US 12,404,237 B2
Method of treating excessive sleepiness and/or cataplexy using n-{2-(([1,1′-biphenyl]-3-yl)methyl)pyrrolidin-3-yl}sulfonamide derivatives
Yasushi Hattori, Kanagawa (JP); Yuhei Miyanohana, Kanagawa (JP); Yuichi Kajita, Kanagawa (JP); Tatsuki Koike, Kanagawa (JP); Yasutaka Hoashi, Kanagawa (JP); Norihito Tokunaga, Kanagawa (JP); Alexander Martin Pawliczek, Kanagawa (JP); Tsuneo Oda, Kanagawa (JP); Tohru Miyazaki, Kanagawa (JP); Yoshiteru Ito, Kanagawa (JP); Kohei Takeuchi, Kanagawa (JP); Keisuke Imamura, Kanagawa (JP); and Takahiro Sugimoto, Kanagawa (JP)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (JP)
Filed by TAKEDA PHARMACEUTICAL COMPANY LIMITED, Osaka (JP)
Filed on Mar. 13, 2025, as Appl. No. 19/079,199.
Application 19/079,199 is a continuation of application No. 18/520,037, filed on Nov. 27, 2023, abandoned.
Application 18/520,037 is a continuation of application No. 18/175,215, filed on Feb. 27, 2023, abandoned.
Application 18/175,215 is a continuation of application No. 17/239,191, filed on Apr. 23, 2021, abandoned.
Application 17/239,191 is a continuation of application No. 16/777,273, filed on Jan. 30, 2020, granted, now 11,028,048, issued on Jun. 8, 2021.
Claims priority of application No. 2019-015488 (JP), filed on Jan. 31, 2019.
Prior Publication US 2025/0243157 A1, Jul. 31, 2025
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 207/14 (2006.01); C07D 403/06 (2006.01); C07D 407/08 (2006.01); C07D 417/06 (2006.01)
CPC C07D 207/14 (2013.01) [C07D 403/06 (2013.01); C07D 407/08 (2013.01); C07D 417/06 (2013.01)] 19 Claims
 
1. A method of treating excessive sleepiness, cataplexy, or a combination thereof, in a patient in need thereof, the method comprising administering to the patient a compound selected from the group consisting of:
N′-{(2S,3R,4S)-1-(azetidine-1-carbonyl)-4-fluoro-2-[(2-fluoro-3′-methyl[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}-N,N-dimethylsulfuric diamide;
N-[(2S,3R)-2-[(2,3′-difluoro[1,1′-biphenyl]-3-yl)methyl]-4,4-difluoro-1-(2-methylpropanoyl)pyrrolidin-3-yl]ethanesulfonamide;
N-{(2S,3R)-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)-2-[(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide;
N-{(2S,3R)-4,4-difluoro-1-(2-hydroxy-2-methylpropanoyl)-2-[(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}methanesulfonamide;
N-{(2S,3R)-1-(bicyclo[1.1.1]pentane-1-carbonyl)-4,4-difluoro-2-[(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}methanesulfonamide;
N-{(2S,3R)-1-(cyclopropanecarbonyl)-4,4-difluoro-2-[(2,3′,5′-trifluoro[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide;
N-{(2S,3R)-4,4-difluoro-1-((1s,3R)-3-fluorocyclobutane-1-carbonyl)-2-[(2,3′,5′-trifluoro[1, l′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}ethanesulfonamide;
N-{(2S,3R)-4,4-difluoro-1-((1s,3R)-3-fluorocyclobutane-1-carbonyl)-2-[(2,3′,5′-trifluoro[1, l′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}methanesulfonamide; and
N′-{(2S,3R)-1-(azetidine-1-carbonyl)-4,4-difluoro-2-[(2-fluoro-3′-methyl[1,1′-biphenyl]-3-yl)methyl]pyrrolidin-3-yl}-N,N-dimethylsulfuric diamide;
or a salt thereof.