IP Library Granted Patent US 10,940,177
Granted Patent B2
US 10,940,177 · App. 16/822,412 · Granted Mar 9, 2021

Lisinopril formulations

Inventors: Gerold L. Mosher (Kansas City, MO); David W. Miles (Kansas City, MO)
Assignee: SILVERGATE PHARMACEUTICALS, INC.
A61K38/05A61K9/0053A61K9/0095A61K31/401A61K38/005A61K45/06A61K47/02A61K47/12A61K47/26
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Quick Facts
Patent No.
US 10,940,177
App. No.
16/822,412
Granted
Mar 9, 2021
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 (35)

1. 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 pharmaceutically acceptable salts thereof;

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

(iv) 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 of the formulation is between about 4 and about 5.2.

4. The formulation of claim 1 , wherein the pH of the formulation is higher than 4.

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

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

7. The formulation of claim 1 , wherein the sweetener is xylitol, sucralose, or saccharin.

8. The formulation of claim 7 , wherein the xylitol is present in the formulation at about 140 mg/ml to about 160 mg/ml.

9. The formulation of claim 7 , wherein the xylitol is present in the formulation at about 150 mg/ml.

10. The formulation of claim 7 , wherein the sucralose is present in the formulation at about 0.5 mg/ml to about 3 mg/ml.

11. The formulation of claim 7 , wherein the sucralose is present in the formulation at about 0.7 mg/ml.

12. The formulation of claim 1 , wherein the preservative is present in the formulation at about 0.1 mg/ml to about 2 mg/ml.

13. The formulation of claim 1 , wherein the preservative is present in the formulation at about 0.8 mg/ml.

14. A stable oral liquid formulation, consisting of:

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

(ii) about 150 mg/ml of a sweetener, wherein the sweetener is xylitol, mannitol, sucralose, saccharin, a pharmaceutically acceptable salt thereof, or a combination thereof;

(iii) about 0.8 mg/ml of a preservative, wherein the preservative is sodium benzoate, benzoic acid, sorbic acid, methylparaben, propylparaben, a pharmaceutically acceptable salts thereof, or a combination thereof; and

(iv) water;

wherein the pH of the formulation is between about 4 and about 5; and

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

15. The formulation of claim 14 , wherein the preservative is sodium benzoate.

16. The formulation of claim 14 , wherein the sweetener is xylitol.

17. The formulation of claim 1 , wherein the lisinopril or a pharmaceutically acceptable salt or solvate thereof functions as a buffer.

18. The formulation of claim 14 , wherein the lisinopril or a pharmaceutically acceptable salt or solvate thereof functions as a buffer.

19. A stable oral liquid formulation, consisting essentially of:

(i) about 0.5 w/w to about 1% w/w lisinopril or a pharmaceutically acceptable salt or solvate thereof;

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

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

(iv) water;

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

Assignments (7)
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 →
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 Sep 20, 2021
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 057531/0556 →
SECURITY INTEREST Recorded Apr 16, 2021
From: SILVERGATE PHARMACEUTICALS, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 055938/0895 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 31, 2020
From: MOSHER, GEROLD L.; MILES, DAVID W.
To: SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 055759/0725 →