Method of treating COVID-19

Inventors: Robert Louis Hoffman (San Diego, CA); Robert Steven Kania (Del Mar, CA); Dafydd Rhys Owen (Concord, MA); Martin Youngjin Pettersson (Littleton, MA); Matthew Forrest Sammons (Quincy, MA); Jamison Bryce Tuttle (Marblehead, MA)

Assignee: Pfizer Inc.

A61K38/005 A61K31/167 A61K31/405 A61K31/513 A61K31/519 A61K31/573 A61K31/609 A61K31/706 A61K39/00 A61P31/14

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Quick Facts

Patent No.: US 12,485,157
App. No.: 17/906,109
Granted: Dec 2, 2025
Kind: B2

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Abstract

The invention relates to methods of treating COVID-19 in a patient by administering therapeutically effective amounts of certain SARS-CoV-2 inhibitor compounds or pharmaceutical compositions containing them to a patient in need thereof. The invention also relates to inhibiting SARS-CoV-2 coronavirus viral replication activity comprising contacting SARS-CoV-2-related coronavirus protease with a therapeutically effective amount of a SARS-Cov-2 protease inhibitor, such as a SARS-Cov-2 3CL protease inhibitor and compositions comprising the same.

Claims (53)

1 . A method of treating COVID-19 in a patient, the method comprising administering to a patient in need thereof a therapeutically effective amount of a compound selected from the group consisting of:

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl pivalate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl benzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-methylbenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-fluorobenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-cyanobenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-methoxybenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-chlorobenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dichlorobenzoate;

(3S)-3-({N-[(4-methoxy-1H-Indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dimethylbenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-difluorobenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2,6-dimethoxybenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-chloro-2-hydroxybenzoate;

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-cyano-2-fluorobenzoate; and

(3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2-cyanobenzoate;

or a pharmaceutically acceptable salt thereof.

2 . The method of claim 1 wherein the compound or pharmaceutically acceptable salt thereof is administered orally, by inhalation or intranasally.

3 . The method of claim 2 wherein the compound or pharmaceutically acceptable salt thereof is administered orally.

4 . The method of claim 2 wherein the compound or pharmaceutically acceptable salt thereof is administered by inhalation or intranasally.

5 . The method of claim 1 wherein the compound or pharmaceutically acceptable salt thereof is administered sublingually.

6 . The method of claim 1 wherein the compound or pharmaceutically acceptable salt thereof is administered one to four times over a 24-hour period.

7 . The method of claim 6 further comprising the administration of one or more additional therapeutic agents.

8 . The method of claim 7 wherein the additional therapeutic agent is selected from the group consisting of remdesivir and dexamethasone.

9 . A method of treating COVID-19 in a patient, the method comprising administering to a patient in need thereof a pharmaceutical composition, the pharmaceutical composition comprising a therapeutically effective amount of a compound selected from the group consisting of: