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(12) Patent Application Publication (10) Pub. No.: US 2009/0099225A1 Freund Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2009/0099225A1 Freund Et Al US 20090099225A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0099225A1 Freund et al. (43) Pub. Date: Apr. 16, 2009 (54) METHOD FOR THE PRODUCTION OF Related U.S. Application Data PROPELLANT GAS-FREE AEROSOLS FROM (63) Continuation of application No. 1 1/506,128, filed on AQUEOUSMEDICAMENT PREPARATIONS Aug. 17, 2006, now Pat. No. 7,470,422, which is a continuation of application No. 10/417.766, filed on (75) Inventors: Bernhard Freund, Gau-Algesheim Apr. 17, 2003, now abandoned, which is a continuation (DE); Bernd Zierenberg, Bingen of application No. 09/331,023, filed on Sep. 15, 1999, am Rhein (DE) now abandoned. (30) Foreign Application Priority Data Correspondence Address: MICHAEL P. MORRIS Dec. 20, 1996 (DE) ............................... 19653969.2 BOEHRINGERINGELHEMI USA CORPORA Dec. 16, 1997 (EP) ......................... PCT/EP97/07062 TION Publication Classification 900 RIDGEBURY RD, P. O. BOX 368 RIDGEFIELD, CT 06877-0368 (US) (51) Int. Cl. A63L/46 (2006.01) (73) Assignee: Boehringer Ingelheim Pharma A63L/437 (2006.01) KG, Ingelheim (DE) (52) U.S. Cl. ......................................... 514/291; 514/299 (57) ABSTRACT (21) Appl. No.: 12/338,812 The present invention relates to pharmaceutical preparations in the form of aqueous solutions for the production of propel (22) Filed: Dec. 18, 2008 lant-free aerosols. US 2009/0099225A1 Apr. 16, 2009 METHOD FOR THE PRODUCTION OF 0008 All substances which are suitable for application by PROPELLANT GAS-FREE AEROSOLS FROM inhalation and which are soluble in the specified solvent can AQUEOUSMEDICAMENT PREPARATIONS be used as pharmaceuticals in the new preparations. Pharma ceuticals for the treatment of diseases of the respiratory pas RELATED APPLICATIONS sages are of especial interest. Therefore, of especial interest are betamimetics, anticholinergics, antiallergics, antihista 0001. This application is a continuation of U.S. Ser. No. mines, and steroids, as well as combinations of these active 1 1/506,128, filed Aug. 17, 2006, which is a continuation of ingredients. U.S. Ser. No. 10/417,766, filed Apr. 17, 2003, now aban doned, which is a continuation of U.S. Ser. No. 09/331,023, 0009. It was found, in a series of examinations, that the filed Sep.15, 1999, now abandoned, which is a filing under 35 nebulizers described above can feature spraying anomalies U.S.C. S. 371 of PCT/EP97/07062, filed Dec. 16, 1997, the when using aqueous pharmaceutical solutions (generally, entireties of which are incorporated herein by reference. double distilled or demineralized (ion exchanged) water is used as a solvent). These spraying anomalies represent an BACKGROUND AND SUMMARY OF THE alteration of the spraying pattern of the aerosol, with the INVENTION consequence that in extreme cases an exact dose can no longer be guaranteed to the patient as a result of the altered 0002 The present invention relates to pharmaceutical mean droplet size distribution (alteration to the lung acces preparations in the form of aqueous solutions for the produc sible part of the aerosol). These spraying anomalies espe tion of propellant-free aerosols for inhalation. cially occur when the nebulizers is used at intervals, for 0003. In the last 20 years, the use of dosage aerosols has example, with breaks of approximately 3 or more days become a strong part of the therapy of obstructive lung dis between utilization. It is possible that these spraying anoma eases, especially asthma. Usually, fluorochlorohydrocarbons lies, which in extreme cases can lead to a dysfunction of the are used as propellant gases. Following the recognition of the nebulizers, are as a result of microscopic deposits in the area oZone damaging potential of these propellant gases, attempts of the jet opening. to develop alternatives have increased. One alternative is the development of nebulizers, where aqueous solutions of phar 0010 Surprisingly, it was discovered that these spraying macologically active Substance are sprayed under high pres anomalies no longer occur when the aqueous pharmaceutical sure so that a mist of inhalable particles results. The advan preparations which are to be sprayed contain a defined effec tage of these nebulizers is that they completely dispense with tive quantity of a complexing agent, especially of EDTA the use of propellant gases. (ethylenediamine tetraacetic acid) or salts thereof. The aque 0004 Such nebulizers are, for example, described in PCT ous pharmaceutical preparations according to the invention Patent Application WO 91/14468 (the Weston Nebulizer), contain water as a solvent, but if necessary, ethanol can be herein incorporated by reference. With the nebulizers added to increase the solubility up to 70% (by volume), pref described here, active ingredients solutions in defined vol erably between 30% and 60% (by volume). umes are sprayed through Small jets under high pressure, so 0011. Other pharmacological adjuvants such as preserva that inhalable aerosols with a mean particle size of between 3 tives, especially benzalkonium chloride, can be added. The and 10 micrometers result. A further developed embodiment preferred quantity of preservative, especially benzalkonium of the aforementioned nebulizer is described in PCT/EP967 chloride, is between 8 and 12 mg/100 ml solution. 04351 (the Jaeger Nebulizer A). The nebulizer portrayed in FIG. 6 of PCT/EP96/04351 (the Jaeger Nebulizer B) carries 0012 Suitable complexing agents are those which are the trademark Respimat(R). pharmacologically acceptable, especially those which are 0005 Usually, pharmaceuticals intended for inhalation already approved by medical regulating authorities. EDTA, are dissolved in an aqueous or ethanolic Solution, and accord nitrilotriacetic acid, citric acid, and ascorbic acid and their ing to the Solution characteristics of the active Substances, salts are especially suitable. The disodium salt of ethylenedi solvent mixtures of water and ethanol may also be suitable. aminetetraacetic acid is especially preferred. 0006. Other components of the solvent are, apart from 0013 The quantity of complexing agent is selected so that water and/or ethanol, optionally other cosolvents, and also the an effective quantity of complexing agent is added to prevent pharmaceutical preparation may also additionally contain fla further occurrence of spraying anomalies. vourings and other pharmacological additives. Examples of 0014. The effective quantity of the complexing agent Na cosolvents are those which contain hydroxyl groups or other EDTA is between 10 and 1000 mg/100 ml solution, especially polar groups, for example, alcohols, especially isopropyl between 10 and 100 mg/100 ml solution. The preferred range alcohol, glycols, especially propylene glycol, polyethylene of the quantity of complexing agent is between 25 and 75 glycol, polypropylene glycol, glycol ether, glycerol, poly mg/100 ml solution, especially between 25 and 50 mg/100 ml oxyethylene alcohols, and polyoxyethylene fatty acid esters. Solution. Cosolvents are suitable for increasing the solubility of adju 0015 The following named compounds can principally be vant materials and, if necessary, active ingredients. used as active ingredients, singly or in combination, in the 0007. The proportion of dissolved pharmaceutical in the aqueous pharmaceutical preparation according to the inven finished pharmaceutical preparation is between 0.001% and tion. In individual cases, it may be required to add a higher 30% preferably between 0.05% and 3%, especially 0.01% quantity of ethanol or a solution mediator to improve solubil to 2% (weight/volume). The maximum concentration of ity. pharmaceutical is dependent on the Solubility in solvent and 0016 Tiotropium bromide, 3-(hydroxydi-2-thieny on the dosage required to achieve the desired therapeutical lacetyl)oxy-8,8-dimethyl-8-azoniabicyclo3.2.1]oct-6-ene effect. bromide US 2009/0099225A1 Apr. 16, 2009 0017. As betamimetics: and 9-O-chloro-6-C.-fluoro-11-3-17-O-dihydroxy-16-O-me thyl-3-oxo-1,4-androstadiene-17-f-carboxylic acid-methyl ester-17-propionate. 0025. Other especially suitable active ingredients for the Bambuterol Bitolterol Carbuterol Formoterol Clenbuterol Fenoterol Hexoprenaline Procaterol production of aqueous pharmaceutical preparations for appli Ibuterol Pirbuterol Salmeterol Tulobuterol cations by inhalation are: Reproterol Salbutamol Sulfonterol Terbutaline B-Sympatico-mimetics, e.g. Fenoterol, Salbutamol. Formot erol, or Terbutalin; 0018 1-(2-Fluoro-4-hydroxyphenyl)-2-[4-(1-benzimida Anticholinergics, e.g. patropium, OXitropium, or Tiotro zolyl)-2-methyl-2-butylaminoethanol, pium; droxy-8-(1-hydroxy-2-isopropylaminobutyl)-2H-1,4- Steroids, e.g., Beclomethasone dipropionate, Budesonide, or benzoxazin-3-(4H)-one, Flunisolide; 0019 1-(4-Amino-3-chloro-5-trifluoromethylphenyl)-2- Peptides, e.g., insulin; and tert.-butyl-amino)ethanol, and Pain killers, e.g., Fentanyl. 0020 1-(4-Ethoxycarbonylamino-3-cyano-5-fluorophe 0026. It is obvious that those pharmacologically accept nyl)-2-(tert-butylamino)ethanol. able salts will be used which dissolve in the solvent according 0021 As anticholinergics: to the invention if necessary. Ipratropium bromide, Oxitropium bromide, Trospium chlo 0027. In the following text, the advantage of the pharma ride, and N-B-fluoroethylene nortropine benzylate methobro ceutical preparation according to the invention will be mide explained more clearly with Examples. 0022. As steroids: 0028. As a pharmaceutical solution, Ipratropium bromide Budesonide, Beclometasone (or the
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