US3155574A - Aerosol composition - Google Patents

Aerosol composition Download PDF

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Publication number
US3155574A
US3155574A US197284A US19728462A US3155574A US 3155574 A US3155574 A US 3155574A US 197284 A US197284 A US 197284A US 19728462 A US19728462 A US 19728462A US 3155574 A US3155574 A US 3155574A
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US
United States
Prior art keywords
nitroglycerin
propellant
composition
aerosol
glycol
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.)
Expired - Lifetime
Application number
US197284A
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English (en)
Inventor
John E Silson
Frangos John
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Revlon Inc
Original Assignee
Revlon Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE632504D priority Critical patent/BE632504A/xx
Application filed by Revlon Inc filed Critical Revlon Inc
Priority to US197284A priority patent/US3155574A/en
Priority to GB18354/63A priority patent/GB970027A/en
Priority to FR934743A priority patent/FR2735M/fr
Priority to ES300000A priority patent/ES300000A3/es
Application granted granted Critical
Publication of US3155574A publication Critical patent/US3155574A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates

Definitions

  • This invention relates to aerosol compositions, and to methods for making and using the same.
  • this invention relates to aerosol compositions containing nitroglycerin, to methods of making the same, and to the use of such aerosol compositions in inhalation therapy.
  • nitroglycerin in relieving the pain associated with angina pectoris has long been known in the art. Although numerous other medicaments have been prescribed for the treatment of anginal pain, nitroglycerin remains the most effective and medically safest -therapeutic agent in this field.
  • nitroglycerin is relatively involatile, and not suitable to administration by direct inhalation of its fumes.
  • a solid desensitizing agent e.g., a therapeutically inert substance such as mannitol
  • nitroglycerin is of little value because the time required for the drug to be absorbed into the blood stream and carried to the coronary arterioles usually far exceeds the duration of the paroxysm of anginal pain which the drug is intended to relieve, and the drug is rapidly destroyed in the gastro-intestinal tract or is removed by the liver.
  • Sublingual administration suffers from similar limitations.
  • the speed of action of sublingual administration may be as long as 2 to 3 minutes.
  • sublingual administration is erratic, since there is no control over the amount of nitroglycerin eiiectively absorbed by the mucous membranes of the mouth.
  • the nitroglycerin present in the uncoated tablets of the prior art is gradually decomposed on exposure to air and the efiicacy of the tablets is reduced with time. This lack of stability of the tablets is not only undesirable from a marketing standpoint, but also contributes to the problem of erratic dosing.
  • the present invention concerns methods for treating anginal pain associated with constriction of the coronary arteries with nitroglycerin by inhalation therapy, specifically by inhalation of a nitroglycerin-containing aerosol composition.
  • safe, controlled, and speedy administration of nitroglycerin can be effected.
  • Inhalation therapy with pulmonary absorption of nitroglycerin into the bloodstream, is comparable in speed to intravenous administration, and insures prompt delivery of the nitroglycerin to the coronary arterioles in about 30 seconds or so.
  • the use of metered valves with aerosol packages of the compositions of the invention insures that a controlled dose of the drug is administred.
  • the compositions retain their potency and efiicacy at original levels, making the product not only more accurate for dosing purposes, but more desirable from a marketing viewpoint.
  • compositions of the present invention comprise 3,155,574 Patented Nov. 3, 1964 from about 30 to about percent by weight of a nontoxic volatile liquefied and/or liquid propellant, preferably from about 65 to about 95 percent, in admixture with about 5 to about 50 percent, preferably about 5 to about 25 percent, by Weight of a non-toxic substance solubilizing a desensitized nitroglycerin component in the propellant, the balance being a stabilized nitroglycerin component in which component about 1 to about 10 percent by weight, preferably about 5 to 10 percent, is the therapeutically active nitroglycerin and the balance is a nontoxic non-volatile liquid desensitizing agent for the nitroglycerin.
  • Suitable non-toxic volatile liquid or liquefied propellants are Well known in the aerosol art. These materials are generally fluorinated, chlorinated, or fiuorochlorinated saturated lower aliphatic hydrocarbons, or liquefied petroleurn gases. Suitably halogenated lower alkanes containing 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms, and at least 1 fluorine atom, are often generically referred to as fiuorohydrocarbon propellants, and are commercially available under the trade names Freons, Genetrons, Ucons, etc. These materials include such particularly useful propellants as dichlorodifluoromethane (Freon 12), dichlorotetrafiuoroethane (Freon 114),
  • propellants are ethyl chloride, 1,1,l-trichloroethane, butane, isobutane, propane, etc.
  • propellants are such as produce a desirable vapor pressure for the composition between about 15 and about 60 pounds per square inch at room temperatures (20-25 0.), preferably between about 35 and about 40 pounds per square inch at these temperatures.
  • a combination of propellants particularly suitable for use in the present invention comprises a mixture of about 60 parts by Weight of Freon 12 with 40 parts by weight of Freon 11.
  • individual Freons or mixtures of Freons can be employed in the invention in various amounts with the other ingredients mentioned before so that the resulting mixtures show a pressure within the limits recited.
  • ethyl alcohol As the non-toxic agent solubilizing the stabilized nitroglycerin component, in the propellants just mentioned, ethyl alcohol has proved to be particularly suitable. This substance promotes the formation of uniform, homogeneous mixtures of the nitroglycerin-containing component with the propellants, and is unobjectionable from a clinical standpoint.
  • the alcohol is suitably employed in amounts sufiicient to prevent separation of the nitroglycerin from the propellant but insufficient to reduce the volatility of the final composition below the pressure limits mentioned earlier as desirable in areosol packages.
  • the nitroglycerin-containing component which is a mixture of nitroglycerin with one or more non-toxic nonvolatile liquid desensitizing agents, is compounded to contain from 5 to 10 percent by weight of nitroglycerin. If the amount of nitroglycerin is much in excess of the latter figure, the sensitivity of the composition may increase to a point at which the highly safe properties of the present compositions are lost. On the other hand, decreasing the amount of nitroglycerin in the composition merely increases the amount of therapeutically inactive desensitizing agent administered.
  • the desensitizing agents are preferably those non-toxic non-volatile liquid compounds having at least 3 carbon atoms and characterized by the structural formula XO(RO),,Y, in which R is alkylene, ketoalkylene or hydroxyalkylene having from 2 to 6 carbon atoms, X and Y may be different and are alkyl, ketoalkyl, hydroxyalkyl,
  • acyl, oxy-substituted acyl, and hydrogen and n is an integer from 1 to 10.
  • desensitizing substances of this class are the following: propanediol-1,2; diethylene glycol; polypropylene glycol (M.W. 400); diethylene glycol diacetate; polyethylene glycol (M.W. 200); diethyleneglycol butyl ether; glycol monoethyl ether; diethyleneglycol diethyl ether; diacetone alcohol; triethylene glycol; polyethylene glycol (M.W.
  • hydroxyethyl acetate diethyleneglycol ethyl ether; dimethoxytetraglycol; trimethylene glycol; glycol diethyl ether; ethoxyethyl acetoxyethyl ether; diethyleneglycol methyl ether; methoxyethyl acetoxyethyl ether; glycol monomethyl ether; bis- (methoxyethyl) formal; bis(methoxyethyl) acetal; 2- methoxymethyl-2,4-dimethylpentane diol-1,5; butanedioi- 1,3; Z-methyl-pentanediol-2,4, and the like.
  • propanediol-1,2 has proved particularly suitable for use in the compositions of the invention, not only because of its excellent desensitizing properties, but also because of its extremely low toxicity.
  • the glycol is compatible with the propellants commonly used in aerosol compositions, and blends well with the remaining components of the aerosol compositions of the invention with the formation of a homogeneous solution.
  • sensitizing agents described above particularly other glycols
  • other of the sensitizing agents described above can be used in compounding the compositions of the invention.
  • sensitizing agent dispensed in practicing the inhalation therapy of nitroglycerin according to certain methods of the present invention toxicity problems are minimized, and many materials otherwise considered unsuitable for inhalation can be employed.
  • a dose of nitroglycerin of between about 0.05 to about 1.0 milligram, preferably 0.1 to 0.4 milligram, as contemplated by the present invention, as little as about 0.45 milligram of the desensitizing agent is inhaled.
  • nonvolatile is defined as having vapor pressure characteristics such that evaporation of a mixture of nitroglycerin and the desensitizer in the proportions contemplated herein will not leave a nitroglycerin residue, e.g., the desensitizer has vapor pressure characteristics similar to those of nitroglycerin.
  • compositions of the invention are conveniently prepared by dissolving a pharmaceutical grade of nitroglycerin in a suitable liquid desensitizer. This combination is then mixed with a solubilizing agent such as absolute ethyl alcohol. This mixture may then be combined with the propellants and put into containers, or the mixture and propellants may be separately put into containers by conventional cold fill or pressure methods.
  • a solubilizing agent such as absolute ethyl alcohol
  • the amounts of propellant and active ingredients in the aerosol composition and the quantity of composition delivered by the valve are, relatively, such that a desired predetermined dose of active ingredient is delivered.
  • Administration is suitably effected by directing the orifice of the aerosol unit into the mouth and simultaneously inhaling and activating the metered valve.
  • Example 1 An aerosol composition suitable for inhalation therapy and having a pressure of 53 p.s.i.g. at 70 F. was prepared by combining 4 weight percent of a combination of propanediol-l,2 and nitroglycerin containing 10 weight percent of nitroglycerin with 10 parts by weight of anhydrous ethyl alcohol, 51.6 parts by weight of dichlorodifluoromethane (Propellant 12), and 34.4 parts of dichloromonofluoromethane (Propellant 11).
  • Butanediol-LZ, propanediol-L3 or polypropylene glycol (MFN. about 300) can be substituted for propanediol-1,2 as desensitizers.
  • Example 2 A composition having a vapor pressure of 45 p.s.i.g. was prepared from 1.43 parts by Weight of a mixture containing 10 percent nitroglycerin (N6) in propanediol- 1,2 (PG), 10 parts of anhydrous ethanol, 53.13 parts of ropellant 12, and 35.44 parts of Propellant 11.
  • Example3 10% NG/PG 10.0 Anhydrous ethanol 25.0 Propellant 12 26.0 Propellant 11 39.0
  • Example4 5% NG/PG 10.0 Anhydrous ethanol 25.0 Propellant l2 39.0 Propellant 11 26.0
  • Example6 10% NG/PG 10.0 Anhydrous ethanol 35.0 Propellant 12 20.0 Ethyl chloride 35.0
  • Example7 10% NG/PG 10.0 Anhydrous ethanol 40.0 Propellant 11 30.0 Isobutane 20.0
  • Example8 10% NG/PG 10.0 Anhydrous ethanol 50.0 Propellant 12 30.0 1,1,1-trichloroethane 10.0
  • Example9 10% NG/PG 10.0 Anhydrous ethanol 25.0 Propellant l2 8.0 Propellant 11 32.0 Dichlorotctrafluoroethane (Propellant 114) 25.0
  • Example 11 10% NG/PG 10.0 Anhydrous ethanol 25.0 1,1-difluoroethane 65.0
  • Example 12 10% NG/PG 10.0 Anhydrous ethanol 25.0 l-chloro-l,l-difluoroethane 65.0
  • An aerosol composition comprising a liquefied propellant, nitroglycerin and a non-volatile liquid desensitizing agent therefor, and an agent solubiiizing said nitroglycerin in said propellant.
  • An aerosol composition comprising a liquefied propellant, ethyl alcohol, nitroglycerin and a non-volatile liquid desensitizing agent therefor of the formula in which R is selected from the group consisting of alkylene, ketoalkylene, and hydroxyalkylene having 2-6 carbon atoms, X and Y are individually selected from the group consisting of alkyl, ketoalkyl, hydroxyalkyl, acyl, oxy-substitutcd acyl, and hydrogen, and n is an integer from 1 to 10.
  • composition as in claim 2 wherein said desensitizing agent is a glycol.
  • a desensitized nitroglycerin-containing areosol composition comprising about 30-95 percent by weight of a volatile non-toxic liquefied propellant, about 5-50 percent by weight of ethyl alcohol, the balance being a mixture containing about 1-10 percent by weight of nitroglycerin with a non-toxic non-volatile liquid glycol.
  • composition as in claim 4 wherein said glycol is propanediol-LZ.
  • the method of treating anginal pain by inhalation therapy which comprises inhaling between about 0.05-1.0 milligram of nitroglycerin in an aerosol composition containing the same, said composition comprising a volatile non-toxic liquefied propellant, ethyl alcohol, and nitroglycerin, and a non-toxic non-volatile liquid desensitizing agent therefor.
  • non-toxic liquefied propellant is selected from the group consisting of fluorinated and fluorochlorinated saturated lower aliphatic hydrocarbons and said desensitizing agent is a glycol.
  • the method of treating anginal pain which comprises inhaling between 0.05-1.0 milligram of nitroglycerin in an aerosol composition containing the same, said composition comprising about 30-95 percent by weight of a volatile non-toxic liquefied propellant selected from the group consisting of liquefied petroleum gases, chlorinated, fluorinated and fluorochlorinated saturated lower aliphatic hydrocarbons, about 5-50 percent by weight of ethyl alcohol, the balance being a mixture containing about 1-10 percent by weight of nitroglycerin with a non-toxic non-volatile glycol.
  • a volatile non-toxic liquefied propellant selected from the group consisting of liquefied petroleum gases, chlorinated, fluorinated and fluorochlorinated saturated lower aliphatic hydrocarbons, about 5-50 percent by weight of ethyl alcohol, the balance being a mixture containing about 1-10 percent by weight of nitroglycerin with a non-toxic non-volatile glycol.
  • composition has a vapor pressure of about 15-60 pounds per square inch at room temperatures and said propellant is at least one fluorochlorinated saturated lower aliphatic hydrocarbon.

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
US197284A 1962-05-24 1962-05-24 Aerosol composition Expired - Lifetime US3155574A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE632504D BE632504A (el) 1962-05-24
US197284A US3155574A (en) 1962-05-24 1962-05-24 Aerosol composition
GB18354/63A GB970027A (en) 1962-05-24 1963-05-09 Aerosol compositions
FR934743A FR2735M (fr) 1962-05-24 1963-05-14 Composition pour aérosols, utilisable pour soulager la douleur accompagnant l'angine de poitrine.
ES300000A ES300000A3 (es) 1962-05-24 1964-05-19 Un procedimiento para preparar una composición para aerosoles

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US197284A US3155574A (en) 1962-05-24 1962-05-24 Aerosol composition

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US3155574A true US3155574A (en) 1964-11-03

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BE (1) BE632504A (el)
ES (1) ES300000A3 (el)
FR (1) FR2735M (el)
GB (1) GB970027A (el)

Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3445564A (en) * 1965-01-04 1969-05-20 Ely A Kirschner Rapidly drying lower aliphatic alcohol-acetone sanitizing composition and method
US3456052A (en) * 1965-09-28 1969-07-15 Garrett Lab Inc Aerosol composition containing butoxymonoether of a polyoxyalkylene glycol
US4323577A (en) * 1979-11-13 1982-04-06 Nippon Kayaku Kabushiki Kaisha Aqueous solution of nitroglycerin
US4380505A (en) * 1978-11-11 1983-04-19 Von Treu Ag Apparatus for producing aerosol product
US4581225A (en) * 1984-04-25 1986-04-08 Eli Lilly And Company Sustained release intranasal formulation and method of use thereof
US4919919A (en) * 1987-09-30 1990-04-24 Nippon Kayaku Kabushiki Kaisha Nitroglycerin spray
US4976965A (en) * 1987-04-30 1990-12-11 Kali-Chemie Pharma Gmbh Coronary affecting medicinal composition
EP0461505A1 (de) * 1990-06-13 1991-12-18 Schwarz Pharma Ag Nitroglycerin-Spray
DE4026072A1 (de) * 1990-08-17 1992-02-20 Sanol Arznei Schwarz Gmbh Nitroglycerinhaltiger, hydrophiler, waessriger pumpspray
US5370862A (en) * 1990-06-13 1994-12-06 Schwarz Pharma Ag Pharmaceutical hydrophilic spray containing nitroglycerin for treating angina
WO1997038687A1 (en) * 1996-04-12 1997-10-23 Flemington Pharmaceutical Corporation Buccal, non-polar spray for nitroglycerin
US20030077229A1 (en) * 1997-10-01 2003-04-24 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing cardiovascular or renal drugs
US20030077228A1 (en) * 1997-10-01 2003-04-24 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating endocrine disorders
US20030077227A1 (en) * 1997-10-01 2003-04-24 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the central nervous system
US20030082107A1 (en) * 1997-10-01 2003-05-01 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating an infectious disease or cancer
US20030095925A1 (en) * 1997-10-01 2003-05-22 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating metabolic disorders
US20030095926A1 (en) * 1997-10-01 2003-05-22 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract
US20030095927A1 (en) * 1997-10-01 2003-05-22 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating muscular and skeletal disorders
US20030190286A1 (en) * 1997-10-01 2003-10-09 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating allergies or asthma
US6676931B2 (en) 1997-10-01 2004-01-13 Novadel Pharma Inc. Buccal, polar and non-polar spray or capsule
US20040120896A1 (en) * 1997-10-01 2004-06-24 Novadel Pharma, Inc. Buccal, polar and non-polar spray or capsule containing drugs for treating pain
US20040136913A1 (en) * 1997-10-01 2004-07-15 Dugger Harry A. Buccal, polar and non-polar spray containing sumatriptan
US20040136914A1 (en) * 1997-10-01 2004-07-15 Dugger Harry A. Buccal, polar and non-polar spray containing ondansetron
US20040141923A1 (en) * 1997-10-01 2004-07-22 Dugger Harry A. Buccal, polar and non-polar spray containing alprazolam
US20040265239A1 (en) * 1997-10-01 2004-12-30 Novadel Pharma Inc. Buccal, polar and non-polar spray containing zolpidem
US20050002867A1 (en) * 1997-10-01 2005-01-06 Novadel Pharma Inc. Buccal, polar and non-polar sprays containing propofol
US20050163719A1 (en) * 1997-10-01 2005-07-28 Dugger Harry A.Iii Buccal, polar and non-polar spray containing diazepam
US20050180923A1 (en) * 1997-10-01 2005-08-18 Dugger Harry A.Iii Buccal, polar and non-polar spray containing testosterone
US20050281752A1 (en) * 1997-10-01 2005-12-22 Dugger Harry A Iii Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the central nervous system
US20050287075A1 (en) * 1997-10-01 2005-12-29 Dugger Harry A Iii Buccal, polar and non-polar spray or capsule containing drugs for treating pain
US20070048229A1 (en) * 1997-10-01 2007-03-01 Novadel Pharma Inc. Buccal, polar and non-polar spray containing atropine
WO2007088327A1 (en) * 2006-02-03 2007-08-09 Futura Medical Developments Limited Composition for promoting vascular smooth muscle relaxation
US20070248548A1 (en) * 2006-04-19 2007-10-25 Blondino Frank E Stable hydroalcoholic oral spray formulations and methods
US20080171089A1 (en) * 2006-12-22 2008-07-17 Blondino Frank E Stable anti-nausea oral spray formulations and methods
DE202008007318U1 (de) 2008-03-14 2008-07-31 G. Pohl-Boskamp Gmbh & Co. Kg Langzeitstabile pharmazeutische Zubereitung mit dem Wirkstoff Glyceroltrinitrat
US20080280947A1 (en) * 2007-05-10 2008-11-13 Blondino Frank E Anti-insomnia compositions and methods
WO2012016691A1 (en) 2010-08-03 2012-02-09 G. Pohl-Boskamp Gmbh & Co. Kg Use of glyceryl trinitrate for treating traumatic edema
EP2767163A1 (en) 2005-02-17 2014-08-20 Abbott Laboratories Transmucosal administration of drug compositions for treating and preventing disorders in animals
EP2878310A1 (en) 2013-11-29 2015-06-03 G. Pohl-Boskamp GmbH & Co. KG Sprayable aqueous composition comprising glyceryl trinitrate
US9101592B2 (en) 2011-02-25 2015-08-11 G. Pohl-Boskamp Gmbh & Co. Kg Stabilized granules containing glyceryl trinitrate
US9248099B2 (en) 2012-05-31 2016-02-02 Desmoid Aktiengesellschaft Use of stabilized granules containing glyceryl trinitrate for arteriogenesis
US11166931B2 (en) 2012-05-31 2021-11-09 G. Pohl-Boskamp Gmbh & Co. Kg Induction of arteriogenesis with an NO (nitric oxide) donor

Families Citing this family (8)

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DE3326089A1 (de) * 1983-07-20 1985-02-07 Gödecke AG, 1000 Berlin Zur inhalation bestimmte darreichungsform von calcium-antagonisten
EP0175671A1 (de) * 1984-08-23 1986-03-26 Kuhlemann & Co. Pharmazeutische Zubereitung sowie Verfahren zum Darreichen dieser pharmazeutischen Zubereitung
HU199678B (en) * 1988-07-08 1990-03-28 Egyt Gyogyszervegyeszeti Gyar Process for producing aerosols containing nitroglicerol
GB9118830D0 (en) * 1991-09-03 1991-10-16 Minnesota Mining & Mfg Medical aerosol formulations
ES2183001T3 (es) 1995-06-27 2003-03-16 Boehringer Ingelheim Pharma Nuevo preparado medicamentoso estable para la produccion de aerosoles exentos de gas propulsor.
US6413496B1 (en) 1996-12-04 2002-07-02 Biogland Ireland (R&D) Limited Pharmaceutical compositions and devices for their administration
US6197280B1 (en) 1997-09-09 2001-03-06 Bioglan Laboratories Limited Pharmaceutical compositions and devices for their administration
GB2592376A (en) * 2020-02-25 2021-09-01 Aer Beatha Ltd Canister

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US2648698A (en) * 1949-07-29 1953-08-11 Hercules Powder Co Ltd Desensitized liquid explosives
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US3014844A (en) * 1957-01-31 1961-12-26 Riker Laboratories Inc Self-propelling powder dispensing compositions

Patent Citations (3)

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US2648698A (en) * 1949-07-29 1953-08-11 Hercules Powder Co Ltd Desensitized liquid explosives
US2868691A (en) * 1956-03-21 1959-01-13 Riker Laboratories Inc Self-propelling compositions for inhalation therapy containing a salt of isoproterenol or epinephrine
US3014844A (en) * 1957-01-31 1961-12-26 Riker Laboratories Inc Self-propelling powder dispensing compositions

Cited By (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3445564A (en) * 1965-01-04 1969-05-20 Ely A Kirschner Rapidly drying lower aliphatic alcohol-acetone sanitizing composition and method
US3456052A (en) * 1965-09-28 1969-07-15 Garrett Lab Inc Aerosol composition containing butoxymonoether of a polyoxyalkylene glycol
US4380505A (en) * 1978-11-11 1983-04-19 Von Treu Ag Apparatus for producing aerosol product
US4323577A (en) * 1979-11-13 1982-04-06 Nippon Kayaku Kabushiki Kaisha Aqueous solution of nitroglycerin
US4581225A (en) * 1984-04-25 1986-04-08 Eli Lilly And Company Sustained release intranasal formulation and method of use thereof
US4976965A (en) * 1987-04-30 1990-12-11 Kali-Chemie Pharma Gmbh Coronary affecting medicinal composition
US4919919A (en) * 1987-09-30 1990-04-24 Nippon Kayaku Kabushiki Kaisha Nitroglycerin spray
EP0461505A1 (de) * 1990-06-13 1991-12-18 Schwarz Pharma Ag Nitroglycerin-Spray
DE4018919A1 (de) * 1990-06-13 1991-12-19 Sanol Arznei Schwarz Gmbh Nitroglycerin-spray
US5370862A (en) * 1990-06-13 1994-12-06 Schwarz Pharma Ag Pharmaceutical hydrophilic spray containing nitroglycerin for treating angina
DE4026072A1 (de) * 1990-08-17 1992-02-20 Sanol Arznei Schwarz Gmbh Nitroglycerinhaltiger, hydrophiler, waessriger pumpspray
US5744124A (en) * 1990-08-17 1998-04-28 Schwarz Pharma Ag Nitroglycerin-containing hydrophilic aqueous pumpable spray composition
WO1997038687A1 (en) * 1996-04-12 1997-10-23 Flemington Pharmaceutical Corporation Buccal, non-polar spray for nitroglycerin
US20050287075A1 (en) * 1997-10-01 2005-12-29 Dugger Harry A Iii Buccal, polar and non-polar spray or capsule containing drugs for treating pain
US20060216240A1 (en) * 1997-10-01 2006-09-28 Novadel Pharma Inc. Buccal, polar and non-polar spray containing zolpidem
US20030077227A1 (en) * 1997-10-01 2003-04-24 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the central nervous system
US20030082107A1 (en) * 1997-10-01 2003-05-01 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating an infectious disease or cancer
US20030095925A1 (en) * 1997-10-01 2003-05-22 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating metabolic disorders
US20030095926A1 (en) * 1997-10-01 2003-05-22 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating disorders of the gastrointestinal tract or urinary tract
US20030095927A1 (en) * 1997-10-01 2003-05-22 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating muscular and skeletal disorders
US20030190286A1 (en) * 1997-10-01 2003-10-09 Dugger Harry A. Buccal, polar and non-polar spray or capsule containing drugs for treating allergies or asthma
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BE632504A (el)
GB970027A (en) 1964-09-16
FR2735M (fr) 1964-08-17
ES300000A3 (es) 1964-11-16

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