IP Library Granted Patent US 10,799,476
Granted Patent B2
US 10,799,476 · App. 16/883,553 · Granted Oct 13, 2020

Enalapril formulations

Inventors: Gerold L. Mosher (Kansas City, MO); David W. Miles (Kansas City, MO)
Assignee: Silvergate Pharmaceuticals, Inc.
A61K31/401A61K9/0053A61K9/0095A61K47/12A61K47/26
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Quick Facts
Patent No.
US 10,799,476
App. No.
16/883,553
Granted
Oct 13, 2020
Kind
B2
Abstract

Provided herein are stable enalapril oral liquid formulations. Also provided herein are methods of using enalapril oral liquid formulations for the treatment of certain diseases including hypertension, heart failure and asymptomatic left ventricular dysfunction.

Claims (21)

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

(i) about 1.0 mg/ml of enalapril maleate;

(ii) a buffer comprising citric acid and disodium hydrogenphosphate, wherein the buffer is present in the oral liquid formulation at a concentration of between about 5 mM and about 20 mM;

(iii) about 1 mg/ml of a preservative that is sodium benzoate;

(iv) a sweetener, wherein the sweetener is sucralose and is present at about 0.7 mg/ml in the oral liquid formulation;

(v) a flavoring agent; and

(vi) water;

wherein the oral liquid formulation maintains about 95% w/w or greater of the initial enalapril amount at the end of a storage period of at least 12 months at about 5±3° C.

2. The oral liquid formulation of claim 1 , wherein the flavoring agent has strawberry flavor.

3. The oral liquid formulation of claim 1 , wherein the citric acid is anhydrous.

4. The oral liquid formulation of claim 1 , wherein the citric acid is present at about 1.82 mg/mL in the oral liquid formulation.

5. The oral liquid formulation of claim 1 , wherein the buffer is present in the oral liquid formulation at a concentration of between about 10 mM and about 20 mM.

6. The oral liquid formulation of claim 1 , wherein the buffer is present in the oral liquid formulation at a concentration of about 10 mM.

7. The oral liquid formulation of claim 1 , wherein the buffer is present in the oral liquid formulation at a concentration of about 11 mM.

8. The oral liquid formulation of claim 1 , wherein the pH of the oral liquid formulation is below 4.5.

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

10. The oral liquid formulation of claim 1 , wherein the pH of the oral liquid formulation is about 3.3.

11. The oral liquid formulation of claim 1 , wherein the pH of the oral liquid formulation is adjusted by HCl, NaOH, or both.

12. The oral liquid formulation of claim 1 , wherein the oral liquid formulation maintains about 95% w/w or greater of the initial enalapril amount at the end of a storage period of at least 18 months at about 5±3° C.

13. The oral liquid formulation of claim 1 , wherein the oral liquid formulation maintains about 95% w/w or greater of the initial enalapril amount at the end of a storage period of at least 24 months at about 5±3° C.

14. The oral liquid formulation of claim 1 , wherein the oral liquid formulation maintains about 95% w/w or greater of the initial enalapril amount at the end of a storage period of at least 6 months at about 25±5° C.

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 →
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: AZURITY PHARMACEUTICALS, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 057532/0424 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2021
From: SILVERGATE PHARMACEUTICALS, INC.
To: AZURITY PHARMACEUTICALS, INC.
Reel/Frame 056430/0743 →
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 Aug 5, 2020
From: MOSHER, GEROLD L.; MILES, DAVID W.
To: SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 053413/0112 →