IP Library Granted Patent US 12,428,397
Granted Patent B2
US 12,428,397 · App. 17/920,943 · Granted Sep 30, 2025

Factor XI activation inhibitors

Inventors: Jacqueline D. Hicks (Watchung, NJ); John S. Debenham (Scotch Plains, NJ); Amjad Ali (Freehold, NJ); Ying-Duo Gao (Middletown, NJ); Lan Wei (Berkeley Heights, NJ); Dexi Yang (Livingston, NJ); Rongze Kuang (Green Brook, NJ); Alan Hruza (Hackettstown, NJ); Peter Nizner (Fanwood, NJ); Daniel A. Tatosian (Berkeley Heights, NJ)
Assignee: Merck Sharp & Dohme LLC
C07D401/14C07D417/14
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Quick Facts
Patent No.
US 12,428,397
App. No.
17/920,943
Granted
Sep 30, 2025
Kind
B2
Abstract

The present invention provides a compound of Formula (I) and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XI activation inhibitors.

Claims (23)

1. A compound of the formula:

wherein

R 1 is phenyl or heteroaryl, which may be monocyclic or bicyclic, wherein said phenyl and heteroaryl groups are optionally substituted with one to three substituents independently selected from the group consisting of halo, oxo, cyano, R 4 and OR 4 ;

R 2 is piperidinyl or NR 4 R 5 , wherein said piperidinyl group is optionally substituted with one to three halo;

R 3 is heterocyclyl, which is optionally substituted with one to three substituents independently selected from the group consisting of halo, cyano, R 4 , OR 4 and R 6 ;

R 4 is hydrogen or C 1-6 alkyl, which is optionally substituted with one to three halo;

R 5 is hydrogen or C 1-6 alkyl, which is optionally substituted with one to three halo;

R 6 is phenyl, C 3-6 cycloalkyl, heterocyclyl or heteroaryl, wherein said heteroaryl is optionally substituted with one to three substituents independently selected from the group consisting of C 1-6 alkyl and halo;

n is an integer from one to three;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 wherein R 1 is selected from benzothiazolyl, phenyl or pyridinyl wherein said groups are optionally substituted with one or two substituents independently selected from the group consisting of chloro, cyano and CF 3 ; or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 wherein R 2 is piperidinyl, or a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 wherein R 3 is piperidinyl, which is optionally substituted with one or two substituents independently selected from the group consisting of cyano, pyrazolyl, methylpyrazolyl, phenyl and triazolyl; or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 wherein R 3 is piperidinyl, which is optionally substituted with cyano and phenyl; or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 wherein n is one; or a pharmaceutically acceptable salt thereof.

7. The compound selected from

or a pharmaceutically acceptable salt thereof.

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

9. A method for inhibiting thrombus formation in blood or treating thrombus formation in blood comprising administering a composition of claim 8 to a mammal in need of thereof.

10. A method for preventing thrombus formation in blood comprising administering a composition of claim 8 to a mammal in need thereof.

11. A method of treating venous thromboembolism or pulmonary embolism in a mammal comprising administering a composition of claim 8 to a mammal in need thereof.

12. A method of treating deep vein thrombosis in a mammal comprising administering a composition of claim 8 to a mammal in need thereof.

13. A method of treating thromboembolic stroke in a mammal comprising administering a composition of claim 1 to a mammal in need thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2022
From: HICKS, JACQUELINE D.; DEBENHAM, JOHN S.; ALI, AMJAD; GAO, YING-DOU; WEI, LAN; YANG, DEXI; KUANG, RONGZE; HRUZA, ALAN; NIZNER, PETER; TATOSIAN, DANIEL S.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061549/0290 →
MERGER Recorded Oct 26, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061549/0443 →
Continuity (2)
Provisional Application 63023587 · May 12, 2020
Related Publication 20230167085A1 · Jun 1, 2023
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