US 12,295,945 B2
Enantiomers of substituted thiazoles as antiviral compounds
Gerald Kleymann, Bad Salzuflen (DE); and Christian Gege, Ehingen (DE)
Filed by Innovative Molecules GmbH, Munich (DE)
Filed on Jan. 21, 2022, as Appl. No. 17/581,166.
Application 17/581,166 is a continuation of application No. 16/753,814, granted, now 11,278,534, previously published as PCT/EP2018/077022, filed on Oct. 4, 2018.
Claims priority of application No. 17195047 (EP), filed on Oct. 5, 2017.
Prior Publication US 2022/0152008 A1, May 19, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/4439 (2006.01); A61K 31/426 (2006.01); A61K 45/06 (2006.01); A61P 31/22 (2006.01); C07D 277/46 (2006.01); C07D 417/12 (2006.01)
CPC A61K 31/4439 (2013.01) [A61K 31/426 (2013.01); A61K 45/06 (2013.01); A61P 31/22 (2018.01); C07D 277/46 (2013.01); C07D 417/12 (2013.01)] 10 Claims
 
1. Compounds according to the formula

OG Complex Work Unit Chemistry
wherein
R20 is selected from C1-4-alkyl and C3-6-cycloalkyl, wherein alkyl and cycloalkyl is unsubstituted or substituted with 1 to 3 substituents independently selected from the group consisting of F or Me;
R21 is selected from F, Cl, OH, Me, OMe, CHF2, CF3, OCHF2, OCF3; and
Y is selected from nitrogen or carbon;
or a tautomer, N-oxide, solvate and pharmaceutically acceptable salt thereof,
which are characterized by an IC50 value (HSV-1/Vero) in an in vitro activity selectivity assay HSV-1 on Vero cells of IC50 below 100 μM.