CA2614631C - Compositions pharmaceutiques contenant des anticholinergiques et des corticosteroides sous la forme d'une suspension ou d'une solution inhalable - Google Patents

Compositions pharmaceutiques contenant des anticholinergiques et des corticosteroides sous la forme d'une suspension ou d'une solution inhalable Download PDF

Info

Publication number: CA2614631C
Authority: CA; Canada
Prior art keywords: pharmaceutical composition; composition according; present; propellant; inhalable
Prior art date: 2000-10-31
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

Application number

CA2614631A

Other languages

English (en)

Other versions

CA2614631A1 (fr

Inventor

Michel Pairet

Michael Paul Pieper

Christopher John Montague Meade

Richard Reichl

Christel Schmelzer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Boehringer Ingelheim Pharma GmbH and Co KG

Priority date (The priority date 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 date listed.)

2000-10-31

Filing date

2001-10-23

Publication date

2011-06-14

2000-12-15 Priority claimed from DE10062712A external-priority patent/DE10062712A1/de

2001-10-23 Application filed by Boehringer Ingelheim Pharma GmbH and Co KG filed Critical Boehringer Ingelheim Pharma GmbH and Co KG

2001-10-23 Priority to CA2733294A priority Critical patent/CA2733294C/fr

2001-10-23 Priority claimed from CA002436540A external-priority patent/CA2436540C/fr

2002-05-10 Publication of CA2614631A1 publication Critical patent/CA2614631A1/fr

2011-06-14 Application granted granted Critical

2011-06-14 Publication of CA2614631C publication Critical patent/CA2614631C/fr

2021-10-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 52
239000000725 suspension Substances 0.000 title claims abstract description 20
239000003246 corticosteroid Substances 0.000 title abstract description 9
229960001334 corticosteroids Drugs 0.000 title abstract description 9
229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 title abstract description 7
239000000812 cholinergic antagonist Substances 0.000 title abstract description 7
239000000203 mixture Substances 0.000 claims description 40
239000000443 aerosol Substances 0.000 claims description 35
239000003380 propellant Substances 0.000 claims description 20
239000004615 ingredient Substances 0.000 claims description 16
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 claims description 13
150000003431 steroids Chemical class 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 10
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 claims description 8
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 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
229960003728 ciclesonide Drugs 0.000 claims description 8
230000002757 inflammatory effect Effects 0.000 claims description 8
230000000414 obstructive effect Effects 0.000 claims description 8
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 7
229960004436 budesonide Drugs 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
150000004677 hydrates Chemical class 0.000 claims description 7
210000002345 respiratory system Anatomy 0.000 claims description 7
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
239000003963 antioxidant agent Substances 0.000 claims description 5
229960002714 fluticasone Drugs 0.000 claims description 5
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 5
229960001664 mometasone Drugs 0.000 claims description 5
QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone 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)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
239000003381 stabilizer Substances 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone 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-DVTGEIKXSA-N 0.000 claims description 3
229940092705 beclomethasone Drugs 0.000 claims description 3
229960003957 dexamethasone Drugs 0.000 claims description 3
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 3
229960000676 flunisolide Drugs 0.000 claims description 3
150000005826 halohydrocarbons Chemical class 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
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 3
239000004094 surface-active agent Substances 0.000 claims description 3
229960005294 triamcinolone Drugs 0.000 claims description 3
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 3
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical class C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
239000001273 butane Chemical class 0.000 claims description 2
239000001282 iso-butane Substances 0.000 claims description 2
239000000314 lubricant Substances 0.000 claims description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
239000001294 propane Chemical class 0.000 claims description 2
229910021653 sulphate ion Inorganic materials 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 2
150000003842 bromide salts Chemical class 0.000 claims 2
239000006184 cosolvent Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
150000004682 monohydrates Chemical class 0.000 claims 1
238000000034 method Methods 0.000 abstract description 10
208000018569 Respiratory Tract disease Diseases 0.000 abstract description 2
239000013543 active substance Substances 0.000 description 40
239000000243 solution Substances 0.000 description 28
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 description 23
239000000843 powder Substances 0.000 description 23
229960000257 tiotropium bromide Drugs 0.000 description 23
238000009472 formulation Methods 0.000 description 22
239000000546 pharmaceutical excipient Substances 0.000 description 20
150000001875 compounds Chemical class 0.000 description 14
239000007789 gas Substances 0.000 description 13
150000003839 salts Chemical class 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000002775 capsule Substances 0.000 description 11
239000002253 acid Substances 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 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
239000002245 particle Substances 0.000 description 8
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 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
239000012530 fluid Substances 0.000 description 7
229960001375 lactose Drugs 0.000 description 7
239000008101 lactose Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
-1 GW 215864 Chemical compound 0.000 description 6
229940110309 tiotropium Drugs 0.000 description 6
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 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
235000006708 antioxidants Nutrition 0.000 description 4
235000010323 ascorbic acid Nutrition 0.000 description 4
239000011668 ascorbic acid Substances 0.000 description 4
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OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 description 4
NVOYVOBDTVTBDX-PMEUIYRNSA-N oxitropium Chemical class CC[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1 NVOYVOBDTVTBDX-PMEUIYRNSA-N 0.000 description 4
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HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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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 2
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
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CA2614631A 2000-10-31 2001-10-23 Compositions pharmaceutiques contenant des anticholinergiques et des corticosteroides sous la forme d'une suspension ou d'une solution inhalable Expired - Fee Related CA2614631C (fr)

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CA2733294A CA2733294C (fr)	2000-10-31	2001-10-23	Combinaison pharmaceutique constituee d'un sel de tiotropium et de ciclesonide

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Application Number	Priority Date	Filing Date	Title
DE10054042		2000-10-31
DE10054042.2		2000-10-31
DE10062712.9		2000-12-15
DE10062712A DE10062712A1 (de)	2000-12-15	2000-12-15	Neue Arzneimittelkompositionen auf der Basis von Anticholinergika und Corticosteroiden
CA002436540A CA2436540C (fr)	2000-10-31	2001-10-23	Composition pharmaceutique a base d'anticholinergiques et de corticosteroides

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Publication	Publication Date	Title
CA2733294C (fr)	2011-12-20	Combinaison pharmaceutique constituee d'un sel de tiotropium et de ciclesonide
CA2431565C (fr)	2008-02-19	Nouvelles compositions pharmaceutiques a base d'anticholinergiques et de ciclesonide
US20120189556A1 (en)	2012-07-26	Pharmaceutical compositions based on anticholinergics and corticosteroids
US7994188B2 (en)	2011-08-09	Compounds for treating inflammatory diseases
US20030018019A1 (en)	2003-01-23	Pharmaceutical compositions based on anticholinergics, corticosteroids and betamimetics
US6608054B2 (en)	2003-08-19	Pharmaceutical compositions based on anticholinergics and endothelin antagonists
US20090088408A1 (en)	2009-04-02	Pharmaceutical compositions on anticholinergics, corticosteroids and betamimetics
US20040010003A1 (en)	2004-01-15	Medicaments comprising betamimetics and a novel anticholinergic
US20020193392A1 (en)	2002-12-19	Pharmaceutical compositions based on tiotropium salts of salts of salmeterol
US7084153B2 (en)	2006-08-01	Medicaments comprising steroids and a novel anticholinergic
IL155718A (en)	2010-06-30	Medicament compositions based on tiotropium salts and on salmeterol salts
EP1551405A1 (fr)	2005-07-13	Sels de tiotropium utilises pour reduire le taux de mortalite respiratoire
US20020122773A1 (en)	2002-09-05	Pharmaceutical compositions based on anticholinergics and dopamine agonists
CA2481268C (fr)	2011-07-12	Medicaments comprenant des steroides et un nouvel anticholinergique
US20020193394A1 (en)	2002-12-19	Compounds for treating inflammatory diseases
CA2568834A1 (fr)	2006-01-12	Medicaments pour inhalation comprenant des steroides et un anticholinergique
CA2534128C (fr)	2012-10-23	Combinaison d'un anticholinergique et d'un steroide et leur utilisation dans le traitement de troubles respiratoires par inhalation
CA2582207A1 (fr)	2006-06-01	Medicaments administres par inhalation contenant un anticholinergique, du salmeterol et un steroide du groupe ciclesonide ou mometasone furoate
CA2614631C (fr)	2011-06-14	Compositions pharmaceutiques contenant des anticholinergiques et des corticosteroides sous la forme d'une suspension ou d'une solution inhalable
CA2582153A1 (fr)	2006-06-01	Medicaments administres par inhalation contenant un nouvel anticholinergique, du formoterol et un steroide
CA2430592C (fr)	2008-02-26	Nouvelles compositions medicamenteuses a base d'anticholinergiques et d'agonistes de la dopamine
EP1654001A2 (fr)	2006-05-10	Medicament pour inhalation comprenant des steroides et un betamimetique
CA2533792C (fr)	2012-09-11	Medicaments d'inhalation contenant des steroides et des esters d'acide carboxylique de fluorene