IP Library Granted Patent US 12,344,616
Granted Patent B2
US 12,344,616 · App. 17/286,525 · Granted Jul 1, 2025

Factor XIa inhibitors

Inventors: Amjad Ali (Freehold, NJ); John S. Debenham (Scotch Plains, NJ); Cheng Zhu (Edison, NJ)
Assignee: Merck Sharp & Dohme LLC
C07D487/08
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Quick Facts
Patent No.
US 12,344,616
App. No.
17/286,525
Granted
Jul 1, 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 XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.

Claims (46)

1. A compound of the formula:

wherein

R 1 is OCHF 2 when X 1 is N, or R 1 is a pyrazole optionally substituted with R 4 when X 1 is CH;

R 2 is chloro or fluoro;

R 3 is hydrogen or fluoro;

R 4 is CHF 2 or CF 3 ;

X 1 is CH or N;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 of the formula:

wherein

R 2 is chloro or fluoro;

R 3 is hydrogen or fluoro;

R 4 is CHF 2 or CF 3 ;

R 5 is a pyrazole optionally substituted with R 4 ;

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 of the formula:

wherein

R 2 is chloro or fluoro;

R 3 is hydrogen or fluoro;

R 4 is CHF 2 or CF 3 ;

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 of the formula:

wherein

R 2 is chloro or fluoro;

R 3 is hydrogen or fluoro;

R 4 is CHF 2 or CF 3 ;

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 of the formula:

wherein

R 2 is chloro;

R 3 is hydrogen;

or a pharmaceutically acceptable salt thereof.

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

7. The compound of claim 1 wherein X 1 is N; or a pharmaceutically acceptable salt thereof.

8. The compound of claim 1 wherein R 1 is OCHF 2 ; or a pharmaceutically acceptable salt thereof.

9. The compound of claim 1 wherein R 1 is pyrazole optionally substituted with R 4 ; or a pharmaceutically acceptable salt thereof.

10. The compound of claim 1 wherein R 2 is fluoro; or a pharmaceutically acceptable salt thereof.

11. The compound of claim 1 wherein R 2 is chloro; or

a pharmaceutically acceptable salt thereof.

12. The compound of claim 1 wherein R 3 is hydrogen; or a pharmaceutically acceptable salt thereof.

13. The compound of claim 1 wherein R 3 is fluoro; or a pharmaceutically acceptable salt thereof.

14. The compound of claim 1 wherein R 4 is CHF 2 ; or a pharmaceutically acceptable salt thereof.

15. The compound of claim 1 wherein R 4 is CF 3 ; or a pharmaceutically acceptable salt thereof.

16. The compound of claim 1 selected from:

or a pharmaceutically acceptable salt thereof.

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

Assignments (2)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2021
From: ALI, AMJAD; DEBENHAM, JOHN S.; ZHU, CHENG
To: MERCK SHARP & DOHME CORP.
Reel/Frame 055955/0377 →