IP Library Granted Patent US 10,695,329
Granted Patent B2
US 10,695,329 · App. 15/726,901 · Granted Jun 30, 2020

Amlodipine formulations

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Quick Facts
Patent No.
US 10,695,329
App. No.
15/726,901
Granted
Jun 30, 2020
Kind
B2
Abstract

Provided herein are stable amlodipine oral liquid formulations. Also provided herein are methods of using amlodipine oral liquid formulations for the treatment of certain diseases including hypertension and Coronary Artery Disease (CAD).

Claims (24)

1. An oral liquid formulation, comprising:

(i) amlodipine benzoate in an amount corresponding to 1.0 mg/ml amlodipine freebase;

(ii) 3 mM of a citrate buffer;

(iii) 0.2 mg/ml to about 10 mg/ml of sodium benzoate;

(iv) 0.5 mg/ml of silicon dioxide;

(v) 7.5 mg/ml of hydroxypropyl methylcellulose;

(vi) 0.15 mg/ml simethicone;

(vii) 1.0 mg/ml of polysorbate 80; and

(viii) water;

wherein the pH of the formulation is between 4 and about 6, and

wherein the formulation is stable at 5±5° C. for at least 12 months; and wherein the stable oral liquid formulation has 95% w/w or greater of the initial amlodipine amount and 5% w/w or less total impurities or related substances at the end of the given storage period.

2. The formulation of claim 1 , wherein the amlodipine benzoate is formed in situ.

3. The formulation of claim 2 , wherein the amlodipine benzoate is formed by a reaction of a pharmaceutically acceptable salt of amlodipine that is more soluble in aqueous media than amlodipine benzoate with a molar excess of sodium benzoate.

4. The formulation of claim 3 , wherein the salt of amlodipine that is more soluble in aqueous media than amlodipine benzoate is selected from amlodipine besylate, amlodipine tosylate, amlodipine mesylate, amlodipine succinate, amlodipine salicylate, amlodipine maleate, amlodipine acetate, and amlodipine hydrochloride.

5. The formulation of claim 2 , wherein the amlodipine benzoate is formed by the reaction of amlodipine besylate with a molar excess of sodium benzoate.

6. The formulation of claim 1 , wherein the formulation further comprises a flavoring agent.

7. The formulation of claim 1 , wherein the formulation further comprises a sweetener.

8. The formulation of claim 7 , wherein the sweetener is sucralose.

9. The formulation of claim 1 , wherein the formulation is in the form of a suspension.

10. The formulation of claim 1 , wherein the pH is between 5 and 6.

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

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

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

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

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 →
RELEASE OF SECURITY INTEREST Recorded Sep 20, 2021
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: AZURITY PHARMACEUTICALS, INC.
Reel/Frame 057531/0403 →
SECURITY INTEREST Recorded Sep 20, 2021
From: AZURITY PHARMACEUTICALS, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 057532/0424 →
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: AZURITY PHARMACEUTICALS, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 055938/0859 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2021
From: SILVERGATE PHARMACEUTICALS, INC.
To: AZURITY PHARMACEUTICALS, INC.
Reel/Frame 055805/0685 →
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 Oct 13, 2017
From: BRAUER, SCOTT; MOSHER, GEROLD L.
To: SILVERGATE PHARMACEUTICALS, INC.
Reel/Frame 043866/0190 →