CA2024916C - Respiratory disorder medicaments comprising salmeterol and fluticasone propionate - Google Patents
Respiratory disorder medicaments comprising salmeterol and fluticasone propionate Download PDFInfo
- Publication number
- CA2024916C CA2024916C CA002024916A CA2024916A CA2024916C CA 2024916 C CA2024916 C CA 2024916C CA 002024916 A CA002024916 A CA 002024916A CA 2024916 A CA2024916 A CA 2024916A CA 2024916 C CA2024916 C CA 2024916C
- Authority
- CA
- Canada
- Prior art keywords
- salmeterol
- fluticasone propionate
- physiologically acceptable
- inhalation
- acceptable salt
- 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
Links
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 title claims abstract description 28
- 208000023504 respiratory system disease Diseases 0.000 title claims abstract description 12
- 229940021597 salmeterol and fluticasone Drugs 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title description 5
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229960004017 salmeterol Drugs 0.000 claims abstract description 29
- 229960000289 fluticasone propionate Drugs 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 21
- 239000000843 powder Substances 0.000 claims description 11
- 229940071648 metered dose inhaler Drugs 0.000 claims description 8
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical class C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 14
- ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 13
- 208000006673 asthma Diseases 0.000 description 13
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 9
- 229940029284 trichlorofluoromethane Drugs 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 7
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 7
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 229940124630 bronchodilator Drugs 0.000 description 6
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 229960002052 salbutamol Drugs 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000003246 corticosteroid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 208000024696 nocturnal asthma Diseases 0.000 description 4
- 230000029058 respiratory gaseous exchange Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 208000005392 Spasm Diseases 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 229950000210 beclometasone dipropionate Drugs 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-M 1-hydroxy-2-naphthoate Chemical compound C1=CC=C2C(O)=C(C([O-])=O)C=CC2=C1 SJJCQDRGABAVBB-UHFFFAOYSA-M 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-M 4-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-M 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000536565 Disteganthus basilateralis Species 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010047924 Wheezing Diseases 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000019406 chloropentafluoroethane Nutrition 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 208000024711 extrinsic asthma Diseases 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 201000010659 intrinsic asthma Diseases 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8920392.1 | 1989-09-08 | ||
| GB898920392A GB8920392D0 (en) | 1989-09-08 | 1989-09-08 | Medicaments |
| GB898923644A GB8923644D0 (en) | 1989-10-20 | 1989-10-20 | Medicaments |
| GB8923644.2 | 1989-10-20 | ||
| SG166294A SG166294G (en) | 1989-09-08 | 1994-11-18 | Inhalation medicaments for treating respiratory disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2024916A1 CA2024916A1 (en) | 1991-03-09 |
| CA2024916C true CA2024916C (en) | 2002-07-09 |
Family
ID=27264677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002024916A Expired - Lifetime CA2024916C (en) | 1989-09-08 | 1990-09-07 | Respiratory disorder medicaments comprising salmeterol and fluticasone propionate |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0416951B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP3042867B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE99941T1 (cg-RX-API-DMAC7.html) |
| BE (1) | BE1003053A3 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2024916C (cg-RX-API-DMAC7.html) |
| CH (1) | CH680983C9 (cg-RX-API-DMAC7.html) |
| DE (2) | DE19975040I2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK0416951T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2062392T3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2651677B1 (cg-RX-API-DMAC7.html) |
| HK (1) | HK18695A (cg-RX-API-DMAC7.html) |
| HU (1) | HU211272A9 (cg-RX-API-DMAC7.html) |
| IE (1) | IE65535B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL95590A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1241996B (cg-RX-API-DMAC7.html) |
| LU (1) | LU90392I2 (cg-RX-API-DMAC7.html) |
| NL (1) | NL990012I2 (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ235221A (cg-RX-API-DMAC7.html) |
| PH (1) | PH27594A (cg-RX-API-DMAC7.html) |
| SG (1) | SG166294G (cg-RX-API-DMAC7.html) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5270305A (en) | 1989-09-08 | 1993-12-14 | 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 |
| HU227519B1 (en) * | 1991-12-18 | 2011-07-28 | Astra Ab | Synergic pharmaceutical composition containing combination of formoterol and budesonide |
| SE9703407D0 (sv) | 1997-09-19 | 1997-09-19 | Astra Ab | New use |
| SE9802073D0 (sv) | 1998-06-11 | 1998-06-11 | Astra Ab | New use |
| NZ511527A (en) | 1998-11-13 | 2002-10-25 | Jago Res A | Dry powder for inhalation |
| GB9903759D0 (en) * | 1999-02-18 | 1999-04-14 | Novartis Ag | Organic compounds |
| GB9904919D0 (en) | 1999-03-03 | 1999-04-28 | Novartis Ag | Organic compounds |
| GB2354007B (en) | 1999-09-11 | 2003-10-22 | Glaxo Group Ltd | Pharmaceutical formulation of fluticasone propionate |
| JP2003518484A (ja) * | 1999-12-24 | 2003-06-10 | グラクソ グループ リミテッド | サルメテロールおよびプロピオン酸フルチカゾンの医薬用エアゾル製剤 |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
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| BRPI0720846A2 (pt) | 2006-12-22 | 2014-03-04 | Almirall Lab | Dispositivo de inalação para fármacos na forma de pó |
| CN101744792B (zh) * | 2008-12-17 | 2013-04-17 | 张凯 | 氟替卡松丙酸酯和沙美特罗昔萘酸酯复方干粉吸入剂及其制备工艺 |
| US8815258B2 (en) | 2009-05-29 | 2014-08-26 | Pearl Therapeutics, Inc. | Compositions, methods and systems for respiratory delivery of two or more active agents |
| KR20170070274A (ko) | 2009-05-29 | 2017-06-21 | 펄 테라퓨틱스 인코포레이티드 | 지속형 무스카린 안타고니스트 및 지속형 ｂ₂아드레날린 수용체 아고니스트의 폐 전달용 조성물, 및 연관된 방법 및 시스템 |
| JP6454323B2 (ja) | 2013-03-15 | 2019-01-16 | パール セラピューティクス，インコーポレイテッド | 粒子状結晶性材料のコンディショニングのための方法及びシステム |
| KR20160003183A (ko) * | 2013-04-29 | 2016-01-08 | 사노피 에스에이 | 흡입식 약학적 조성물 및 그를 포함하는 흡입기 장치 |
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|---|---|---|---|---|
| GB2107715B (en) * | 1981-10-19 | 1985-11-13 | Glaxo Group Ltd | Micronised beclomethasone dipropionate monohydrate and powder inhalation compositions containing it |
| ZW6584A1 (en) * | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| FR2588474B1 (fr) * | 1985-10-16 | 1987-11-27 | Cird | Compositions synergetiques anti-inflammatoires a base d'un corticosteroide et d'un beta agoniste |
-
1990
- 1990-09-05 IL IL9559090A patent/IL95590A/en not_active IP Right Cessation
- 1990-09-07 DK DK90309846.5T patent/DK0416951T3/da active
- 1990-09-07 DE DE1990605951 patent/DE19975040I2/de active Active
- 1990-09-07 NZ NZ235221A patent/NZ235221A/en unknown
- 1990-09-07 DE DE69005951T patent/DE69005951T2/de not_active Expired - Lifetime
- 1990-09-07 ES ES90309846T patent/ES2062392T3/es not_active Expired - Lifetime
- 1990-09-07 EP EP90309846A patent/EP0416951B1/en not_active Expired - Lifetime
- 1990-09-07 BE BE9000862A patent/BE1003053A3/fr not_active IP Right Cessation
- 1990-09-07 AT AT90309846T patent/ATE99941T1/de active
- 1990-09-07 IE IE325690A patent/IE65535B1/en not_active IP Right Cessation
- 1990-09-07 JP JP2235997A patent/JP3042867B2/ja not_active Expired - Lifetime
- 1990-09-07 PH PH41153A patent/PH27594A/en unknown
- 1990-09-07 CA CA002024916A patent/CA2024916C/en not_active Expired - Lifetime
- 1990-09-07 IT IT48260A patent/IT1241996B/it active Protection Beyond IP Right Term
- 1990-09-07 FR FR909011142A patent/FR2651677B1/fr not_active Expired - Lifetime
- 1990-09-07 CH CH2906/90A patent/CH680983C9/de not_active IP Right Cessation
-
1994
- 1994-11-18 SG SG166294A patent/SG166294G/en unknown
-
1995
- 1995-02-09 HK HK18695A patent/HK18695A/xx not_active IP Right Cessation
- 1995-06-02 HU HU95P/P00150P patent/HU211272A9/hu unknown
-
1999
- 1999-04-14 NL NL990012C patent/NL990012I2/nl unknown
- 1999-04-26 LU LU90392C patent/LU90392I2/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL990012I2 (nl) | 1999-09-01 |
| CA2024916A1 (en) | 1991-03-09 |
| BE1003053A3 (fr) | 1991-11-05 |
| NZ235221A (en) | 1992-11-25 |
| FR2651677A1 (fr) | 1991-03-15 |
| JPH03167120A (ja) | 1991-07-19 |
| IE903256A1 (en) | 1991-03-13 |
| DE19975040I2 (de) | 2006-07-13 |
| DK0416951T3 (da) | 1994-02-14 |
| IL95590A0 (en) | 1991-09-16 |
| CH680983C1 (cg-RX-API-DMAC7.html) | 2008-06-25 |
| DE69005951D1 (de) | 1994-02-24 |
| HK18695A (en) | 1995-02-17 |
| ATE99941T1 (de) | 1994-01-15 |
| EP0416951A1 (en) | 1991-03-13 |
| EP0416951B1 (en) | 1994-01-12 |
| IL95590A (en) | 1996-06-18 |
| ES2062392T3 (es) | 1994-12-16 |
| IT9048260A1 (it) | 1992-03-07 |
| IT9048260A0 (it) | 1990-09-07 |
| HU211272A9 (en) | 1995-11-28 |
| LU90392I2 (fr) | 1999-06-28 |
| NL990012I1 (nl) | 1999-07-01 |
| DE69005951T2 (de) | 1994-05-26 |
| FR2651677B1 (fr) | 1993-08-06 |
| PH27594A (en) | 1993-08-31 |
| JP3042867B2 (ja) | 2000-05-22 |
| IT1241996B (it) | 1994-02-02 |
| IE65535B1 (en) | 1995-11-01 |
| CH680983C9 (cg-RX-API-DMAC7.html) | 2008-08-15 |
| SG166294G (en) | 1995-06-16 |
| CH680983A5 (cg-RX-API-DMAC7.html) | 1992-12-31 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKEX | Expiry |