IP Library Granted Patent US 10,265,370
Granted Patent B2
US 10,265,370 · App. 16/053,164 · Granted Apr 23, 2019

Lisinopril formulations

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Quick Facts
Patent No.
US 10,265,370
App. No.
16/053,164
Granted
Apr 23, 2019
Kind
B2
Abstract

Provided herein are stable lisinopril oral liquid formulations. Also provided herein are methods of using lisinopril oral liquid formulations for the treatment of certain diseases including hypertension, heart failure and acute myocardial infarction.

Claims (38)

1. A stable oral liquid formulation, comprising:

(i) about 1 mg/ml lisinopril or a pharmaceutically acceptable salt or solvate thereof;

(ii) a sweetener;

(iii) a buffer comprising citric acid and sodium citrate;

(iv) a preservative selected from the group consisting of sodium benzoate, benzoic acid, sorbic acid, methylparaben, propylparaben, and salts thereof; and

(v) water;

wherein the formulation is stable at about 25±5° C. for at least 6 months.

2. The formulation of claim 1 , wherein the lisinopril is lisinopril dihydrate.

3. The formulation of claim 1 , wherein the pH is between about 4 and about 5.2.

4. The formulation of claim 1 , wherein the pH is about 4.9.

5. The formulation of claim 1 , wherein the pH is about 5.2.

6. The formulation of claim 1 , wherein the formulation is stable at about 25±5° C. for at least 12 months.

7. The formulation of claim 1 , wherein the formulation is stable at about 25±5° C. for at least 18 months.

8. The formulation of claim 1 , wherein the formulation is stable at about 25±5° C. for at least 24 months.

9. The formulation of claim 1 , wherein the buffer concentration is from about 5 to about 50 mM.

10. The formulation of claim 1 , wherein the buffer concentration is about 10 mM.

11. The formulation of claim 1 , wherein the sweetener is a sugar.

12. The formulation of claim 11 , wherein the sugar is selected from the group consisting of glucose, fructose, sucrose, xylitol, tagatose, sucralose, maltitol, isomaltulose, lactitol, sorbitol, erythritol, trehalose, maltodextrin, polydextrose, and salts thereof.

13. The formulation of claim 1 , wherein the sweetener is selected from the group consisting of glycerin, inulin, erythritol, maltol, acesulfame, alitame, aspartame, neotame, sodium cyclamate, saccharin, and salts thereof.

14. The formulation of claim 13 , wherein the amount of sweetener is about 0.5 to about 3 mg/ml.

15. The formulation of claim 1 , wherein the preservative is sodium benzoate.

16. The formulation of claim 1 , wherein the amount of the preservative is about 0.5 to about 1.2 mg/ml.

17. The formulation of claim 1 , wherein the preservative is methylparaben or propylparaben or salts thereof.

18. The formulation of claim 17 , wherein the amount of the paraben is about 0.1 to about 2 mg/ml.

19. A stable oral liquid formulation, comprising:

(i) about 1 mg/ml lisinopril or a pharmaceutically acceptable salt or solvate thereof;

(ii) a sweetener selected from the group consisting of xylitol, mannitol, sucralose, saccharin, and salts thereof;

(iii) a buffer comprising citric acid and sodium citrate;

(iv) a preservative; and

(v) water;

wherein the formulation is stable at about 25±5° C. for at least 6 months.

20. A stable oral liquid formulation, comprising:

(i) about 1 mg/ml lisinopril or a pharmaceutically acceptable salt or solvate thereof;

(ii) a sweetener;

(iii) a buffer comprising citric acid and sodium citrate;

(iv) a preservative; and

(v) water;

wherein the formulation is stable at about 25±5° C. for at least 6 months.

Assignments (9)
CONFIRMATORY GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Mar 17, 2025
From: ARBOR PHARMACEUTICALS, LLC; AZURITY PHARMACEUTICALS, INC.; AZURITY PHARMACEUTICALS IRELAND LIMITED; SILVERGATE PHARMACEUTICALS, INC.
To: HPS INVESTMENT PARTNERS, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 070531/0487 →
RELEASE OF SECURITY INTEREST Recorded Mar 14, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: AZURITY PHARMACEUTICALS, INC.; SILVERGATE PHARMACEUTICALS, INC.; ARBOR PHARMACEUTICALS, LLC; SLAYBACK PHARMA LIMITED LIABILITY COMPANY
Reel/Frame 070521/0299 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2023
From: SILVERGATE PHARMACEUTICALS, INC.
To: AZURITY PHARMACEUTICALS, INC.
Reel/Frame 064817/0471 →
RELEASE OF SECURITY INTEREST Recorded Sep 20, 2021
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 057531/0556 →
SECURITY INTEREST Recorded Sep 20, 2021
From: SILVERGATE PHARMACEUTICALS, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 057532/0550 →
RELEASE OF SECURITY INTEREST Recorded Aug 23, 2021
From: GOLDMAN SACHS BANK USA
To: AZURITY PHARMACEUTICALS, INC.; SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 057253/0348 →
SECURITY INTEREST Recorded Apr 16, 2021
From: SILVERGATE PHARMACEUTICALS, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 055938/0895 →
SECURITY INTEREST Recorded May 17, 2019
From: CUTISPHARMA, INC.; SILVERGATE PHARMACEUTICALS, INC.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 049209/0272 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 5, 2018
From: MOSHER, GEROLD L.; MILES, DAVID W.
To: SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 047479/0828 →
Cited By (2)
US 12,186,360 US 12,433,931