IP Library Granted Patent US 9,616,096
Granted Patent B1
US 9,616,096 · App. 15/268,095 · Granted Apr 11, 2017

Lisinopril formulations

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Quick Facts
Patent No.
US 9,616,096
App. No.
15/268,095
Granted
Apr 11, 2017
Kind
B1
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 (41)

1. A method of treating hypertension in a subject comprising administering to that subject a therapeutically effective amount of a stable oral liquid formulation, comprising:

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

(ii) about 150 mg/ml of a sweetener that is xylitol;

(iii) a buffer comprising about 0.86 mg/ml citric acid and about 1.44 mg/ml sodium citrate;

(iv) about 0.8 mg/ml of a preservative that is sodium benzoate; and

(v) 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 12 months.

2. The method of claim 1 , wherein lisinopril is lisinopril dihydrate.

3. The method of claim 1 , wherein the pH is about 4.9.

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

5. The method of claim 1 , wherein the hypertension is primary (essential) hypertension.

6. The method of claim 1 , wherein the hypertension is secondary hypertension.

7. The method of claim 1 , wherein the subject has blood pressure values greater than or equal to 140/90 mmm Hg.

8. The method of claim 1 , wherein the subject is elderly.

9. The method of claim 1 , wherein the subject is a child.

10. The method of claim 1 , wherein the formulation is further administered in combination with an agent selected from the group consisting of diuretics, beta blockers, alpha blockers, mixed alpha and beta blockers, calcium channel blockers, angiotensin II receptor antagonists, ACE inhibitors, aldosterone antagonists, and alpha-2 agonists.

11. A method of treating heart failure in a subject comprising administering to that subject a therapeutically effective amount of a stable oral liquid formulation, comprising:

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

(ii) about 150 mg/nil of a sweetener that is xylitol;

(iii) a buffer comprising about 0.86 mg/ml citric acid and about 1.44 mg/ml sodium citrate;

(iv) about 0.8 mg/ml of a preservative that is sodium benzoate; and

(v) 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 12 months.

12. The method of claim 11 , wherein lisinopril is lisinopril dihydrate.

13. The method of claim 11 , wherein the pH is about 4.9.

14. The method of claim 11 , wherein the formulation is stable at about 25±5° C. for at least 24 months.

15. The method of claim 11 , wherein the subject is not responding adequately to diuretics and digitalis.

16. A method of treating a hemodynamically stable subject within 24 hours of acute myocardial infarction comprising administering to that subject a therapeutically effective amount of a stable oral liquid formulation, comprising:

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

(ii) about 150 mg/ml of a sweetener that is xylitol;

(iii) a buffer comprising about 0.86 mg/ml citric acid and about 1.44 mg/ml sodium citrate;

(iv) about 0.8 mg/ml of a preservative that is sodium benzoate; and

(v) 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 12 months.

17. The method of claim 16 , wherein lisinopril is lisinopril dihydrate.

18. The method of claim 16 , wherein the pH is about 4.9.

19. The method of claim 16 , wherein the formulation is stable at about 25±5° C. for at least 24 months.

20. The method of claim 16 , wherein the formulation is further administered in combination with an agent selected from the group consisting of beta blockers, aspirin, and thrombolytics.

Assignments (11)
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded May 17, 2019
From: WHITE OAK HEALTHCARE FINANCE, LLC, AS AGENT
To: ARGENTUM HOLDINGS, LLC; SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 049211/0188 →
SECURITY INTEREST Recorded May 17, 2019
From: CUTISPHARMA, INC.; SILVERGATE PHARMACEUTICALS, INC.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 049209/0272 →
SECURITY INTEREST Recorded Dec 19, 2018
From: ARGENTUM HOLDINGS, LLC; SILVERGATE PHARMACEUTICALS, INC.
To: WHITE OAK HEALTHCARE FINANCE, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 047815/0615 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2016
From: MOSHER, GEROLD L.; MILES, DAVID W.
To: SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 040066/0323 →