IP Library › Granted Patent US 10,596,113
Granted Patent B2
US 10,596,113 · App. 14/585,533 · Granted Mar 24, 2020

Stable pressurized aerosol solution composition of glycopyrronium bromide and formoterol combination

Inventors: Sauro Bonelli (Parma, IT); Diego Copelli (Parma, IT); Massimiliano Dagli Alberi (Parma, IT); Francesca Usberti (Parma, IT); Enrico Zambelli (Parma, IT)
Assignee: CHIESI FARMACEUTICI S.p.A.
A61K9/124A61K9/008A61K31/167A61K31/40A61K31/573A61K31/58A61K45/06A61M15/009A61M15/0021A61M15/0071A61M15/0086A61M39/22A61M2039/226A61M2205/0238
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Quick Facts
Patent No.
US 10,596,113
App. No.
14/585,533
Granted
Mar 24, 2020
Kind
B2
Abstract

Aerosol solution compositions intended for use with a pressurized metered dose inhaler, comprising glycopyrronium bromide and formoterol, or a salt thereof or a solvate of said salt, optionally in combination with one or more additional active ingredients, and stabilized by a selected amount of a mineral acid, exhibit improved stability when contained in a can internally coated by a resin comprising a fluorinated ethylene propylene (FEP) polymer.

Claims (21)

1. A method to lower the amount of degradation product N-(3-bromo)-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl)propan-2-ylamino]ethyl] phenyl]formamide (DP3) formed during the shelf-life of a pharmaceutical aerosol solution composition intended for use in a pressurized metered dose inhaler comprising:

(a) glycopyrronium bromide at a dosage in the range 5 to 26 μg per actuation;

(b) formoterol, or a salt thereof or a solvate of said salt, at a dosage in the range from 1 to 25 μg per actuation;

(c) a HFA propellant;

(d) a co-solvent;

(e) a stabilizing amount of a mineral acid; and

(f) optionally, an inhalation corticosteroid;

said method comprising containing said composition in an aerosol can internally coated by a resin comprising a fluorinated ethylene propylene (FEP) polymer.

2. A method according to claim 1 , wherein the overall level of formoterol degradation products formed, when said composition is stored in accelerated conditions at 25° C. and 60% relative humidity for at least 6 months, is lower than 10% w/w with respect to the theoretical formoterol fumarate content of 6 μg/actuation, and wherein the residual level of formoterol fumarate, when said composition is stored in accelerated conditions at 25° C. and 60% relative humidity for at least 6 months, is higher than 90 w/w with respect to its initial content.

3. A method according to claim 1 , wherein the overall level of formoterol degradation products formed, when said composition is stored in accelerated conditions at 25° C. and 60% relative humidity for at least 6 months, is lower than 2% w/w with respect to the theoretical formoterol fumarate content of 6 μg/actuation, and wherein the residual level of formoterol fumarate, when said composition is stored in accelerated conditions at 25° C. and 60% relative humidity for at least 6 months, is higher than 95% w/w with respect to its initial content.

4. A method according to claim 1 , wherein the pharmaceutical aerosol solution composition comprises:

(a) glycopyrronium bromide in an amount sufficient to deliver 5 to 26 μg per actuation;

(b) formoterol fumarate in an amount sufficient to deliver 1 to 24 μg per actuation; and

(c) beclometasone dipropionate in an amount sufficient to deliver 50 to 250 μg per actuation;

dissolved in HFA-134a and ethanol, wherein:

the composition comprises hydrochloric acid in an amount equivalent to 0.18 to 0.26 μg/μl of 1M HCl;

the composition comprises ethanol in an amount of 10 to 15% w/w of the composition; and

the composition comprises HFA-134a in an amount of 85 to 90% w/w of the composition.

5. A method according to claim 4 , wherein:

when said composition is stored in accelerated conditions at 25° C. and 60% relative humidity for at least 6 months showed a N-(3-bromo)-[2-hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl) propan-2-ylamino]ethyl]phenyl]formamide level of less than 0.10% w/w with respect to a theoretical formoterol fumarate content of 6 μg/actuation; and

containing said composition in an aerosol can internally coated by a resin comprising a fluorinated ethylene propylene (FEP) polymer comprises performing an oxygen purging step by vacuum crimping.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2015
From: BONELLI, SAURO; COPELLI, DIEGO; ALBERI, MASSIMILIANO DAGLI; USBERTI, FRANCESCA; ZAMBELLI, ENRICO
To: CHIESI FARMACEUTICI S.P.A.
Reel/Frame 035299/0687 →
Priority Claims (1)
EP 13199784 · Dec 30, 2013 · regional
Continuity (1)
Related Publication 20150182450A1 · Jul 2, 2015