TW200817011A - Aerosol formulation for the inhalation of beta agonists - Google Patents
Aerosol formulation for the inhalation of beta agonists Download PDFInfo
- Publication number
- TW200817011A TW200817011A TW096130614A TW96130614A TW200817011A TW 200817011 A TW200817011 A TW 200817011A TW 096130614 A TW096130614 A TW 096130614A TW 96130614 A TW96130614 A TW 96130614A TW 200817011 A TW200817011 A TW 200817011A
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- active substance
- ethyl
- enantiomers
- mixture
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 112
- 238000009472 formulation Methods 0.000 title claims abstract description 70
- 239000000443 aerosol Substances 0.000 title abstract description 16
- 229940125388 beta agonist Drugs 0.000 title 1
- 239000013543 active substance Substances 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 119
- 239000008194 pharmaceutical composition Substances 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 56
- 239000002253 acid Substances 0.000 claims description 40
- 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 36
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 36
- 235000019441 ethanol Nutrition 0.000 claims description 28
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 23
- -1 decyloxy, ethoxy Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 20
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000473 propyl gallate Substances 0.000 claims description 18
- 235000010388 propyl gallate Nutrition 0.000 claims description 18
- 229940075579 propyl gallate Drugs 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 235000006708 antioxidants Nutrition 0.000 claims description 9
- 239000002207 metabolite Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- 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 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 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 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 7
- 229960001860 salicylate Drugs 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
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- 239000000460 chlorine Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 229960003728 ciclesonide Drugs 0.000 claims description 5
- 235000015165 citric acid Nutrition 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 5
- 229940095064 tartrate Drugs 0.000 claims description 5
- 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 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229960004436 budesonide Drugs 0.000 claims description 4
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- 229960002714 fluticasone Drugs 0.000 claims description 4
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- 208000024891 symptom Diseases 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
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- ANGKOCUUWGHLCE-HKUYNNGSSA-N [(3s)-1,1-dimethylpyrrolidin-1-ium-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical class C1[N+](C)(C)CC[C@@H]1OC(=O)[C@](O)(C=1C=CC=CC=1)C1CCCC1 ANGKOCUUWGHLCE-HKUYNNGSSA-N 0.000 claims description 3
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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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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| US20050255050A1 (en) * | 2004-05-14 | 2005-11-17 | Boehringer Ingelheim International Gmbh | Powder formulations for inhalation, comprising enantiomerically pure beta agonists |
| US7220742B2 (en) * | 2004-05-14 | 2007-05-22 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, process for the manufacture thereof and use thereof as medicaments |
| MX2008001976A (es) | 2005-08-15 | 2008-03-25 | Boehringer Ingelheim Int | Procedimiento para la preparacion de betamimeticos. |
| KR20140012989A (ko) | 2011-02-17 | 2014-02-04 | 시플라 리미티드 | 글리코피롤레이트 및 베타2-효능제의 조합 |
| EP3318247A1 (en) | 2011-08-12 | 2018-05-09 | Boehringer Ingelheim Vetmedica GmbH | Taste masked pharmaceutical composition |
| WO2014016548A2 (en) | 2012-07-27 | 2014-01-30 | Cipla Limited | Pharmaceutical composition |
| LT2934479T (lt) | 2012-12-21 | 2018-12-27 | Boehringer Ingelheim Vetmedica Gmbh | Ciklezonidas, skirtas arklių kvėpavimo takų ligų gydymui |
| ES2909039T3 (es) * | 2012-12-21 | 2022-05-05 | Boehringer Ingelheim Vetmedica Gmbh | Formulación farmacéutica que comprende ciclesonida |
| CA2952701C (en) | 2014-06-18 | 2023-09-19 | Boehringer Ingelheim Vetmedica Gmbh | Muscarinic antagonists and combinations thereof for the treatment of airway disease in horses |
| US11701478B2 (en) | 2015-10-09 | 2023-07-18 | Boehringer Ingelheim International Gmbh | Method for coating microstructured components |
| US20210220367A1 (en) * | 2020-01-20 | 2021-07-22 | Cai Gu Huang | Inhalable formulation of a solution containing glycopyrrolate and olodaterol hydrochloride |
| US20210393521A1 (en) * | 2020-06-23 | 2021-12-23 | Cai Gu Huang | Preparation of a pharmaceutical composition of olodaterol, tiotropium bromide and budesonide |
| CN115989032A (zh) | 2020-07-31 | 2023-04-18 | 化学研究有限公司 | 用于吸入施用的组合疗法 |
| CN117679423A (zh) | 2022-09-05 | 2024-03-12 | 立生医药(苏州)有限公司 | 预防或治疗呼吸系统疾病的吸入用药物组合物 |
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| DE19653969A1 (de) * | 1996-12-20 | 1998-06-25 | Boehringer Ingelheim Kg | Neue wässrige Arzneimittelzubereitung zur Erzeugung treibgasfreier Aerosole |
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| DE10253282A1 (de) * | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung |
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| DE102004019540A1 (de) * | 2004-04-22 | 2005-11-10 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen |
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| DK1781298T3 (da) * | 2004-04-22 | 2012-05-07 | Boehringer Ingelheim Int | Lægemiddelkombinationer indeholdende benzoxazin til behandling af luftvejs-sygdomme |
| DE102004024454A1 (de) * | 2004-05-14 | 2005-12-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Enantiomerenreine Betaagonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| US7220742B2 (en) * | 2004-05-14 | 2007-05-22 | Boehringer Ingelheim International Gmbh | Enantiomerically pure beta agonists, process for the manufacture thereof and use thereof as medicaments |
| WO2006023457A1 (en) * | 2004-08-16 | 2006-03-02 | Theravance, Inc. | COMPOUNDS HAVING β2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY |
| TWI482772B (zh) * | 2006-08-21 | 2015-05-01 | Astrazeneca Ab | 適合口服且包含三唑并[4,5-d]嘧啶衍生物之組合物 |
-
2007
- 2007-08-15 UY UY30542A patent/UY30542A1/es not_active Application Discontinuation
- 2007-08-16 US US11/839,809 patent/US20080041369A1/en not_active Abandoned
- 2007-08-16 AU AU2007285747A patent/AU2007285747A1/en not_active Abandoned
- 2007-08-16 MX MX2009001759A patent/MX2009001759A/es not_active Application Discontinuation
- 2007-08-16 KR KR1020097005575A patent/KR20090057393A/ko not_active Ceased
- 2007-08-16 PE PE2007001102A patent/PE20081319A1/es not_active Application Discontinuation
- 2007-08-16 JP JP2009525030A patent/JP2010501022A/ja active Pending
- 2007-08-16 SG SG2011057254A patent/SG174058A1/en unknown
- 2007-08-16 EP EP07819952A patent/EP2054084A1/de not_active Withdrawn
- 2007-08-16 WO PCT/EP2007/058518 patent/WO2008020057A1/de not_active Ceased
- 2007-08-16 NZ NZ575425A patent/NZ575425A/en not_active IP Right Cessation
- 2007-08-16 CA CA002660488A patent/CA2660488A1/en not_active Abandoned
- 2007-08-16 BR BRPI0715761-4A2A patent/BRPI0715761A2/pt not_active IP Right Cessation
- 2007-08-17 TW TW096130614A patent/TW200817011A/zh unknown
- 2007-08-17 AR ARP070103673A patent/AR062425A1/es not_active Application Discontinuation
-
2009
- 2009-01-28 NO NO20090407A patent/NO20090407L/no not_active Application Discontinuation
- 2009-02-12 IL IL197025A patent/IL197025A0/en unknown
- 2009-03-18 CO CO09028168A patent/CO6170341A2/es not_active Application Discontinuation
-
2011
- 2011-11-11 US US13/294,449 patent/US20120058980A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2054084A1 (de) | 2009-05-06 |
| AU2007285747A1 (en) | 2008-02-21 |
| KR20090057393A (ko) | 2009-06-05 |
| AR062425A1 (es) | 2008-11-05 |
| BRPI0715761A2 (pt) | 2013-09-24 |
| PE20081319A1 (es) | 2008-10-16 |
| UY30542A1 (es) | 2008-03-31 |
| MX2009001759A (es) | 2009-02-25 |
| JP2010501022A (ja) | 2010-01-14 |
| US20120058980A1 (en) | 2012-03-08 |
| IL197025A0 (en) | 2009-11-18 |
| NO20090407L (no) | 2009-04-29 |
| SG174058A1 (en) | 2011-09-29 |
| CO6170341A2 (es) | 2010-06-18 |
| US20080041369A1 (en) | 2008-02-21 |
| NZ575425A (en) | 2011-12-22 |
| WO2008020057A1 (de) | 2008-02-21 |
| CA2660488A1 (en) | 2008-02-21 |
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