IP Library › Granted Patent US 12,304,908
Granted Patent B2
US 12,304,908 · App. 17/324,520 · Granted May 20, 2025

Azabenzimidazoles and their use as AMPA receptor modulators

Inventors: Michael K. Ameriks (San Diego, CA); Cynthia G. B. Berry (San Diego, CA); Gang Chen (San Diego, CA); Fabrice Loic Jourdan (Olias del Rey, ES); Terry Patrick Lebold (San Diego, CA); David Wei Lin (San Diego, CA); Miguel Angel Pena Piñon (Olias del Rey, ES); Suchitra Ravula (San Diego, CA); Bradley M. Savall (San Diego, CA); Devin M. Swanson (Carlsbad, CA); Dongpei Wu (San Diego, CA); Wei Zhang (San Diego, CA)
Assignee: Rapport Therapeutics, Inc.
C07D471/04A61P25/00C07D471/14C07C2601/02C07C2601/04C07C2601/08C07C2601/14C07C2601/16
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,304,908
App. No.
17/324,520
Granted
May 20, 2025
Kind
B2
Abstract

Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, Also provided herein are pharmaceutical compositions comprising compounds of Formula (I) and methods of using compounds of Formula (I).

Claims (2)

1. A compound, wherein the compound is 3-(7-chloro-1H-indazol-5-yl)-2,5-bis(trifluoromethyl)imidazo[4,5-b]pyridine, or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein the compound is 3-(7-chloro-1H-indazol-5-yl)-2,5-bis(trifluoromethyl)imidazo[4,5-b]pyridine.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2023
From: JANSSEN PHARMACEUTICA NV
To: RAPPORT THERAPEUTICS, INC.
Reel/Frame 063079/0430 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2023
From: JANSSEN PHARMACEUTICA NV
To: PRECISION NEUROSCIENCE NEWCO, INC.
Reel/Frame 062404/0771 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 21, 2022
From: AMERIKS, MICHAEL K.; BERRY, CYNTHIA G.B.; CHEN, GANG; LEBOLD, TERRY PATRICK; LIN, DAVID WEI; RAVULA, SUCHITRA; SAVALL, BRADLEY M.; SWANSON, DEVIN M.; WU, DONGPEI; ZHANG, WEI
To: JANSSEN PHARMACEUTICA NV
Reel/Frame 059324/0720 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 21, 2022
From: JOURDAN, FABRICE LOIC; PINON, MIGUEL ANGEL PENA
To: NOVALIX SAS
Reel/Frame 059324/0771 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 21, 2022
From: NOVALIX SAS
To: JANSSEN PHARMACEUTICA NV
Reel/Frame 059324/0849 →
Continuity (3)
Continuation 15569299
Provisional Application 62154313 · Apr 29, 2015
Related Publication 20210284641A1 · Sep 16, 2021
References Cited (112)
US 4370340A · Ueda et al. · 1983 [cited by applicant]
US 5565483A · Hewawasam et al. · 1996 [cited by applicant]
US 5688809A · Macor · 1997 [cited by applicant]
US 5886008A · Macor · 1999 [cited by applicant]
US 6124285A · Watjen et al. · 2000 [cited by applicant]
US 6548576B1 · Winter · 2003 [cited by applicant]
US 6613777B1 · Chen et al. · 2003 [cited by applicant]
US 7842698B2 · Rueckle · 2010 [cited by applicant]
US 8283364B2 · Budzik et al. · 2012 [cited by applicant]
US 8299056B2 · Bahmanyar et al. · 2012 [cited by applicant]
US 8362018B2 · Macleod et al. · 2013 [cited by applicant]
US 8575154B2 · Kori et al. · 2013 [cited by applicant]
US 9120788B2 · Chappie et al. · 2015 [cited by applicant]
US 9908886B2 · Nacro et al. · 2018 [cited by applicant]
US 10087185B2 · Ameriks et al. · 2018 [cited by applicant]
US 10100045B2 · Ameriks et al. · 2018 [cited by applicant]
US 10155769B2 · Ameriks et al. · 2018 [cited by applicant]
US 11312712B2 · Ameriks et al. · 2022 [cited by applicant]
US 20100137276A1 · Bradley et al. · 2010 [cited by applicant]
US 20150344468A1 · Gardinier et al. · 2015 [cited by applicant]
US 20160289238A1 · He et al. · 2016 [cited by applicant]
CA 2357042 · 2000 [cited by applicant]
CN 1094727A · 1994 [cited by applicant]
CN 1142823A · 1997 [cited by applicant]
CN 1144800A · 1997 [cited by applicant]
CN 1051313C · 2000 [cited by applicant]
CN 101052640A · 2007 [cited by applicant]
CN 101939315A · 2011 [cited by applicant]
CN 102056904A · 2011 [cited by applicant]
CN 101321736A · 2012 [cited by applicant]
EP 869958 · 1998 [cited by applicant]
IN 777DELNO2007 · 2007 [cited by applicant]
JP 2000501432 · 2000 [cited by applicant]
JP 2002507613 · 2002 [cited by applicant]
JP 2008511589 · 2008 [cited by applicant]
JP 2010508328 · 2010 [cited by applicant]
JP 2010536825 · 2010 [cited by applicant]
JP 2013535408 · 2013 [cited by applicant]
WO WO199521836 · 1995 [cited by applicant]
WO WO200001376 · 2000 [cited by applicant]
WO WO200210170 · 2002 [cited by applicant]
WO WO200214294 · 2002 [cited by applicant]
WO WO2006023109 · 2006 [cited by applicant]
WO WO2007135529 · 2007 [cited by applicant]
WO WO2008053031 · 2008 [cited by applicant]
WO WO2008113795 · 2008 [cited by applicant]
WO WO2008148832 · 2008 [cited by applicant]
WO WO2009067607 · 2009 [cited by applicant]
WO WO2010005528 · 2010 [cited by applicant]
WO WO2010066658 · 2010 [cited by applicant]
WO WO2010069684 · 2010 [cited by applicant]
WO WO2011056985 · 2011 [cited by applicant]
WO WO2011100607A1 · 2011 [cited by applicant]
WO WO2011156245 · 2011 [cited by applicant]
WO WO2011163355A1 · 2011 [cited by applicant]
WO WO2012021382 · 2012 [cited by applicant]
WO WO2013064984 · 2013 [cited by applicant]
WO WO2013130501A8 · 2014 [cited by applicant]
WO WO2014085153 · 2014 [cited by applicant]
WO WO2014128585 · 2014 [cited by applicant]
WO WO2015183673A1 · 2015 [cited by applicant]
WO WO2019198692A1 · 2019 [cited by applicant]
WO WO2020159285A1 · 2020 [cited by applicant]
International Search Report for PCT/US2016/029801 dated Oct. 17, 2016. [cited by applicant]
International Search Report for PCT/US2016/029780 dated Jun. 14, 2016. [cited by applicant]
International Search Report for PCT/US2016/029791 dated Jun. 9, 2016. [cited by applicant]
International Search Report for PCT/US2016/029805 dated Jun. 8, 2016. [cited by applicant]
Hanan et al., “Mild and General One-Pot Reduction and Cyclization of Aromatic and Heteroaromatic 2-Nitroamines to Bicyclic 2H-Imidazoles”, Synlett 2010, No. 18, pp. 2759-2764. [cited by applicant]
Bagshawe, Drug Dev Res. 1995, 34, 220-230. [cited by applicant]
Bertolini, et al., J Med Chem. 1997, 40, 2011-2016. [cited by applicant]
Bodor, Adv Drug Res. 1984, 13, 224-331. [cited by applicant]
Brewer, G. J. (1997). “Isolation and culture of adult rat hippocampal neurons.” Journal of Neuroscience Methods 71(2): 143-155. [cited by applicant]
Chen et al., Bipolar Disord., 13:1-15, 2011. [cited by applicant]
Cho et al. (2007). “Two families of TARP isoforms that have distinct effects on the kinetic properties of AMPA receptors and synaptic currents.” Neuron 55(6): 890-904. [cited by applicant]
Database Registry, 2011, RN 1309289-50-6, Retrieved from STN international [online] retrieved on Feb. 6, 2020. [cited by applicant]
Du et al., J Neurosci 24: 6578-6589, 2004. [cited by applicant]
Du et al., J Neurosci 28: 68-79, 2008. [cited by applicant]
Engin and Treit, Behav Pharmacol 18:365-374, 2007. [cited by applicant]
Fleisher et al., Adv Drug Delivery Rev., 1996, 19, 115-130. [cited by applicant]
G.D. Considine, ed., Van Nostrand's Encyclopedia of Chemistry, p. 261, 5 [cited by applicant]
Gill and Bredt., Neuropsychopharmacology 36(1): 362-363 (2011). [cited by applicant]
Harrison, Brain 125:1428-1449, 2002. [cited by applicant]
Heckers and Konradi, Curr Top Behav Neurosci. 4:529-553, 2010. [cited by applicant]
Kambe, Tohru; Correia, Bruno E.; Niphakis, Micah J.; Cravatt, Benjamin F., Journal of the American Chemical Society (2014), 136(30), 10777-10782. [cited by applicant]
Lazzaro et al. (2002). “Functional characterization of CP-465,022, a selective, noncompetitive AMPA receptor antagonist.” Neuropharmacology 42(2): 143-153. [cited by applicant]
Macor et al., “The discovery of a novel and potent benzodiazepine receptor pharmacophore”, Bioorganic & Medicinal Chemistry Letters, Pergamon, Amsterdam, NL, vol. 5, No. 20, Oct. 19, 1995 (Oct. 19, 1995), pp. 2397-2402. [cited by applicant]
Mcnaughton et al., Behav Pharmacol 18: 329-346, 2007. [cited by applicant]
Nolen and Bloemkolk, Neuropsychobiology, 42 Suppl 1:11-7, 2000. [cited by applicant]
Pirotte et al., “AMPA receptor positive allosteric modulators: a patent review”, Expert Opinion Therapeutic Patents, vol. 23, No. 5, 2013, pp. 615-628. [cited by applicant]
Robinson et al., J. Med Chem., 1996, 39(1), 10-18. [cited by applicant]
Rogawski et al., Epilepsy Currents, 2011, vol. 11(2), pp. 56-63. [cited by applicant]
Rowe, Raymond C, Paul J. Sheskey, and Marian E Quinn. Handbook of Pharmaceutical Excipients. London: Pharmaceutical Press, 6th Edition, 2009, p. 17 (Year: 2009). [cited by applicant]
S. Paulekuhn, et al., “Trends in Active Pharmaceutical Ingredient Salt Selection based on Analysis of the Orange Book Database”, J. Med. Chem., 2007, 50:6665-72. [cited by applicant]
S.M. Berge, et al., “Pharmaceutical Salts”, J Pharm Sci., 1977, 66:1-19. [cited by applicant]
Schobel et al., Arch Gen Psych, 66:938-946, 2009. [cited by applicant]
Shan, et al., J Pharm Sci. 1997, 86 (7), 765-767. [cited by applicant]
Shi et al.(2009) “The stoichiometry of AMPA receptors and TARPs varies by neuronal cell type.” Neuron 62(5): 633-640. [cited by applicant]
Small et al., Nat. Rev. Neurosci. 12:585-601, 2011. [cited by applicant]
Strange et al. (2006). “Functional characterisation of homomeric ionotropic glutamate receptors GluR1-GluR6 in a fluorescence-based high throughput screening assay.” Comb Chem High Throughput Screen 9(2): 147-158. [cited by applicant]
Tikhonova et al., “Virtual screening of organic molecule databases . Design of focused libraries of potential I igands of NMDA and AMPA receptors”, Russian Chemical Bulletin , Kluwer Academic Publishers—Plenum Publisher… [cited by applicant]
Tomita et al. (2003). “Functional studies and distribution define a family of transmembrane AMPA receptor regulatory proteins.” J Cell Biol 161(4): 805-816.2003. [cited by applicant]
Tregellas et al., Am J Psychiatry 171: 549-556, 2014. [cited by applicant]
Yeung et al., Hippocampus 23:278-286, 2013. [cited by applicant]
Yeung et al., Neuropharmacology 62: 155-160, 2012. [cited by applicant]
STN Chemical Structure Search Results (dated Feb. 24, 2022) (11 pages). [cited by applicant]
K.R. Gogas, et al., Comprehensive Medicinal Chemistry II: Therapeutic Areas I: Central Nervous System, Pain, Metabolic Syndrome, Urology, Gastrointestinal and Cardiovascular, 2007, 85-116. [cited by applicant]
International Search Report for PCT/US2017/057572 dated Jan. 12, 2018. [cited by applicant]
International Search Report for PCT/US2017/057566 dated Feb. 22, 2018. [cited by applicant]
International Search Report for PCT/US2017/057564 dated Febrauary 28, 2018. [cited by applicant]
Gray's Neuropsychological Theory of Anxiety (2003) abstract. [cited by applicant]
Kaur, T., and Cadenhead, K.S. (2010). Curr. Top. Behav. Neurosci. 4, 97-121. [cited by applicant]
Simon JA Grove et al., “Postive modulators of the AMPA receptor,” Expert Opinion on Therapeutic Patents., vol. 10, No. 10, Oct. 1, 2000, pp. 1539-1548. [cited by applicant]