CA2427583C - Inhalable formulation of a solution containing a tiotropium salt - Google Patents
Inhalable formulation of a solution containing a tiotropium salt Download PDFInfo
- Publication number
- CA2427583C CA2427583C CA002427583A CA2427583A CA2427583C CA 2427583 C CA2427583 C CA 2427583C CA 002427583 A CA002427583 A CA 002427583A CA 2427583 A CA2427583 A CA 2427583A CA 2427583 C CA2427583 C CA 2427583C
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutical preparation
- preparation according
- tiotropium
- acid
- 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 - Fee Related
Links
- 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
- 239000000203 mixture Substances 0.000 title abstract description 61
- 238000009472 formulation Methods 0.000 title abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 45
- 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 compound 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 abstract description 30
- 229960000257 tiotropium bromide Drugs 0.000 claims abstract description 30
- MQLXPRBEAHBZTK-SEINRUQRSA-M tiotropium bromide hydrate Chemical compound 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 abstract description 13
- 239000013543 active substance Substances 0.000 claims description 39
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 31
- 229940110309 tiotropium Drugs 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 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
- 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 16
- 239000002253 acid Substances 0.000 claims description 16
- 229960004436 budesonide Drugs 0.000 claims description 16
- 150000003431 steroids Chemical class 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 13
- 229940037001 sodium edetate Drugs 0.000 claims description 13
- -1 1-(((R)-3-(3-(2-(2,3-dichlorothieno[3,2-b]pyridin-5-yl)-(E)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl Chemical group 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000003755 preservative agent Substances 0.000 claims description 9
- 229960002714 fluticasone Drugs 0.000 claims description 8
- 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 8
- 239000002671 adjuvant Substances 0.000 claims description 7
- 239000000739 antihistaminic agent Substances 0.000 claims description 7
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 7
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- 229960000676 flunisolide Drugs 0.000 claims description 6
- 230000002335 preservative effect Effects 0.000 claims description 6
- 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 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 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 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 235000010323 ascorbic acid Nutrition 0.000 claims description 5
- 239000011668 ascorbic acid Substances 0.000 claims description 5
- 229960005070 ascorbic acid Drugs 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 229950000210 beclometasone dipropionate Drugs 0.000 claims description 5
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 5
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical group [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 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 claims description 4
- 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
- 230000003266 anti-allergic effect Effects 0.000 claims description 4
- 230000001387 anti-histamine Effects 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 235000006708 antioxidants Nutrition 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 229960003449 epinastine Drugs 0.000 claims description 4
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical compound 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
- 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
- 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
- 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
- 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
- 229960005042 mequitazine Drugs 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
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-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
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000019155 vitamin A Nutrition 0.000 claims description 2
- 239000011719 vitamin A Substances 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 229940045997 vitamin a Drugs 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 47
- 239000000443 aerosol Substances 0.000 abstract description 19
- 239000000243 solution Substances 0.000 description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- 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
- 238000003860 storage Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
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- 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
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- 235000015165 citric acid Nutrition 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 239000008194 pharmaceutical composition 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
- 230000008901 benefit Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 239000000043 antiallergic agent Substances 0.000 description 3
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- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
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- 229960000391 sorbitan trioleate Drugs 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-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
- 150000001298 alcohols Chemical class 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940009662 edetate Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- XWTIDFOGTCVGQB-FHIVUSPVSA-N fluocortin butyl Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)C(=O)OCCCC)[C@@]2(C)C[C@@H]1O XWTIDFOGTCVGQB-FHIVUSPVSA-N 0.000 description 2
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Otolaryngology (AREA)
- Emergency Medicine (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10054042.2 | 2000-10-31 | ||
| DE10054042 | 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 |
|---|---|
| CA2427583A1 CA2427583A1 (en) | 2002-05-10 |
| CA2427583C true CA2427583C (en) | 2008-02-12 |
Family
ID=7661727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002427583A Expired - Fee Related CA2427583C (en) | 2000-10-31 | 2001-10-24 | Inhalable formulation of a solution containing a tiotropium salt |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP1335729A2 (hr) |
| JP (1) | JP4559703B2 (hr) |
| KR (1) | KR100983208B1 (hr) |
| CN (1) | CN1237970C (hr) |
| AR (1) | AR038765A1 (hr) |
| AU (2) | AU2174102A (hr) |
| BG (1) | BG66425B1 (hr) |
| BR (1) | BR0115016A (hr) |
| CA (1) | CA2427583C (hr) |
| CZ (1) | CZ305033B6 (hr) |
| DE (1) | DE10152369A1 (hr) |
| EA (1) | EA009068B1 (hr) |
| EC (1) | ECSP034570A (hr) |
| EE (1) | EE05343B1 (hr) |
| HK (1) | HK1060569A1 (hr) |
| HR (1) | HRP20030337A2 (hr) |
| HU (1) | HUP0301377A3 (hr) |
| IL (2) | IL155676A0 (hr) |
| ME (1) | ME00242B (hr) |
| MX (1) | MXPA03003750A (hr) |
| MY (1) | MY132777A (hr) |
| NO (1) | NO332524B1 (hr) |
| NZ (1) | NZ526024A (hr) |
| PE (1) | PE20020518A1 (hr) |
| PL (1) | PL361001A1 (hr) |
| SA (1) | SA01220503B1 (hr) |
| SK (1) | SK288031B6 (hr) |
| TW (1) | TWI296934B (hr) |
| UA (1) | UA76435C2 (hr) |
| UY (1) | UY26991A1 (hr) |
| WO (1) | WO2002036591A2 (hr) |
| YU (1) | YU33103A (hr) |
| ZA (1) | ZA200303045B (hr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA02010565A (es) | 2000-04-28 | 2004-05-17 | Kosan Biosciences Inc | Produccion de policetidos. |
| 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 |
| AU2004279438A1 (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. |
| EP2034990A4 (en) * | 2006-05-26 | 2013-03-06 | Dey L P | DIRTIBLE COMPOSITIONS OF QUATERNARY AMMONIUM MUSCARIN 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 |
| 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 |
| 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 |
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 |
| DK0835098T3 (da) * | 1995-06-27 | 2002-10-07 | Boehringer Ingelheim Pharma | Stabilt lægemiddelpræparat til frembringlese af drivgasfrie aerosoler |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| CA2256721A1 (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 |
| ATE234604T1 (de) * | 1998-08-04 | 2003-04-15 | Jago Res 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 |
-
2001
- 2001-10-24 AU AU2174102A patent/AU2174102A/xx active Pending
- 2001-10-24 JP JP2002539350A patent/JP4559703B2/ja not_active Expired - Lifetime
- 2001-10-24 CN CNB018183271A patent/CN1237970C/zh not_active Expired - Lifetime
- 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 IL IL15567601A patent/IL155676A0/xx unknown
- 2001-10-24 WO PCT/EP2001/012296 patent/WO2002036591A2/de active IP Right Grant
- 2001-10-24 NZ NZ526024A patent/NZ526024A/en not_active IP Right Cessation
- 2001-10-24 MX MXPA03003750A patent/MXPA03003750A/es active IP Right Grant
- 2001-10-24 SK SK526-2003A patent/SK288031B6/sk not_active IP Right Cessation
- 2001-10-24 YU YU33103A patent/YU33103A/sh unknown
- 2001-10-24 EA EA200300483A patent/EA009068B1/ru not_active IP Right Cessation
- 2001-10-24 DE DE10152369A patent/DE10152369A1/de not_active Withdrawn
- 2001-10-24 AU AU2002221741A patent/AU2002221741B2/en not_active Expired
- 2001-10-24 HU HU0301377A patent/HUP0301377A3/hu unknown
- 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 PL PL01361001A patent/PL361001A1/xx not_active Application Discontinuation
- 2001-10-24 EE EEP200300202A patent/EE05343B1/xx unknown
- 2001-10-24 EP EP01992710A patent/EP1335729A2/de not_active Ceased
- 2001-10-24 KR KR1020037006001A patent/KR100983208B1/ko active IP Right Grant
- 2001-10-24 BR BR0115016-2A patent/BR0115016A/pt active Pending
- 2001-10-29 TW TW090126752A patent/TWI296934B/zh not_active IP Right Cessation
- 2001-10-29 MY MYPI20014987A patent/MY132777A/en unknown
- 2001-10-29 PE PE2001001072A patent/PE20020518A1/es active IP Right Grant
- 2001-10-29 UY UY26991A patent/UY26991A1/es not_active Application Discontinuation
- 2001-10-31 AR ARP010105088A patent/AR038765A1/es not_active Ceased/Invalidation/Refusal/Rejection/Nullification
- 2001-11-03 SA SA01220503A patent/SA01220503B1/ar unknown
-
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
-
2004
- 2004-05-20 HK HK04103587A patent/HK1060569A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20201026 |