IP Library Granted Patent US 10,899,714
Granted Patent B2
US 10,899,714 · App. 16/680,359 · Granted Jan 26, 2021

6-aminoisoquinoline compounds

Inventors: Mitchell A. deLong (Chapel Hill, NC); Susan M. Royalty (Davis, CA); Jill Marie Sturdivant (Chapel Hill, NC); Geoffrey Richard Heintzelman (Durham, NC)
Assignee: Aerie Pharmaceuticals, Inc.
C07D217/02C07D215/38C07D217/04C07D401/12C07D405/12C07D409/12C07D417/12
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Quick Facts
Patent No.
US 10,899,714
App. No.
16/680,359
Granted
Jan 26, 2021
Kind
B2
Abstract

6-Amino isoquinoline compounds are provided that influence, inhibit or reduce the action of a kinase. Pharmaceutical compositions including therapeutically effective amounts of the 6-aminoisoquinoline compounds and pharmaceutically acceptable carriers are also provided. Various methods using the compounds and/or compositions to affect disease states or conditions such as cancer, obesity and glaucoma are also provided.

Claims (36)

1. A compound, wherein the compound is a pharmaceutically acceptable salt of Formula IV:

wherein,

A is a substituted or unsubstituted chain containing from one to four member atoms selected from the group consisting of carbon, nitrogen, oxygen and sulphur, wherein the chain may be mono- or di-substituted with halogen, cyano, nitro, or C 1 -C 4 alkyl, or the substituted atoms may attach back to the main chain to form a ring;

R 1 and R 2 are, independently, hydrogen, hydroxyl, halogen, or cyano; and

R 3 is hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, amino, cyano, cycloalkyl, heterocycloalkyl, aryl, C 1 -C 4 alkyl aryl, heteroaryl, C 1 -C 4 alkyl heteroaryl, carbonyl, carbonylamino, thioalkyl, sulfonyl, sulfonylamino, acyl, or carboxyl.

2. The compound of claim 1 , wherein R 1 and R 2 are hydrogen.

3. The compound of claim 1 , wherein A is methylene or ethylene.

4. The compound of claim 1 , wherein A is —O—CH 2 — or —NH—CH 2 —.

5. The compound of claim 1 , wherein R 3 is alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl, C 1 -C 4 alkyl aryl, heteroaryl, C 1 -C 4 alkyl heteroaryl, carbonyl, or carbonylamino.

6. The compound of claim 1 , wherein R 3 is aryl.

7. The compound of claim 6 , wherein R 3 is substituted with heteroaryl, acyl, carboxyl, carbonylamino, nitro, amino, cyano, halogen, alkoxy, or hydroxyl.

8. The compound of claim 6 , wherein R 3 is phenyl.

9. The compound of claim 1 , wherein the compound is a pharmaceutically acceptable salt of:

10. A pharmaceutical composition comprising:

a) the compound of claim 1 ; and

b) a pharmaceutically acceptable carrier.

11. The pharmaceutical composition of claim 10 , wherein the carrier is a systemic or topical carrier.

12. The pharmaceutical composition of claim 11 , wherein the composition comprises about 0.001% to 10% of the compound and 90% to 99.999% of the systemic carrier.

13. A method of treating an eye disease in a subject in need thereof, comprising administering to the subject an effective amount of a compound, wherein the compound is a pharmaceutically acceptable salt of Formula IV:

wherein,

A is a substituted or unsubstituted chain containing from one to four member atoms selected from the group consisting of carbon, nitrogen, oxygen and sulphur, wherein the chain may be mono- or di-substituted with halogen, cyano, nitro, or C 1 -C 4 alkyl, or the substituted atoms may attach back to the main chain to form a ring;

R 1 and R 2 are, independently, hydrogen, hydroxyl, halogen, or cyano; and

R 3 is hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, amino, cyano, cycloalkyl, heterocycloalkyl, aryl, C 1 -C 4 alkyl aryl, heteroaryl, C 1 -C 4 alkyl heteroaryl, carbonyl, carbonylamino, thioalkyl, sulfonyl, sulfonylamino, acyl, or carboxyl.

14. The method of claim 13 , wherein R 1 and R 2 are hydrogen.

15. The method of claim 13 , wherein A is methylene or ethylene.

16. The method of claim 13 , wherein A is —O—CH 2 — or —NH—CH 2 —.

17. The method of claim 13 , wherein R 3 is alkyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl, C 1 -C 4 alkyl aryl, heteroaryl, C 1 -C 4 alkyl heteroaryl, carbonyl, or carbonylamino.

18. The method of claim 13 , wherein R 3 is aryl.

19. The method of claim 18 , wherein R 3 is substituted with heteroaryl, acyl, carboxyl, carbonylamino, nitro, amino, cyano, halogen, alkoxy, or hydroxyl.

20. The method of claim 18 , wherein R 3 is phenyl.

21. The method of claim 13 , wherein the compound is a pharmaceutically acceptable salt of:

22. The method of claim 13 , wherein the subject is administered a pharmaceutical composition comprising:

a) the effective amount of the compound; and

b) a pharmaceutically acceptable carrier.

23. The method of claim 22 , wherein the pharmaceutically acceptable carrier is a systemic or topical carrier.

24. The method of claim 23 , wherein the composition comprises about 0.001% to 10% of the compound and 90% to 99.999% of the systemic carrier.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2024
From: AERIE PHARMACEUTICALS, INC.
To: ALCON INC.
Reel/Frame 067822/0168 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 13, 2019
From: DELONG, MITCHELL A.; ROYALTY, SUSAN M.; STURDIVANT, JILL MARIE; HEINTZELMAN, GEOFFREY RICHARD
To: AERIE PHARMACEUTICALS, INC.
Reel/Frame 051001/0367 →