IP Library Granted Patent US 11,865,111
Granted Patent B2
US 11,865,111 · App. 17/819,178 · Granted Jan 9, 2024

Antiviral drugs targeting the N-terminal domain (NTD) of the coronavirus spike receptor binding domain (RBD)

Inventors: Jonathan A. Bohmann (San Antonio, TX); Nadean M. Gutierrez (Devine, TX); Joseph A. McDonough (Helotes, TX); Robert Francis Campbell (Edgemere, MD); Michael Gordon Joyce (Silver Spring, MD); Rekha Panchal (Fort Detrick, MD); Rajeshwer Sankhala (Bethesda, MD); Allen Duplantier (Stafford, VA)
Assignees: Southwest Research Institute; The Henry M. Jackson Foundation for the Advancement of Military Medicine, Inc.; The Government of the United States, as Represented by the Secretary of the Army
A61K31/445
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Quick Facts
Patent No.
US 11,865,111
App. No.
17/819,178
Granted
Jan 9, 2024
Kind
B2
Abstract

Antiviral drugs targeting the N-terminal domain (NTD) of the spike receptor binding domain (RBD) and methods of treating a subject suffering from coronavirus.

Claims (13)

1. A method for treatment of SARS-COV-1, SARS-CoV-2 (Covid-19) and MERS-CoV, and variants within each, in a mammalian subject in need thereof, comprising administering to the subject an effective amount of the following benzimidazole compounds:

wherein, X can be —CH 2 — or C═O, and R can be —OCH 3 or —NHCH 3 , or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.

2. The method of claim 1 wherein said benzimidazole compound comprises methyl 3-(((3-(5-(1H-benzo[d]imidazol-2-yl)thiophen-3-yl)benzyl)amino)methyl)benzoate.

3. The method of claim 1 wherein said benzimidazole compound comprises 3-(((3-(5-(1H-benzo[d]imidazol-2-yl)thiophen-3-yl)benzyl)amino)methyl)-N-methylbenzamide.

4. The method of claim 1 wherein said benzimidazole compound comprises methyl 3-((3-(5-(1H-benzo[d]imidazol-2-yl)thiophen-3-yl)benzamido)methyl)benzoate.

5. An antiviral drug for treatment of SARS-COV-1, SARS-CoV-2 (Covid-19) and MERS-CoV, and variants within each, in a mammalian subject in need thereof, comprising methyl 3-(((3-(5-(1H-benzo [d]imidazol-2-yl)thiophen-3-yl)benzyl)amino)methyl)benzoate.

6. A method for treatment of SARS-COV-1, SARS-CoV-2 (Covid-19) and MERS-CoV, and variants within each, in a mammalian subject in need thereof, comprising administering to the subject an effective amount of the following piperdine compounds selected from the group consisting of:

1-(3-ethoxy-4-hydroxybenzyl)-N-(3′-fluoro-[1,1′-biphenyl]-3-yl)piperidine-4-carboxamide;

1-(3-ethoxy-4-hydroxybenzyl)-N-(3′-(trifluoromethyl)-[1,1′-biphenyl]-3-yl)piperidine-4-carboxamide;

1-(3-ethoxy-4-hydroxybenzyl)-N-(3′-methoxy-[1,1′-biphenyl]-3-yl)piperidine-4-carboxamide;

N-(3′-chloro-[1,1′-biphenyl]-3-yl)-1-(3-hydroxy-4-methoxybenzyl)piperidine-4-carboxamide;

N-(3′-chloro-[1,1′-biphenyl]-3-yl)-1-(3-ethoxy-4-hydroxybenzyl)piperidine-4-carboxamide; or

N-(4′-chloro-[1,1′-biphenyl]-3-yl)-1-(3-ethoxy-4-hydroxybenzyl)piperidine-4-carboxamide.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2023
From: BOHMANN, JONATHAN A.; GUTIERREZ, NADEAN M.; MCDONOUGH, JOSEPH A.
To: SOUTHWEST RESEARCH INSTITUTE
Reel/Frame 063108/0702 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2023
From: JOYCE, MICHAEL GORDON; SANKHALA, RAJESHWER
To: THE HENRY M. JACKSON FOUNDATION FOR THE ADVANCEMENT OF MILITARY MEDICINE, INC.
Reel/Frame 063108/0774 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2023
From: CAMPBELL, ROBERT F.; PANCHAL, REKHA
To: THE GOVERNMENT OF THE UNITED STATES, AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 062404/0967 →
CONFIRMATORY LICENSE Recorded Sep 1, 2022
From: HENRY M. JACKSON FDN FOR THE ADV MIL/MED
To: UNITED STATES GOVERNMENT
Reel/Frame 060965/0542 →
Continuity (2)
Provisional Application 63260342 · Aug 17, 2021
Related Publication 20230074535A1 · Mar 9, 2023