IP Library Granted Patent US 12,698,283
Granted Patent B2
US 12,698,283 · App. 18/003,758 · Granted Aug 4, 2026

Quinoline derivatives, pharmaceutically acceptable salts, and methods of use thereof

Inventor: Bapu Gaddam (Ellicott City, MD)
Assignee: vTv Therapeutics LLC
C07D471/04
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 12,698,283
App. No.
18/003,758
Filed
Dec 29, 2022
Granted
Aug 4, 2026
Kind
B2
Art Unit
1624
USPC
514/250
Abstract

The present disclosure relates to the compound trans-4-[1-(3-chlorophenyl)-7-methoxy-2,4-dioxo-pyrimido[5,4-c]quinolin-3-yl]cyclohexanecarboxylic acid, pharmaceutically acceptable salts, and use thereof as a therapeutic agent including treatment of inflammatory disorders.

Claims (6)

1 . A compound having the Formula (I):

or a pharmaceutically acceptable salt thereof.

2 . The compound of claim 1 , wherein the compound is a compound of Formula (I).

3 . The compound of claim 1 , wherein the compound is an acid salt of the compound of Formula (I).

4 . The compound of claim 3 , wherein the compound is an HCl salt of the compound of Formula (I).

5 . A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2024
From: GADDAM, BAPU
To: VTV THERAPEUTICS LLC
Reel/Frame 066563/0839 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2024
From: GADDAM, BAPU
To: VTV THERAPEUTICS LLC
Reel/Frame 066543/0589 →
Continuity (2)
Provisional Application 63045240 · Jun 29, 2020
Related Publication 20230265089A1 · Aug 24, 2023
References Cited (61)
US 4927820A · Shutske et al. · 1990 [cited by applicant]
US 5834485A · Dyke et al. · 1998 [cited by applicant]
US 7964608B2 · Mjalli et al. · 2011 [cited by applicant]
US 8329715B2 · Mjalli et al. · 2012 [cited by applicant]
US 8853226B2 · Mjalli et al. · 2014 [cited by applicant]
US 9163022B2 · Mjalli et al. · 2015 [cited by applicant]
US 9393245B2 · Mjalli et al. · 2016 [cited by applicant]
US 9687489B2 · Mjalli et al. · 2017 [cited by applicant]
US 9833457B2 · Mjalli et al. · 2017 [cited by applicant]
US 10085990B2 · Mjalli et al. · 2018 [cited by applicant]
US 10391097B2 · Mjalli et al. · 2019 [cited by applicant]
US 10568888B2 · Mjalli et al. · 2020 [cited by applicant]
US 12545676B2 · Gaddam et al. · 2026 [cited by applicant]
US 20030105129A1 · Mortlock et al. · 2003 [cited by applicant]
US 20040171593A1 · Keating et al. · 2004 [cited by applicant]
US 20050065116A1 · Carson et al. · 2005 [cited by applicant]
US 20080255209A1 · Klein et al. · 2008 [cited by applicant]
US 20090018333A1 · Grauert et al. · 2009 [cited by applicant]
US 20100190808A1 · Mjalli et al. · 2010 [cited by applicant]
US 20110160234A1 · Mjalli et al. · 2011 [cited by applicant]
US 20120028932A1 · Nickolaus et al. · 2012 [cited by applicant]
US 20120035143A1 · Nickolaus et al. · 2012 [cited by applicant]
US 20180360839A1 · Mjalli et al. · 2018 [cited by applicant]
US 20230312559A1 · Gaddam et al. · 2023 [cited by applicant]
EP 0143001A2 · 1985 [cited by applicant]
PL 193012B1 · 2007 [cited by applicant]
WO WO9857936A1 · 1998 [cited by applicant]
WO WO03024489A2 · 2003 [cited by applicant]
WO WO03062238A1 · 2003 [cited by applicant]
WO WO2007004958A1 · 2007 [cited by applicant]
WO WO2009094528A1 · 2009 [cited by applicant]
WO WO2009125809A1 · 2009 [cited by applicant]
WO WO2011124524A1 · 2011 [cited by applicant]
WO WO2011124525A1 · 2011 [cited by applicant]
WO WO2022005494A1 · 2022 [cited by applicant]
WO WO2022026350A1 · 2022 [cited by applicant]
Byrn et al. Pharmaceutical Solids: A Strategic Approach to Regulatory Considerations. Pharmaceutical Research 12(7):945-954 (1995). [cited by applicant]
Berge et al. Pharmaceutical Salts. Journal of Pharmaceutical Sciences 66(1):1-19 (Jan. 1977). [cited by applicant]
Chemical Abstracts Registry Entry 375362-97-3, entered Dec. 14, 2001. [cited by applicant]
Geis et al. Tricyclic theophylline derivatives with high water-solubility: structure-activity relationships at adenosine receptors, phosphodiesterases, and benzodiazepine binding sites. Pharmazie 50(5):333-336 (1995). [cited by applicant]
Haede et al., Herstellung Kondensierter 2-Alkylthio-4-hydroxypyrimidine J. Heterocyclic Chem. 18(7):1417-1419 (1981). [cited by applicant]
Haider et al., Product Class 9: Cinnolines in Science of Synthesis. ChemInform 16:251-313 (2004). [cited by applicant]
Katritzky et al., Polycyclic Heteroaromatics from Reactions of Acylbenzotriazoles with Aryl Isocyanates, J. Org. Chem., 65:8069-8073 (2000). [cited by applicant]
Landells et al. A biochemical and functional assessment of monocyte phosphodiesterase activity in healthy and asthmatic subjects. Pulm Pharmacol Ther 13(5):231-239 (2000). [cited by applicant]
Lewgowd et al., Determination of Lipophilicity, pKa Measurement and Action on the Central Nervous System of Some Pyrimido[5,4-c]quinolines Acta Poloniae Pharm., 62(4):271-281 (2005). [cited by applicant]
Lewgowd et al., Synthesis and cytotoxicity of new potential intercalators based on tricyclic systems of some pyrimido[5,4-c]cinnoline and pyrimido[5,4-c]quinoline derivatives. Part I Acta Poloniae Pharm., 62(2):105-110 … [cited by applicant]
Menon et al., Synthesis and Antimicrobial Properties of Pyrimido[5,4-c]cinolin-2,4(1H,3H)-diones J. Indian Chem. Soc., 72(10):731-733 (1995). [cited by applicant]
Nargund et al. Synthesis and antimicrobial and anti-inflammatory activities of substituted 2-mercapto-3-(N-aryl)pyrimido[5,4-c]cinnolin-4-(3H)-ones. J Pharm Sci 81(4):365-366 (1992). [cited by applicant]
PCT/US2009/031819 International Search Report and Written Opinion dated Mar. 25, 2009. [cited by applicant]
PCT/US2020/044410 International Search Report and Written Opinion dated Mar. 25, 2021. [cited by applicant]
PCT/US2021/043111 International Search Report and Written Opinion dated Nov. 5, 2021. [cited by applicant]
Peter et al. Inhibition of cyclooxygenase-2 prevents adverse effects induced by phosphodiesterase type 4 inhibitors in rats. Br J Pharmacol 162(2):415-427 (2011). [cited by applicant]
PubChem CID 5213595, create date, Oct. 7, 2005. [cited by applicant]
Reimund et al. Anti-TNF-alpha properties of new 9-benzyladenine derivatives with selective phosphodiesterase-4-inhibiting properties. Biochem Biophys Res Commun 288(2):427-434 (2001). [cited by applicant]
Shindo et al., Synthesis of Heterocyclic Compounds Isosterically Related to Pyrazolo[4,3-c]quinolines as Benzodiazepine Receptor Ligands. Heterocycles 29(5):899-912 (1989). [cited by applicant]
Spina. PDE4 inhibitors: current status. Br J Pharmacol155:308-315 (2008). [cited by applicant]
Stanczak et al., Comparison of pharmacophore cinnoline and quinoline systems on the basis of computer calculation and pharmacological screening of their condensed systems. Pharmazie 56(6):501-505 (2001). [cited by applicant]
Stanczak et al., Determination of the Lipophilicity of Pyrimido[5,4-c]quinoline Derivatives by Reversed-Phase Thin-Layer Chromatography. Part 1. Lipophilicity of Pyrimido[5,4-c]quinolin-4(3H)-ones and 1,2,3,4-Tetrahydro… [cited by applicant]
Stanczak et al., Synthesis and biological activity of some 4-amino-3-cinnoline carboxylic acid derivatives. Pharmazie 53(3):156-161 (1998). [cited by applicant]
Sturton et al. Phosphodiesterase 4 inhibitors for the treatment of COPD. Chest 121(5 Suppl):192S-196S (2002). [cited by applicant]
Zahran et al. Synthesis of some pyrimidines and their benzo-derivatives via 6 pi-electron cyclization reactions. Afinidad 52(460:415-418 (1995). [cited by applicant]