CA2563302C - Combinations of glycopyrrolate and beta2 adrenoceptor agonists - Google Patents
Combinations of glycopyrrolate and beta2 adrenoceptor agonists Download PDFInfo
- Publication number
- CA2563302C CA2563302C CA2563302A CA2563302A CA2563302C CA 2563302 C CA2563302 C CA 2563302C CA 2563302 A CA2563302 A CA 2563302A CA 2563302 A CA2563302 A CA 2563302A CA 2563302 C CA2563302 C CA 2563302C
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- clo
- alkyl
- glycopyrrolate
- medicament
- 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
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 title claims abstract description 23
- 229940015042 glycopyrrolate Drugs 0.000 title claims abstract description 21
- 239000000556 agonist Substances 0.000 title description 5
- 102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 title description 4
- 108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 title description 4
- 239000003814 drug Substances 0.000 claims abstract description 51
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 150000003839 salts Chemical group 0.000 claims abstract description 14
- 239000012453 solvate Chemical group 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- -1 cyclopentyl-hydroxyphenylacetyl Chemical group 0.000 claims description 20
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 14
- 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 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 12
- 239000008101 lactose Substances 0.000 claims description 12
- IREJFXIHXRZFER-PCBAQXHCSA-N indacaterol maleate Chemical compound OC(=O)\C=C/C(O)=O.N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 IREJFXIHXRZFER-PCBAQXHCSA-N 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 8
- 239000002552 dosage form Substances 0.000 claims description 7
- 235000019359 magnesium stearate Nutrition 0.000 claims description 7
- 238000002648 combination therapy Methods 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 2
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 2
- 229960004436 budesonide Drugs 0.000 claims description 2
- 229960003728 ciclesonide Drugs 0.000 claims description 2
- 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 claims description 2
- 229960000289 fluticasone propionate Drugs 0.000 claims description 2
- QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960002744 mometasone furoate Drugs 0.000 claims description 2
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 51
- 230000002757 inflammatory effect Effects 0.000 abstract description 15
- 208000027771 Obstructive airways disease Diseases 0.000 abstract description 12
- 208000027866 inflammatory disease Diseases 0.000 abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 239000000443 aerosol Substances 0.000 description 24
- 125000005843 halogen group Chemical group 0.000 description 20
- 208000006673 asthma Diseases 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- 239000003380 propellant Substances 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 239000002775 capsule Substances 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- 229960001375 lactose Drugs 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000006199 nebulizer Substances 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 4
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 4
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000004067 bulking agent Substances 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229960001021 lactose monohydrate Drugs 0.000 description 4
- 229940071648 metered dose inhaler Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000000414 obstructive effect Effects 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 206010047924 Wheezing Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 150000003842 bromide salts Chemical class 0.000 description 3
- 230000003182 bronchodilatating effect Effects 0.000 description 3
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 150000003431 steroids Chemical class 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
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- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/402—1-aryl substituted, e.g. piretanide
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Compositions Of Oxide Ceramics (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0411056.5A GB0411056D0 (en) | 2004-05-18 | 2004-05-18 | Organic compounds |
| GB0411056.5 | 2004-05-18 | ||
| PCT/EP2005/005354 WO2005110402A1 (en) | 2004-05-18 | 2005-05-17 | Combinations of glycopyrrolate and beta2 adrenoceptor agonists |
Publications (2)
| Publication Number | Publication Date |
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| CA2563302A1 CA2563302A1 (en) | 2005-11-24 |
| CA2563302C true CA2563302C (en) | 2012-08-28 |
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| CA2563302A Expired - Lifetime CA2563302C (en) | 2004-05-18 | 2005-05-17 | Combinations of glycopyrrolate and beta2 adrenoceptor agonists |
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Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| HRP20160373T1 (hr) * | 2005-03-16 | 2016-05-06 | Meda Pharma Gmbh & Co. Kg | Kombinacija antikolinergika i antagonista leukotrien receptora za liječenje bolesti dišnog sustava |
| CA2607391A1 (en) * | 2005-04-23 | 2006-11-02 | Boehringer Ingelheim International Gmbh | Combination of medicaments to be inhaled, containing a betamimetic agent and a steroid in addition to an anticholinergic agent |
| GB0511065D0 (en) * | 2005-05-31 | 2005-07-06 | Novartis Ag | Organic compounds |
| GB0523655D0 (en) * | 2005-11-21 | 2005-12-28 | Novartis Ag | Organic compounds |
| GB0523656D0 (en) * | 2005-11-21 | 2005-12-28 | Novartis Ag | Organic compounds |
| EP1878722A1 (en) * | 2006-07-13 | 2008-01-16 | Novartis AG | Quinolinone derivatives and their pharmaceutical compositions |
| CN101479245B (zh) | 2006-06-30 | 2013-05-22 | 诺瓦提斯公司 | 喹啉酮衍生物和其药物组合物 |
| EP1938822A1 (en) * | 2006-12-21 | 2008-07-02 | Novartis AG | Combination therapy for the treatment of airways disease |
| CN107669664B (zh) | 2009-05-29 | 2020-07-10 | 珍珠治疗公司 | 经呼吸递送活性剂的组合物及相关方法和系统 |
| US8815258B2 (en) | 2009-05-29 | 2014-08-26 | Pearl Therapeutics, Inc. | Compositions, methods and systems for respiratory delivery of two or more active agents |
| EP2440196A4 (en) * | 2009-06-09 | 2013-01-02 | Elevation Pharmaceuticals Inc | TREATMENT OF CHRONIC OBSTRUCTIVE PULMONARY DISEASE BY ADMINISTRATION OF BETA 2 NEBULIZED AGONIST OR A COMBINATION OF BETA 2 NEBULIZED AGONIST AND ANTICHOLINERGIC |
| RU2561052C2 (ru) | 2009-12-23 | 2015-08-20 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Комбинированное лечение хронического обструктивного заболевания легких |
| PH12012501066A1 (en) | 2009-12-23 | 2016-03-02 | Chiesi Farm Spa | Combination therapy for copd |
| WO2012110770A2 (en) | 2011-02-17 | 2012-08-23 | Cipla Limited | Pharmaceutical composition |
| KR101317924B1 (ko) * | 2011-05-17 | 2013-10-16 | 김동진 | 글리코피롤레이트의 합성방법 및 이 활성성분을 함유하는 약학적 조성물의 제조방법 |
| WO2014007766A1 (en) | 2012-07-05 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Dry powder inhalers comprising a carrier other than lactose |
| WO2014007767A1 (en) | 2012-07-05 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Dry powder inhalers comprising a carrier other than lactose and a ternary component |
| KR101460694B1 (ko) * | 2012-09-07 | 2014-11-11 | 성광제약주식회사 | 글리코피롤레이트의 신규 합성방법 및 이 활성성분을 함유하는 약학적 조성물 |
| CN103784401A (zh) * | 2012-10-29 | 2014-05-14 | 北京市丰硕维康技术开发有限责任公司 | 一种治疗呼吸道疾病的溶液型定量吸入气雾剂及制备方法 |
| KR20160081989A (ko) | 2013-02-28 | 2016-07-08 | 더미라, 인코포레이티드 | 글리코피롤레이트 염 |
| US8558008B2 (en) | 2013-02-28 | 2013-10-15 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
| US9006462B2 (en) | 2013-02-28 | 2015-04-14 | Dermira, Inc. | Glycopyrrolate salts |
| 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 |
| WO2015101576A1 (en) | 2013-12-30 | 2015-07-09 | Chiesi Farmaceutici S.P.A. | Stable pressurised aerosol solution composition of glycopyrronium bromide and formoterol combination |
| EP3191081B1 (en) | 2014-09-09 | 2020-03-25 | Vectura Limited | Formulation comprising glycopyrrolate, method and apparatus |
| KR20180128450A (ko) * | 2016-04-11 | 2018-12-03 | 수벤 라이프 사이언시스 리미티드 | 글리코피롤레이트의 국소 스프레이 포뮬레이션 |
| US10098837B2 (en) | 2016-07-28 | 2018-10-16 | Chiesi Farmaceutici S.P.A. | Combination therapy for COPD |
| WO2020217143A1 (en) * | 2019-04-23 | 2020-10-29 | Glenmark Pharmaceutical Limited | Inhalable dry powder composition comprising gly copyrronium, indacaterol and fluticasone |
| US20200375945A1 (en) * | 2019-06-03 | 2020-12-03 | Cai Gu Huang | Inhalable formulation of a solution containing indacaterol maleate and glycopyrronium bromide |
| PH12022551243A1 (en) | 2019-12-02 | 2023-09-11 | Chiesi Farm Spa | Stainles steel can for pressurised metered dose inhalers |
Family Cites Families (188)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956062A (en) | 1959-02-26 | 1960-10-11 | Robins Co Inc A H | Esters of amino alcohols |
| US6204261B1 (en) | 1995-12-20 | 2001-03-20 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β Converting enzyme inhibitors |
| GB1219606A (en) | 1968-07-15 | 1971-01-20 | Rech S Et D Applic Scient Soge | Quinuclidinol derivatives and preparation thereof |
| IT1016489B (it) | 1974-03-18 | 1977-05-30 | Isf Spa | Inalatore |
| JPS6235216A (ja) | 1985-08-09 | 1987-02-16 | Noritoshi Nakabachi | 不均質物質層の層厚非破壊測定方法および装置 |
| GB8916480D0 (en) | 1989-07-19 | 1989-09-06 | Glaxo Group Ltd | Chemical process |
| GB8923590D0 (en) | 1989-10-19 | 1989-12-06 | Pfizer Ltd | Antimuscarinic bronchodilators |
| US5416013A (en) | 1990-04-04 | 1995-05-16 | Sterling Winthrop Inc. | Interleukin 1β protease and interleukin 1β protease inhibitors |
| PT100441A (pt) | 1991-05-02 | 1993-09-30 | Smithkline Beecham Corp | Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso |
| US5451700A (en) | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
| CA2071674C (en) | 1991-06-21 | 2003-08-19 | Kevin T. Chapman | Peptidyl derivatives as inhibitors of interleukin-1.beta. converting enzyme |
| WO1993005071A1 (en) | 1991-08-30 | 1993-03-18 | Sterling Winthrop Inc. | INTERLEUKIN 1β PROTEASE AND INTERLEUKIN 1β PROTEASE INHIBITORS |
| EP0547699A1 (en) | 1991-12-19 | 1993-06-23 | Merck & Co. Inc. | Peptidyl derivatives as inhibitors of interleukin-1B converting enzyme |
| WO1993014777A1 (en) | 1992-01-31 | 1993-08-05 | Merck & Co., Inc. | PEPTIDYL DERIVATIVES AS INHIBITORS OF INTERLEUKIN-1β CONVERTING ENZYME |
| EP0627926B1 (en) | 1992-02-21 | 1998-08-05 | Merck & Co., Inc. (a New Jersey corp.) | PEPTIDYL DERIVATIVES AS INHIBITORS OF INTERLEUKIN-1$g(b) CONVERTING ENZYME |
| WO1993018007A1 (en) | 1992-03-13 | 1993-09-16 | Tokyo Tanabe Company Limited | Novel carbostyril derivative |
| WO1993019749A1 (en) | 1992-04-02 | 1993-10-14 | Smithkline Beecham Corporation | Compounds useful for treating allergic and inflammatory diseases |
| MX9301942A (es) | 1992-04-02 | 1994-08-31 | Smithkline Beecham Corp | Derivados de ciclohexan-ilideno novedosos. |
| WO1993019750A1 (en) | 1992-04-02 | 1993-10-14 | Smithkline Beecham Corporation | Compounds useful for treating allergic or inflammatory diseases |
| JPH08500242A (ja) | 1992-06-24 | 1996-01-16 | メルク エンド カンパニー インコーポレーテッド | インターロイキン１β前駆体の転換酵素をコードするＤＮＡ |
| WO1994003480A1 (en) | 1992-07-31 | 1994-02-17 | Pfizer Inc. | Peptidyl 4-amino-2,2-difluoro-3-oxo-1,6-hexanedioic acid derivatives as antiinflammatory agents |
| US5395958A (en) | 1992-09-30 | 1995-03-07 | Mitsubishi Kasei Corporation | Cyclopropene derivatives |
| CA2109646C (en) | 1992-11-24 | 2000-03-07 | Gaston O. Daumy | Para-nitroanilide peptides |
| GB9301000D0 (en) | 1993-01-20 | 1993-03-10 | Glaxo Group Ltd | Chemical compounds |
| US5656600A (en) | 1993-03-25 | 1997-08-12 | Corvas International, Inc. | α-ketoamide derivatives as inhibitors of thrombosis |
| US5411985A (en) | 1993-05-17 | 1995-05-02 | Merck & Co., Inc. | Gamma-pyrone-3-acetic acid as an inhibitor or interleukin-1 β inventory enzyme |
| JPH0789951A (ja) | 1993-06-03 | 1995-04-04 | Sterling Winthrop Inc | インターロイキン−１β転換酵素阻害剤 |
| ES2122145T3 (es) | 1993-06-04 | 1998-12-16 | Vertex Pharma | Fosfiniloximetil-cetonas peptidicas como inhibidores de la enzima convertida de la interleuquina-1 beta. |
| ES2114654T3 (es) | 1993-06-08 | 1998-06-01 | Vertex Pharma | Piridazinas como inhibidores de la enzima de conversion de la interleuquina-1beta. |
| DE4326959C2 (de) | 1993-08-12 | 1995-07-06 | Henkel Kgaa | Verwendung von Fettsäure-N-alkylpolyhydroxyalkylamiden |
| US6596260B1 (en) | 1993-08-27 | 2003-07-22 | Novartis Corporation | Aerosol container and a method for storage and administration of a predetermined amount of a pharmaceutically active aerosol |
| US5716929A (en) | 1994-06-17 | 1998-02-10 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
| US5756466A (en) | 1994-06-17 | 1998-05-26 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
| GB9414193D0 (en) | 1994-07-14 | 1994-08-31 | Glaxo Group Ltd | Compounds |
| GB9414208D0 (en) | 1994-07-14 | 1994-08-31 | Glaxo Group Ltd | Compounds |
| US5565430A (en) | 1994-08-02 | 1996-10-15 | Sterling Winthrop Inc. | Azaaspartic acid analogs as interleukin-1β converting enzyme inhibitors |
| CA2392466C (en) | 1995-12-07 | 2004-05-04 | Jago Research Ag | Inhaler for multiple dosed administration of a pharmacological dry powder |
| US5843904A (en) | 1995-12-20 | 1998-12-01 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1βconverting enzyme |
| WO1998011109A1 (en) | 1996-09-12 | 1998-03-19 | Idun Pharmaceuticals, Incorporated | Novel tricyclic compounds for the inhibition of the ice/ced-3 protease family of enzymes |
| EP0929311B8 (en) | 1996-09-12 | 2006-02-01 | Idun Pharmaceuticals, Inc. | INHIBITION OF APOPTOSIS USING INTERLEUKIN-1 beta-CONVERTING ENZYME (ICE)/CED-3 FAMILY INHIBITORS |
| AU739321B2 (en) | 1996-09-12 | 2001-10-11 | Idun Pharmaceuticals, Incorporated | C-terminal modified (N-substituted)-2-indolyl dipeptides as inhibitors of the ICE/ced-3 family of cysteine proteases |
| US6610683B2 (en) | 1996-09-12 | 2003-08-26 | Idun Pharmaceuticals, Inc. | Treatment of infectious disease using interleukin-1β-converting enzyme (ICE)/CED-3 family inhibitors |
| GB9622386D0 (en) | 1996-10-28 | 1997-01-08 | Sandoz Ltd | Organic compounds |
| US6613795B2 (en) * | 1996-11-11 | 2003-09-02 | Christian Noe | Enantiomerically pure basic arylcycloalkylhydroxycarboxylic esters, processes for their preparation and their use in medicaments |
| AU745331B2 (en) * | 1996-11-11 | 2002-03-21 | Meda Pharma Gmbh & Co. Kg | Pure enantiomer basic aryl-cycloalkyl-hydroxycarboxylic acid esters, process for preparing the same and their use in medicaments |
| TW528755B (en) | 1996-12-24 | 2003-04-21 | Glaxo Group Ltd | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| IL131815A0 (en) | 1997-03-18 | 2001-03-19 | Basf Ag | Methods and compositions for modulating responsiveness to corticosteroids |
| US6054487A (en) | 1997-03-18 | 2000-04-25 | Basf Aktiengesellschaft | Methods and compositions for modulating responsiveness to corticosteroids |
| AR016384A1 (es) | 1997-07-30 | 2001-07-04 | Smithkline Beecham Corp | Inhibidores de caspasas, composiciones farmaceuticas que comprenden dichos inhibidores de caspasas y uso de los inhibidores de caspasas para prepararun medicamento util para el tratamiento de apoptosis y desordenes asociados con excesiva actividad de la convertosa il-1 beta. |
| AU9281298A (en) | 1997-10-01 | 1999-04-23 | Kyowa Hakko Kogyo Co. Ltd. | Benzodioxole derivatives |
| GB9723590D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723566D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723589D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| YU44900A (sh) | 1998-01-31 | 2003-01-31 | Glaxo Group Limited | Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola |
| PE20000270A1 (es) | 1998-02-14 | 2000-05-20 | Glaxo Group Ltd | Derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol |
| DE69939689D1 (de) | 1998-03-19 | 2008-11-20 | Vertex Pharma | Caspase inhibitoren |
| US6362371B1 (en) | 1998-06-08 | 2002-03-26 | Advanced Medicine, Inc. | β2- adrenergic receptor agonists |
| AR019322A1 (es) | 1998-06-18 | 2002-02-13 | Smithkline Beecham Corp | Derivados de sulfonilo sustituido por heterociclo-etanodionanilina sustituida por heterociclo, composicion farmaceutica que los contiene y su uso para lamanufactura de un medicamento |
| GB9813535D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| BR9911482A (pt) | 1998-06-23 | 2002-01-22 | Glaxo Group Ltd | Composto, composição farmacêutica, uso do composto, e, processos para o tratamento ou profilaxia de doenças inflamatórias, e para a preparação de um composto |
| GB9813540D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| GB9813565D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| AU8180398A (en) | 1998-06-30 | 2000-01-17 | Dow Global Technologies Inc. | Polymer polyols and a process for the production thereof |
| EP1100465B1 (de) | 1998-07-24 | 2004-11-24 | Jago Research Ag | Medizinische aerosolformulierungen |
| ES2264826T3 (es) | 1998-10-16 | 2007-01-16 | Pfizer Inc. | Derivados de adenina. |
| EP1283036B2 (de) * | 1998-11-13 | 2020-01-01 | Jagotec AG | Multidosis-Trockenpulverinhalator mit Pulverreservoir |
| GB9902689D0 (en) | 1999-02-08 | 1999-03-31 | Novartis Ag | Organic compounds |
| DE19921693A1 (de) | 1999-05-12 | 2000-11-16 | Boehringer Ingelheim Pharma | Neuartige Arzneimittelkompositionen auf der Basis von anticholinergisch wirksamen Verbindungen und ß-Mimetika |
| GB9913083D0 (en) * | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| YU25500A (sh) | 1999-05-11 | 2003-08-29 | Pfizer Products Inc. | Postupak za sintezu analoga nukleozida |
| US20040002548A1 (en) | 1999-05-12 | 2004-01-01 | Boehringer Ingelheim Pharma Kg | Medicament compositions containing anticholinergically-effective compounds and betamimetics |
| US6683115B2 (en) | 1999-06-02 | 2004-01-27 | Theravance, Inc. | β2-adrenergic receptor agonists |
| GB9913932D0 (en) | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
| US6322771B1 (en) | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
| TR200909479T2 (tr) | 1999-08-21 | 2012-02-21 | Nycomed Gmbh | Sinerjistik kombinasyon. |
| WO2001019373A2 (en) | 1999-09-17 | 2001-03-22 | Basf Aktiengesellschaft | Methods and compositions for modulating responsiveness to corticosteroids |
| CO5180581A1 (es) | 1999-09-30 | 2002-07-30 | Pfizer Prod Inc | Compuestos para el tratamiento de la isquemia ciones farmaceuticas que los contienen para el tratamiento de la isquemia |
| GB9924361D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Ltd | Purine derivatives |
| GB9924363D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Central Res | Purine derivatives |
| OA11558A (en) | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
| GB0003960D0 (en) | 2000-02-18 | 2000-04-12 | Pfizer Ltd | Purine derivatives |
| US6369115B1 (en) | 2000-03-20 | 2002-04-09 | Dura Pharmaceuticals, Inc. | Stabilized powder formulations |
| GB0008660D0 (en) | 2000-04-07 | 2000-05-31 | Arakis Ltd | The treatment of respiratory diseases |
| HUP0300832A2 (hu) | 2000-04-27 | 2003-08-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Új, lassú hatású bétamimetikumok, eljárás előállításukra és alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények |
| TWI227240B (en) | 2000-06-06 | 2005-02-01 | Pfizer | 2-aminocarbonyl-9H-purine derivatives |
| GB0015727D0 (en) | 2000-06-27 | 2000-08-16 | Pfizer Ltd | Purine derivatives |
| US6916828B2 (en) | 2000-06-27 | 2005-07-12 | Laboratorios S.A.L.V.A.T., S.A. | Carbamates derivatived from arylakylamines |
| GB0015876D0 (en) | 2000-06-28 | 2000-08-23 | Novartis Ag | Organic compounds |
| DE10038639A1 (de) | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| WO2002012266A1 (en) | 2000-08-05 | 2002-02-14 | Glaxo Group Limited | 17.beta.-carbothioate 17.alpha.-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents |
| GB0022695D0 (en) | 2000-09-15 | 2000-11-01 | Pfizer Ltd | Purine Derivatives |
| US20020193392A1 (en) | 2000-11-13 | 2002-12-19 | Christel Schmelzer | Pharmaceutical compositions based on tiotropium salts of salts of salmeterol |
| GB0028383D0 (en) | 2000-11-21 | 2001-01-03 | Novartis Ag | Organic compounds |
| GB0029562D0 (en) | 2000-12-04 | 2001-01-17 | Novartis Ag | Organic compounds |
| PL362989A1 (en) | 2000-12-22 | 2004-11-15 | Almirall Prodesfarma Ag | Quinuclidine carbamate derivatives and their use as m3 antagonists |
| KR100869721B1 (ko) | 2000-12-28 | 2008-11-21 | 알미랄 에이쥐 | 신규한 퀴누클리딘 유도체 및 그를 함유한 의약 조성물 |
| US20020179087A1 (en) | 2001-02-01 | 2002-12-05 | Karl-Heinz Bozung | Pharmaceutical compositions containing an oxitropium salt and a betamimetic |
| GB0103630D0 (en) | 2001-02-14 | 2001-03-28 | Glaxo Group Ltd | Chemical compounds |
| EP1366025B1 (en) | 2001-03-08 | 2007-06-27 | Glaxo Group Limited | Agonists of beta-adrenoreceptors |
| EP1241176A1 (en) | 2001-03-16 | 2002-09-18 | Pfizer Products Inc. | Purine derivatives for the treatment of ischemia |
| EP1370521B1 (en) | 2001-03-22 | 2007-12-19 | Glaxo Group Limited | Formanilide derivatives as beta2-adrenoreceptor agonists |
| CA2443600A1 (en) | 2001-04-19 | 2002-10-31 | Vertex Pharmaceuticals Incorporated | Heterocyclyldicarbamides as caspase inhibitors |
| ES2314052T3 (es) | 2001-04-30 | 2009-03-16 | Glaxo Group Limited | Derivados de ester de 17beta-carbotioato de androstano con un grupo ester ciclico en la posicion 17alfa. |
| IL158774A0 (en) | 2001-05-25 | 2004-05-12 | Pfizer | An adenosine a2a receptor agonist and an anticholinergic agent in combination for treating obstructive airways diseases |
| EP1395604B1 (en) | 2001-06-12 | 2008-06-25 | Glaxo Group Limited | Novel anti inflammatory 17.alpha.-heterocyclic-esters of 17.beta.-carbothioate androstane derivatives |
| CA2445046C (en) | 2001-06-21 | 2009-11-24 | Diversa Corporation | Nitrilases |
| ITMI20010357U1 (it) | 2001-06-28 | 2002-12-30 | Plastiape Spa | Dispositivo inalatore |
| JP4191034B2 (ja) | 2001-09-14 | 2008-12-03 | グラクソ グループ リミテッド | 呼吸器疾患の治療のためのフェネタノールアミン誘導体 |
| CA2462980A1 (en) | 2001-10-17 | 2003-04-24 | Ucb, S.A. | Quinuclidine derivatives, processes for preparing them and their uses as m2 and/or m3 muscarinic receptor inhibitors |
| GB0125259D0 (en) | 2001-10-20 | 2001-12-12 | Glaxo Group Ltd | Novel compounds |
| MY130622A (en) | 2001-11-05 | 2007-07-31 | Novartis Ag | Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (pde4) inhibitors |
| MXPA04004388A (es) | 2001-11-09 | 2005-05-16 | Cv Therapeutics Inc | Antagonistas del receptor a2b de adenosina. |
| TWI249515B (en) | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| WO2003042160A1 (en) | 2001-11-13 | 2003-05-22 | Theravance, Inc. | Aryl aniline beta-2 adrenergic receptor agonists |
| AU2002356759A1 (en) | 2001-12-01 | 2003-06-17 | Glaxo Group Limited | 17.alpha. -cyclic esters of 16-methylpregnan-3,20-dione as anti-inflammatory agents |
| ES2425347T3 (es) | 2001-12-20 | 2013-10-14 | Chiesi Farmaceutici S.P.A. | Derivados de carbamato de 1-alquil-1-azoniabiciclo[2.2.2]octano y su uso como antagonistas de receptores muscarínicos |
| WO2003072592A1 (en) | 2002-01-15 | 2003-09-04 | Glaxo Group Limited | 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents |
| WO2003062259A2 (en) | 2002-01-21 | 2003-07-31 | Glaxo Group Limited | Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents |
| GB0202216D0 (en) | 2002-01-31 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| GB0204719D0 (en) | 2002-02-28 | 2002-04-17 | Glaxo Group Ltd | Medicinal compounds |
| US6933410B2 (en) | 2002-03-08 | 2005-08-23 | Novartis Ag | Process for preparing 5,6-diethyl-2,3-dihydro-1H-inden-2-amine |
| WO2003082280A1 (en) | 2002-03-26 | 2003-10-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| EP1490317A1 (en) | 2002-03-26 | 2004-12-29 | Boehringer Ingelheim Pharmaceuticals Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| EP1496911B1 (en) | 2002-04-10 | 2007-12-19 | University Of Virginia Patent Foundation | Use of a combination comprising a2a adenosine receptor agonists and anti-pathogenic agents for the treatment of inflammatory diseases |
| ATE496620T1 (de) | 2002-04-11 | 2011-02-15 | Merck Sharp & Dohme | 1h-benzo(f)indazol-5-yl-derivate als selektive glucocorticoid-rezeptor-modulatoren |
| ES2206021B1 (es) | 2002-04-16 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de pirrolidinio. |
| ATE381535T1 (de) | 2002-04-25 | 2008-01-15 | Glaxo Group Ltd | Phenethanolaminderivate |
| EP1507754A1 (en) | 2002-05-28 | 2005-02-23 | Theravance, Inc. | Alkoxy aryl beta-2 adrenergic receptor agonists |
| ES2201907B1 (es) | 2002-05-29 | 2005-06-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos. |
| US7186864B2 (en) | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| DE10224888A1 (de) | 2002-06-05 | 2003-12-24 | Merck Patent Gmbh | Pyridazinderivate |
| US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| DE10225574A1 (de) | 2002-06-10 | 2003-12-18 | Merck Patent Gmbh | Aryloxime |
| DE10227269A1 (de) | 2002-06-19 | 2004-01-08 | Merck Patent Gmbh | Thiazolderivate |
| WO2004000814A1 (en) | 2002-06-25 | 2003-12-31 | Merck Frosst Canada & Co. | 8-(biaryl) quinoline pde4 inhibitors |
| JP2005538972A (ja) | 2002-07-02 | 2005-12-22 | メルク フロスト カナダ アンド カンパニー | ジアリール置換エタンピリドンｐｄｅ４阻害剤 |
| ES2204295B1 (es) | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| PT1521733E (pt) | 2002-07-08 | 2014-10-29 | Pfizer Prod Inc | Moduladores do recetor de glucocorticoides |
| GB0217225D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicinal compounds |
| AR040661A1 (es) | 2002-07-26 | 2005-04-13 | Theravance Inc | Diclorhidrato cristalino de n-{2-[-((r)-2-hidroxi-2-feniletilamino)fenil]etil}-(r)-2hidroxi-2-(3-formamido-4-hidroxifenil)etilamina, agonista del receptor adrenergico beta 2 |
| PE20050130A1 (es) * | 2002-08-09 | 2005-03-29 | Novartis Ag | Compuestos organicos |
| WO2004018449A1 (en) | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Piperidine-derivatives as pde4 inhibitors |
| US20060166995A1 (en) | 2002-08-10 | 2006-07-27 | Altana Pharma Ag | Piperidine-n-oxide-derivatives |
| JP2005538138A (ja) | 2002-08-10 | 2005-12-15 | アルタナ ファルマ アクチエンゲゼルシャフト | Ｐｄｅ４インヒビターとしてのピリダジノン誘導体 |
| CA2494613C (en) | 2002-08-10 | 2011-06-28 | Altana Pharma Ag | Pyrrolidinedione substituted piperidine-phthalazones as pde4 inhibitors |
| WO2004018465A2 (en) | 2002-08-17 | 2004-03-04 | Altana Pharma Ag | Benzonaphthyridines with pde 3/4 inhibiting activity |
| JP2005537312A (ja) | 2002-08-17 | 2005-12-08 | アルタナ ファルマ アクチエンゲゼルシャフト | 新規のフェナントリジン |
| GB0219512D0 (en) | 2002-08-21 | 2002-10-02 | Norton Healthcare Ltd | Inhalation compositions with high drug ratios |
| US6858627B2 (en) | 2002-08-21 | 2005-02-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| WO2004018422A1 (en) | 2002-08-23 | 2004-03-04 | Ranbaxy Laboratories Limited | Fluoro and sulphonylamino containing 3,6-disubstituted azabicyclo (3.1.0) hexane derivatives as muscarinic receptor antagonists |
| KR20050036982A (ko) | 2002-08-29 | 2005-04-20 | 베링거 인겔하임 파마슈티칼즈, 인코포레이티드 | 염증, 알러지 및 증식성 질환의 치료에 글루코코르티코이드모사체로 사용하기 위한 3-(설폰아미도에틸)-인돌 유도체 |
| AU2003255493B8 (en) | 2002-08-29 | 2009-03-26 | Takeda Gmbh | 2-hydroxy-6-phenylphenanthridines as PDE-4 inhibitors |
| ATE353217T1 (de) | 2002-08-29 | 2007-02-15 | Altana Pharma Ag | 3-hydroxy-6-phenylphenanthridine als pde-4 inhibitoren |
| GB0220730D0 (en) | 2002-09-06 | 2002-10-16 | Glaxo Group Ltd | Medicinal compounds |
| JP2006096662A (ja) | 2002-09-18 | 2006-04-13 | Sumitomo Pharmaceut Co Ltd | 新規６−置換ウラシル誘導体及びアレルギー性疾患の治療剤 |
| JP2004107299A (ja) | 2002-09-20 | 2004-04-08 | Japan Energy Corp | 新規１−置換ウラシル誘導体及びアレルギー性疾患の治療剤 |
| US20050245588A1 (en) | 2002-09-20 | 2005-11-03 | Amjad Ali | Octahydro-2-h-naphtho[1,2-f]indole-4-carboxamide derivatives as selective glucocorticoid receptor modulators |
| DE10246374A1 (de) | 2002-10-04 | 2004-04-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Betamimetika mit verlängerter Wirkungsdauer, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| AP2005003283A0 (en) | 2002-10-11 | 2005-06-30 | Pfizer | Indole derivatives useful for the treatment os diseases |
| ATE369353T1 (de) | 2002-10-22 | 2007-08-15 | Glaxo Group Ltd | Medizinisch verwendbare arylethanolamin verbindungen |
| DE60317918T2 (de) | 2002-10-23 | 2009-01-29 | Glenmark Pharmaceuticals Ltd. | Tricyclische verbindungen zur behandlung von entzündlichen und allergischen erkrankungen verfahren zu deren herstellung und sie enthaltende pharmazeutische zusammensetzungen |
| CA2503588A1 (en) | 2002-10-28 | 2004-05-06 | Glaxo Group Limited | Phenethanolamine derivative for the treatment of respiratory diseases |
| GB0225287D0 (en) | 2002-10-30 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
| GB0225535D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Medicinal compounds |
| GB0225540D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Medicinal compounds |
| DE10253282A1 (de) | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung |
| DE10253220A1 (de) | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Dihydroxy-Methyl-Phenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE10253426B4 (de) | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
| DE10261874A1 (de) | 2002-12-20 | 2004-07-08 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| CA2513081C (en) | 2003-01-09 | 2011-04-19 | Astellas Pharma Inc. | Pyrrolopyridazine derivatives |
| CA2512987C (en) | 2003-01-21 | 2011-06-14 | Merck & Co., Inc. | 17-carbamoyloxy cortisol derivatives as selective glucocorticoid receptor modulators |
| TWI324150B (en) | 2003-02-28 | 2010-05-01 | Novartis Ag | Process for preparing 5-[(r)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-(1h)-quinolin-2-one salt |
| EP1460064A1 (en) | 2003-03-14 | 2004-09-22 | Pfizer Limited | Indole-2-carboxamide derivatives useful as beta-2 agonists |
| PE20050211A1 (es) | 2003-04-02 | 2005-04-27 | Novartis Ag | Procedimiento para preparar oxi-(1h)-quinolin-2-onas 5-(alfa-haloacetil)-8-sustituidas |
| AU2004226824B2 (en) | 2003-04-04 | 2008-05-01 | Novartis Ag | Quinoline-2-one-derivatives for the treatment of airways diseases |
| TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| BRPI0410660A (pt) | 2003-06-04 | 2006-06-20 | Pfizer | derivados de 2-amino-piridina como agonistas de adrenoreceptor ß2 |
| GB0312832D0 (en) | 2003-06-04 | 2003-07-09 | Pfizer Ltd | 2-amino-pyridine derivatives useful for the treatment of diseases |
| WO2004108720A1 (en) | 2003-06-11 | 2004-12-16 | Merck Frosst Canada Ltd. | 7- (1, 3-thiazol-2-yl)thio!-coumarin derivatives and their use as leukotriene biosynthesis inhibitors |
| TW200510298A (en) | 2003-06-13 | 2005-03-16 | Theravance Inc | Substituted pyrrolidine and related compounds |
| WO2004111044A1 (en) | 2003-06-17 | 2004-12-23 | Glenmark Pharmaceuticals Ltd. | Tricyclic compounds useful for the treatment of inflammatory and allergic disorders:process for their preparation |
| SE527189C2 (sv) * | 2003-06-19 | 2006-01-17 | Microdrug Ag | Inhalatoranordning samt kombinerade doser för formaterol och ett antikolinergiskt medel |
| GB0316290D0 (en) | 2003-07-11 | 2003-08-13 | Glaxo Group Ltd | Novel compounds |
| WO2005082413A2 (en) * | 2004-02-27 | 2005-09-09 | Altana Pharma Ag | Ciclesonide and glycopyrronium combination |
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| US20060239935A1 (en) * | 2005-04-23 | 2006-10-26 | Boehringer Ingelheim International Gmbh | Compositions for inhalation |
| EP2778064A1 (en) | 2013-03-14 | 2014-09-17 | Airbus Operations GmbH | Passenger services provisioning for a means of transport |
| WO2016046150A1 (en) | 2014-09-25 | 2016-03-31 | Boehringer Ingelheim Vetmedica Gmbh | Combination treatment of sglt2 inhibitors and dopamine agonists for preventing metabolic disorders in equine animals |
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