US 11,730,714 B2
Compounds for the treatment of neuromuscular disorders
Thomas Holm Pedersen, Risskov (DK); Lars J. S. Knutsen, Essex (GB); Nicholas M. Kelly, Bagsværd (DK); Martin Broch-Lips, Skødstrup (DK); Claus Elsborg Olesen, Åbyhøj (DK); Marc Labelle, Bedford, NH (US); Ole Bækgaard Nielsen, Egå (DK); and Rajesh Kumar, Winnipeg (CA)
Assigned to NMD PHARMA A/S, Århus N (DK)
Filed by NMD PHARMA A/S, Århus N (DK)
Filed on Dec. 14, 2018, as Appl. No. 16/220,640.
Application 16/220,640 is a continuation in part of application No. 15/842,807, filed on Dec. 14, 2017, granted, now 11,147,788.
Prior Publication US 2019/0183834 A1, Jun. 20, 2019
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/216 (2006.01); A61P 37/06 (2006.01); A61P 25/28 (2006.01)
CPC A61K 31/216 (2013.01) [A61P 25/28 (2018.01); A61P 37/06 (2018.01)] 20 Claims
 
1. A compound of Formula (Ha):

OG Complex Work Unit Chemistry
wherein:
R1 is selected from the group consisting of F, Cl, Br, I, —CN, —CF3, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C4 cycloalkyl and —S—CH3;
R2 is independently selected from the group consisting of hydrogen, deuterium, F, Cl, Br, I, —CN, —CF3 and -oxime optionally substituted with C1 alkyl;
R3 is selected from the group consisting of C2-5 alkynyl, and C4-5 cycloalkyl, each of which may be optionally substituted with one or more, identical or different, substituents R5;
R4 is selected from the group consisting of H, C1-5 alkyl optionally substituted with one or more, identical or different, substituents R7, C3-6 cycloalkyl optionally substituted with one or more, identical or different, substituents R7, phenyl optionally substituted with one or more, identical or different, substituents R8 and benzyl optionally substituted with one or more, identical or different, substituents R8;
R5 is independently selected from the group consisting of deuterium, F, OC1-5 alkyl optionally substituted with one or more, identical or different, substituents R7, OC3-5 cycloalkyl optionally substituted with one or more, identical or different, substituents R7, and OH;
R6 is independently selected from the group consisting of hydrogen and deuterium;
R7 is independently selected from the group consisting of deuterium and F;
R8 is independently selected from the group consisting of deuterium, methoxy, nitro, cyano, Cl, Br, I and F; and
n is an integer 0, 1, 2, 3 or 4;
or a pharmaceutically acceptable salt, hydrate, polymorph, tautomer, or solvate thereof.