US 12,295,970 B2
Imidazoquinoline compounds and prodrugs thereof
Laird Forrest, Lawrence, KS (US); Daniel Aires, Mission Hills, KS (US); Ryan Moulder, Lawrence, KS (US); Ruolin Lu, Lawrence, KS (US); Jordan Hunt, Lawrence, KS (US); Peter Kleindl, Lawrence, KS (US); Ti Zhang, Lawrence, KS (US); Chad Groer, Lawrence, KS (US); and Shuang Cai, Lawrence, KS (US)
Assigned to UNIVERSITY OF KANSAS, Lawrence, KS (US); and HYLAPHARM, LLC, Lawrence, KS (US)
Appl. No. 17/598,160
Filed by UNIVERSITY OF KANSAS, Lawrence, KS (US); and HYLAPHARM, LLC, Lawrence, KS (US)
PCT Filed Apr. 16, 2020, PCT No. PCT/US2020/028468
§ 371(c)(1), (2) Date Sep. 24, 2021,
PCT Pub. No. WO2020/214783, PCT Pub. Date Oct. 22, 2020.
Claims priority of provisional application 62/835,408, filed on Apr. 17, 2019.
Prior Publication US 2022/0177472 A1, Jun. 9, 2022
Int. Cl. A61K 33/243 (2019.01); A61K 45/06 (2006.01); A61K 47/36 (2006.01); A61K 47/61 (2017.01); A61P 29/00 (2006.01); A61P 35/00 (2006.01); C07D 471/04 (2006.01); C07F 15/00 (2006.01)
CPC A61K 33/243 (2019.01) [A61K 45/06 (2013.01); A61K 47/36 (2013.01); A61K 47/61 (2017.08); A61P 29/00 (2018.01); A61P 35/00 (2018.01); C07D 471/04 (2013.01); C07F 15/0093 (2013.01)] 29 Claims
 
1. A composition comprising
(a) compound of Formula I

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein
X1 is H, halo, hydroxy, amino, cyano, trifluoromethyl, thiol, alkylthio, sulfoxide, sulfone, nitro, pentafluorosulfanyl, carboxylate, amide, ester, C1-C6 alkyl, C1-C6 alkoxy, aryl, aryloxy, C1-C6 alkanoyl, C1-C8 alkanoyloxy, aryloyl, aryloyloxy,

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where R1 and R2 are each independently H, or

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X2 is H, hydroxyl,

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where R1 and R2 are each independently H, or

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m is 1, 2, 3, 4, 5, 6, 7, or 8;
n is 1, 2, or 3;
p is 1, 2, 3, 4, 5, 6, 7, or 8; and
X3 is CH2 or O;
provided that at least one of X1 and X2 is not

OG Complex Work Unit Chemistry
and wherein the compound of Formula I is not

OG Complex Work Unit Chemistry
(b) a pharmaceutically acceptable carrier; and
(c) a hyaluronan-tocopherol conjugate of Formula II, III, IV, V, or a mixture of any two or more thereof:

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or a pharmaceutically acceptable salt thereof,

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or a pharmaceutically acceptable salt thereof,

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or a pharmaceutically acceptable salt thereof,

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein a is independently at each occurrence from 1 to 800 and b is independently at each occurrence from 18 to 2540.