IP Library Granted Patent US 12,286,408
Granted Patent B2
US 12,286,408 · App. 18/338,096 · Granted Apr 29, 2025

KV7 channel activators compositions and methods of use

Inventors: Michael E. Bozik (Wexford, PA); Scott S. Harried (Sun Prairie, CT); Lynn Resnick (Pittsburgh, PA); George T. Topalov (Pittsburgh, PA); Justin K. Belardi (Pittsburgh, PA); Charles A. Flentge (Mars, PA); David A. Mareska (Pittsburgh, PA); James S. Hale (Pittsburgh, PA)
Assignee: Biohaven Therapeutics Ltd.
C07D235/30A61K31/4184C07D405/04C07D471/04
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Quick Facts
Patent No.
US 12,286,408
App. No.
18/338,096
Granted
Apr 29, 2025
Kind
B2
Abstract

Provided herein are optionally substituted benzoimidazol-1,2-yl amides, pharmaceutical compositions comprising a therapeutically effective amount of such compounds and a pharmaceutically acceptable excipient, and methods of treating Kv7 associated diseases, such as, epilepsy, amyotrophic lateral sclerosis, various types of pain, hyperexcitability, a dyskinesia, dystonia, mania and tinnitus with such compounds and pharmaceutical compositions.

Claims (43)

1. A method of treating a Kv7 associated disorder selected from the group consisting of epilepsy, pain, neuropathic pain, inflammatory pain, persistent pain, cancer pain, postoperative pain, tinnitus, epileptic encephalopathy, treatment-resistant epilepsy, congenital neurological disorder with intellectual disability or epileptic encephalopathy, severe epileptic encephalopathies, congenital neurodevelopmental disorder with phenotypes of nonsyndromic intellectual disability or epileptic encephalopathy, epileptic spasms, epileptic encephalopathy, early infantile epileptic encephalopathy 7, early infantile epileptic encephalopathy with delayed psychomotor development, and combinations thereof, in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a compound represented by Formula 8c:

wherein

D is optionally substituted cyclobutyl, optionally substituted phenyl, or optionally substituted C 2-5 alkyl, wherein the optional substituents are selected from —CH 3 and F;

A is C 1 alkyl;

X is substituted cyclobutyl, wherein the substituent is F;

Y is H;

R 1 is selected from H, C 3 hydroxyalkyl, CN, F, or Cl;

R 2 is selected from H, CN, F, Br, or —OCF 3 ;

R 3 is selected from H, F, or —OCH 3 ;

R 4 is H or F;

wherein when X is substituted with 2 fluorine atoms, the fluorine atoms are not geminal;

or a pharmaceutically acceptable salt thereof; and

wherein the subject is treated.

2. The method of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

3. The method of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

4. The method of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

5. The method of claim 2 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

6. The method of claim 2 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

7. The method of claim 2 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

8. The method of claim 3 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

9. The method of claim 3 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

10. The method of claim 4 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

11. The method of claim 4 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

12. The method of claim 4 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

13. The method of claim 4 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

14. The method of claim 4 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

15. The method of claim 4 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

16. The method of claim 4 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

Continuity (8)
Continuation 17570536 · Jan 7, 2022
Continuation 17077068 · Oct 22, 2020
Continuation 16358642 · Mar 19, 2019
Provisional Application 62697198 · Jul 12, 2018
Provisional Application 62663438 · Apr 27, 2018
Provisional Application 62644902 · Mar 19, 2018
Provisional Application 62644932 · Mar 19, 2018
Related Publication 20240002349A1 · Jan 4, 2024
References Cited (53)
US 6855714B2 · Blume et al. · 2005 [cited by applicant]
US 7501447B2 · Liu et al. · 2009 [cited by applicant]
US 8466201B2 · Edwards et al. · 2013 [cited by applicant]
US 9481653B2 · Resnick et al. · 2016 [cited by applicant]
US 9914708B2 · Harried et al. · 2018 [cited by applicant]
US 10385025B2 · Resnick et al. · 2019 [cited by applicant]
US 10851067B2 · Bozik · 2020 [cited by examiner]
US 11261162B2 · Bozik · 2022 [cited by examiner]
US 11724990B2 · Bozik · 2023 [cited by examiner]
US 20080214613A1 · Renton et al. · 2008 [cited by applicant]
US 20110124858A1 · Iwata et al. · 2011 [cited by applicant]
US 20170114022A1 · Harried et al. · 2017 [cited by applicant]
US 20180148419A1 · Resnick et al. · 2018 [cited by applicant]
US 20220323417A1 · Bozik · 2022 [cited by examiner]
EP 2218718A1 · 2010 [cited by applicant]
JP 07072181B · 2015 [cited by applicant]
WO 1996001833A1 · 1996 [cited by applicant]
WO 2004108712A1 · 2004 [cited by applicant]
WO 2009085230A1 · 2009 [cited by applicant]
WO 2010051819A1 · 2010 [cited by applicant]
WO 2010080503A1 · 2010 [cited by applicant]
WO 2012004698A1 · 2012 [cited by applicant]
WO 2012018668A1 · 2012 [cited by applicant]
WO 2016040952A3 · 2016 [cited by applicant]
Chemical Abstracts Registry No. 1298059-85-4, indexed in the Registry file on STN CAS Online May 20, 2011. [cited by applicant]
Chemical Abstracts Registry No. 1370729-32-0, indexed in the Registry file on STN CAS Online Apr. 27, 2012. [cited by applicant]
Chemical Abstracts Registry No. 1390407-52-9, indexed in the Registry file on STN CAS Online Aug. 13, 2012. [cited by applicant]
Chemical Abstracts Registry No. 1445709-80-7, indexed in the Registry file on STN CAS Online Jul. 19, 2013. [cited by applicant]
Chemical Abstracts Registry No. 689297-99-2, indexed in the Registry file on STN CAS Online Jun. 4, 2004. [cited by applicant]
Dadiboyena et al. “Parallel synthesis of aminobenzimidazole-tethered lhiazoles” Synthesis 44, No. 02 (2012): 215-218. [cited by applicant]
Ding Kejia et al. “Aryl-substituted aminobenzimidazoles targeting the hepatitis C virus internal ribosome entry site” Bioorganic & Medicinal Chemistry Letters, vol. 24, No. 14, May 14, 2014 (May 14, 2014), pp. 3113-3117… [cited by applicant]
International Search Report and Written Opinion for PCT/US2015/050027 dated Mar. 2, 2016. [cited by applicant]
International Search Report and Written Opinion for PCT/US2017/059393 dated Feb. 28, 2018. [cited by applicant]
International Search Report and Written Opinion for PCT/US2019/023039 dated Jul. 29, 2019. [cited by applicant]
Internet Archive WayBack Machine, Dec. 4, 2011, https://web.archive.org/web/20111204050304/http://www.uorsy.com:80/screening.php—accessed Dec. 13, 2018. [cited by applicant]
PubChem CID 118938248, National Center for Biotechnology Information, Pub Chem Compound Database, CID=118938248, https://pubchem.ncbi.nlm.nih.gov/compound/118938248 (accessed Mar. 11, 2020); created Apr. 9, 2016. [cited by applicant]
PubChem CID 129075695, National Center for Biotechnology Information, Pub Chem Compound Database, CID=129075695, https://pubchem.ncbi.nlm.nih.gov/compound/129075695 (accessed Mar. 11, 2020); created Aug. 4, 2017. [cited by applicant]
PubChem CID 129075701, National Center for Biotechnology Information, Pub Chem Compound Database, CID=129075701, https://pubchem.ncbi.nlm.nih.gov/compound/129075701 (accessed Mar. 11, 2020); created Aug. 4, 2017. [cited by applicant]
PubChem CID 21428920, National Center for Biotechnology Information. PubChem Compound Database; CID=21428920, https://pubchem.ncbi.nlm.nih.gov/compound/21428920 (accessed Apr. 27, 2016), create date Dec. 5, 2007. [cited by applicant]
PubChem CID 47251124, National Center for Biotechnology Information. PubChem Compound Database; CID=47251124, https://pubchem.ncbi.nlm.nih.gov/compound/47251124 (accessed Apr. 27, 2016), create dale Nov. 26, 2010. [cited by applicant]
PubChem CID 52655712, National Center for Biotechnology Information. PubChem Compound Database; CID=52655712, https://pubchem.ncbi.nlm.nih.gov/compound/52655712 (accessed Apr. 27, 2016), create date May 20, 2011. [cited by applicant]
PubChem CID 53531705, National Center for Biotechnology Information. PubChem Compound Database; CID=53531705, https://pubchem.ncbi.nlm.nih.gov/compound/53531705 {accessed Apr. 27, 2016), create dale Dec. 3, 2011. [cited by applicant]
PubChem CID 60339539, National Center for Biotechnology Information. PubChem Compound Database; CID=60339539, https://pubchem.ncbi.nlm.nih.gov/compound/60339539 (accessed Apr. 27, 2016), create dale Oct. 18, 2012. [cited by applicant]
PubChem CID 60339611, National Center for Biotechnology Information. PubChem Compound Database; CID=60339611, https://pubchem.ncbi.nlm.nih.gov/compound/60339611 {accessed Apr. 27, 2016), create dale Oct. 18, 2012. [cited by applicant]
Pubchem. Substance Record for SID 128950369. Deposit Date: Dec. 4, 2011 [retrieved on Oct. 15, 2015]. Retrieved rom the Internet. < URL: hllps://pubchem.ncbi.nlm.nih.gov/subslance/128950369/version/1>. entire document. [cited by applicant]
Pubchem. Substance Record for SID 131669753. Deposit Date: Jan. 24, 2012. [retrieved on Nov. 30, 2015]. Retrieved from the Internet. <URL: https://pubchem.ncbi.nlm.nih.gov/substance/131669753/version/1#section=To- p >. … [cited by applicant]
Pubmed Compound Summary for CID 1111771, “N-{a-Ethylbenzimidazol-2-yl)acetamide”, U.S. National Library of Medicine, Jul. 10, 2005, pp. 1-8 (<https://pubchem.ncbi.nlm.nih.gov/compound/1111771>). [cited by applicant]
SciFinder Search 2, downloaded 2014. [cited by applicant]
SciFinder Search 3, downloaded 2014. [cited by applicant]
SciFinder Search, downloaded 2014. [cited by applicant]
Supplementary European Search Report and Written Opinion for EP 15840730.4 dated Dec. 22, 2017. [cited by applicant]
Uorsy, Internet Archive WayBack Machine, Dec. 4, 2011, https://web.archive.org/web/20111204050304 http://www.uorsy.com:80/screening.php access Dec. 13, 2018. [cited by applicant]
Palumbo et al. “The Management and Outcomes of Pharmacological Treatments for Tinnitus” 2015, Current Neuropharmacology 13:692-700. [cited by applicant]