US20110014134A1 - Suspension aerosol formulations of pharmaceutical products - Google Patents
Suspension aerosol formulations of pharmaceutical products Download PDFInfo
- 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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- US
- 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
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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)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Otolaryngology (AREA)
- Pulmonology (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)
- Cosmetics (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Detergent Compositions (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:
- 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.
- Ipratropium bromide
- Oxitropium bromide
- Trospium chloride
- Benzilic acid-N-β-fluoroethylnortropine ester
- methobromide
- Budesonide
- Beclomethasone (or the 17, 21-dipropionate thereof)
- Dexamethason-21-isonicotinate
- Flunisolide
- Disodium cromoglycate
- Nedocromil
- 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.
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 |
---|---|---|---|
DE4003270A DE4003270A1 (en) | 1990-02-03 | 1990-02-03 | NEW SPEED GASES AND THEIR USE IN MEDICINE PREPARATIONS |
DEP4003270.1 | 1990-02-03 | ||
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 |
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 (26)
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) | 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 (2)
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 |
Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4003270A1 (en) * | 1990-02-03 | 1991-08-08 | Boehringer Ingelheim Kg | NEW SPEED GASES AND THEIR USE IN MEDICINE PREPARATIONS |
MX9203481A (en) * | 1990-10-18 | 1992-07-01 | Minnesota Mining & Mfg | FORMULATIONS. |
CA2094266C (en) * | 1990-10-18 | 1999-06-01 | Robert K. Schultz | Aerosol formulations of beclomethasone-17,21-dipropionate |
DK0656206T3 (en) † | 1991-06-10 | 2001-10-08 | Schering Corp | Aerosol formulations without chlorofluorocarbon compounds |
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 |
US5653962A (en) * | 1991-12-12 | 1997-08-05 | 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 |
US5674471A (en) * | 1991-12-12 | 1997-10-07 | Glaxo Group Limited | Aerosol formulations containing P134a and salbutamol |
US5658549A (en) * | 1991-12-12 | 1997-08-19 | Glaxo Group Limited | Aerosol formulations containing propellant 134a and fluticasone propionate |
ES2079210T3 (en) * | 1991-12-12 | 1996-01-01 | Glaxo Group Ltd | PHARMACEUTICAL FORMULATION OF AEROSOL. |
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 |
CA2125666C (en) | 1991-12-12 | 2002-07-16 | Rachel Ann Akehurst | Medicaments |
US7101534B1 (en) | 1991-12-18 | 2006-09-05 | 3M Innovative Properties Company | Suspension aerosol formulations |
US20030103907A1 (en) * | 1991-12-18 | 2003-06-05 | Schultz Robert K. | Suspension aerosol formulations |
AU675633B2 (en) * | 1991-12-18 | 1997-02-13 | Minnesota Mining And Manufacturing Company | Suspension aerosol formulations |
US7105152B1 (en) | 1991-12-18 | 2006-09-12 | 3M Innovative Properties Company | Suspension aerosol formulations |
WO1993019117A1 (en) * | 1992-03-26 | 1993-09-30 | Great Lakes Chemical Corporation | Azeotrope-like compositions of 1,1,1,2,3,3,3-heptafluoropropane and 1,1-difluoroethane |
RO117414B1 (en) * | 1992-12-09 | 2002-03-29 | Jager Paul D Waterbury | Pharmaceutical composition of gas dispersoid in solution |
DE69424181T2 (en) * | 1993-12-20 | 2000-10-19 | Minnesota Mining And Mfg. Co., Saint Paul | FLUNISOLIDE AEROSOL FORMULATIONS |
EP0806940B1 (en) | 1994-12-22 | 2003-04-09 | AstraZeneca AB | Aerosol drug formulations |
US6135628A (en) * | 1995-10-13 | 2000-10-24 | Boehringer Ingelheim Pharmceuticals, Inc. | Method and apparatus for homogenizing aerosol formulations |
US6054488A (en) * | 1996-06-11 | 2000-04-25 | 3M Innovative Properties Company | Medicinal aerosol formulations of formoterol |
US6039932A (en) * | 1996-09-27 | 2000-03-21 | 3M Innovative Properties Company | Medicinal inhalation aerosol formulations containing budesonide |
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US8357352B2 (en) | 2004-07-02 | 2013-01-22 | 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 |
US8518377B2 (en) * | 2006-04-11 | 2013-08-27 | Boehringer Ingelheim Pharma Gbmh Co. Kg | Aerosol suspension formulations with TG 227 ea or TG 134 a as propellant |
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