IP Library Granted Patent US 9,695,184
Granted Patent B2
US 9,695,184 · App. 14/768,038 · Granted Jul 4, 2017

Therapeutic compounds and uses thereof

Inventors: Winston Zapanta Ong (Stoneham, MA); Pawel Wojciech Nowak (Woodcliff Lake, NJ); Ben C Askew (Marshfield, MA)
Assignee: Kala Pharmaceuticals, Inc.
C07D491/107C07D405/12C07D405/14C07D413/14
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Quick Facts
Patent No.
US 9,695,184
App. No.
14/768,038
Granted
Jul 4, 2017
Kind
B2
Abstract

Described herein are compounds of Formula (I) pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Methods of using the compounds or pharmaceutical compositions thereof for treating diseases are also provided.

Claims (103)

1. A compound of Formula (II):

or a pharmaceutically acceptable salt thereof,

wherein:

R 1 is hydrogen or optionally substituted C 1-6 alkyl;

R 2 is:

(1) a heterocyclyl when:

(a) X is —O—, or —C(═O)— and n is independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; or

(b) X is a bond and n is 6, 7, 8, 9, or 10; or

(2) an eight or nine membered heterocyclyl, when X is a bond and n is 0, 1, 2, 3, 4, or 5;

wherein each instance of R 3 is independently hydrogen, F, Cl , Br, I, CN, and OH;

Y is CH or N;

m is independently 0, 1, 2, 3, or 4;

each instance of R 4 is independently hydrogen, optionally substituted C 1-6 alkyl, F, Cl, Br, I, or CN; and

j is 0, 1, or 2.

2. The compound of claim 1 , wherein the compound is of Formula (II-a):

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein the compound is of Formula (II-b):

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 , wherein the compound is of Formula (II-c):

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 , wherein the compound is of Formula (II-c1):

or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 , wherein the compound is of Formula (II-c2):

or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1 , wherein the compound is of Formula (II-c3):

or a pharmaceutically acceptable salt thereof.

8. The compound of claim 1 , wherein the compound is of Formula (II-c4):

or a pharmaceutically acceptable salt thereof.

9. A compound of Formula (III-c):

or a pharmaceutically acceptable salt thereof,

wherein:

R 2 is:

(1) a heterocyclyl when:

(a) X is —O—, or —C(═O)— and n is independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; or

(b) X is a bond and n is 6, 7, 8, 9, or 10; or

(2) an eight or nine membered heterocyclyl, when X is a bond and n is 0, 1, 2, 3, 4, or 5; and

Y is CH or N.

10. The compound of claim 9 , wherein the compound is of Formula (III-c1):

or a pharmaceutically acceptable salt thereof.

11. The compound of claim 9 , wherein the compound is of Formula (III-c2):

or a pharmaceutically acceptable salt thereof.

12. The compound of claim 9 , wherein the compound is of Formula (III-c3):

or a pharmaceutically acceptable salt thereof.

13. The compound of claim 9 , wherein the compound is of Formula (III-c4):

or a pharmaceutically acceptable salt thereof.

14. A compound of Formula (IV-a1-ii):

or a pharmaceutically acceptable salt thereof;

wherein R 2 is a heterocyclyl;

Y is CH is N; and

Z 1 is branched or unbranched, acyclic of cyclic C 1-6 alkyl.

15. The compound of claim 14 , wherein the compound is of Formula (IV-a1-iii):

or a pharmaceutically acceptable salt thereof.

16. The compound of claim 14 , wherein the compound is of Formula (IV-a1-iv):

or a pharmaceutically acceptable salt thereof.

17. A compound of Formula (V):

or a pharmaceutically acceptable salt thereof,

wherein:

R 1 is hydrogen or optionally substituted C 1-6 alkyl;

R 2 is:

(1) a heterocyclyl when:

(a) X is —O—, of —C(═O)— and n is independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; or

(b) X is a bond and n is 6,7, 8, 9, or 10; or

(2) an eight or nine membered heterocyclyl, when X is a bond and n is 0, 1, 2, 3, 4, or 5;

wherein each instance of R 3 is independently hydrogen, F, Cl, Br, I, CN, or OH;

m is independently 0, 1, 2, 3, or 4,

Y is CH or N; and

each of e and f is independently 1, 2, or 3.

18. The compound of claim 17 , wherein the compound is of Formula (V-a):

or a pharmaceutically acceptable salt thereof.

19. The compound of claim 17 , wherein the compound is of Formula (V-a1):

or a pharmaceutically acceptable salt thereof.

20. The compound of claim 17 , wherein the compound is of Formula (V-a1-i):

or a pharmaceutically acceptable salt thereof.

21. The compound of claim 17 , wherein the compound is of Formula (V-a1-ii):

or a pharmaceutically acceptable salt thereof.

22. The compound of claim 17 , wherein the compound is of Formula (V-a1-iii):

or a pharmaceutically acceptable salt thereof.

23. The compound of claim 17 , wherein the compound is of Formula (V-a1-iv):

or a pharmaceutically acceptable salt thereof.

24. The compound of claim 17 , wherein the compound is of Formula (V-b):

or a pharmaceutically acceptable salt thereof.

25. The compound of claim 17 , wherein the compound is of Formula (V-b1):

or a pharmaceutically acceptable salt thereof.

26. The compound of claim 17 , wherein the compound is of Formula (V-b1-i):

or a pharmaceutically acceptable salt thereof.

27. The compound of claim 17 , wherein the compound is of Formula (V-b1-ii):

or a pharmaceutically acceptable salt thereof.

28. The compound of claim 17 , wherein the compound is of Formula (V-b1-iii):

or a pharmaceutically acceptable salt thereof.

29. The compound of claim 17 , wherein the compound is of Formula (V-b1-iv):

or a pharmaceutically acceptable salt thereof.

30. The compound of claim 1 , wherein R 2 is of formula:

wherein each instance of p and q is independently 0, 1, 2, 3, or 4.

31. The compound of claim 30 , wherein R 2 is of the formula:

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

wherein each instance of p, q, s, and t is independently 0, 1, 2, 3, or 4.

33. The compound of claim 32 , wherein R 2 is of the formula:

34. A compound of one of the following formulae:

35. A pharmaceutical composition comprising a compound of one of claims 1 , 9 , 14 , 17 , or 34 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

36. The pharmaceutical composition of claim 35 , wherein the pharmaceutical composition is suitable for delivery to the eye.

37. The compound of one of claims 1 , 9 , 14 , or 17 , wherein R 1 is methyl.

38. The compound of claim 32 , wherein R 2 is of the formula:

39. The compound of any one of claims 1 , 9 , or 17 , wherein R 2 is a spiro-heterocyclyl when X is a bond, —O—, or —C(═O)— and n is independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

Assignments (8)
CHANGE OF NAME Recorded Sep 21, 2023
From: KALA PHARMACEUTICALS, INC.
To: KALA BIO, INC.
Reel/Frame 065017/0488 →
FIRST AMENDMENT TO IP SECURITY AGREEMENT Recorded Dec 22, 2022
From: KALA PHARMACEUTICALS, INC.
To: OXFORD FINANCE LLC
Reel/Frame 062205/0883 →
SECURITY INTEREST Recorded May 6, 2021
From: KALA PHARMACEUTICALS, INC.
To: OXFORD FINANCE LLC
Reel/Frame 056168/0602 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS AT REEL AND FRAME: 047602 / 0480 & 047172 / 0481 Recorded May 5, 2021
From: ATHYRIUM OPPORTUNITIES III ACQUISITION LP
To: KALA PHARMACEUTICALS, INC
Reel/Frame 056151/0092 →
SECURITY INTEREST Recorded Oct 1, 2018
From: KALA PHARMACEUTICALS, INC.
To: ATHYRIUM OPPORTUNITIES III ACQUISITION LP
Reel/Frame 047172/0481 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2015
From: ONG, WINSTON Z.; NOWAK, PAWEL W.; KIM, JINSOO
To: KALA PHARMACEUTICALS, INC.
Reel/Frame 036661/0915 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2015
From: ASKEW, BEN C.
To: BREAKTHROUGH CHEMISTRY ADVISORS, LLC
Reel/Frame 036661/0974 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2015
From: BREAKTROUGH CHEMISTRY ADVISORS, LLC
To: KALA PHARMACEUTICALS, INC.
Reel/Frame 036662/0081 →
Continuity (2)
Provisional Application 61765487 · Feb 15, 2013
Related Publication 20160002254A1 · Jan 7, 2016