US20020071812A1 - Propellent gases and their use in pharmaceutical preparations - Google Patents

Propellent gases and their use in pharmaceutical preparations Download PDF

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Publication number
US20020071812A1
US20020071812A1 US10/072,400 US7240002A US2002071812A1 US 20020071812 A1 US20020071812 A1 US 20020071812A1 US 7240002 A US7240002 A US 7240002A US 2002071812 A1 US2002071812 A1 US 2002071812A1
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specified
active substances
propellent gases
pharmaceutical preparations
combination
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US10/072,400
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Hans-Hermann Weil
Ottfried Daab
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Priority to US10/072,400 priority Critical patent/US20020071812A1/en
Publication of US20020071812A1 publication Critical patent/US20020071812A1/en
Priority to US10/638,987 priority patent/US20040028618A1/en
Priority to US10/934,611 priority patent/US7160538B2/en
Priority to US11/553,508 priority patent/US20070065370A1/en
Priority to US12/179,785 priority patent/US20090104127A1/en
Priority to US12/891,076 priority patent/US20110014134A1/en
Abandoned legal-status Critical Current

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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/12—Aerosols; Foams
    • A61K9/124—Aerosols; Foams characterised by the propellant
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols

Definitions

  • the invention relates to new propellent gases which contain as a typical ingredient 1,1,1,2,3,3,3-heptafluoropropane (TG 227), the use of these propellent gases in pharmaceutical preparations suitable for producing aerosols, and these pharmaceutical preparations themselves.
  • TG 227 1,1,1,2,3,3,3-heptafluoropropane
  • Aerosols of powdered (micronised) drugs are used widely in therapy, e.g. in the treatment of obstructive diseases of the respiratory tract. If such aerosols are not produced by atomising the pharmaceutical powder or by spraying solutions, suspensions of the drugs in liquefied propellent gases are used.
  • the latter consist primarily of mixtures of TG 11 (trichlorofluoromethane), TG 12 (dichlorodifluoromethane) and TG 114 (1,2-dichloro-1,1,2,2-tetrafluoroethane), optionally with the addition of lower alkanes such as butane or pentane, or with the addition of DME (dimethylether). Mixtures of this kind are known for example from German Patent 1178975.
  • TG 227 (1,1,1,2,3,3,3-heptafluoropropane, optionally in admixture with one of more propellent gases from the group comprising TG 11 (trichlorofluoromethane), TG 12 (dichlorodifluoro-methane), TG 114 (1,2-dichloro-1,1,2,2-tetrafluoroethane), propane, butane, pentane and DME (dimethylether) is particularly suitable for use in therapeutic preparations.
  • the compounds to be used in addition to TG 227 are added if the properties of the propellent gas are to be modified, e.g. if the liquefied propellents gas is to have a different density, different pressure or different solubility characteristics.
  • Pharmaceutical preparations based on the propellent gas contain an active substance in finely divided form, usually as a suspension, and generally also contain surface-active substances, e.g. a phospholipid (such as lecithin), an ester of a polyalcohol (such as sorbitol) with higher saturated or unsaturated fatty acids (e.g.
  • the ratios of quantities of the individual ingredients of the propellent gas mixture may be varied within wide limits.
  • the proportion (in percent by weight) is 10 to 100% in the case of TG 227.
  • the mixture may also contain up to 50% propane and/or butane and/or pentane and/or DME and/or TG 11 and/or TG 12 and/or TG 114. Within the limits specified the ingredients are chosen to add up to 100%.
  • Propellent gas mixtures which contain 30 to 100% TG 227 are preferred.
  • the proportion of suspended drug in the finished preparation is between 0.001 and 5%, preferably between 0.005 and 3%, more particularly between 0.01 and 2%.
  • the surface-active substances are added in amounts of from 0.01 to 10%, preferably 0.05 to 5%, more particularly 0.1 to 3% (here, as in the case of the pharmaceutical substances, the percentage by weight of the finished preparation is given).
  • the pharmaceutical substances used in the new preparations may be any of the substances suitable for use by inhalation or possibly for intranasal administration. They include, therefore, in particular betamimetics, anticholinergics, steroids, antiallergics, PAF-antagonists and combinations of these active substances.
  • the active substances may also be combined, e.g. betamimetics plus anticholinergics or betamimetics plus antiallergics.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Detergent Compositions (AREA)

Abstract

Pharmaceutical preparations for producing powder aerosols using as the propellant gas TG 227.

Description

  • The invention relates to new propellent gases which contain as a typical ingredient 1,1,1,2,3,3,3-heptafluoropropane (TG 227), the use of these propellent gases in pharmaceutical preparations suitable for producing aerosols, and these pharmaceutical preparations themselves. [0001]
  • Aerosols of powdered (micronised) drugs are used widely in therapy, e.g. in the treatment of obstructive diseases of the respiratory tract. If such aerosols are not produced by atomising the pharmaceutical powder or by spraying solutions, suspensions of the drugs in liquefied propellent gases are used. The latter consist primarily of mixtures of TG 11 (trichlorofluoromethane), TG 12 (dichlorodifluoromethane) and TG 114 (1,2-dichloro-1,1,2,2-tetrafluoroethane), optionally with the addition of lower alkanes such as butane or pentane, or with the addition of DME (dimethylether). Mixtures of this kind are known for example from German Patent 1178975. [0002]
  • Owing to their harmful effect on the earth's atmosphere (destruction of the ozone layer, Greenhouse effect) the use of chlorofluorocarbons has become a problem, with the result that the search is on for other propellent gases or propellent gas mixtures which do not have the above-mentioned harmful effects or, at least, have them to a lesser degree. [0003]
  • However, this search has come up against major problems, since propellent gases for therapeutic use have to satisfy numerous criteria which cannot easily be reconciled, e.g. in terms of toxicity, stability, vapour pressure, density and solubility characteristics. [0004]
  • As has now been found, TG 227 (1,1,1,2,3,3,3-heptafluoropropane, optionally in admixture with one of more propellent gases from the group comprising TG 11 (trichlorofluoromethane), TG 12 (dichlorodifluoro-methane), TG 114 (1,2-dichloro-1,1,2,2-tetrafluoroethane), propane, butane, pentane and DME (dimethylether) is particularly suitable for use in therapeutic preparations. [0005]
  • The compounds to be used in addition to TG 227 are added if the properties of the propellent gas are to be modified, e.g. if the liquefied propellents gas is to have a different density, different pressure or different solubility characteristics. Pharmaceutical preparations based on the propellent gas contain an active substance in finely divided form, usually as a suspension, and generally also contain surface-active substances, e.g. a phospholipid (such as lecithin), an ester of a polyalcohol (such as sorbitol) with higher saturated or unsaturated fatty acids (e.g. stearic, palmitic or oleic acid), such as sorbitan trioleate, or a polyethoxysorbitan ester of a higher, preferably unsaturated fatty acid. The adjuvant may be present in the mixture in dissolved or undissolved form. In some cases, the suspensions produced with the new propellent gas have a tendency to separate out. However, it has been found that the separated suspensions can easily be uniformly distributed again in the suspension medium simply by shaking. [0006]
  • The ratios of quantities of the individual ingredients of the propellent gas mixture may be varied within wide limits. The proportion (in percent by weight) is 10 to 100% in the case of TG 227. The mixture may also contain up to 50% propane and/or butane and/or pentane and/or DME and/or TG 11 and/or TG 12 and/or TG 114. Within the limits specified the ingredients are chosen to add up to 100%. Propellent gas mixtures which contain 30 to 100% TG 227 are preferred. [0007]
  • The proportion of suspended drug in the finished preparation is between 0.001 and 5%, preferably between 0.005 and 3%, more particularly between 0.01 and 2%. The surface-active substances are added in amounts of from 0.01 to 10%, preferably 0.05 to 5%, more particularly 0.1 to 3% (here, as in the case of the pharmaceutical substances, the percentage by weight of the finished preparation is given). The pharmaceutical substances used in the new preparations may be any of the substances suitable for use by inhalation or possibly for intranasal administration. They include, therefore, in particular betamimetics, anticholinergics, steroids, antiallergics, PAF-antagonists and combinations of these active substances.[0008]
  • The following are given as specific examples: [0009]
  • Examples of Betamimetics [0010]
  • Bambuterol [0011]
  • Bitolterol [0012]
  • Carbuterol [0013]
  • Clenbuterol [0014]
  • Fenoterol [0015]
  • Hexoprenalin [0016]
  • Ibuterol [0017]
  • Pirbuterol [0018]
  • Procaterol [0019]
  • Reproterol [0020]
  • Salbutamol [0021]
  • Salmeterol [0022]
  • Sulfonterol [0023]
  • Terbutalin [0024]
  • Tulobuterol [0025]
  • 1-(2-fluoro-4-hydroxyphenyl)-2-[4-(1-benzimidazolyl)-2-methyl-2-butylamino]ethanol [0026]
  • erythro-5′-hydroxy-8′-(1-hydroxy-2-isopropylaminobutyl)-2H-1,4-benzoxazin-3-(4H)-one [0027]
  • 1-(4-amino-3-chloro-5-trifluoromethylphenyl)-2-tert.-butylamino)ethanol [0028]
  • 1-(4-ethoxycarbonylamino-3-cyano-5-fluorophenyl)-2-(tert.-butylamino)ethanol. [0029]
  • Examples of Anticholinergics [0030]
  • Ipratropium bromide [0031]
  • Oxitropium bromide [0032]
  • Trospium chloride [0033]
  • Benzilic acid-N-β-fluoroethylnortropine ester [0034]
  • methobromide [0035]
  • Examples of Steroids [0036]
  • Budesonide [0037]
  • Beclomethasone (or the 17,21-dipropionate thereof) [0038]
  • Dexamethason-21-isonicotinate [0039]
  • Flunisolide [0040]
  • Examples of Antiallergics [0041]
  • Disodium cromoglycate [0042]
  • Nedocromil [0043]
  • Examples of PAF-antagonists [0044]
  • WEB 2086 [0045]
  • WEB 2170 [0046]
  • WEB 2347 [0047]
  • The active substances may also be combined, e.g. betamimetics plus anticholinergics or betamimetics plus antiallergics. [0048]
  • Examples of Preparations According to the Invention (Amounts Given in Percent by Weight) [0049]
  • 1) 0.10% Oxitropium bromide [0050]
  • 0.01% Soya lecithin [0051]
  • 4.0% Pentane [0052]
  • 95.89% TG 227 [0053]
  • 2) 0.3% Fenoterol [0054]
  • 0.1% Soya lecithin [0055]
  • 10.0% Pentane [0056]
  • 70.0% TG 227 [0057]
  • 19.6% TG 134a [0058]
  • 3) 0.1% Ipratropium bromide [0059]
  • 0.1% Soya lecithin [0060]
  • 20.0% Pentane [0061]
  • 20.0% Butane [0062]
  • 49.8% TG 11 [0063]
  • 4) 0.3% Fenoterol [0064]
  • 0.1% Soya lecithin [0065]
  • 30.0% TG 11 [0066]
  • 69.6 TG 227 [0067]
  • 5) 1.5% Disodium cromoglicate [0068]
  • 0.1% Tween 20 [0069]
  • 98.4% TG 227 [0070]
  • 1.4% Butane [0071]
  • 6) 0.3% Salbutamol [0072]
  • 0.2% Span 85 [0073]
  • 20.0% Pentane [0074]
  • 60.0% TG 227 [0075]
  • 19.5% TG 12 [0076]
  • 7) 0.15% Fenoterol [0077]
  • 0.06% Ipratropium-bromide [0078]
  • 0.10% Soya lecithin [0079]
  • 40.00% TG 11 [0080]
  • 19.69% Propane [0081]
  • 40.00% TG 227 [0082]
  • 8) 0.1% Ipratropium-bromide [0083]
  • 0.1% Soya lecithin [0084]
  • 15.3% Propane [0085]
  • 30.5% TG 11 [0086]
  • 54.0% TG 227 [0087]

Claims (11)

1. Propellent gases characterised in that they contain TG 227, optionally in admixture with one of more propellent gases from the group comprising TG 11, TG 12, TG 114, propane, butane, pentane and DME.
2. Propellent gases according to claim 1, characterised in that they additionally contain at least one surface-active substance.
3. Propellent gases according to claim 2, characterised in that the surface-active substance is a phospholipid, a sorbitan ester with a higher saturated or unsaturated fatty acid or a polyethoxysorbitan ester of a higher, preferably unsaturated fatty acid.
4. Propellent gases according to claim 2, characterised in that the surface-active substance is a lecithin, a polyethoxyethylenesorbitan oleate or sorbitan trioleate.
5. Pharmaceutical preparations for producing powder aerosols based on propellent gases according to claim 1, 2, 3 or 4, characterised in that they contain as active substance a betamimetic, an anticholinergic, a steroid, an antiallergic or a PAF-antagonist or a combination of such compounds.
6. Pharmaceutical preparations according to claim 5, characterised in that the betamimetic used is:
Bambuterol
Bitolterol
Carbuterol
Clenbuterol
Fenoterol
Hexoprenalin
Ibuterol
Pirbuterol
Procaterol
Reproterol
Salbutamol
Salmeterol
Sulfonterol
Terbutalin
Tulobuterol
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.-butylamino)ethanol
1-(4-ethoxycarbonylamino-3-cyano-5-fluorophenyl)-2-(tert.-butylamino)ethanol
the anticholinergic used is:
Ipratropium bromide
Oxitropium bromide
Trospium chloride
Benzilic acid-N-β-fluoroethylnortropine ester methobromide
the steroid used is:
Budesonide
Beclomethasone (or the 17, 21-dipropionate thereof)
Dexamethason-21-isonicotinate
Flunisolide
The antiallergic agent is:
Disodium cromoglycate
Nedocromil
The PAF-antagonist is:
WEB 2086
WEB 2170
WEB 2347.
7. Pharmaceutical preparations according to claim 5, characterised in that the combination of the active substances comprises one of the betamimetics specified in claim 6 and one of the anticholinergics specified in claim 6.
8. Pharmaceutical preparation according to claim 5, characterised in that the combination of the active substances comprises one of the betamimetics specified in claim 6 and disodium chromoglycate.
9. Pharmaceutical preparation according to claim 5,. characterised in that the combination of the active substances contains one of the betamimetics specified in claim 6 and one of the PAF-antagonists specified in claim 6.
10. Pharmaceutical preparation according to claim 5, characterised in that the combination of the active substances comprises disodium chromoglycate and one of the PAF-antagonists specified in claim 6.
11. Process for preparing pharmaceutical preparations according to claims 5 to 10, characterised in that pharmaceutically active substances micronised by conventional methods are suspended in a liquefied propellent gas mixture according to claim 1, 2, 3 or 4, optionally with the addition of surface-active substances.
US10/072,400 1990-01-31 2002-02-06 Propellent gases and their use in pharmaceutical preparations Abandoned US20020071812A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US10/072,400 US20020071812A1 (en) 1990-01-31 2002-02-06 Propellent gases and their use in pharmaceutical preparations
US10/638,987 US20040028618A1 (en) 1990-02-03 2003-08-12 Suspension aerosol formulations of pharmaceutical products
US10/934,611 US7160538B2 (en) 1990-02-03 2004-09-03 Suspension aerosol formulations of pharmaceutical products
US11/553,508 US20070065370A1 (en) 1990-02-03 2006-10-27 Suspension aerosol formulationis of pharmaceutical products
US12/179,785 US20090104127A1 (en) 1990-02-03 2008-07-25 Suspension aerosol formulations of pharmaceutical products
US12/891,076 US20110014134A1 (en) 1990-02-03 2010-09-27 Suspension aerosol formulations of pharmaceutical products

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DEP4003270.1 1990-02-03
DE4003270A DE4003270A1 (en) 1990-02-03 1990-02-03 NEW SPEED GASES AND THEIR USE IN MEDICINE PREPARATIONS
EPPCT/EP91/00178 1991-01-31
PCT/EP1991/000178 WO1991011496A1 (en) 1990-02-03 1991-01-31 Novel vehicle gases and their use in medical preparations
US09/525,431 US6419899B1 (en) 1990-01-31 2000-03-14 Suspension aerosol formulations of pharmaceutical products
US10/072,400 US20020071812A1 (en) 1990-01-31 2002-02-06 Propellent gases and their use in pharmaceutical preparations

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US09/525,431 Division US6419899B1 (en) 1990-01-31 2000-03-14 Suspension aerosol formulations of pharmaceutical products

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/638,987 Continuation US20040028618A1 (en) 1990-02-03 2003-08-12 Suspension aerosol formulations of pharmaceutical products

Publications (1)

Publication Number Publication Date
US20020071812A1 true US20020071812A1 (en) 2002-06-13

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Family Applications (7)

Application Number Title Priority Date Filing Date
US09/525,431 Expired - Fee Related US6419899B1 (en) 1990-01-31 2000-03-14 Suspension aerosol formulations of pharmaceutical products
US10/072,400 Abandoned US20020071812A1 (en) 1990-01-31 2002-02-06 Propellent gases and their use in pharmaceutical preparations
US10/638,987 Abandoned US20040028618A1 (en) 1990-02-03 2003-08-12 Suspension aerosol formulations of pharmaceutical products
US10/934,611 Expired - Lifetime US7160538B2 (en) 1990-02-03 2004-09-03 Suspension aerosol formulations of pharmaceutical products
US11/553,508 Abandoned US20070065370A1 (en) 1990-02-03 2006-10-27 Suspension aerosol formulationis of pharmaceutical products
US12/179,785 Abandoned US20090104127A1 (en) 1990-02-03 2008-07-25 Suspension aerosol formulations of pharmaceutical products
US12/891,076 Abandoned US20110014134A1 (en) 1990-02-03 2010-09-27 Suspension aerosol formulations of pharmaceutical products

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US09/525,431 Expired - Fee Related US6419899B1 (en) 1990-01-31 2000-03-14 Suspension aerosol formulations of pharmaceutical products

Family Applications After (5)

Application Number Title Priority Date Filing Date
US10/638,987 Abandoned US20040028618A1 (en) 1990-02-03 2003-08-12 Suspension aerosol formulations of pharmaceutical products
US10/934,611 Expired - Lifetime US7160538B2 (en) 1990-02-03 2004-09-03 Suspension aerosol formulations of pharmaceutical products
US11/553,508 Abandoned US20070065370A1 (en) 1990-02-03 2006-10-27 Suspension aerosol formulationis of pharmaceutical products
US12/179,785 Abandoned US20090104127A1 (en) 1990-02-03 2008-07-25 Suspension aerosol formulations of pharmaceutical products
US12/891,076 Abandoned US20110014134A1 (en) 1990-02-03 2010-09-27 Suspension aerosol formulations of pharmaceutical products

Country Status (26)

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US (7) US6419899B1 (en)
EP (1) EP0513099B1 (en)
JP (1) JP3497162B2 (en)
KR (1) KR920703034A (en)
AT (1) ATE185587T1 (en)
AU (1) AU656129B2 (en)
CA (1) CA2075060C (en)
CZ (1) CZ285209B6 (en)
DE (2) DE4003270A1 (en)
DK (1) DK0513099T3 (en)
ES (1) ES2139574T3 (en)
FI (1) FI103348B1 (en)
GR (1) GR3032176T3 (en)
HK (1) HK1010737A1 (en)
HR (1) HRP940737B1 (en)
HU (1) HU218664B (en)
IL (1) IL97024A0 (en)
NO (1) NO302420B1 (en)
NZ (1) NZ236974A (en)
PT (1) PT96635B (en)
RU (1) RU2118170C1 (en)
SI (1) SI9110155B (en)
SK (1) SK281440B6 (en)
WO (1) WO1991011496A1 (en)
YU (1) YU48509B (en)
ZA (1) ZA91756B (en)

Cited By (9)

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US20030198600A1 (en) * 1991-12-12 2003-10-23 Glaxo Group Limited Aerosol formulation containing particulate formoterol, propellant and polar cosolvent
US20030223939A1 (en) * 2002-04-17 2003-12-04 Andreas Kordikowski Particulate materials
US6743413B1 (en) 1991-12-18 2004-06-01 3M Company Suspension aerosol formulations
US6932962B1 (en) 1994-12-22 2005-08-23 Astrazeneca Ab Aerosol drug formulations containing hydrofluoroalkanes and alkyl saccharides
US7101534B1 (en) 1991-12-18 2006-09-05 3M Innovative Properties Company Suspension aerosol formulations
US7105152B1 (en) 1991-12-18 2006-09-12 3M Innovative Properties Company Suspension aerosol formulations
US20060239908A1 (en) * 2005-04-23 2006-10-26 Boehringer Ingelheim International Gmbh Compositions for inhalation
US20080287451A1 (en) * 2007-02-11 2008-11-20 Cook Robert O Method of therapeutic administration of DHE to enable rapid relief of migraine while minimizing side effect profile
US8080236B2 (en) 2002-04-17 2011-12-20 Nektar Therapeutics Uk, Ltd Particulate materials

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DE4003270A1 (en) * 1990-02-03 1991-08-08 Boehringer Ingelheim Kg NEW SPEED GASES AND THEIR USE IN MEDICINE PREPARATIONS
DK0553298T3 (en) * 1990-10-18 1995-04-18 Minnesota Mining & Mfg Aerosol formulation comprising beclomethasone 17,21 dipropionate
MX9203481A (en) * 1990-10-18 1992-07-01 Minnesota Mining & Mfg FORMULATIONS.
PT656207E (en) † 1991-06-10 2001-11-30 Schering Corp AEROSOLS FORMULATIONS WITHOUT CHLOROFLUOROCARBONETS
US5221492A (en) * 1991-08-23 1993-06-22 E. I. Du Pont De Nemours And Company Azeotropic mixture of perfluoropropane and dimethyl ether
GB9118830D0 (en) * 1991-09-03 1991-10-16 Minnesota Mining & Mfg Medical aerosol formulations
IL104068A (en) * 1991-12-12 1998-10-30 Glaxo Group Ltd Surfactant-free pharmaceutical aerosol formulation comprising 1,1,1,2-tetrafluoroethane or 1,1,1,2,3,3,3-heptafluoro-n- propane as propellant
US5658549A (en) * 1991-12-12 1997-08-19 Glaxo Group Limited Aerosol formulations containing propellant 134a and fluticasone propionate
US5744123A (en) * 1991-12-12 1998-04-28 Glaxo Group Limited Aerosol formulations containing P134a and particulate medicaments
US5736124A (en) * 1991-12-12 1998-04-07 Glaxo Group Limited Aerosol formulations containing P134a and particulate medicament
JP3280974B2 (en) * 1991-12-12 2002-05-13 グラクソ、グループ、リミテッド Medicine
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