IP Library Granted Patent US 11,180,503
Granted Patent B2
US 11,180,503 · App. 16/624,545 · Granted Nov 23, 2021

[1,2,4]Triazolo[4,3-A]pyrazin-6(5H)-one derivatives

Inventors: Michael James Genin (Danville, IN); William Glen Holloway (Brownsburg, IN); Richard Duane Johnston (Greenfield, IN); John Richard Morphy (Surrey, GB); Qing Shi (Carmel, IN)
Assignee: ELI LILLY AND COMPANY
C07D471/14
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Quick Facts
Patent No.
US 11,180,503
App. No.
16/624,545
Granted
Nov 23, 2021
Kind
B2
Abstract

The present invention provides a compound of Formula (I), wherein X is H or C1-C3 alkyl optionally substituted with hydroxyl; Y is H, hydroxy, or methyl; R is ethyl, n-propyl, cyclopropyl, or Formula (II); and A is methyl, cyclopropyl or trifluoromethyl; or a pharmaceutically acceptable salt thereof; with the proviso that when X and Y are both H and R is n-propyl, then A is other than methyl; for use as a human PDE1 inhibitor.

Claims (19)

1. A compound of the formula:

wherein X is H or C1-C3 alkyl optionally substituted with hydroxyl;

Y is H, hydroxy, or methyl;

R is ethyl, n-propyl, cyclopropyl, or

and

A is methyl, cyclopropyl or trifluoromethyl;

or a pharmaceutically acceptable salt thereof;

with the proviso that when X and Y are both H and R is n-propyl, then A is other than methyl.

2. The compound or salt according to claim 1 wherein X is methyl.

3. The compound or salt according to claim 1 wherein Y is H.

4. The compound or salt according to claim 1 wherein R is n-propyl.

5. The compound or salt according to claim 1 wherein A is cyclopropyl.

6. The compound according to claim 1 wherein the compound is in the free base form.

7. The compound or salt according to claim 1 wherein the compound is of the formula:

8. The compound according to claim 1 wherein the compound is of the formula:

9. The compound or salt according to claim 1 wherein the compound is of the formula:

10. The compound according to claim 1 wherein the compound is of the formula:

11. A pharmaceutical composition, comprising a compound or a pharmaceutically-acceptable salt thereof according to claim 1 , with one or more pharmaceutically acceptable carriers, diluents, or excipients.

12. A process for preparing a pharmaceutical composition, comprising admixing a compound according to claim 1 , or a pharmaceutically-acceptable salt thereof, with one or more pharmaceutically acceptable carriers, diluents, or excipients.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2019
From: GENIN, MICHAEL JAMES; HOLLOWAY, WILLIAM GLEN; JOHNSTON, RICHARD DUANE; MORPHY, JOHN RICHARD; SHI, QING
To: ELI LILLY AND COMPANY
Reel/Frame 051333/0399 →
Continuity (2)
Provisional Application 62540122 · Aug 2, 2017
Related Publication 20200123154A1 · Apr 23, 2020