AU2002221741B2 - Inhalative solution formulation containing a tiotropium salt - Google Patents
Inhalative solution formulation containing a tiotropium salt Download PDFInfo
- Publication number
- AU2002221741B2 AU2002221741B2 AU2002221741A AU2002221741A AU2002221741B2 AU 2002221741 B2 AU2002221741 B2 AU 2002221741B2 AU 2002221741 A AU2002221741 A AU 2002221741A AU 2002221741 A AU2002221741 A AU 2002221741A AU 2002221741 B2 AU2002221741 B2 AU 2002221741B2
- Authority
- AU
- Australia
- Prior art keywords
- pharmaceutical preparation
- preparation according
- tiotropium
- concentration
- active substance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 63
- 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 45
- 238000009472 formulation Methods 0.000 title description 44
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 239000013543 active substance Substances 0.000 claims description 40
- 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 31
- 229960000257 tiotropium bromide Drugs 0.000 claims description 31
- 229940110309 tiotropium Drugs 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 23
- 150000003839 salts Chemical group 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
- 150000003431 steroids Chemical class 0.000 claims description 16
- 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 15
- 239000002253 acid Substances 0.000 claims description 15
- 229960004436 budesonide Drugs 0.000 claims description 15
- 229940037001 sodium edetate Drugs 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 12
- -1 (6,7-difluoro-2-quinolinyl)ethenyl Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 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 11
- 239000000739 antihistaminic agent Substances 0.000 claims description 10
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000003755 preservative agent Substances 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims description 7
- 230000003266 anti-allergic effect Effects 0.000 claims description 7
- 208000006673 asthma Diseases 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000043 antiallergic agent Substances 0.000 claims description 5
- 229940125715 antihistaminic agent Drugs 0.000 claims description 5
- 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
- 239000008139 complexing agent Substances 0.000 claims description 5
- 239000006184 cosolvent Substances 0.000 claims description 5
- 229960000676 flunisolide Drugs 0.000 claims description 5
- 230000002335 preservative effect Effects 0.000 claims description 5
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 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 4
- 239000003963 antioxidant agent Substances 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
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical group O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 229960004583 pranlukast Drugs 0.000 claims description 4
- 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 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-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
- 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
- 239000003814 drug Substances 0.000 claims description 3
- 229960005042 mequitazine Drugs 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 229960004764 zafirlukast Drugs 0.000 claims description 3
- KVVDRQDTODKIJD-UHFFFAOYSA-N 2-cyclopropylacetic acid Chemical compound OC(=O)CC1CC1 KVVDRQDTODKIJD-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- 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 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
- 229960000265 cromoglicic acid Drugs 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
- 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 5
- 230000001387 anti-histamine Effects 0.000 claims 5
- 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
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 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 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000243 solution Substances 0.000 description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- 239000000443 aerosol Substances 0.000 description 18
- 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 12
- 238000003860 storage Methods 0.000 description 9
- 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
- 239000012530 fluid Substances 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 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
- 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
- 150000007513 acids Chemical class 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
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- 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 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
- 235000006708 antioxidants Nutrition 0.000 description 3
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- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 3
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- 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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- 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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Landscapes
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- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10054042 | 2000-10-31 | ||
| DE10054042.2 | 2000-10-31 | ||
| PCT/EP2001/012296 WO2002036591A2 (de) | 2000-10-31 | 2001-10-24 | Inhalative lösungsformulierung mit einem tiotropiumsalz |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002221741A1 AU2002221741A1 (en) | 2002-07-18 |
| AU2002221741B2 true AU2002221741B2 (en) | 2007-04-05 |
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| AU2174102A Pending AU2174102A (en) | 2000-10-31 | 2001-10-24 | Inhalative solution formulation containing a tiotropium salt |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2174102A Pending AU2174102A (en) | 2000-10-31 | 2001-10-24 | Inhalative solution formulation containing a tiotropium salt |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP1335729A2 (ru) |
| JP (1) | JP4559703B2 (ru) |
| KR (1) | KR100983208B1 (ru) |
| CN (1) | CN1237970C (ru) |
| AR (1) | AR038765A1 (ru) |
| AU (2) | AU2002221741B2 (ru) |
| BG (1) | BG66425B1 (ru) |
| BR (1) | BR0115016A (ru) |
| CA (1) | CA2427583C (ru) |
| CZ (1) | CZ305033B6 (ru) |
| DE (1) | DE10152369A1 (ru) |
| EA (1) | EA009068B1 (ru) |
| EC (1) | ECSP034570A (ru) |
| EE (1) | EE05343B1 (ru) |
| HK (1) | HK1060569A1 (ru) |
| HR (1) | HRP20030337A2 (ru) |
| HU (1) | HUP0301377A3 (ru) |
| IL (2) | IL155676A0 (ru) |
| ME (1) | ME00242B (ru) |
| MX (1) | MXPA03003750A (ru) |
| MY (1) | MY132777A (ru) |
| NO (1) | NO332524B1 (ru) |
| NZ (1) | NZ526024A (ru) |
| PE (1) | PE20020518A1 (ru) |
| PL (1) | PL361001A1 (ru) |
| SA (1) | SA01220503B1 (ru) |
| SK (1) | SK288031B6 (ru) |
| TW (1) | TWI296934B (ru) |
| UA (1) | UA76435C2 (ru) |
| UY (1) | UY26991A1 (ru) |
| WO (1) | WO2002036591A2 (ru) |
| YU (1) | YU33103A (ru) |
| ZA (1) | ZA200303045B (ru) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070092334A (ko) | 2000-04-28 | 2007-09-12 | 코산 바이오사이언시즈, 인코포레이티드 | 폴리케타이드의 제조방법 |
| 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 |
| CA2544733A1 (en) * | 2003-10-09 | 2005-04-21 | Inverseon, Inc. | Methods for treating diseases and conditions with inverse agonists and for screening for agents acting as inverse agonists |
| SE0303269L (sv) * | 2003-12-03 | 2005-06-04 | Microdrug Ag | Medicinsk produkt |
| SI1863476T1 (sl) * | 2005-03-16 | 2016-05-31 | Meda Pharma Gmbh & Co. Kg | Kombinacija antiholinergikov in antagonistov receptorja levkotriena za zdravljenje respiratornih bolezni |
| CA2653744C (en) * | 2006-05-26 | 2018-01-16 | 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 |
| CN116196298A (zh) * | 2018-07-26 | 2023-06-02 | 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 |
| CN111936124A (zh) * | 2018-07-26 | 2020-11-13 | 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ES2183001T3 (es) * | 1995-06-27 | 2003-03-16 | Boehringer Ingelheim Pharma | Nuevo preparado medicamentoso estable para la produccion de aerosoles exentos de gas propulsor. |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| JPH11511758A (ja) * | 1996-06-04 | 1999-10-12 | ザ、プロクター、エンド、ギャンブル、カンパニー | 鼻腔用ステロイドと抗ヒスタミン剤を含む鼻腔内噴霧薬 |
| 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 |
| WO2000007567A1 (de) * | 1998-08-04 | 2000-02-17 | 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
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- 2001-10-24 YU YU33103A patent/YU33103A/sh unknown
- 2001-10-24 UA UA2003054960A patent/UA76435C2/uk unknown
- 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 HU HU0301377A patent/HUP0301377A3/hu unknown
- 2001-10-24 SK SK526-2003A patent/SK288031B6/sk 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 PL PL01361001A patent/PL361001A1/xx not_active Application Discontinuation
- 2001-10-24 AU AU2174102A patent/AU2174102A/xx active Pending
- 2001-10-24 CN CNB018183271A patent/CN1237970C/zh not_active Expired - Lifetime
- 2001-10-24 MX MXPA03003750A patent/MXPA03003750A/es active IP Right Grant
- 2001-10-24 EA EA200300483A patent/EA009068B1/ru not_active IP Right Cessation
- 2001-10-24 CZ CZ2003-1487A patent/CZ305033B6/cs not_active IP Right Cessation
- 2001-10-24 ME MEP-2008-407A patent/ME00242B/me unknown
- 2001-10-24 WO PCT/EP2001/012296 patent/WO2002036591A2/de active IP Right Grant
- 2001-10-24 EP EP01992710A patent/EP1335729A2/de not_active Ceased
- 2001-10-24 DE DE10152369A patent/DE10152369A1/de not_active Withdrawn
- 2001-10-24 BR BR0115016-2A patent/BR0115016A/pt active Pending
- 2001-10-29 UY UY26991A patent/UY26991A1/es not_active Application Discontinuation
- 2001-10-29 PE PE2001001072A patent/PE20020518A1/es active IP Right Grant
- 2001-10-29 MY MYPI20014987A patent/MY132777A/en unknown
- 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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