IP Library › Granted Patent US 10,011,606
Granted Patent B2
US 10,011,606 · App. 15/615,380 · Granted Jul 3, 2018

Imidazopyrazinones as PDE1 inhibitors

Inventors: Jan Kehler (Lyngby, DK); Lars Kyhn Rasmussen (Vanløse, DK); Morten Langgård (Glostrup, DK); Mikkel Jessing (Frederiksberg, DK)
Assignee: H. Lundbeck A/S
C07D487/04C07D519/00
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Quick Facts
Patent No.
US 10,011,606
App. No.
15/615,380
Granted
Jul 3, 2018
Kind
B2
Abstract

The present invention provides imidazopyrazinones as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.

Claims (92)

1. A compound selected from the group consisting of:

(A) (4) 7-(Cyclohexylmethyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(5) 7-(3-Fluorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(6) 3-Cyclopropyl-7-(3-fluorobenzyl)imidazo[1,5-a]pyrazin-8(7H)-one;

(7) 7-(Cyclopentylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8(7H)-one;

(8) 7-(Cyclohexylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8(7H)-one;

(9) 7-(3-Fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(10) 7-(Cyclopentylmethyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(11) 7-(Cyclohexylmethyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(12) 7-(Cycloheptylmethyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(13) 7-(Cycloheptylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8(7H)-one;

(14) 7-(4-Chlorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(15) 6-Bromo-7-(3-fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(16) 7-Benzyl-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(17) 7-(2-Fluorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(18) 7-(3-Chlorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(19) 7-(2-Chlorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(20) 7-(3-Methoxybenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(21) 6-Methyl-7-(2-methylbenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(22) 6-Methyl-7-(4-methylbenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(23) 7-(4-Methoxybenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

(24) 7-(4-Fluorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one; and

(25) 6-Methyl-7-(3-methylbenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or

(B) a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein the compound is:

(4) 7-(Cyclohexylmethyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein the compound is:

(5) 7-(3-Fluorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 , wherein the compound is:

(6) 3-Cyclopropyl-7-(3-fluorobenzyl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 , wherein the compound is:

(7) 7-(Cyclopentylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 , wherein the compound is:

(8) 7-(Cyclohexylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1 , wherein the compound is:

(9) 7-(3-Fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

8. The compound of claim 1 , wherein the compound is:

(10) 7-(Cyclopentylmethyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

9. The compound of claim 1 , wherein the compound is:

(11) 7-(Cyclohexylmethyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

10. The compound of claim 1 , wherein the compound is:

(12) 7-(Cycloheptylmethyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

11. The compound of claim 1 , wherein the compound is:

(13) 7-(Cycloheptylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

12. The compound of claim 1 , wherein the compound is:

(14) 7-(4-Chlorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

13. The compound of claim 1 , wherein the compound is:

(15) 6-Bromo-7-(3-fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

14. The compound of claim 1 , wherein the compound is:

(16) 7-Benzyl-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

15. The compound of claim 1 , wherein the compound is:

(17) 7-(2-Fluorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

16. The compound of claim 1 , wherein the compound is:

(18) 7-(3-Chlorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

17. The compound of claim 1 , wherein the compound is:

(19) 7-(2-Chlorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

18. The compound of claim 1 , wherein the compound is:

(20) 7-(3-Methoxybenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

19. The compound of claim 1 , wherein the compound is:

(21) 6-Methyl-7-(2-methylbenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

20. The compound of claim 1 , wherein the compound is:

(22) 6-Methyl-7-(4-methylbenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

21. The compound of claim 1 , wherein the compound is:

(23) 7-(4-Methoxybenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

22. The compound of claim 1 , wherein the compound is:

(24) 7-(4-Fluorobenzyl)-6-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

23. The compound of claim 1 , wherein the compound is:

(25) 6-Methyl-7-(3-methylbenzyl)-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazin-8(7H)-one;

or a pharmaceutically acceptable salt thereof.

24. A pharmaceutical composition comprising a therapeutically effective amount of the compound of claim 1 and one or more pharmaceutically acceptable carriers.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2017
From: KEHLER, JAN; RASMUSSEN, LARS KYHN; LANGGARD, MORTEN; JESSING, MIKKEL; JUHL, KARSTEN; VITAL, PAULO JORGE VIEIRA
To: H. LUNDBECK A/S
Reel/Frame 044497/0073 →
Priority Claims (3)
DK 201500261 · Apr 30, 2015 · national
DK 201500666 · Oct 29, 2015 · national
DK 201600202 · Apr 4, 2016 · national
Continuity (2)
Continuation 15142116 · Apr 29, 2016
Related Publication 20170291903A1 · Oct 12, 2017