US 12,246,024 B2
Compositions and methods for controlling cerumen production
Stephen L. Segebrecht, Lawrence, KS (US)
Assigned to Free State Pharma Inc, Lawrence, KS (US)
Filed by Free State Pharma Inc, Lawrence, KS (US)
Filed on Dec. 13, 2019, as Appl. No. 16/713,303.
Prior Publication US 2021/0177858 A1, Jun. 17, 2021
Int. Cl. A61K 31/5386 (2006.01); A61K 9/00 (2006.01); A61K 47/10 (2017.01); A61P 27/16 (2006.01)
CPC A61K 31/5386 (2013.01) [A61K 47/10 (2013.01); A61P 27/16 (2018.01); A61K 9/0046 (2013.01)] 21 Claims
OG exemplary drawing
 
1. A liquid composition for the treatment and/or prevention of excessive cerumen, comprising;
a compound or pharmaceutically acceptable prodrug or salt thereof, wherein the compound or a combination thereof is selected from the group consisting of

OG Complex Work Unit Chemistry
wherein A is a group selected from

OG Complex Work Unit Chemistry
R1 and R2 are each independently hydrogen, C1-C4-alkyl optionally substituted with hydroxy or halogen;
R3 is hydroxy, C1-C4-alkyl, C1-C4-alkoxy, CF3, or fluorine;
X− denotes an anion selected from among chlorine, bromine, iodine, methanesulphonate or trifluoromethanesulphonate; and
Ar is phenyl, naphthyl, thienyl, and furyl, each optionally mono- or disubstituted with one or two groups selected from C1-C4-alkyl, C1-C4-alkoxy, hydroxy, fluorine, chlorine, bromine, or CF3;
wherein the compound is present in a total amount of 0.005% to 15% by weight of the liquid composition;
an otologically acceptable topical carrier, wherein the otologically acceptable topical carrier is propylene glycol and, wherein the otologically acceptable topical carrier is present in an amount of about 50% to about 99.995% by weight of the liquid composition; and
wherein the liquid composition is formulated for topical administration to the external ear canal.