CA2477881A1 - Formoterol superfine formulation - Google Patents
Formoterol superfine formulation Download PDFInfo
- Publication number
- CA2477881A1 CA2477881A1 CA002477881A CA2477881A CA2477881A1 CA 2477881 A1 CA2477881 A1 CA 2477881A1 CA 002477881 A CA002477881 A CA 002477881A CA 2477881 A CA2477881 A CA 2477881A CA 2477881 A1 CA2477881 A1 CA 2477881A1
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- CA
- Canada
- Prior art keywords
- pharmaceutical formulation
- formulation according
- hfa
- pharmaceutical
- comprised
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
Abstract
The present invention relates to a pharmaceutical formulation for use in the administration of a long-acting .szlig.2-agonist by inhalation. In particular this invention relates to a chemically stable highly efficient formoterol HFA
solution formulation to be administered by pressurised metered dose inhalers (pMDIs) characterized by a deep lung penetration. The invention also relates to methods for the preparation of said formulation and to its use in respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD).
solution formulation to be administered by pressurised metered dose inhalers (pMDIs) characterized by a deep lung penetration. The invention also relates to methods for the preparation of said formulation and to its use in respiratory diseases such as asthma and chronic obstructive pulmonary disease (COPD).
Claims (22)
1. A pharmaceutical aerosol formulation to be administered by pressurized metered dose inhalers which comprises an active ingredient selected from formoterol or a stereoisomer, physiologically acceptable salt and solvate thereof, in a solution of a liquefied HFA propellant and a co-solvent, characterised in that the amount of residual water is less than 1500 ppm on the total weight of the formulation.
2. A pharmaceutical formulation according to claim 1 wherein the amount of residual water is less than 1000 ppm.
3. A pharmaceutical formulation according to claim 1 wherein the amount of residual water is less than 500 ppm.
4. A pharmaceutical formulation according to claims 1-3 wherein the fraction of particles equal or less than 1.1 µm delivered on actuation of the inhaler is higher or equal than 30% as defined by the content of the stages S6-AF of an Andersen Cascade Impactor, relatively to the content of the stages S6-AF, according to the method referred to in the description on page 17 lines 4 to 12.
5. A pharmaceutical formulation according to claims 1-4 wherein the superfine fraction is higher than 50%.
6. A pharmaceutical formulation according to claims 1-5 wherein the active ingredient is (R,R)-(~)-formoterol fumarate in a concentration comprised between 0.003 and 0.192 % w/v.
7. A pharmaceutical formulation according to claim 6 wherein the active ingredient is in a concentration comprised between 0.006 and 0.048% w/v.
8. A pharmaceutical formulation according to any preceding claim wherein the pH is comprised between 2.5 and 5Ø
9. A pharmaceutical formulation according to claim 8 wherein the pH is comprised between 3.5 and 4Ø
10. A pharmaceutical formulation according to claims 8 and 9 wherein the pH is adjusted by adding hydrochloric acid.
11. A pharmaceutical formulation according to any preceding claim, wherein the propellant includes one or more hydrofluoroalkanes [HFAs]
selected from the group comprising HFA 134a and HFA 227.
selected from the group comprising HFA 134a and HFA 227.
12. A pharmaceutical formulation according to any preceding claim, wherein the co-solvent is selected from the group of lower alkyl (C1-C4) alcohols, polyols, polyalkylene glycols, (poly)alkoxy derivatives and their combinations.
13. A pharmaceutical formulation according to claim 12 wherein the co-solvent is ethanol.
14. A pharmaceutical formulation according to claim 13 wherein ethanol is in anhydrous form.
15. A pharmaceutical formulation according to claims 13-14 wherein the concentration of ethanol is comprised between 10 and 20% w/w.
16. A pharmaceutical formulation according to any preceding claim filled in a canister having part or all of its internal metallic surfaces made of standard aluminium, stainless steel, anodised aluminium or lined with an inert organic coating.
17. A pharmaceutical formulation according to claim 15 comprising 0.012-0.048% w/v formoterol fumarate, 12% w/w anhydrous ethanol, 0.037% w/w HCl 1 M and HFA 134a.
18. A pharmaceutical formulation according to claim 15 comprising 0.006-0.024% w/v formoterol fumarate, 12% w/w anhydrous ethanol, 0.023% w/w HCl 1 M and HFA 134a.
19. A pharmaceutical formulation according to any preceding claim comprising a further active ingredient selected from the class of steroids such as beclomethasone dipropionate, fluticasone propionate, ciclesonide, budesonide and its 22R-epimer or anticholinergic atropine-like derivatives such as ipratropium bromide, oxitropium bromide, tiotropium bromide.
20. A pharmaceutical formulation according to any preceding claim filled in a pressurized metered dose inhaler overwrapped in a package capable of resisting water ingress.
21. A pharmaceutical formulation according to claim 20 wherein the package further incorporates a material able to adsorb any propellant and cosolvent which may leak from the canister such as a molecular sieve.
22. A method of preparing the pharmaceutical formulations of claims 1-19, the method comprising:
(a) preparing of a solution of one or more active ingredients in one or more co-solvents;
(b) optionally adjusting the pH of the solution;
(c) filling of the device with said solution;
(d) crimping with valves and gassing;
(e) adding a propellant containing a hydrofluoroalkane (HFA).
(a) preparing of a solution of one or more active ingredients in one or more co-solvents;
(b) optionally adjusting the pH of the solution;
(c) filling of the device with said solution;
(d) crimping with valves and gassing;
(e) adding a propellant containing a hydrofluoroalkane (HFA).
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02004786A EP1340492A1 (en) | 2002-03-01 | 2002-03-01 | Aerosol formulations for pulmonary administration of medicaments having systemic effects |
| EP02004786.6 | 2002-03-01 | ||
| EP02023589A EP1415647A1 (en) | 2002-10-23 | 2002-10-23 | "Long-acting beta-2 agonists ultrafine formulations" |
| EP02023589.1 | 2002-10-23 | ||
| PCT/EP2003/001964 WO2003074024A1 (en) | 2002-03-01 | 2003-02-26 | Formoterol superfine formulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2477881A1 true CA2477881A1 (en) | 2003-09-12 |
| CA2477881C CA2477881C (en) | 2011-02-01 |
Family
ID=27790093
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2477881A Expired - Lifetime CA2477881C (en) | 2002-03-01 | 2003-02-26 | Formoterol superfine formulation |
| CA2477885A Expired - Fee Related CA2477885C (en) | 2002-03-01 | 2003-02-27 | Pressurised metered dose inhalers containing solutions of beta-2 agonists |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2477885A Expired - Fee Related CA2477885C (en) | 2002-03-01 | 2003-02-27 | Pressurised metered dose inhalers containing solutions of beta-2 agonists |
Country Status (36)
| Country | Link |
|---|---|
| US (4) | US20050152846A1 (en) |
| EP (6) | EP3536344B1 (en) |
| JP (3) | JP2005523905A (en) |
| KR (2) | KR100947409B1 (en) |
| CN (2) | CN100398094C (en) |
| AR (2) | AR038641A1 (en) |
| AT (1) | ATE465712T1 (en) |
| AU (2) | AU2003222753B2 (en) |
| BR (2) | BRPI0308274B8 (en) |
| CA (2) | CA2477881C (en) |
| CO (2) | CO5611091A2 (en) |
| CY (4) | CY1111133T1 (en) |
| DE (1) | DE60332321D1 (en) |
| DK (4) | DK3536344T3 (en) |
| EA (2) | EA007735B1 (en) |
| ES (4) | ES2780127T3 (en) |
| GE (2) | GEP20063986B (en) |
| HK (1) | HK1079425A1 (en) |
| HR (2) | HRP20040752B1 (en) |
| HU (3) | HUE048310T2 (en) |
| IL (3) | IL163843A0 (en) |
| LT (3) | LT3536344T (en) |
| MA (1) | MA27175A1 (en) |
| ME (3) | ME00077B (en) |
| MX (2) | MXPA04008372A (en) |
| MY (2) | MY143517A (en) |
| NO (2) | NO20043625L (en) |
| NZ (2) | NZ535018A (en) |
| PE (2) | PE20030827A1 (en) |
| PL (2) | PL209212B1 (en) |
| PT (4) | PT3384931T (en) |
| RS (2) | RS52387B (en) |
| SI (4) | SI3384931T1 (en) |
| TN (2) | TNSN04149A1 (en) |
| TW (2) | TWI347197B (en) |
| WO (2) | WO2003074024A1 (en) |
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| JP5392880B2 (en) * | 2000-05-22 | 2014-01-22 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | Stable pharmaceutical solution formulation for pressurized metered dose inhalers |
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| EP1415647A1 (en) * | 2002-10-23 | 2004-05-06 | CHIESI FARMACEUTICI S.p.A. | "Long-acting beta-2 agonists ultrafine formulations" |
| EP1340492A1 (en) * | 2002-03-01 | 2003-09-03 | CHIESI FARMACEUTICI S.p.A. | Aerosol formulations for pulmonary administration of medicaments having systemic effects |
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| KR20070000476A (en) * | 2004-02-27 | 2007-01-02 | 키에시 파르마슈티시 엣스. 피. 에이. | Stable pharmaceutical solution formulations for pressurized metered dose inhalers |
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| CA2571519C (en) * | 2004-07-02 | 2013-05-14 | Boehringer Ingelheim International Gmbh | Aerosol suspension formulations containing tg 227 ea or tg 134 a as a propellant |
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| CA2594127C (en) * | 2005-02-25 | 2013-10-15 | Chiesi Farmaceutici S.P.A. | Pharmaceutical aerosol formulations for pressurized metered dose inhalers comprising a sequestering agent |
| DE102006017320A1 (en) * | 2006-04-11 | 2007-10-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosol suspension formulations with TG 227 ea or TG 134 a as propellant |
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