US20030165435A1 - Stable pharmaceutical budesonide preparation for producing propellant-free aerosols - Google Patents
Stable pharmaceutical budesonide preparation for producing propellant-free aerosols Download PDFInfo
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- US20030165435A1 US20030165435A1 US10/373,515 US37351503A US2003165435A1 US 20030165435 A1 US20030165435 A1 US 20030165435A1 US 37351503 A US37351503 A US 37351503A US 2003165435 A1 US2003165435 A1 US 2003165435A1
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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
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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
- A61K9/0012—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
- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- 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
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
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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
- A61K9/0012—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]
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
Definitions
- the present invention relates to pharmaceutical preparations in the form of stable ethanolic solutions of active substances for producing propellant-free aerosols.
- nebulisers are described, for example, in PCT Patent Application WO91/14468, the contents of which are referred to hereinafter.
- solutions of defined volumes containing active substances are sprayed, using high pressures through small nozzles so as to produce inhalable aerosols with a preferred particle size of between 1 and 10, preferably between 2 and 5 micrometers.
- Suitable solvents for the pharmaceutical preparation within the scope of the present inventions are solutions containing at least 70% (v/v) of ethanol; solutions containing at least 85% (v/v) are preferred whilst solutions having an ethanol content of more than 95% (v/v) are particularly preferred.
- the concentration is given in percent by volume (v/v), the remainder being water.
- Most particularly preferred is ethanol which already contains small amounts of water, e.g. 96% ethanol, so that it is no longer hygroscopic and evaporates azeotropically.
- the solvent may include other cosolvents and the pharmaceutical preparation may also contain flavourings and other pharmacological excipients.
- cosolvents are those which contain hydroxyl groups or other polar groups, e.g. alcohols, especially isopropyl alcohol, glycols, particularly propylene glycol, polyethylene glycol, polypropylene glycol, glycol ether, glycerol, polyoxyethylene alcohols and esters of polyoxyethylene fatty acids.
- Cosolvents are suitable for increasing the solubility of the excipients and possibly the active substances.
- the proportion of dissolved pharmaceutical substance in the finished pharmaceutical preparation is between 0.001 and 5%, preferably between 0.05 and 3%, most particularly 0.01 to 2%, where the figures refer to the percentage by weight.
- the maximum concentration of pharmaceutical substance depends on the solubility in the solvent and on the dosage required to achieve the desired therapeutic effect.
- any substances which are suitable for administration by inhalation and which are soluble in the solvent specified may include, in particular, betamimetics, anticholinergics, antiallergics, PAF-antagonists and particularly steroids and combinations of active substances thereof.
- WEB 2086 (4-(2-chlorophenyl)-9-methyl-2-[3-(4-morpholinyl)-3-propanon-1-yl]-6H-thieno-[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine)
- WEB 2170 (6-(2-chlorophenyl)-8,9-dihydro-1-methyl-8-[(4-morpholinyl)carbonyl]-4H,7H-cyclopenta[4,5]thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine)
- compositions according to the invention may contain other excipients such as soya lecithin or surface-active substances.
- inorganic acids include, for example: hydrochloric acid, sulphuric acid or phosphoric acid
- organic acids include ascorbic acid, malic acid, citric acid, tartaric acid, maleic acid, succinic acid, fumaric acid, acetic acid, formic acid, propionic acid, etc.
- the amount of acid in the finished pharmaceutical preparation is in every case selected so that the pH of the solution is between 2.0 and 7.0, especially between 3.0 and 4.0.
- the pharmaceutical preparation also contains a complex forming agent.
- complex forming agents include EDTA, citric acid, nitrilo triacetic acid and the salts thereof.
- the quantity of complex forming agent is between 0.1 and 3 mg/100 ml, preferably between 0.2 and 2 mg/100 ml, particularly between 0.9 and 1.1 mg/100 ml, based on the finished pharmaceutical preparation.
- steroids which may be used as an active substance in the pharmaceutical preparation according to the invention are: Seratrodast Mycophenolate mofetil Pranlukast Zileuton Butixocort Budesonide Deflazacort Fluticasone Promedrol Mometasone furoate Tipredane Beclomethasone, Douglas Icomethasone enbutate Ciclometasone Cloprednol Fluocortin butyl Halometasone Deflazacort Alclometasone Ciclometasone Alisactide Prednicarbate Hydrocortisone butyrate Tixocortol pivalate Alclometasone dipropionate Lotrisone Canesten-HC Deprodone Fluticasone propionate Methylprednisolone- Halopredone acetate Aceponate Mometasone Mometasone furoate Hydrocortisone aceponate Mometasone Ulobeta
- Flunisolide hemihydrate-6 ⁇ -fluoro-11 ⁇ ,16 ⁇ ,17 ⁇ ,21-tetrahydropregna-1,4-diene-3,20-16 acetonide hemihydrate has a molecular weight of 442.5.
- 250 ⁇ g of Flunisolide are dissolved, per dose, in 15 ⁇ l of solution so as to give a concentration of 1.667% (g/100 ml).
- the finished pharmaceutical preparation contains 1 mg/100 ml of disodium-EDTA.
- the pH value of the pharmaceutical preparation is adjusted to pH 4 using 0.1N HCl.
- the Flunisolide-hemihydrate content was 1,666.7 mg/100 ml.
- the pH of the solution was adjusted using 1N HCl and was determined using a pH meter, pH 1162 Radiometer Copenhagen.
- the samples were transferred into 5 ml glass ampoules and stored at 80° C. away from light.
- the combination AC showed the lowest amount of decomposition product after 30 days' storage.
Abstract
The invention relates to ethanol-containing pharmaceutical preparations for the production of propellant-free aerosols.
Description
- The present invention relates to pharmaceutical preparations in the form of stable ethanolic solutions of active substances for producing propellant-free aerosols.
- In the last 20 years, the use of metering aerosols has become an established component of the treatment of obstructive lung diseases, particularly asthma. Usually, fluorochlorohydrocarbons have been used as propellant gases. Since the ozone-damaging potential of these propellant gases was recognised, more and more efforts have been made to develop alternatives. One alternative is the development of nebulisers in which aqueous solutions of pharmacologically-active substances are sprayed under high pressure so as to produce a mist of inhalable particles. The advantage of these nebulisers is that there is no need to use any propellant gases whatsoever.
- Some nebulisers are described, for example, in PCT Patent Application WO91/14468, the contents of which are referred to hereinafter. In the nebulisers described therein, solutions of defined volumes containing active substances are sprayed, using high pressures through small nozzles so as to produce inhalable aerosols with a preferred particle size of between 1 and 10, preferably between 2 and 5 micrometers.
- Hitherto, it has been assumed that, with conventional metering aerosols containing propellant gas, the optimum level of lung-bound particles is obtained in the aerosol. It has now been found, surprisingly, that by using ethanolic active substance solutions in combination with, for example, the above-mentioned nebulisers it is possible to generate a significantly better spectrum of inhalable particles than is usually the case with metering aerosols which contain propellant gas.
- Suitable solvents for the pharmaceutical preparation within the scope of the present inventions are solutions containing at least 70% (v/v) of ethanol; solutions containing at least 85% (v/v) are preferred whilst solutions having an ethanol content of more than 95% (v/v) are particularly preferred. The concentration is given in percent by volume (v/v), the remainder being water. Most particularly preferred is ethanol which already contains small amounts of water, e.g. 96% ethanol, so that it is no longer hygroscopic and evaporates azeotropically.
- Apart from water, the solvent may include other cosolvents and the pharmaceutical preparation may also contain flavourings and other pharmacological excipients. Examples of cosolvents are those which contain hydroxyl groups or other polar groups, e.g. alcohols, especially isopropyl alcohol, glycols, particularly propylene glycol, polyethylene glycol, polypropylene glycol, glycol ether, glycerol, polyoxyethylene alcohols and esters of polyoxyethylene fatty acids. Cosolvents are suitable for increasing the solubility of the excipients and possibly the active substances.
- The proportion of dissolved pharmaceutical substance in the finished pharmaceutical preparation is between 0.001 and 5%, preferably between 0.05 and 3%, most particularly 0.01 to 2%, where the figures refer to the percentage by weight. The maximum concentration of pharmaceutical substance depends on the solubility in the solvent and on the dosage required to achieve the desired therapeutic effect.
- As pharmaceutically active agent in the new preparations, it is possible to use any substances which are suitable for administration by inhalation and which are soluble in the solvent specified. These may include, in particular, betamimetics, anticholinergics, antiallergics, PAF-antagonists and particularly steroids and combinations of active substances thereof.
- The following are mentioned specifically by way of example:
- Tiotropium bromide, 3-[(hydroxyl-2-thienylacetyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3,2,1]oct-6-en-bromide
As betamimetics: Bambuterol Bitolterol Carbuterol Formoterol Clenbuterol Fenoterol Hexoprenaline Procaterol Ibuterol Pirbuterol Salmeterol Tulobuterol Reproterol Salbutamol Sulfonterol Terbutaline - 1-(2-fluoro-4-hydroxyphenyl)-2-[4-(1-benzimidazolyl)-2-methyl-2-butylamino]ethanol,
- erythro-5′-hydroxy-8′-(1-hydroxy-2-isopropylaminobutyl)-2H-1,4-benzoxazin-3-(4H)-one,
- 1-(4-amino-3-chloro-5-trifluoromethylphenyl)-2-tert.-butyl-amino)ethanol,
- 1-(4-ethoxycarbonylamino-3-cyano-5-fluorophenyl)-2-(tert.-butylamino)ethanol.
- As anticholinergics:
- Ipratropium bromide
- Oxitropium bromide
- Trospium chloride
- N-β-fluorethylnortropine benzilate methobromide
- As steroids:
- Budesonide
- Beclomethasone (or the 17,21-dipropionate)
- Dexamethasone-21-isonicotinate
- Flunisolide
- As antiallergics:
- Disodium cromoglycate
- Nedocromil
- Epinastin
- As PAF-antagonists:
- WEB 2086 (4-(2-chlorophenyl)-9-methyl-2-[3-(4-morpholinyl)-3-propanon-1-yl]-6H-thieno-[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine)
- WEB 2170 (6-(2-chlorophenyl)-8,9-dihydro-1-methyl-8-[(4-morpholinyl)carbonyl]-4H,7H-cyclopenta[4,5]thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine)
- The pharmaceutical preparations according to the invention may contain other excipients such as soya lecithin or surface-active substances.
- Surprisingly, it has also been found that the addition of an organic or inorganic acid, preferably in conjunction with a complex forming agent, leads to an improvement in the stability (shelf life) of steroid-containing preparations. This has been found particularly useful for pharmaceutical preparations which contain as active substance Flunisolide or the hydrate or hemihydrate thereof or Budenoside, and which contain ethanol as solvent.
- Examples of inorganic acids include, for example: hydrochloric acid, sulphuric acid or phosphoric acid; examples of organic acids include ascorbic acid, malic acid, citric acid, tartaric acid, maleic acid, succinic acid, fumaric acid, acetic acid, formic acid, propionic acid, etc.
- The amount of acid in the finished pharmaceutical preparation is in every case selected so that the pH of the solution is between 2.0 and 7.0, especially between 3.0 and 4.0.
- In a preferred embodiment, the pharmaceutical preparation also contains a complex forming agent. Examples of complex forming agents include EDTA, citric acid, nitrilo triacetic acid and the salts thereof. The quantity of complex forming agent is between 0.1 and 3 mg/100 ml, preferably between 0.2 and 2 mg/100 ml, particularly between 0.9 and 1.1 mg/100 ml, based on the finished pharmaceutical preparation.
- The preferred complex forming agent is EDTA (ethylene diamine tetraacetic acid or a salt thereof, such as the disodium salt). A preferred pharmaceutical preparation according to the present invention contains 1.667% Flunisolide in the ethanol (96% v/v) as solvent, which contains 0.01% (v/v) EDTA as complex forming agent and is adjusted by the addition of acid to a pH of between 3.0 and 4.0.
- Examples of steroids which may be used as an active substance in the pharmaceutical preparation according to the invention are:
Seratrodast Mycophenolate mofetil Pranlukast Zileuton Butixocort Budesonide Deflazacort Fluticasone Promedrol Mometasone furoate Tipredane Beclomethasone, Douglas Icomethasone enbutate Ciclometasone Cloprednol Fluocortin butyl Halometasone Deflazacort Alclometasone Ciclometasone Alisactide Prednicarbate Hydrocortisone butyrate Tixocortol pivalate Alclometasone dipropionate Lotrisone Canesten-HC Deprodone Fluticasone propionate Methylprednisolone- Halopredone acetate Aceponate Mometasone Mometasone furoate Hydrocortisone aceponate Mometasone Ulobetasol propionate Aminoglutethimide Triamcinolone Hydrocortisone Meprednisone Fluorometholone Dexamethasone Betamethasone Medrysone Fluclorolofle acetonide Fluocinolone acetonide paramethasone acetate Deprodone Propionate Aristocort diacetate Fluocinonide Mazipredone Difluprednate Betamethasone valerate Dexamethasonisonicotinate Beclomethasone dipropionate Fluocortoloncapronate Formocortal Triamcinolon hexacetonide Cloprednol Formebolone Clobetason Endrisone Flunisolide Halcinonide Fluazacort Clobetasol Hydrocortisome-17-butyrate Diflorasone Flucortin Amcinonide Betamethasone dipropionate Cortivazol Betamethasone adamantoate Fluodexan Triiostane Budesonide Clobetasone Demetex Trimacinolon Benetonide - 9α-chloro-6α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-1,4-androstadiene-17β-carboxylic acid methylester-17-propionate.
- Table 1 shows a comparison of a deposition study which was carried out on the one hand with a standard commercial metering aerosol Inhacort® (Flunisolide, dichloromethane, trichlorofluoromethane, cryofluoran, sorbitane triolate)=MDI, and on the other hand with the pharmaceutical preparation according to the invention containing Flunisolide in 96% (v/v) ethanol, which was carried out with a nebuliser as in the above-mentioned PCT Application WO 91/14468 (BINEB®; technical data: volume of drug preparation administered 15 μl, pressure approx. 300 bar, 2 jets squeezed out of two nozzle openings measuring 5×8 μm).
TABLE 1 Table 1: Deposition study BINEB ® MDI Lung (%) 39.7 (9.9) 15.3 (5.1) Mouthpiece (%) 39.9 (9.4) 66.9 (7.1) Exhaled part (%) 10.4 (4.9) 1.4 (1.3) Central lung region (%) 10.7 (2.5) 4.5 (1.8) Middle lung region (%) 14.9 (3.6) 5.4 (1.9) Peripheral lung region (%) 14.1 (4.3) 5.4 (1.4) Peripheral zone/central 1.3 (0.2) 1.3 (0.2) zone ratio - The Table clearly shows the advantage of the pharmaceutical preparation according to the invention which was administered with the nebuliser described.
- Flunisolide hemihydrate-6α-fluoro-11β,16α,17α,21-tetrahydropregna-1,4-diene-3,20-16 acetonide hemihydrate has a molecular weight of 442.5. When used in BINEB, 250 μg of Flunisolide are dissolved, per dose, in 15 μl of solution so as to give a concentration of 1.667% (g/100 ml).
- 96% ethanol is used as solvent. In addition, the finished pharmaceutical preparation contains 1 mg/100 ml of disodium-EDTA. The pH value of the pharmaceutical preparation is adjusted to pH 4 using 0.1N HCl.
- Analogously to the above experiment, formulations were prepared containing Budesonide as active substance.
- The following mixtures of pharmaceutical preparations were made up, containing Flunisolide-hemihydrate as active substance.
TABLE II Quantity of Ethanol disodium Experiment content EDTA in No. Combination (v/v) % pH mg/100 ml 1 1 85 3.6 0 2 A 96 3.6 0 3 B 85 7.0 0 4 AB 96 7.0 0 5 C 85 3.6 1 6 AC 96 3.6 1 7 BC 85 7.0 1 8 ABC 96 7.0 1 - The Flunisolide-hemihydrate content was 1,666.7 mg/100 ml. The pH of the solution was adjusted using 1N HCl and was determined using a pH meter, pH 1162 Radiometer Copenhagen. The samples were transferred into 5 ml glass ampoules and stored at 80° C. away from light. The combination AC showed the lowest amount of decomposition product after 30 days' storage.
- Further examples of formulations which additionally contain disodium EDTA as complex forming agent are shown in Table III.
TABLE III I II III IV Amount in Amount in Amount in Amount in Ingredients mg/100 ml mg/100 ml mg/100 ml mg/100 ml Flunisolide 1667 1667 1667 1667 hemihydrate Disodium 1 1 1 1 EDTA 0.1 N HCl ad pH 3.6 ad pH 3.2 ad pH 4.0 ad pH 3.6 Menthol — — — 667 Ethanol 96% ad 100 ml ad 100 ml ad 100 ml ad 100 ml - The adjuvant menthol was added in order to mask the bitter flavour of the steroid where necessary.
- The formulations described above were packaged in 5 ml glass ampoules and stored at 80° C. The preferred preparation, on account of the small amount of decomposition product, is preparation III.
- Table IV shows some examples of formulations for Budenoside.
TABLE IV I II III IV V Amount in Amount in Amount in Amount in Amount in Ingredients mg/100 ml mg/100 ml mg/100 ml mg/100 ml mg/100 ml Budesonide 1333 1333 1333 1333 1333 Disodium 1 — 1 1 — EDTA 0.1 N HCl 3.2 3.2 3.6 4.0 4.0 ad pH Ethanol 96% 100 100 100 100 100 ad - After 3 months' storage at 80° C. in sealed glass ampoules the amount of decomposition product was determined by HPLC. Formulations IV and V showed the smallest amount of decomposition product.
Claims (20)
1. A pharmaceutical preparation for use in producing propellant-free aerosols which comprises a pharmacologically active substance, and if necessary, pharmacologically-harmless adjuvants and/or flavourings, characterised in that the pharmaceutical preparation contains at least 70% (v/v) ethanol as a solvent.
2. A pharmaceutical preparation according to claim 1 , characterised in that it contains 96% (v/v) ethanol as a solvent.
3. A pharmaceutical preparation according to claim 1 or 2, characterised in that the active substance is suitable for administration by inhalation and is selected from the group comprising betamimetics, anticholinergics, antiallergics and/or PAF-antagonists.
4. A pharmaceutical preparation according to claims 1 to 3 , characterised in that the proportion of dissolved pharmaceutical product in the pharmaceutical preparation is between 0.001 and 5.0 percent by volume.
5. A pharmaceutical preparation for the production of propellant-free aerosols, comprising a steroid and, if necessary, pharmacologically-harmless adjuvants and/or flavourings, characterised in that the pharmaceutical preparation contains at least 85% (v/v) ethanol as a solvent, and if necessary, a complex forming agent.
6. A pharmaceutical preparation according to claim 5 , characterised in that the solvent is 96% (v/v) ethanol.
7. A pharmaceutical preparation according to claim 6 , characterised in that the complex forming agent is EDTA or a salt thereof.
8. A pharmaceutical preparation according to claim 5 or claim 7 , characterised in that the quantity of complex forming agent is between 0.1 and 5 mg/100 ml of solution.
9. A pharmaceutical preparation according to one of claims 5 to 8 , characterised in that the pH value of the preparation is adjusted to a level between 3.2 and 4.5.
10. A pharmaceutical preparation according to one of claims 5 to 9 , characterised in that the active substance is Flunisolide or Budesonide.
11. A pharmaceutical preparation according to one of claims 1 to 6 , characterised in that the active substance is Tiotropium or an acid addition salt thereof.
12. A pharmaceutical preparation according to one of claims 1 to 6 , characterised in that the active substance is 3-[(hydroxyl-2-thienylacetyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3,2,1]oct-6-ene or an acid addition salt thereof.
13. A pharmaceutical preparation for use in producing a propellant-free metering aerosol containing, per 100 ml of 96% (v/v) ethanol, 1.667 g of Flunisolide hemihydrate and 1 mg of disodium EDTA, the pH value of the pharmaceutical preparation being adjusted to 4.0.
14. A pharmaceutical preparation for use in producing a propellant-free metering aerosol containing, per 100 ml of 90% (v/v) ethanol, 1.667 g of Flunisolide hemihydrate and 1 mg of disodium EDTA, the pH value of the pharmaceutical preparation being adjusted to 4.0.
15. A pharmaceutical preparation for use in producing a propellant-free metering aerosol containing, per 100 ml of 96% (v/v) ethanol, 1.333 g of Budesonide and 1 mg of disodium EDTA, the pH value of the pharmaceutical preparation being adjusted to 4.0.
16. A pharmaceutical preparation for use in producing a propellant-free metering aerosol containing, per 100 ml of 90% (v/v) ethanol, 1.333 g of Budesonide and 1 mg of disodium EDTA, the pH value of the pharmaceutical preparation being adjusted to 4.0.
17. Use of a pharmaceutical preparation comprising a pharmacologically active substance in a solution containing at least 79% ethanol by volume in the preparation of a propellant-free composition for administration by inhalation.
18. Use of a pharmaceutical preparation as defined in one of claims 1 to 16 as a propellant-free composition for administration by inhalation.
19. A process for preparing a pharmaceutical preparation as defined in claim 1 which comprises dissolution of a pharmacologically active substance in at least 70% v/v.
20. A delivery system for a pharmacologically active substance which comprises a preparation as defined in any one of claims 1 to 16 in combination with a propellant-free nebuliser.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/373,515 US20030165435A1 (en) | 1995-06-27 | 2003-02-25 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
US11/351,095 US20060127322A1 (en) | 1995-06-27 | 2006-02-09 | Stable pharmaceutical Budesonide preparation for producing propellant-free aerosols |
US11/968,903 US8062626B2 (en) | 1995-06-27 | 2008-01-03 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19523207.0 | 1995-06-27 | ||
DE19523207 | 1995-06-27 | ||
US97392198A | 1998-02-03 | 1998-02-03 | |
US09/396,673 US6491897B1 (en) | 1995-06-27 | 1999-09-09 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
US10/102,495 US20020141944A1 (en) | 1995-06-27 | 2002-03-20 | Stable pharmaceutical budersonide preparation for producing propellant-free aerosols |
US10/373,515 US20030165435A1 (en) | 1995-06-27 | 2003-02-25 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US10/102,495 Continuation US20020141944A1 (en) | 1995-06-27 | 2002-03-20 | Stable pharmaceutical budersonide preparation for producing propellant-free aerosols |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US11/351,095 Continuation US20060127322A1 (en) | 1995-06-27 | 2006-02-09 | Stable pharmaceutical Budesonide preparation for producing propellant-free aerosols |
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US20030165435A1 true US20030165435A1 (en) | 2003-09-04 |
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Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
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US09/396,673 Expired - Lifetime US6491897B1 (en) | 1995-06-27 | 1999-09-09 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
US10/102,495 Abandoned US20020141944A1 (en) | 1995-06-27 | 2002-03-20 | Stable pharmaceutical budersonide preparation for producing propellant-free aerosols |
US10/373,515 Abandoned US20030165435A1 (en) | 1995-06-27 | 2003-02-25 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
US11/351,095 Abandoned US20060127322A1 (en) | 1995-06-27 | 2006-02-09 | Stable pharmaceutical Budesonide preparation for producing propellant-free aerosols |
US11/968,903 Expired - Fee Related US8062626B2 (en) | 1995-06-27 | 2008-01-03 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/396,673 Expired - Lifetime US6491897B1 (en) | 1995-06-27 | 1999-09-09 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
US10/102,495 Abandoned US20020141944A1 (en) | 1995-06-27 | 2002-03-20 | Stable pharmaceutical budersonide preparation for producing propellant-free aerosols |
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US11/351,095 Abandoned US20060127322A1 (en) | 1995-06-27 | 2006-02-09 | Stable pharmaceutical Budesonide preparation for producing propellant-free aerosols |
US11/968,903 Expired - Fee Related US8062626B2 (en) | 1995-06-27 | 2008-01-03 | Stable pharmaceutical budesonide preparation for producing propellant-free aerosols |
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SI (1) | SI0835098T1 (en) |
SK (1) | SK282468B6 (en) |
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UA (1) | UA62917C2 (en) |
WO (1) | WO1997001329A1 (en) |
ZA (1) | ZA965411B (en) |
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- 1996-06-21 DK DK96923883T patent/DK0835098T3/en active
- 1996-06-21 CZ CZ19974192A patent/CZ288337B6/en not_active IP Right Cessation
- 1996-06-21 WO PCT/EP1996/002700 patent/WO1997001329A1/en active IP Right Grant
- 1996-06-21 AU AU64144/96A patent/AU721566B2/en not_active Expired
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- 1996-06-21 AT AT96923883T patent/ATE223203T1/en active
- 1996-06-21 UA UA98010415A patent/UA62917C2/en unknown
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- 1996-06-21 RU RU98101470/15A patent/RU2223750C2/en active
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- 1996-06-21 IL IL12275296A patent/IL122752A/en not_active IP Right Cessation
- 1996-06-21 DE DE59609627T patent/DE59609627D1/en not_active Expired - Lifetime
- 1996-06-21 HU HU9901710A patent/HU223072B1/en active IP Right Grant
- 1996-06-21 NZ NZ312662A patent/NZ312662A/en not_active IP Right Cessation
- 1996-06-21 PT PT96923883T patent/PT835098E/en unknown
- 1996-06-21 SI SI9630544T patent/SI0835098T1/en unknown
- 1996-06-21 ES ES96923883T patent/ES2183001T3/en not_active Expired - Lifetime
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- 1996-06-21 TR TR97/01711T patent/TR199701711T1/en unknown
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- 1996-06-26 ZA ZA965411A patent/ZA965411B/en unknown
- 1996-06-27 MY MYPI96002634A patent/MY116535A/en unknown
- 1996-06-27 EG EG59696A patent/EG23912A/en active
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1998
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1999
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2002
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2006
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2008
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