HRP20030337A2 - Inhalative solution formulation containing a tiotropium salt - Google Patents
Inhalative solution formulation containing a tiotropium salt Download PDFInfo
- Publication number
- HRP20030337A2 HRP20030337A2 HR20030337A HRP20030337A HRP20030337A2 HR P20030337 A2 HRP20030337 A2 HR P20030337A2 HR 20030337 A HR20030337 A HR 20030337A HR P20030337 A HRP20030337 A HR P20030337A HR P20030337 A2 HRP20030337 A2 HR P20030337A2
- Authority
- HR
- Croatia
- Prior art keywords
- preparation according
- drug preparation
- drug
- tiotropium
- acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 60
- 238000009472 formulation Methods 0.000 title claims description 44
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 title claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
- 238000002360 preparation method Methods 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 239000013543 active substance Substances 0.000 claims description 41
- 229940079593 drug Drugs 0.000 claims description 34
- 239000003814 drug Substances 0.000 claims description 34
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical group C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims description 27
- 229960000257 tiotropium bromide Drugs 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 24
- -1 monomethyl ester Chemical class 0.000 claims description 22
- 229940110309 tiotropium Drugs 0.000 claims description 20
- 239000000443 aerosol Substances 0.000 claims description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical group 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 230000002349 favourable effect Effects 0.000 claims description 15
- 150000003431 steroids Chemical class 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 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 14
- 229960004436 budesonide Drugs 0.000 claims description 14
- 229940037001 sodium edetate Drugs 0.000 claims description 13
- MQLXPRBEAHBZTK-SEINRUQRSA-M tiotropium bromide hydrate Chemical group O.[Br-].C[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 MQLXPRBEAHBZTK-SEINRUQRSA-M 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 8
- 230000003266 anti-allergic effect Effects 0.000 claims description 7
- 239000000739 antihistaminic agent Substances 0.000 claims description 7
- 229960002714 fluticasone Drugs 0.000 claims description 7
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone 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)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 7
- 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 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000003380 propellant Substances 0.000 claims description 6
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 5
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 4
- 230000001387 anti-histamine Effects 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 229950000210 beclometasone dipropionate Drugs 0.000 claims description 4
- 229960003449 epinastine Drugs 0.000 claims description 4
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical group C1C2=CC=CC=C2C2CN=C(N)N2C2=CC=CC=C21 WHWZLSFABNNENI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical group CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims description 3
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000043 antiallergic agent Substances 0.000 claims description 3
- 229940125715 antihistaminic agent Drugs 0.000 claims description 3
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000889 atomisation Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229960002881 clemastine Drugs 0.000 claims description 3
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 claims description 3
- 229960000265 cromoglicic acid Drugs 0.000 claims description 3
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims description 3
- 239000013583 drug formulation Substances 0.000 claims description 3
- 229960005127 montelukast Drugs 0.000 claims description 3
- 229960004398 nedocromil Drugs 0.000 claims description 3
- RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004583 pranlukast Drugs 0.000 claims description 3
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 claims description 3
- 229960004764 zafirlukast Drugs 0.000 claims description 3
- PSILZZNMGXTOOP-UHFFFAOYSA-N 2-[2-[[2-(4-tert-butyl-1,3-thiazol-2-yl)-1-benzofuran-5-yl]oxymethyl]phenyl]acetic acid Chemical compound CC(C)(C)C1=CSC(C=2OC3=CC=C(OCC=4C(=CC=CC=4)CC(O)=O)C=C3C=2)=N1 PSILZZNMGXTOOP-UHFFFAOYSA-N 0.000 claims description 2
- KVVDRQDTODKIJD-UHFFFAOYSA-N 2-cyclopropylacetic acid Chemical compound OC(=O)CC1CC1 KVVDRQDTODKIJD-UHFFFAOYSA-N 0.000 claims description 2
- 229960000428 carbinoxamine Drugs 0.000 claims description 2
- OJFSXZCBGQGRNV-UHFFFAOYSA-N carbinoxamine Chemical compound C=1C=CC=NC=1C(OCCN(C)C)C1=CC=C(Cl)C=C1 OJFSXZCBGQGRNV-UHFFFAOYSA-N 0.000 claims description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical group [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims 2
- 239000006184 cosolvent Substances 0.000 claims 2
- 230000002335 preservative effect Effects 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 239000000243 solution Substances 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 238000001994 activation Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- 239000012669 liquid formulation Substances 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000004147 Sorbitan trioleate Substances 0.000 description 3
- 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 3
- 239000000654 additive Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
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- 150000001768 cations Chemical class 0.000 description 3
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- 210000004072 lung Anatomy 0.000 description 3
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- 235000019337 sorbitan trioleate Nutrition 0.000 description 3
- 229960000391 sorbitan trioleate Drugs 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 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 2
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- UYVYDRXVNVNQEA-BJTOFBPUSA-N [2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 4-(acetamidomethyl)cyclohexane-1-carboxylate Chemical compound O=C([C@]1(O)[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)COC(=O)C1CCC(CNC(C)=O)CC1 UYVYDRXVNVNQEA-BJTOFBPUSA-N 0.000 description 2
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- NBMKJKDGKREAPL-CXSFZGCWSA-N (8s,9r,10s,11s,13s,14s,16r,17r)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one 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)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-CXSFZGCWSA-N 0.000 description 1
- KQZSMOGWYFPKCH-UJPCIWJBSA-N (8s,9s,10r,11s,13s,14s,17r)-17-acetyl-11,17-dihydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)C[C@@H]2O KQZSMOGWYFPKCH-UJPCIWJBSA-N 0.000 description 1
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Classifications
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- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
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- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
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- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
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- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
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- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10054042 | 2000-10-31 | ||
| PCT/EP2001/012296 WO2002036591A2 (de) | 2000-10-31 | 2001-10-24 | Inhalative lösungsformulierung mit einem tiotropiumsalz |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20030337A2 true HRP20030337A2 (en) | 2005-04-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20030337A HRP20030337A2 (en) | 2000-10-31 | 2003-04-28 | Inhalative solution formulation containing a tiotropium salt |
Country Status (33)
| Country | Link |
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| EP (1) | EP1335729A2 (ja) |
| JP (1) | JP4559703B2 (ja) |
| KR (1) | KR100983208B1 (ja) |
| CN (1) | CN1237970C (ja) |
| AR (1) | AR038765A1 (ja) |
| AU (2) | AU2174102A (ja) |
| BG (1) | BG66425B1 (ja) |
| BR (1) | BR0115016A (ja) |
| CA (1) | CA2427583C (ja) |
| CZ (1) | CZ305033B6 (ja) |
| DE (1) | DE10152369A1 (ja) |
| EA (1) | EA009068B1 (ja) |
| EC (1) | ECSP034570A (ja) |
| EE (1) | EE05343B1 (ja) |
| HK (1) | HK1060569A1 (ja) |
| HR (1) | HRP20030337A2 (ja) |
| HU (1) | HUP0301377A3 (ja) |
| IL (2) | IL155676A0 (ja) |
| ME (1) | ME00242B (ja) |
| MX (1) | MXPA03003750A (ja) |
| MY (1) | MY132777A (ja) |
| NO (1) | NO332524B1 (ja) |
| NZ (1) | NZ526024A (ja) |
| PE (1) | PE20020518A1 (ja) |
| PL (1) | PL361001A1 (ja) |
| SA (1) | SA01220503B1 (ja) |
| SK (1) | SK288031B6 (ja) |
| TW (1) | TWI296934B (ja) |
| UA (1) | UA76435C2 (ja) |
| UY (1) | UY26991A1 (ja) |
| WO (1) | WO2002036591A2 (ja) |
| YU (1) | YU33103A (ja) |
| ZA (1) | ZA200303045B (ja) |
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| NZ546497A (en) | 2000-04-28 | 2008-04-30 | Kosan Biosciences Inc | Production of polyketides |
| US20030235538A1 (en) | 2002-04-09 | 2003-12-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Method for the administration of an anticholinergic by inhalation |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| WO2005034871A2 (en) * | 2003-10-09 | 2005-04-21 | Inverseon, Inc. | Methods for treating diseases and conditions with inverse agonists |
| SE0303269L (sv) * | 2003-12-03 | 2005-06-04 | Microdrug Ag | Medicinsk produkt |
| MX2007011273A (es) * | 2005-03-16 | 2007-11-08 | Meda Pharma Gmbh & Co Kg | La combinacion de anticolinergicos y antagonistas del receptor de leucotrieno para el tratamiento de enfermedades respiratorias. |
| AU2007267523B2 (en) * | 2006-05-26 | 2012-02-09 | Dey, L.P. | Nebulizable compositions of quaternary ammonium muscarinic receptor antagonists |
| CN100446770C (zh) * | 2007-01-10 | 2008-12-31 | 上海现代药物制剂工程研究中心有限公司 | 丙酸培氯米松水雾剂 |
| TR200907237A2 (tr) * | 2009-09-23 | 2011-04-21 | Bi̇lgi̇ç Mahmut | Tiotropyum kuru toz kombinasyonu |
| CN116173025A (zh) * | 2018-07-26 | 2023-05-30 | 四川海思科制药有限公司 | 一种含格隆铵盐及茚达特罗盐的气雾剂药物组合物及其制备方法与应用 |
| CN111971034A (zh) * | 2018-07-26 | 2020-11-20 | 四川海思科制药有限公司 | 一种含格隆铵盐的气雾剂药物组合物及其制备方法与应用 |
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| EP0504112A3 (en) * | 1991-03-14 | 1993-04-21 | Ciba-Geigy Ag | Pharmaceutical aerosol formulations |
| DE4203306A1 (de) * | 1992-02-06 | 1993-08-12 | Ig Spruehtechnik Gmbh | Asthma oder pulmonal-aerosolzubereitungen mit lecithin |
| KR100392280B1 (ko) * | 1995-06-27 | 2003-11-19 | 베링거 인겔하임 카게 | 추진제비함유흡입성에어로졸을제조하기위한안정한추진제비함유약제학적용액 |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| WO1997046243A1 (en) * | 1996-06-04 | 1997-12-11 | The Procter & Gamble Company | A nasal spray containing an intranasal steroid and an antihistamine |
| DE19653969A1 (de) * | 1996-12-20 | 1998-06-25 | Boehringer Ingelheim Kg | Neue wässrige Arzneimittelzubereitung zur Erzeugung treibgasfreier Aerosole |
| JPH10298107A (ja) * | 1997-04-25 | 1998-11-10 | Taisho Pharmaceut Co Ltd | 医薬組成物 |
| EP1102579B1 (de) * | 1998-08-04 | 2003-03-19 | Jago Research Ag | Medizinische aerosolformulierungen |
| DE19847968A1 (de) * | 1998-10-17 | 2000-04-20 | Boehringer Ingelheim Pharma | Verschlußkappe und Behälter als Zweikammer-Kartusche für Vernebler zur Erzeugung von Aerosolen |
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2001
- 2001-10-24 EP EP01992710A patent/EP1335729A2/de not_active Ceased
- 2001-10-24 YU YU33103A patent/YU33103A/sh unknown
- 2001-10-24 EE EEP200300202A patent/EE05343B1/xx unknown
- 2001-10-24 AU AU2174102A patent/AU2174102A/xx active Pending
- 2001-10-24 MX MXPA03003750A patent/MXPA03003750A/es active IP Right Grant
- 2001-10-24 PL PL01361001A patent/PL361001A1/xx not_active Application Discontinuation
- 2001-10-24 KR KR1020037006001A patent/KR100983208B1/ko active IP Right Grant
- 2001-10-24 SK SK526-2003A patent/SK288031B6/sk not_active IP Right Cessation
- 2001-10-24 NZ NZ526024A patent/NZ526024A/en not_active IP Right Cessation
- 2001-10-24 AU AU2002221741A patent/AU2002221741B2/en not_active Expired
- 2001-10-24 IL IL15567601A patent/IL155676A0/xx unknown
- 2001-10-24 DE DE10152369A patent/DE10152369A1/de not_active Withdrawn
- 2001-10-24 BR BR0115016-2A patent/BR0115016A/pt active Pending
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- 2001-10-24 UA UA2003054960A patent/UA76435C2/uk unknown
- 2001-10-24 WO PCT/EP2001/012296 patent/WO2002036591A2/de active IP Right Grant
- 2001-10-24 CA CA002427583A patent/CA2427583C/en not_active Expired - Fee Related
- 2001-10-24 JP JP2002539350A patent/JP4559703B2/ja not_active Expired - Lifetime
- 2001-10-24 CZ CZ2003-1487A patent/CZ305033B6/cs not_active IP Right Cessation
- 2001-10-24 EA EA200300483A patent/EA009068B1/ru not_active IP Right Cessation
- 2001-10-24 HU HU0301377A patent/HUP0301377A3/hu unknown
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- 2001-10-29 UY UY26991A patent/UY26991A1/es not_active Application Discontinuation
- 2001-10-29 MY MYPI20014987A patent/MY132777A/en unknown
- 2001-10-29 PE PE2001001072A patent/PE20020518A1/es active IP Right Grant
- 2001-10-29 TW TW090126752A patent/TWI296934B/zh not_active IP Right Cessation
- 2001-10-31 AR ARP010105088A patent/AR038765A1/es not_active Ceased/Invalidation/Refusal/Rejection/Nullification
- 2001-11-03 SA SA01220503A patent/SA01220503B1/ar unknown
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2003
- 2003-04-16 BG BG107726A patent/BG66425B1/bg active Active
- 2003-04-17 ZA ZA200303045A patent/ZA200303045B/xx unknown
- 2003-04-28 HR HR20030337A patent/HRP20030337A2/hr not_active Application Discontinuation
- 2003-04-28 EC EC2003004570A patent/ECSP034570A/es unknown
- 2003-04-29 NO NO20031914A patent/NO332524B1/no not_active IP Right Cessation
- 2003-04-30 IL IL155676A patent/IL155676A/en active IP Right Grant
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2004
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