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US20110014134A1 - Suspension aerosol formulations of pharmaceutical products - Google Patents

Suspension aerosol formulations of pharmaceutical products Download PDF

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Publication number
US20110014134A1
US20110014134A1 US12/891,076 US89107610A US2011014134A1 US 20110014134 A1 US20110014134 A1 US 20110014134A1 US 89107610 A US89107610 A US 89107610A US 2011014134 A1 US2011014134 A1 US 2011014134A1
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United States
Prior art keywords
group
methyl
propellent gases
propellent
active substance
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.)
Abandoned
Application number
US12/891,076
Inventor
Hans-Hermann Weil
Ottfried Daab
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.)
Boehringer Ingelheim GmbH
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Boehringer Ingelheim GmbH
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Filing date
Publication date
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Application filed by Boehringer Ingelheim GmbH filed Critical Boehringer Ingelheim GmbH
Priority to US12/891,076 priority Critical patent/US20110014134A1/en
Publication of US20110014134A1 publication Critical patent/US20110014134A1/en
Abandoned 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
    • 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 1,1,1,3,3,3,3-heptafluoropropane (TG 227), the use of these propellent gases in pharmaceutical preparations suitable for producing aerosols, and these pharmaceutical preparations themselves.
  • TG 227 1,1,1,3,3,3,3-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 atomizing 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 TG114 (1, 2-dichloro-1,1,2,2-tetrafluoroehane), optionally with the addition of lower alkanes such as butane or pentane, or with the addition of DME (dimethylether). Mixtures of this kind are knows 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 (dichlorodifluoromethane), 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 propellent 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 phospholipids (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 a acid.
  • the adjuvant may be present in the mixture in dissolved or undissolved form.
  • 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.
  • the ratios of quantities of the individual ingredients of the propellent gas mixtures 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 RG and/or TG 11 and/or TG 12 and/or 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 to 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, 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 anti-allergies.

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

Abstract

Pharmaceutical preparations for producing powder aerosols using propellant gases which use TG 227, and possibly also TG 11, TG 12, TGH 114, propane, butane, pentane or DME.

Description

  • The invention relates to new propellent gases which contain as a typical ingredient 1,1,1,3,3,3,3-heptafluoropropane (TG 227), the use of these propellent gases in pharmaceutical preparations suitable for producing aerosols, and these pharmaceutical preparations themselves.
  • 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 atomizing 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 TG114 (1, 2-dichloro-1,1,2,2-tetrafluoroehane), optionally with the addition of lower alkanes such as butane or pentane, or with the addition of DME (dimethylether). Mixtures of this kind are knows for example from German Patent 1178975.
  • 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.
  • 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.
  • 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 (dichlorodifluoromethane), 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 propellent 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 phospholipids (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 a 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.
  • The ratios of quantities of the individual ingredients of the propellent gas mixtures 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 RG and/or TG 11 and/or TG 12 and/or 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 to 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, steroids, antiallergics, PAF-antagonists and combinations of these active substances.
  • The following are given as specific examples:
    • EXAMPLES OF BETAMIMETICS
  • 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-ter.-butylamino) ethanol
  • 1-(4-ethoxyc arbonylamino-3-cyano-5-fluorophenyl-2-(tert.-butylamino)ethanol.
    • Examples of Anticholinergics:
  • Ipratropium bromide
  • Oxitropium bromide
  • Trospium chloride
  • Benzilic acid-N-β-fluoroethylnortropine ester
  • methobromide
    • Examples of Steroids:
  • Budesonide
  • Beclomethasone (or the 17, 21-dipropionate thereof)
  • Dexamethason-21-isonicotinate
  • Flunisolide
    • Examples of Anti-Allergies:
  • Disodium cromoglycate
  • Nedocromil
    • Examples of PAF-Antagonists:
  • 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.
  • 3-(Morpholin-4-yl-carbonyl)-5-(2-chlorphenyl)-10-methyl-7H-cyclopental[4.5]thieno-[3.2-f][1.2.4]triazolo [4.3-a][1.4]diazepine
  • 3-(Di-n-propylamincarbonyl)-5-(2-chlorphenyl)-10-methyl-7H-cyc lopental [4.5]thieno-[3.2-f][1.2.4]triazolo [4.3-a][1.4]diazepine
  • The active substances may also be combined, e.g., betamimetics plus anticholinergics or betamimetics plus anti-allergies.
  • Examples of preparations according to the invention (amounts given in percent by weight):
  •
    1) 0.10% Oxitropium bromide 2) 0.3% Fenoterol
    0.01% Soya lecithin 0.1% Soyalecithin
    4.0% Pentane 10.0% Pentane
    95.89% TG 227 70.0% TG 227
    19.6% TG 134a
    3) 0.1% Ipratropium bromide 4) 0.3% Fenoterol
    0.1% Soya lecithin 0.1% Soya lecithin
    20.0% Pentane 30.0% TG 11
    20.0% Butane 69.6% TG 227
    49.8% TG 11
    5) 1.5% Disodium cromoglicate 6) 0.3% Salbutamol
    0.1% Tween 20 0.2% Span 85
    98.4% TG 227 20.0% Pentane
    1.4% Butane 60.0% TG 227
    19.5% TG 12
    7) 0.15% Fenoterol 8) 0.1% Ipratropium bromide
    0.06% Ipratropium bromide 0.1% Soya lecithin
    0.10% Soya lecithin 15.3% Propane
    40.00% TG 11 30.5% TG 11
    19.69% Propane 54.0% TG 227
    40.00% TG 227

Claims (7)

1. Propellent gases characterised in that they contain TG 227, in admixture with one or 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 prospholipid, 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 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 selected from the group consisting of 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, and 1-(4-ethoxycarbonylamino-3-cyano-5-fluorophenyl)-2-(tert.-butylamino)ethanol;
the anticholinergic used is selected from the group consisting of Ipratropium bromide, Oxitropium bromide, Trospium chloride, Benzilic acid-N-β-fluoroethylnortropine ester, and methobromide;
The steroid used is selected from the group consisting Budesonide, Beclomethasone or the 17, 21-dipropionate thereof, Dexamethason-21-isonicotinate, and Flunisolide;
the antiallergic agent is selected from the group consisting of Disodium cromoglycate and Nedocromil; and
the PAF-antagonist is selected from the group consisting of 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, 3-(Morpholin-4-yl-carbonyl)-5-(2-chlorphenyl)-10-methyl-7H-cyclopental[4.5]thieno-[3.2-f][1.2.4]triazolo[4.3-a][1.4]diazepine, and 3-(Di-n-propylamincarbonyl)-5-(2-chlorphenyl)-10-methyl-7H-cyclopental[4.5]thieno-[3.2-f][1.2.4]triazolo[4.3-a][1.4]diazepine.
7. Process for preparing pharmaceutical preparations according to claim 5, characterised in that pharmaceutically active substances micronised by conventional methods are suspended in a liquefied propellent gas mixture optionally with the addition of surface-active substances.
US12/891,076 1990-02-03 2010-09-27 Suspension aerosol formulations of pharmaceutical products Abandoned US20110014134A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/891,076 US20110014134A1 (en) 1990-02-03 2010-09-27 Suspension aerosol formulations of pharmaceutical products

Applications Claiming Priority (15)

Application Number Priority Date Filing Date Title
EPPCT/EP91/00178 1990-01-31
DE4003270A DE4003270A1 (en) 1990-02-03 1990-02-03 NEW SPEED GASES AND THEIR USE IN MEDICINE PREPARATIONS
DEP4003270.1 1990-02-03
PCT/EP1991/000178 WO1991011496A1 (en) 1990-02-03 1991-01-31 Novel vehicle gases and their use in medical preparations
US91035392A 1992-10-01 1992-10-01
US28240294A 1994-07-28 1994-07-28
US59723096A 1996-02-06 1996-02-06
US99025297A 1997-12-15 1997-12-15
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
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

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US12/179,785 Continuation US20090104127A1 (en) 1990-02-03 2008-07-25 Suspension aerosol formulations of pharmaceutical products

Publications (1)

Publication Number Publication Date
US20110014134A1 true US20110014134A1 (en) 2011-01-20

Family

ID=6399399

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 (6)

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

Country Status (25)

Country Link
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) FI103348B (en)
GR (1) GR3032176T3 (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 (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060002863A1 (en) * 2004-07-02 2006-01-05 Boehringer Ingelheim International Gmbh Aerosol suspension formulations containing TG 227 ea or TG 134 a as propellant
US20090092559A1 (en) * 2006-04-11 2009-04-09 Boehringer Ingelheim Pharma Gbmh Co. Kg Aerosol suspension formulations with TG 227 ea or TG 134 a as propellant

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AU658854B2 (en) * 1990-10-18 1995-05-04 Minnesota Mining And Manufacturing Company Aerosol formulation comprising beclomethasone 17,21 dipropionate
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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
US5674471A (en) * 1991-12-12 1997-10-07 Glaxo Group Limited Aerosol formulations containing P134a and salbutamol
EP0616524B1 (en) 1991-12-12 1998-10-07 Glaxo Group Limited Medicaments
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
US5916540A (en) 1994-10-24 1999-06-29 Glaxo Group Limited Aerosol formulations containing P134A and/or P227 and particulate medicament
US5683676A (en) * 1991-12-12 1997-11-04 Glaxo Group Limited Canister containing aerosol formulations containing P134a and particulate medicaments
NZ246046A (en) * 1991-12-12 1995-12-21 Glaxo Group Ltd Aerosol comprising a particulate medicament in a fluorocarbon or chlorofluorohydrocarbon and a polar cosolvent
US5736124A (en) * 1991-12-12 1998-04-07 Glaxo Group Limited Aerosol formulations containing P134a and particulate medicament
US7101534B1 (en) 1991-12-18 2006-09-05 3M Innovative Properties Company Suspension aerosol formulations
ATE204743T1 (en) 1991-12-18 2001-09-15 Minnesota Mining & Mfg AEROSOL COMPOSITIONS FOR MEDICINAL SUSPENSIONS
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US7105152B1 (en) 1991-12-18 2006-09-12 3M Innovative Properties Company Suspension aerosol formulations
AU3936293A (en) * 1992-03-26 1993-10-21 Great Lakes Chemical Corporation Azeotrope-like compositions of 1,1,1,2,3,3,3-heptafluoropropane and 1,1-difluoroethane
SG52459A1 (en) * 1992-12-09 1998-09-28 Boehringer Ingelheim Pharma Stabilized medicinal aerosol solution formulations
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