IP Library Granted Patent US 10,624,882
Granted Patent B2
US 10,624,882 · App. 15/858,995 · Granted Apr 21, 2020

Rho kinase inhibitors

Inventors: Todd Bosanac (New Milford, CT); John David Ginn (New Milford, CT); Eugene Richard Hickey (Ridgefield, CT); Thomas Martin Kirrane, Jr. (Middlebury, CT); Weimin Liu (Sandy Hook, CT); Anthony S. Prokopowicz (Stormville, NY); Sabine K. Schlyer (New Milford, CT); Cheng-Kon Shih (Danbury, CT); Roger John Snow (Danbury, CT); Michael Robert Turner (Danbury, CT); Frank Wu (Ridgefield, CT); Erick Richard Young (Danbury, CT)
Assignee: Aerie Pharmaceuticals, Inc.
A61K31/472A61K31/4725A61K31/496A61K31/517A61K31/5377A61K31/541A61P9/00A61P27/06C07D217/24C07D239/88C07D239/90C07D401/12C07D401/14C07D403/12C07D405/12C07D409/12C07D413/12C07D487/08
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,624,882
App. No.
15/858,995
Granted
Apr 21, 2020
Kind
B2
Abstract

Disclosed are novel substituted 2H-isoquinolin-1-one and 3H-quinazolin-4-one derivatives useful as inhibitors of Rho kinase and for treating a variety of diseases and disorders that are mediated or sustained through the activity of Rho kinase, including cardiovascular diseases, pharmaceutical compositions comprising such compounds, methods for using such compounds and processes for making such compounds.

Claims (52)

1. A compound selected from:

1-(4-Chloro-phenyl)-cyclopentanecarboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

2-Benzylamino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide;

1-Benzyl-piperidine-4-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

Pyrrolidine-2-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

2-Amino-4-methyl-pentanoic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

(R)-2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-3-phenyl-propionamide;

(S)-2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-3-phenyl-propionamide;

2-(Cyclohexylmethyl-amino)-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide;

2-Methylamino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide;

2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide;

2-Cyclopropylamino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide;

(R)-2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide;

(R)-Pyrrolidine-2-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

(R)-2-Amino-3-methyl-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-butyramide;

2-(Cyclopropylmethyl-amino)-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide;

N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-(2-thiophen-2-yl-ethylamino)-acetamide;

2-(Cyclohexyl-methyl-amino)-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide;

N-(6-Chloro-4-oxo-3,4-dihydro-quinazolin-7-yl)-2-dimethylamino-2-phenyl-acetamide;

N-(6-Chloro-4-oxo-3,4-dihydro-quinazol in-7-yl)-2-cyclopropylamino-2-phenyl-acetamide;

2,5-Dimethyl-2H-pyrazole-3-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

(trans)-4-(3-Bromo-phenyl)-pyrrolidine-3-carboxylic acid (6-chloro-4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

(R)—N-(6-Chloro-4-oxo-3,4-dihydro-quinazolin-7-yl)-2-(4-chloro-phenyl)-2-hydroxy-propionamide;

(R)-2-(4-Chloro-phenyl)-2-hydroxy-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-propionamide;

or a pharmaceutically acceptable salt thereof.

2. A composition comprising the compound of claim 1 .

3. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient or carrier.

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

(R)-2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-3-phenyl-propionamide;

(S)-2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-3-phenyl-propionamide;

(R)-2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide;

(R)-Pyrrolidine-2-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

(R)-2-Amino-3-methyl-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-butyramide;

(trans)-4-(3-Bromo-phenyl)-pyrrolidine-3-carboxylic acid (6-chloro-4-oxo-3,4-dihydro-quinazolin-7-yl)-amide;

(R)—N-(6-Chloro-4-oxo-3,4-dihydro-quinazolin-7-yl)-2-(4-chloro-phenyl)-2-hydroxy-propionamide;

(R)-2-(4-Chloro-phenyl)-2-hydroxy-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-propionamide;

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 , wherein the compound is 1-(4-Chloro-phenyl)-cyclopentanecarboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 , wherein the compound is 2-Benzylamino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1 , wherein the compound is 1-Benzyl-piperidine-4-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide or a pharmaceutically acceptable salt thereof.

8. The compound of claim 1 , wherein the compound is Pyrrolidine-2-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide or a pharmaceutically acceptable salt thereof.

9. The compound of claim 1 , wherein the compound is 2-Amino-4-methyl-pentanoic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide or a pharmaceutically acceptable salt thereof.

10. The compound of claim 1 , wherein the compound is 2-(Cyclohexylmethyl-amino)-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide or a pharmaceutically acceptable salt thereof.

11. The compound of claim 1 , wherein the compound is 2-Methylamino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide or a pharmaceutically acceptable salt thereof.

12. The compound of claim 1 , wherein the compound is 2-Amino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide or a pharmaceutically acceptable salt thereof.

13. The compound of claim 1 , wherein the compound is 2-Cyclopropylamino-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-phenyl-acetamide or a pharmaceutically acceptable salt thereof.

14. The compound of claim 1 , wherein the compound is 2-(Cyclopropylmethyl-amino)-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide or a pharmaceutically acceptable salt thereof.

15. The compound of claim 1 , wherein the compound is N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-2-(2-thiophen-2-yl-ethylamino)-acetamide or a pharmaceutically acceptable salt thereof.

16. The compound of claim 1 , wherein the compound is 2-(Cyclohexyl-methyl-amino)-N-(4-oxo-3,4-dihydro-quinazolin-7-yl)-acetamide or a pharmaceutically acceptable salt thereof.

17. The compound of claim 1 , wherein the compound is N-(6-Chloro-4-oxo-3,4-dihydro-quinazolin-7-yl)-2-dimethylamino-2-phenyl-acetamide or a pharmaceutically acceptable salt thereof.

18. The compound of claim 1 , wherein the compound is N-(6-Chloro-4-oxo-3,4-dihydro-quinazolin-7-yl)-2-cyclopropylamino-2-phenyl-acetamide or a pharmaceutically acceptable salt thereof.

19. The compound of claim 1 , wherein the compound is 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid (4-oxo-3,4-dihydro-quinazolin-7-yl)-amide or a pharmaceutically acceptable salt thereof.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2024
From: AERIE PHARMACEUTICALS, INC.
To: ALCON INC.
Reel/Frame 067822/0168 →
RELEASE OF SECURITY INTEREST Recorded Sep 5, 2019
From: DEERFIELD PRIVATE DESIGN FUND III, L.P.
To: AERIE PHARMACEUTICALS, INC.
Reel/Frame 050276/0807 →
SECURITY INTEREST Recorded Jul 23, 2018
From: AERIE PHARMACEUTICALS, INC.
To: DEERFIELD PRIVATE DESIGN FUND III, L.P.
Reel/Frame 046432/0307 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2017
From: BOSANAC, TODD; GINN, JOHN DAVID; HICKEY, EUGENE RICHARD; KIRRANE, THOMAS MARTIN, JR.; LIU, WEIMIN; PROKOPOWICZ, ANTHONY S.; SCHLYER, SABINE K.; SHIH, CHENG-KON; SNOW, ROGER JOHN; TURNER, MICHAEL ROBERT; WU, FRANK; YOUNG, ERICK RICHARD
To: BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.
Reel/Frame 044508/0328 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2017
From: BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 044508/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2017
From: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
To: AERIE PHARMACEUTICALS, INC.
Reel/Frame 044508/0377 →