US20120309725A1 - Combinations of a muscarinic receptor antagonist and a beta-2 adrenoreceptor agonist - Google Patents
Combinations of a muscarinic receptor antagonist and a beta-2 adrenoreceptor agonist Download PDFInfo
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- US20120309725A1 US20120309725A1 US13/510,962 US201013510962A US2012309725A1 US 20120309725 A1 US20120309725 A1 US 20120309725A1 US 201013510962 A US201013510962 A US 201013510962A US 2012309725 A1 US2012309725 A1 US 2012309725A1
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- ZAGKULCVWQULCM-UHFFFAOYSA-N OC(C1=CC=CC=C1)(C1=CC=CC=C1)C12CC[N+](CCOCC3=CC=CC=C3)(CC1)CC2.[CH3-] Chemical compound OC(C1=CC=CC=C1)(C1=CC=CC=C1)C12CC[N+](CCOCC3=CC=CC=C3)(CC1)CC2.[CH3-] ZAGKULCVWQULCM-UHFFFAOYSA-N 0.000 description 3
- 0 [1*]C.[2*]C.[3*]C.[6*]C([7*]C1=CC=CC=C1)OCOC(O)C1=CC=C(O)C(OC)=C1 Chemical compound [1*]C.[2*]C.[3*]C.[6*]C([7*]C1=CC=CC=C1)OCOC(O)C1=CC=C(O)C(OC)=C1 0.000 description 2
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- 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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
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- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
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- 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
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D75/00—Packages comprising articles or materials partially or wholly enclosed in strips, sheets, blanks, tubes, or webs of flexible sheet material, e.g. in folded wrappers
- B65D75/28—Articles or materials wholly enclosed in composite wrappers, i.e. wrappers formed by associating or interconnecting two or more sheets or blanks
- B65D75/30—Articles or materials enclosed between two opposed sheets or blanks having their margins united, e.g. by pressure-sensitive adhesive, crimping, heat-sealing, or welding
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- This invention relates to pharmaceutical products and compositions for use in the treatment of chronic obstructive pulmonary disease (COPD), asthma and related diseases.
- COPD chronic obstructive pulmonary disease
- this invention relates to the combination of a muscarinic receptor antagonist and a beta-2 adrenoreceptor agonist, and the use of said combination in treating diseases mediated via the M 3 muscarinic acetylcholine receptor and/or the beta-2 adrenoreceptor.
- this invention is concerned with novel pharmaceutical combination products comprising 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate and 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide and the use of said combination products in medicine, particularly in treating diseases mediated via the M 3 muscarinic acetylcholine receptor and/or the beta-2 adrenoreceptor, for example in the prophylaxis and treatment of inflammatory or respiratory tract diseases.
- COPD chronic obstructive pulmonary diseases
- rhinitis respiratory tract infection and upper respiratory tract disease
- beta-2 adrenergic receptor agonists beta-2 adrenergic receptor agonists
- beta-2 agonists beta-2 adrenergic receptor agonists
- short acting compounds for immediate relief such as salbutamol, biltolterol, pirbuterol and terbutaline.
- longer acting compounds such as salmeterol and formoterol.
- Salmeterol is available by prescription for use twice daily in the treatment of asthma.
- inhaled anticholinergic agents have become well established as well-tolerated and effective bronchodilators for the treatment of COPD.
- Treatment with anticholinergics significantly improves FEV 1 , (forced expiratory volume in 1 second) resting and dynamic lung hyperinflation, symptoms and exercise capacity, and reduces COPD exacerbations.
- FEV 1 forced expiratory volume in 1 second
- ipratropium dosed four-times-a-day
- oxitropium bromide oxitropium bromide
- tiotropium tiotropium; dosed once-daily.
- WO 03/024439 describes compounds of the general formula:
- WO2005/104745 specifically describes the compound 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide.
- the present invention provides a novel pharmaceutical combination product comprising the therapeutic agents:
- Compound (II) may refer to the free base depicted above, and/or one or more salts thereof, as dictated by the context.
- the pharmaceutical combination product comprises 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate and 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide.
- 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate and 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide are the sole active ingredients in said pharmaceutical combination product.
- the pharmaceutical combination product of Compound (I) and Compound (II) additionally comprises an inhaled corticosteroid.
- This invention also provides for use of the pharmaceutical combination product in the manufacture of a medicament for the treatment of conditions for which administration of one or more of the therapeutic compounds is indicated.
- the use is for the manufacture of a medicament for the treatment of inflammatory or respiratory tract diseases, by simultaneous or sequential administration of Compound (I) and Compound (II).
- the use is for the manufacture of a medicament for the treatment of chronic obstructive pulmonary disease (COPD) and/or asthma, by simultaneous or sequential administration of Compound (I) and Compound (II).
- COPD chronic obstructive pulmonary disease
- the invention also provides said pharmaceutical combination product for use in the treatment of inflammatory or respiratory tract diseases, such as chronic obstructive pulmonary disease (COPD) and/or asthma.
- COPD chronic obstructive pulmonary disease
- Another embodiment of the invention is a method for the treatment of inflammatory or respiratory tract diseases, comprising administering either sequentially or simultaneously, to a patient in need thereof, a pharmaceutical combination product comprising Compound (I) and Compound (II).
- the inflammatory or respiratory tract disease is selected from the group consisting of chronic obstructive pulmonary disease, chronic bronchitis, asthma, chronic respiratory obstruction, pulmonary fibrosis, pulmonary emphysema, allergic rhinitis, small airways disease, bronchiectasis and cystic fibrosis.
- the pharmaceutical combination product may be used for the treatment of inflammatory or respiratory tract diseases, and more specifically the treatment of chronic obstructive pulmonary disease (COPD) and/or asthma by simultaneous or sequential administration of Compound (I) and Compound (II).
- COPD chronic obstructive pulmonary disease
- the present invention is directed to a pharmaceutical combination product comprising
- the pharmaceutically acceptable anion depicted by X ⁇ may be selected from chloride, bromide, iodide, hydroxide, sulfate, nitrate, phosphate, acetate, trifluoroacetate, fumarate, citrate, tartrate, oxalate, succinate, mandelate, methanesulfonate or p-toluenesulfonate.
- the pharmaceutically acceptable anion X ⁇ is bromide.
- the structural formula for the quaternary moiety (cation) of Compound (I) is also referred to as 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane.
- Compound (I) is 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide (also referred to herein as Compound (I) bromide).
- Pharmaceutically acceptable acid addition salts of Compound (II) include those formed from hydrochloric, hydrobromic, sulphuric, citric, tartaric, phosphoric, lactic, pyruvic, acetic, trifluoroacetic, triphenylacetic, phenylacetic, substituted phenyl acetic eg.
- the pharmaceutically acceptable salt of Compound (II) is selected from the acetate, 1-naphthoate and (R)-mandelate salts.
- the pharmaceutically acceptable salt of Compound (II) is the ⁇ -phenylcinnamate salt.
- the pharmaceutically acceptable salt of Compound (II) is the triphenylacetate salt.
- Compound (II) is 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate (also referred to as Compound (II) triphenylacetate).
- the pharmaceutical combination product of the invention comprises 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide and 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate.
- the pharmaceutical combination product of Compound (I) and Compound (II) additionally comprises an inhaled corticosteroid, e.g. fluticasone propionate, mometasone furoate, budesonide or 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate).
- corticosteroid e.g. fluticasone propionate, mometasone furoate, budesonide or 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate).
- said pharmaceutical combination product comprises 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide, 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate and 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate).
- the pharmaceutical combination product of the invention comprises 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide and 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate as the sole active ingredients.
- Compound (I) specifically 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide has been the subject of studies in animal models, and in humans, and has been found to be a long acting high-affinity pan-active muscarinic receptor antagonist which has potential for once-daily administration.
- Compound (II) specifically 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol and its salts has been extensively tested in animal and human studies and has been found to demonstrate sustained bronchodilation over a 24 hour period in conjunction with a favourable safety profile and thus has the potential for once-daily administration.
- Compound (I) and Compound (II), and the combination thereof, are considered to have potential in the treatment of inflammatory or respiratory tract diseases such as chronic obstructive pulmonary disease, chronic bronchitis, asthma, chronic respiratory obstruction, pulmonary fibrosis, pulmonary emphysema, allergic rhinitis, small airways disease, bronchiectasis and cystic fibrosis.
- inflammatory or respiratory tract diseases such as chronic obstructive pulmonary disease, chronic bronchitis, asthma, chronic respiratory obstruction, pulmonary fibrosis, pulmonary emphysema, allergic rhinitis, small airways disease, bronchiectasis and cystic fibrosis.
- COPD chronic disease characterised by airways obstruction and reduced maximum expiratory flow from the lungs that manifests as persistent daily symptoms, such as shortness of breath (dyspnoea), and limitation of the ability to perform daily activities or exertion. Furthermore, there are periodic exacerbations of the condition that result in worsening of the day-to-day symptoms and activity limitation, and can also lead to hospitalisation of the patient because of the severity of the worsening symptoms/limitation. In addition, there is a progressive decline in lung function (disease progression) over several years.
- Bronchodilator treatment in COPD includes but is not necessarily limited to reducing symptoms, particularly dyspnoea, to allow a patient to undertake more daily activities and other activities that require exertion, and preventing exacerbations.
- Asthma is a chronic condition, which is characterised by widespread, variable and reversible airflow obstruction. Symptoms include coughing, wheezing, breathlessness and/or a tight feeling in the chest. Asthma attacks are generally caused by exposure to a trigger, such as pollen, dust or other allergens, which causes constriction of the airways (bronchoconstriction). It will be appreciated that a subject suffering from a condition such as asthma, may variously from time to time display no overt symptoms of the condition, or may suffer from periodic attacks during which symptoms are displayed or may experience exacerbations or worsening of the condition. In this context the term ‘treatment’ is intended to encompass prevention of such periodic attacks or exacerbations of the existing condition. Such treatment may be referred to as ‘maintenance treatment’ or ‘maintenance therapy’.
- the route of administration is by inhalation via the mouth or nose.
- the route of administration is by inhalation via the mouth.
- Compound (I), and specifically (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide may be administered by inhalation at a dose of from about 1 mcg to about 1000 mcg/daily, e.g. 100, 250 or 500 mcg per day.
- Compound (I) and specifically (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide may be administered by inhalation at a dose of 62.5 mcg or 125 mcg per day. In general Compound (I) will be administered as a once-daily dose.
- Compound (I), and specifically (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide may be administered by inhalation, once-daily, at a dose of 62.5 mcg per day.
- Compound (I), and specifically (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide may be administered by inhalation, once-daily, at a dose of 125 mcg per day.
- Compound (II) may for example be administered by inhalation at a dose of from about 1 mcg to about 400 mcg/day (calculated as the free base).
- Compound (II), and specifically 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate may be administered by inhalation at a dose of from about 1 mcg to 100 mcg/day, for example 3, 6.25, 12.5, 25, 50 or 100 mcg/day (calculated as the free base).
- Compound (II) will be administered as a once-daily dose. In one embodiment Compound (II) may be administered by inhalation at a dose of 12.5 mcg/day. In another embodiment Compound (II) may be administered by inhalation at a dose of 25 mcg/day. In another embodiment Compound (II) may be administered by inhalation at a dose of 50 mcg/day.
- 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate may be administered by inhalation, once-daily, at a dose of 25 mcg per day.
- the present invention provides a pharmaceutical combination product for once-daily administration by inhalation, comprising 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate at a dose of 25 mcg per day, and (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide at a dose of 125 mcg per day.
- the present invention provides a pharmaceutical combination product for once-daily administration by inhalation, comprising 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate at a dose of 25 mcg per day, and (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide at a dose of 62.5 mcg per day.
- the combination additionally includes an inhaled corticosteroid
- this may be used at doses compatible with those known for monotherapy.
- the inhaled corticosteroid is fluticasone furoate this may be administered by inhalation at a dose of from about 25 mcg to about 800 mcg daily, and if necessary in divided doses.
- the daily dose of fluticasone furoate may be for example 25, 50, 100, 200, 300, 400, 600 or 800 mcg, in general as a once-daily dose.
- the daily dose of fluticasone furoate is 100 mcg.
- the daily dose of fluticasone furoate is 50 mcg.
- the individual compounds of the pharmaceutical combination product as described herein may be administered either sequentially or simultaneously in separate or combined pharmaceutical formulations/compositions.
- Compound (I) and Compound (II) may for example, be formulated separately and presented in separate packs or devices, or said individually formulated components may be presented in a single pack or device.
- the individual compounds may be admixed within the same formulation, and presented as a fixed pharmaceutical combination.
- such formulations will include pharmaceutical carriers or excipients as described hereinafter, but combinations of the compounds without any excipients are also within the ambit of this invention.
- the individual compounds of the pharmaceutical combination product may be administered simultaneously in a combined pharmaceutical formulation or composition.
- the pharmaceutical combination product additionally includes an inhaled corticosteroid, eg 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate)
- an inhaled corticosteroid eg 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate)
- this may likewise be formulated separately, either with or without one or more pharmaceutical carriers or excipients, and presented for either sequential or simultaneous administration, or the inhaled corticosteroid may be admixed with either Compound (I) and/or Compound (II).
- a pharmaceutical combination product comprising Compound (I) and Compound (II) presented separately for sequential or simultaneous administration;
- each of Compound (I) and/or Compound (II) may be formulated with or without pharmaceutical carriers or excipients.
- the present invention further provides a pharmaceutical combination product comprising Compound (I) and Compound (II) wherein at least one of Compound (I) and Compound (II) is formulated with a pharmaceutically acceptable carrier or excipient.
- the present invention further provides a pharmaceutical combination product comprising Compound (I) and Compound (II) wherein each of Compound (I) and Compound (II) is formulated with a pharmaceutically acceptable carrier or excipient.
- compositions of Compounds (I) and (II) include those suitable for inhalation, including fine particle powders, or mists which may be generated and administered by means of various types of inhalers for example, reservoir dry powder inhalers, unit-dose dry powder inhalers, pre-metered multi-dose dry powder inhalers, nasal inhalers or pressurized metered dose inhalers, nebulisers or insufflators.
- inhalers for example, reservoir dry powder inhalers, unit-dose dry powder inhalers, pre-metered multi-dose dry powder inhalers, nasal inhalers or pressurized metered dose inhalers, nebulisers or insufflators.
- compositions may be prepared by any of the methods well known in the art of pharmacy. In general, said methods include the step of bringing the active ingredient(s) into association with the carrier which constitutes one or more accessory ingredients. In general the compositions are prepared by uniformly and intimately bringing into association the active ingredient with liquid carriers or finely divided solid carriers or both and then, if necessary, shaping the product into the desired composition.
- Powder compositions generally contain a powder mix for inhalation of the active ingredient and a suitable powder base (carrier/diluent/excipient substance) such as mono-, di or poly-saccharides (e.g. lactose or starch).
- a suitable powder base such as mono-, di or poly-saccharides (e.g. lactose or starch).
- lactose is preferred.
- the lactose may be for example anhydrous lactose or ⁇ -lactose monohydrate.
- the carrier is ⁇ -lactose monohydrate.
- Dry powder compositions may also include, in addition to the active ingredient and carrier, a further excipient (eg a ternary agent) such as a sugar ester, calcium stearate or magnesium stearate.
- a further excipient eg a ternary agent
- the active ingredient may be presented without excipients.
- composition or ‘formulation’ herein refers to the active ingredients either with or without excipients or carriers.
- the present invention further provides a pharmaceutical combination product comprising Compound (I) and Compound (II) wherein Compound (II) is formulated with a pharmaceutically acceptable carrier and a ternary agent.
- the present invention further provides a pharmaceutical combination product for inhaled administration comprising 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate and (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide each formulated separately with a pharmaceutically acceptable carrier and a ternary agent, but held in the same pack or device, for sequential or simultaneous administration.
- said ternary agent is magnesium stearate.
- the present invention further provides a pharmaceutical combination product for inhaled administration comprising 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate and (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide each formulated separately with lactose, as a pharmaceutically acceptable carrier, and magnesium stearate, as a ternary agent, but held in the same pack or device, for sequential or simultaneous administration.
- a pharmaceutical combination product for inhaled administration comprising 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate
- Each capsule, cartridge or blister may generally contain between 1 mcg-1000 mcg, e.g. 100 to 500 mcg of Compound (I) and/or between 1 mcg-400 mcg, e.g 1 to 100 mcg of Compound (II).
- Packaging of the formulation may be suitable for unit dose or multi-dose delivery.
- Compound (I) and Compound (II) may be formulated independently or in admixture. Said compounds may thus be incorporated in separate unit doses or may be combined in a single unit dose with or without additional excipients as deemed necessary.
- each capsule, cartridge or blister may contain 125 mcg or 62.5 mcg of Compound (I) and/or 25 mcg of Compound (II).
- each capsule, cartridge or blister may contain 125 mcg or 62.5 mcg of (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide and/or 25 mcg of 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate.
- a dry powder inhalable composition may also be provided as a bulk reservoir in an inhalation device, the device then being provided with a metering mechanism for metering a dose of the composition from the reservoir to an inhalation channel where the metered dose is able to be inhaled by a patient inhaling at a mouthpiece of the device.
- exemplary marketed devices of this type are TURBUHALERTM of AstraZeneca, TWISTHALERTM of Schering and CLICKHALERTM of Innovata.
- a further delivery method for a dry powder inhalable composition is for metered doses of the composition to be provided in capsules (one dose per capsule) which are then loaded into an inhalation device, typically by the patient on demand.
- the device has means to rupture, pierce or otherwise open the capsule so that the dose is able to be entrained into the patient's lung when they inhale at the device mouthpiece.
- ROTAHALERTM of GlaxoSmithKline
- HANDIHALERTM of Boehringer Ingelheim.
- a dry powder composition may also be presented in a delivery device which permits separate containment of Compound (I) and Compound (II) optionally in admixture with one or more excipients.
- a delivery device permitting separate containment of actives is an inhaler device having two medicament packs in peelable blister strip form, each pack containing pre-metered doses in blister pockets arranged along its length.
- Said device has an internal indexing mechanism which, each time the device is actuated, peels opens a pocket of each strip and positions the packs so that each newly exposed dose of each pack is adjacent a manifold which communicates with a mouthpiece of the device. When the patient inhales at the mouthpiece, each dose is simultaneously drawn out of its associated pocket into the manifold and entrained via the mouthpiece into the patient's respiratory tract. Thus, each time the device is used, the patient is administered a combination therapy consisting of a dose from each medicament pack.
- a further device that permits separate containment of different compounds is DUOHALERTM of Innovata.
- the present invention provides a dry powder inhaler (Inhaler 1) comprising two compositions presented separately, wherein a first composition comprises
- the present invention provides Inhaler 1 wherein each composition is in unit dose form.
- the present invention provides Inhaler 1 wherein the unit dose form is a capsule, cartridge or blister.
- the present invention provides Inhaler 1 wherein 4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide is present in an amount of about 125 mcg/dose.
- the present invention provides Inhaler 1 wherein 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate is present in an amount of about 25 mcg/dose.
- the present invention provides Inhaler 1 wherein the second composition further comprises 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate).
- the present invention provides Inhaler 1 wherein 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate) is present in an amount of about 100 mcg/dose.
- Spray compositions for inhalation may for example be formulated as aqueous solutions or suspensions or as aerosols delivered from pressurised packs, such as a metered dose inhaler, with the use of a suitable liquefied propellant.
- Aerosol compositions suitable for inhalation can be either a suspension or a solution and generally contain the pharmaceutical product and a suitable propellant such as a fluorocarbon or hydrogen-containing chlorofluorocarbon or mixtures thereof, particularly hydrofluoroalkanes, especially 1,1,1,2-tetrafluoroethane, 1,1,1,2,3,3,3-heptafluoro-n-propane or a mixture thereof.
- the aerosol composition may optionally contain additional formulation excipients well known in the art such as surfactants e.g. oleic acid, lecithin or an oligolactic acid derivative e.g. as described in WO94/21229 and WO98/34596 and/or cosolvents e.g. ethanol.
- additional formulation excipients well known in the art such as surfactants e.g. oleic acid, lecithin or an oligolactic acid derivative e.g. as described in WO94/21229 and WO98/34596 and/or cosolvents e.g. ethanol.
- Pressurised formulations will generally be retained in a canister (e.g. an aluminium canister) closed with a valve (e.g. a metering valve) and fitted into an actuator provided with a mouthpiece.
- Another aspect of the invention is a pharmaceutical combination product consisting of Compound (I) and Compound (II) formulated individually or in admixture, with a fluorocarbon or hydrogen-containing chlorofluorocarbon as propellant, optionally in combination with a surface-active agent and/or a cosolvent.
- the propellant is selected from 1,1,1,2-tetrafluoroethane, or 1,1,1,2,3,3,3-heptafluoro-n-propane and mixtures thereof.
- compositions according to the invention may be buffered by the addition of suitable buffering agents.
- Active ingredients for administration by inhalation desirably have a controlled particle size.
- the optimum particle size for inhalation into the bronchial system is usually 1-10 ⁇ m, preferably 2-5 ⁇ m. Particles having a size above 20 ⁇ m are generally too large when inhaled to reach the small airways.
- the particles of the active ingredient as produced may be size reduced by conventional means e.g. by micronization.
- the desired fraction may be separated out by air classification or sieving.
- the particles will be crystalline.
- Magnesium stearate if present in the composition, is generally used in an amount of about 0.2 to 2%, e.g. 0.6 to 2% or 0.5 to 1.75%, e.g. 0.6%, 0.75%, 1%, 1.25% or 1.5% w/w, based on the total weight of the composition.
- the magnesium stearate will typically have a particle size in the range 1 to 50 ⁇ m, and more particularly 1-20 ⁇ m, e.g. 1-10 ⁇ m.
- Commercial sources of magnesium stearate include Peter Greven, Covidien/Mallinckodt and FACI.
- a pharmaceutical combination product comprising Compound (I) and Compound (II) wherein Compound (I) is (4-[hydroxy(diphenyl)methyl]-1- ⁇ 2-[(phenylmethyl)oxy]ethyl ⁇ -1-azoniabicyclo[2.2.2]octane bromide and is presented as a dry powder composition containing magnesium stearate at an amount of 0.6% w/w based on the total weight of the composition.
- a pharmaceutical combination product comprising Compound (I) and Compound (II) wherein Compound (II) is 4- ⁇ (1R)-2-[(6- ⁇ 2-[(2,6-dichlorobenzyl)oxy]ethoxy ⁇ hexyl)amino]-1-hydroxyethyl ⁇ -2-(hydroxymethyl)phenol triphenylacetate and is presented as a dry powder composition containing magnesium stearate at an amount of 1.0% w/w based on the total weight of the composition.
- Intranasal sprays may be formulated with aqueous or non-aqueous vehicles with the addition of agents such as thickening agents, buffer salts or acid or alkali to adjust the pH, isotonicity adjusting agents or anti-oxidants.
- agents such as thickening agents, buffer salts or acid or alkali to adjust the pH, isotonicity adjusting agents or anti-oxidants.
- Solutions for inhalation by nebulization may be formulated with an aqueous vehicle with the addition of agents such as acid or alkali, buffer salts, isotonicity adjusting agents or antimicrobials. They may be sterilized by filtration or heating in an autoclave, or presented as a non-sterile product.
- agents such as acid or alkali, buffer salts, isotonicity adjusting agents or antimicrobials. They may be sterilized by filtration or heating in an autoclave, or presented as a non-sterile product.
- Compound (II) as the ⁇ -phenylcinnamate salt and the triphenylacetate salt has been studied in a number of clinical pharmacology studies, including single- and repeat-dose studies. In addition, these studies have evaluated Compound (II) formulated with lactose and either cellobiose octaacetate or magnesium stearate. In asthmatic patients, a statistically and clinically significant improvement in trough (24-hour) FEV1 was observed for all doses of Compound (II) tested, compared to placebo.
- a combination of Compound (I) bromide and Compound (II) triphenylacetate has been administered to sixteen healthy Japanese volunteers, aged 20 to 65, as part of a clinical trial to assess the safety, tolerability, pharmacokinetics and pharmacodynamics of single inhaled doses of Compound (I) bromide and Compound (II) triphenylacetate as monotherapies and in combination.
- This study was a randomised, double blind, placebo-controlled, four-way crossover study wherein subjects received a single dose of:
- ⁇ -lactose monohydrate sourced from DMV Fronterra Excipients, complying with the requirements of Ph.Eur/USNF may be used. Before use, the ⁇ -lactose monohydrate may be sieved through a coarse screen (for example with a mesh size 500 or 800 microns). The level of fines in the ⁇ -lactose monohydrate, which can be measured by Sympatec, may be 4.5% w/w less than 4.5 micron.
- Compound (I) bromide is micronised before use in an APTM microniser to give a mass median diameter of 1 to 5 microns, such as 2 to 5 microns.
- Pharmaceutical grade magnesium stearate sourced from Peter Greven, complying with the requirements of Ph.Eur/USNF may be used as supplied with a mass median particle size of 8 to 12 microns.
- Lactose monohydrate may be passed through a sieve and then combined with magnesium stearate and blended using either a high shear mixer (a QMM, PMA or TRV series mixer, such as TRV25 or TRV65) or a low shear tumbling blender (a Turbula mixer) to provide a magnesium stearate/lactose premix, hereinafter referred to as blend A.
- a high shear mixer a QMM, PMA or TRV series mixer, such as TRV25 or TRV65
- a Turbula mixer a low shear tumbling blender
- Final blend B may be obtained as follows.
- An quantity of blend A and compound (I) bromide may be screened, for example using a COMILTM, and then blended with the remaining blend A using either a high shear mixer (a QMM, PMA or TRV series mixer, such as TRV25 or TRV65) or a low shear tumbling blender (a Turbula mixer).
- a high shear mixer a QMM, PMA or TRV series mixer, such as TRV25 or TRV65
- a Turbula mixer a Turbula mixer
- the blended composition may then be transferred into blister strips (typical nominal mean quantity of blend per blister is 12.5-13.5 mg) of the type generally used for the supply of dry powder for inhalation and the blister strips were sealed in the customary fashion.
- blister strips typically nominal mean quantity of blend per blister is 12.5-13.5 mg
- ⁇ -lactose monohydrate which can be sourced from DMV Fronterra Excipients, complying with the requirements of Ph.Eur/USNF may be used. Before use, the ⁇ -lactose monohydrate may be sieved through a coarse screen (typical mesh size 500 microns). The level of fines in the ⁇ -lactose monohydrate, which can be measured by Sympatec, may be 4.5% w/w less than 4.5 micron.
- Compound (II) triphenylacetate is micronised before use in an APTM microniser to give a MMD (mass median diameter) of from 1 to 5 microns, such as 2 to 5 microns, for example 1.8 microns.
- MMD mass median diameter
- Magnesium stearate which can be sourced from Peter Greven, complying with the requirements of Ph.Eur/USNF may be used as supplied with a mass median particle size 8 to 12 microns.
- Lactose monohydrate may be passed through a sieve and then combined with magnesium stearate (typically 130 g) and blended using either a high shear mixer (a QMM, PMA or TRV series mixer, such as TRV25 or TRV65) or a low shear tumbling blender (a Turbula mixer) to provide a magnesium stearate/lactose premix, hereinafter referred to as blend A.
- a high shear mixer a QMM, PMA or TRV series mixer, such as TRV25 or TRV65
- a Turbula mixer a low shear tumbling blender
- Final blend B may be obtained as follows.
- An appropriate quantity of blend A and compound (II) triphenylacetate typically 5-165 g may be screened, for example using a COMILTM, and then blended with the remaining blend A using either a high shear mixer (a QMM, PMA or TRV series mixer) or a low shear tumbling blender (a Turbula mixer).
- the final concentration of compound (II) triphenylacetate in the blends is typically in the range 0.02% w/w-0.8% w/w free base equivalent.
- the blended composition is transferred into blister strips (typical nominal mean quantity of blend B per blister is 12.5-13.5 mg) or the type generally used for the supply of dry powder for inhalation and the blister strips are then sealed in the customary fashion.
- Compound (I) bromide and Compound (II) triphenylacetate as an inhalation powder may be administered in a DPI device containing two blister strips.
- One strip contains a blend of micronised Compound (I) bromide (approximately 500 micrograms per blister), magnesium stearate and lactose monohydrate.
- the second strip contains a blend of micronised Compound (II) triphenylacetate (approximately 25 micrograms per blister), magnesium stearate and lactose monohydrate.
- the DPI device will deliver, when actuated, the contents of a single blister simultaneously from each of the two blister strips.
- Each blister strip is a double foil laminate containing 30 blisters per strip.
- Compound (I) bromide and Compound (II) triphenylacetate as an inhalation powder may be administered in a dry powder inhaler device containing two blister strips, wherein one strip contains a blend of micronised Compound (I) bromide (approximately 125 or 62.5 micrograms per blister), magnesium stearate (at an amount of 0.6% w/w of the total powder weight per blister) and lactose monohydrate.
- the second strip contains a blend of micronised Compound (II) triphenylacetate (approximately 25 micrograms per blister), magnesium stearate and lactose monohydrate.
- the second strip optionally further comprises 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate) at an amount of approximately 100 micrograms per blister.
- the DPI device will deliver, when actuated, the contents of a single blister simultaneously from each of the two blister strips.
- Each blister strip is a double foil laminate containing 7, 14 or 30 filled blisters per strip.
- Compound (I) bromide and Compound (II) triphenylacetate as an inhalation powder may be administered in a dry powder inhaler device containing two blister strips, wherein one strip contains a blend of micronised Compound (I) bromide (approximately 125 or 62.5 micrograms per blister), Compound (II) triphenylacetate (approximately 25 micrograms per blister), magnesium stearate and lactose monohydrate.
- the second strip contains a blend of 6 ⁇ ,9 ⁇ -difluoro-17 ⁇ -[(2-furanylcarbonyl)oxy]-11 ⁇ -hydroxy-16 ⁇ -methyl-3-oxo-androsta-1,4-diene-17 ⁇ -carbothioic acid S-fluoromethyl ester (fluticasone furoate) at an amount of approximately 100 micrograms per blister, and lactose monohydrate.
- the DPI device will deliver, when actuated, the contents of a single blister simultaneously from each of the two blister strips.
- Each blister strip is a double foil laminate containing 7, 14 or 30 filled blisters per strip.
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US20130030015A1 (en) * | 2004-04-27 | 2013-01-31 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
WO2015181262A1 (en) | 2014-05-28 | 2015-12-03 | Glaxosmithkline Intellectual Property Development Limited | Fluticasone furoate in the treatment of copd |
US9750726B2 (en) | 2009-12-01 | 2017-09-05 | Glaxo Group Limited | Combinations of a muscarinic receptor antagonist and a beta-2 adrenoreceptor agonist |
US9763965B2 (en) | 2012-04-13 | 2017-09-19 | Glaxosmithkline Intellectual Property Development Limited | Aggregate particles |
US9795561B2 (en) | 2012-12-17 | 2017-10-24 | Glaxo Group Limited | Combination of umeclidinium, fluticasone propionate and salmeterol xinafoate for use in the treatment of inflammatory or respiratory tract diseases |
US11116721B2 (en) | 2009-02-26 | 2021-09-14 | Glaxo Group Limited | Pharmaceutical formulations comprising 4-{(1R)-2-[(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl) phenol |
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US20130157991A1 (en) * | 2010-08-31 | 2013-06-20 | Osama Ahmed Aswania | Dry Powder Inhalation Drug Products Exhibiting Moisture Control Properties and Methods of Administering the Same |
CA2838031A1 (en) * | 2011-06-08 | 2012-12-13 | Glaxo Group Limited | Dry powder inhaler compositions comprising umeclidinium |
AU2012266541A1 (en) * | 2011-06-08 | 2014-01-09 | Glaxo Group Limited | Combination comprising umeclidinium and a corticosteroid |
GB201305825D0 (en) | 2013-03-28 | 2013-05-15 | Vectura Ltd | New use |
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