723,990 B2
Library of pH responsive polymers and nanoprobes thereof
Jinming Gao, Plano, TX (US); Gang Huang, Plano, TX (US); Tian Zhao, Irving, TX (US); Xinpeng Ma, Dallas, TX (US); Yiguang Wang, Dallas, TX (US); Yang Li, Dallas, TX (US); and Baran D. Sumer, Dallas, TX (US)
Assigned to The Board of Regents of The University of Texas System, Austin, TX (US)
Filed by The Board of Regents of the University of Texas System, Austin, TX (US)
Filed on Apr. 15, 2021, as Appl. No. 17/231,922.
Application 17/231,922 is a continuation of application No. 16/114,187, filed on Aug. 27, 2018, granted, now 11,013,818.
Application 16/114,187 is a continuation of application No. 15/369,701, filed on Dec. 5, 2016, granted, now 10,098,971, issued on Oct. 16, 2018.
Application 15/369,701 is a continuation of application No. PCT/US2015/034575, filed on Jun. 5, 2015.
Claims priority of provisional application 62/009,019, filed on Jun. 6, 2014.
Prior Publication US 2021/0338840 A1, Nov. 4, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 8/73 (2006.01); A61K 8/06 (2006.01); A61K 49/00 (2006.01); G01N 21/64 (2006.01); C08F 8/30 (2006.01); C08F 8/32 (2006.01); C08F 8/34 (2006.01); C08F 8/42 (2006.01); C09B 69/10 (2006.01); G01N 33/58 (2006.01); G01N 33/84 (2006.01)
CPC A61K 49/0054 (2013.01) [A61K 49/0021 (2013.01); A61K 49/0032 (2013.01); A61K 49/0041 (2013.01); C08F 8/30 (2013.01); C08F 8/32 (2013.01); C08F 8/34 (2013.01); C08F 8/42 (2013.01); C09B 69/103 (2013.01); C09B 69/105 (2013.01); C09B 69/106 (2013.01); C09B 69/109 (2013.01); G01N 21/643 (2013.01); G01N 21/6428 (2013.01); G01N 21/6456 (2013.01); G01N 33/582 (2013.01); G01N 33/84 (2013.01); G01N 2021/6432 (2013.01); G01N 2021/6439 (2013.01); G01N 2021/6441 (2013.01)] 20 Claims
OG exemplary drawing
 
1. A polymer of the formula:

OG Complex Work Unit Chemistry
wherein:
R1 is hydrogen, alkyl(C≤12), cycloalkyl(C≤12), substituted alkyl(C≤12), substituted cycloalkyl(C≤12), or

OG Complex Work Unit Chemistry
 or a metal chelating group;
n is an integer from 1 to 500;
R2 and R2′ are each independently selected from hydrogen, alkyl(C≤12), cycloalkyl(C≤12), substituted alkyl(C≤12), or substituted cycloalkyl(C≤12);
R3 is a group of the formula:

OG Complex Work Unit Chemistry
wherein:
nx is 1-10;
X1, X2, and X3 are each independently selected from hydrogen, alkyl(C≤12), cycloalkyl(C≤12), substituted alkyl(C≤12), or substituted cycloalkyl(C≤12); and
X4 and X5 are each independently selected from alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤12), heteroaryl(C≤12) or a substituted version of any of these groups, or X4 and X5 are taken together and are alkanediyl(C≤12), alkoxydiyl(C≤12), alkylaminodiyl(C≤12), or a substituted version of any of these groups;
x is an integer from 1 to 150;
R4 is a group of the formula:

OG Complex Work Unit Chemistry
wherein:
ny is 1-10;
X1′, X2′, and X3′ are each independently selected from hydrogen, alkyl(C≤12), cycloalkyl(C≤12), substituted alkyl(C≤12), or substituted cycloalkyl(C≤12); and
X4′ and X5′ are each independently selected from alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤12), heteroaryl(C≤12) or a substituted version of any of these groups, or X4′ and X5′ are taken together and are alkanediyl(C≤12), alkoxydiyl(C≤12), alkylaminodiyl(C≤12), or a substituted version of any of these groups;
y is an integer from 1 to 150;
R5 is a group of the formula:

OG Complex Work Unit Chemistry
wherein:
nz is 1-10;
Y1, Y2, and Y3 are each independently selected from hydrogen, alkyl(C≤12), cycloalkyl(C≤12), substituted alkyl(C≤12), or substituted cycloalkyl(C≤12); and
Y4 is with the following structure:

OG Complex Work Unit Chemistry
z is an integer from 0-6; and
R6 is hydrogen, halo, hydroxy, alkyl(C≤12), or substituted alkyl(C≤12),
wherein R3, R4, and R5 can occur in any order within the polymer, provided that R3 and R4 are not the same group.