US 11,834,418 B2
Benzoimidazol-1,2-yl amides as Kv7 channel activators
Lynn Resnick, Pittsburgh, PA (US); George T. Topalov, Pittsburgh, PA (US); Justin K. Belardi, Pittsburgh, PA (US); James S. Hale, Pittsburgh, PA (US); Scott S. Harried, Pittsburgh, PA (US); Charles A. Flentge, Mars, PA (US); and David A. Mareska, McMurray, PA (US)
Assigned to Biohaven Therapeutics Ltd., Tortola (VG)
Filed by BIOHAVEN THERAPEUTICS LTD., New Haven, CT (US)
Filed on Dec. 18, 2020, as Appl. No. 17/127,231.
Application 17/127,231 is a continuation of application No. 16/460,449, filed on Jul. 2, 2019, granted, now 10,906,877, issued on Feb. 2, 2021.
Application 16/460,449 is a continuation of application No. 15/879,792, filed on Jan. 25, 2018, granted, now 10,385,025, issued on Aug. 20, 2019.
Application 15/879,792 is a continuation of application No. 15/339,590, filed on Oct. 31, 2016, granted, now 9,914,708, issued on Mar. 13, 2018.
Application 15/339,590 is a continuation of application No. 14/853,815, filed on Sep. 14, 2015, granted, now 9,481,653, issued on Nov. 1, 2016.
Application 15/339,590 is a continuation of application No. 17/127,231.
Application 17/127,231 is a continuation of application No. 16/346,292, abandoned, previously published as PCT/US2017/059393, filed on Oct. 31, 2017.
Application 16/346,292 is a continuation in part of application No. 15/339,590, filed on Oct. 31, 2016, granted, now 9,914,708, issued on Mar. 13, 2018.
Claims priority of provisional application 62/050,023, filed on Sep. 12, 2014.
Prior Publication US 2021/0188782 A1, Jun. 24, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 235/30 (2006.01); C07D 413/04 (2006.01); C07D 401/04 (2006.01); C07D 405/12 (2006.01); C07D 403/04 (2006.01); C07D 401/12 (2006.01)
CPC C07D 235/30 (2013.01) [C07D 401/04 (2013.01); C07D 401/12 (2013.01); C07D 403/04 (2013.01); C07D 405/12 (2013.01); C07D 413/04 (2013.01)] 20 Claims
 
1. A compound represented by a formula:

OG Complex Work Unit Chemistry
wherein:
D is optionally substituted cyclobutyl, optionally substituted phenyl, optionally substituted isoxazolyl, optionally substituted pyridinyl, isopropyl, or t-butyl;
A is C1-8 alkyl;
X is optionally substituted phenyl;
Y is OH;
R1 is H, Cl, Br, CN, OCH3, CF3, —CO2CH2CH3, C1-4 alkyl, or C1-4 hydroxyalkyl; and
R2 is H, F, —CH2OH, —CO2Me, or —C(CH3)2OH;
R3 is H, F, Cl, Br, I, or a substituent having a molecular weight of 15 Da to 200 Da and consisting of 2 to 5 chemical elements, wherein the chemical elements are independently C, H, O, N, S, F, Cl, or Br; and
R4 is H, —CH3, or —CF3;
or a pharmaceutically acceptable salt thereof.