IP Library Granted Patent US 11,058,677
Granted Patent B2
US 11,058,677 · App. 14/650,955 · Granted Jul 13, 2021

LFA-1 inhibitor formulations

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Quick Facts
Patent No.
US 11,058,677
App. No.
14/650,955
Granted
Jul 13, 2021
Kind
B2
Abstract

The present invention provides formulations, methods and kits for the treatment of dry eye diseases. In particular, stabilized pharmaceutical compositions comprising the compound of Formula 1 are described herein for a variety of uses including the treatment of dry eye syndrome. In one aspect, methods and ingredients for improving the stability of compositions of the compound of Formula 1 are described.

Claims (42)

1. A composition comprising a compound of Formula 1:

or a salt thereof,

a pharmaceutically acceptable carrier, and

a thiosulfate salt,

wherein the composition has less than about 1% of total degradation products of the compound of Formula 1 when stored at a temperature of about 40° C. for a period of at least one month.

2. The composition of claim 1 , wherein the pharmaceutically acceptable carrier is an aqueous carrier.

3. The composition of claim 2 , wherein the thiosulfate salt is present in an amount of about 0.01% to about 0.5% w/v.

4. The composition of claim 2 , wherein the thiosulfate salt is present in an amount of about 0.3% w/v.

5. The composition of claim 3 , wherein the thiosulfate salt is sodium thiosulfate.

6. The composition of claim 5 , wherein the composition is buffered to a pH of about 6.0 to about 8.5.

7. The composition of claim 6 , wherein the compound of Formula 1 is present in an amount of about 1% to about 5% w/v.

8. The composition of claim 7 , wherein the compound of Formula 1 is present in an amount of about 5% w/v.

9. The composition of claim 8 , wherein the composition exhibits less than about 1% of total degradation products of the compound of Formula 1 upon storage at a temperature of about 40° C. for a time period selected from the group consisting of 2 months, 3 months, 4 months, 5 months, and 6 months.

10. The composition of claim 8 , further comprising a sparged nitrogen gas.

11. The composition of claim 1 , comprising:

about 5% w/v of the compound of Formula 1;

about 0.3% w/v thiosulfate salt;

sodium chloride; and

sodium phosphate,

wherein the composition has a pH of about 7.0 to about 8.0.

12. The composition of claim 11 , wherein the sodium phosphate is dibasic sodium phosphate.

13. A composition comprising:

4 to 10 w/v % compound of Formula 1:

or a salt thereof; and

0.2 to 0.4% antioxidant, the antioxidant being sodium thiosulfate;

wherein the composition is an aqueous solution with the compound of Formula 1 dissolved therein, and

wherein the composition is suitable for topical administration to the eye.

14. A composition comprising:

about 5 w/v % compound of Formula 1:

or a salt thereof;

about 0.3% w/v antioxidant, the antioxidant being sodium thiosulfate;

sodium phosphate for buffering the compositions at a pH of 6.0 to 8.0; and

sodium chloride for providing isotonicity to the composition;

wherein the composition is an aqueous solution having the compound of Formula 1 dissolved therein, and

wherein the composition is suitable for topical administration to the eye.

15. The composition of claim 13 , wherein said thiosulfate salt is the primary antioxidant.

16. The composition of claim 13 , further comprising a sparged inert gas.

17. The composition of claim 16 , wherein the sparged inert gas is nitrogen.

18. The composition of claim 13 , wherein the composition is buffered to a pH of about 7.5.

19. The composition of claim 1 , wherein the composition comprises one or more antioxidants and a sparged inert gas.

20. The composition of claim 1 , wherein the formulation expires in about 1-5 years when stored at or below ambient temperature.

21. The composition of claim 14 , wherein the formulation expires in about 1-5 years when stored at or below ambient temperature.

Assignments (6)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 23, 2025
From: BAUSCH + LOMB IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 074050/0573 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 23, 2025
From: BAUSCH + LOMB IRELAND LIMITED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 074050/0682 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 23, 2025
From: BAUSCH + LOMB IRELAND LIMITED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 074050/0709 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2023
From: NOVARTIS PHARMACEUTICALS CORPORATION
To: BAUSCH + LOMB IRELAND LIMITED
Reel/Frame 065789/0853 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2021
From: NOVARTIS AG
To: NOVARTIS PHARMACEUTICALS CORPORATION
Reel/Frame 056800/0532 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2019
From: SARCODE BIOSCIENCE INC.
To: NOVARTIS AG
Reel/Frame 050900/0268 →