US 12,246,000 B2
Inhibition of protein amyloid aggregation using fluorinated benzenesulfonamides
Daumantas Matulis, Vilnius (LT); Andrius Sakalauskas, Vilnius (LT); Virginija Dudutiene, Vilnius (LT); Mantas Zvirblis, Vilnius (LT); Mantas Ziaunys, Vilnius (LT); and Vytautas Smirnovas, Vilnius (LT)
Assigned to Vilnius University, Vilnius (LT)
Filed by Vilnius University, Vilnius (LT)
Filed on Sep. 20, 2022, as Appl. No. 17/948,251.
Claims priority of application No. 22182182 (EP), filed on Jun. 30, 2022.
Prior Publication US 2024/0000736 A1, Jan. 4, 2024
Int. Cl. A61K 31/196 (2006.01); A61K 31/18 (2006.01); A61K 31/195 (2006.01); A61K 31/63 (2006.01); A61P 25/28 (2006.01)
CPC A61K 31/196 (2013.01) [A61K 31/18 (2013.01); A61K 31/195 (2013.01); A61K 31/63 (2013.01); A61P 25/28 (2018.01)] 10 Claims
OG exemplary drawing
 
1. A composition for treatment of an illness related to amyloid aggregation, wherein the composition comprises an effective amount of a fluorinated benzensulfonamide compound as part of a pharmaceutical formulation, wherein the fluorinated benzensulfonamide compound is of structure I or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Chemistry
wherein X is S, NH or SO2;
NHR2 and F are at ortho and meta positions with respect to the sulfonamide group, such that
when X═S or NH, NHR2 is at ortho position and F is at meta position, and when X═SO2,
NHR2 is at meta position and F is at ortho position;
R1 is selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein n=0, 1, or 2, and COOH is at the position ortho, meta, or para, as shown:

OG Complex Work Unit Chemistry
benzene-dicarboxylic acid, wherein n=0, 1, or 2, and COOH groups are at different positions of benzene ring, as shown:

OG Complex Work Unit Chemistry
and
2-phenylacetic acid, as shown:

OG Complex Work Unit Chemistry
R2 is cycloalkyl wherein cycloalkyl comprises cycloalkanes from cyclooctane to cyclotetradecane (C8-C14),
cycloalkylmethyl wherein cycloalkyl comprises cycloalkanes from cyclohexane to cyclododecane (C6-C12),
alkyl where alkyl comprises alkanes from hexane to tetradecane (C6-C14), or
alkyl where alkyl comprises branched alkanes from C6 to C14.