CA2440010C - Powder inhaler formulations - Google Patents
Powder inhaler formulations Download PDFInfo
- Publication number
- CA2440010C CA2440010C CA2440010A CA2440010A CA2440010C CA 2440010 C CA2440010 C CA 2440010C CA 2440010 A CA2440010 A CA 2440010A CA 2440010 A CA2440010 A CA 2440010A CA 2440010 C CA2440010 C CA 2440010C
- Authority
- CA
- Canada
- Prior art keywords
- powder
- inhalation
- component
- sorbitan
- mixing
- 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
- 239000000843 powder Substances 0.000 title claims abstract description 87
- 239000000203 mixture Substances 0.000 title claims description 51
- 238000009472 formulation Methods 0.000 title description 24
- 238000000034 method Methods 0.000 claims abstract description 52
- 239000003814 drug Substances 0.000 claims abstract description 51
- 239000002552 dosage form Substances 0.000 claims abstract description 24
- 238000002156 mixing Methods 0.000 claims description 38
- 230000008569 process Effects 0.000 claims description 34
- 229940110309 tiotropium Drugs 0.000 claims description 29
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 28
- 239000000194 fatty acid Substances 0.000 claims description 28
- 229930195729 fatty acid Natural products 0.000 claims description 28
- 239000004480 active ingredient Substances 0.000 claims description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 22
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 claims description 19
- 229960001022 fenoterol Drugs 0.000 claims description 19
- 239000004147 Sorbitan trioleate Substances 0.000 claims description 18
- 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 claims description 18
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 14
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 13
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 13
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 13
- 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 claims description 13
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 11
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- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 8
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 8
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 8
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- 238000004519 manufacturing process Methods 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 claims description 6
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- NVOYVOBDTVTBDX-PMEUIYRNSA-N oxitropium Chemical compound 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 claims description 6
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- 229960004129 sorbitan tristearate Drugs 0.000 claims description 6
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 229940035044 sorbitan monolaurate Drugs 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
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- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 claims description 4
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- NVANJYGRGNEULT-BDZGGURLSA-N [(3s,4r,5r)-4-hexadecanoyloxy-5-[(1r)-1-hexadecanoyloxy-2-hydroxyethyl]oxolan-3-yl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)O[C@H](CO)[C@H]1OC[C@H](OC(=O)CCCCCCCCCCCCCCC)[C@H]1OC(=O)CCCCCCCCCCCCCCC NVANJYGRGNEULT-BDZGGURLSA-N 0.000 claims description 2
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- A—HUMAN NECESSITIES
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Landscapes
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| CN102688224A (zh) * | 2003-04-14 | 2012-09-26 | 维克特拉有限公司 | 用于提高剂量效率的药物组合物和装置 |
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| ITMI20040795A1 (it) * | 2004-04-23 | 2004-07-23 | Eratech S R L | Composizione farmaceutica solida secca suo processo di preparazione e sospensione acquosa stabile ottenuta dalla stessa |
| DE102004024451A1 (de) * | 2004-05-14 | 2005-12-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pulverformulierungen für die Inhalation, die Enantiomerenreine Betaagonisten enthalten |
| US9149433B2 (en) * | 2004-11-30 | 2015-10-06 | Basf Corporation | Method for formation of micro-prilled polymers |
| EP3199164B1 (en) | 2005-02-10 | 2020-03-18 | Glaxo Group Limited | Processes for making lactose utilizing pre-classification techniques and pharmaceutical formulations formed therefrom |
| DK1917253T3 (da) | 2005-08-15 | 2015-03-30 | Boehringer Ingelheim Int | Fremgangsmåde til fremstilling af betamimetika |
| EP1925295A1 (de) * | 2006-11-22 | 2008-05-28 | Boehringer Ingelheim Pharma GmbH & Co. KG | Stabile Pulverformulierung enthaltend ein Anticholinergikum |
| JP2010534248A (ja) | 2007-07-21 | 2010-11-04 | アルバニー モレキュラー リサーチ， インコーポレイテッド | ５−ピリジノン置換インダゾール |
| CN103351390A (zh) | 2007-11-21 | 2013-10-16 | 解码遗传Ehf公司 | 用于治疗肺部和心血管病症的联芳基pde4 抑制剂 |
| EP2476680B1 (en) | 2008-01-11 | 2014-08-27 | Albany Molecular Research, Inc. | (1-Azinone)-Substituted Pyridoindoles |
| EP2349224B1 (en) | 2008-10-10 | 2017-05-10 | Probelte Pharma, S.A. | Orally administrable immunostimulant product for aquaculture |
| WO2010059836A1 (en) | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Substituted aza-bridged bicyclics for cardiovascular and cns disease |
| US8673931B2 (en) | 2009-01-26 | 2014-03-18 | Abraham Fisher | Bicyclic heterocyclic spiro compounds |
| WO2010102065A1 (en) | 2009-03-05 | 2010-09-10 | Bend Research, Inc. | Pharmaceutical compositions of dextran polymer derivatives |
| EP3130396B1 (en) | 2009-03-27 | 2021-03-17 | Bend Research, Inc. | Spray-drying process |
| TR200909788A2 (tr) | 2009-12-25 | 2011-07-21 | Bi̇lgi̇ç Mahmut | Tiotropyum içeren inhalasyona uygun kuru toz formülasyonu |
| US8834931B2 (en) | 2009-12-25 | 2014-09-16 | Mahmut Bilgic | Dry powder formulation containing tiotropium for inhalation |
| US9084976B2 (en) | 2010-09-03 | 2015-07-21 | Bend Research, Inc. | Spray-drying apparatus and methods of using the same |
| US8815294B2 (en) | 2010-09-03 | 2014-08-26 | Bend Research, Inc. | Pharmaceutical compositions of dextran polymer derivatives and a carrier material |
| EP2611530B1 (en) | 2010-09-03 | 2019-01-16 | Bend Research, Inc. | Spray-drying apparatus and methods of using the same |
| EP2618924A1 (en) | 2010-09-24 | 2013-07-31 | Bend Research, Inc. | High-temperature spray drying process and apparatus |
| US9084727B2 (en) | 2011-05-10 | 2015-07-21 | Bend Research, Inc. | Methods and compositions for maintaining active agents in intra-articular spaces |
| US10105500B2 (en) | 2012-05-09 | 2018-10-23 | Virginia Commonwealth University | Dry powder inhaler (DPI) designs for producing aerosols with high fine particle fractions |
| ES2588902T3 (es) * | 2012-05-14 | 2016-11-07 | Boehringer Ingelheim International Gmbh | Dispositivo para alojar un blíster de fármacos |
| WO2014007771A2 (en) | 2012-07-05 | 2014-01-09 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Inhalation compositions comprising muscarinic receptor antagonist |
| US10111957B2 (en) * | 2012-07-05 | 2018-10-30 | Arven Ilac Snayi ve Ticaret A.S. | Inhalation compositions comprising glucose anhydrous |
| PT3212169T (pt) | 2014-10-31 | 2021-05-06 | Bend Res Inc | Processo para formar domínios ativos dispersos numa matriz |
| US10806770B2 (en) | 2014-10-31 | 2020-10-20 | Monash University | Powder formulation |
| CN110996912A (zh) * | 2017-08-20 | 2020-04-10 | 福摩莱克斯医药创新有限公司 | 用于鼻内递送的干粉组合物 |
| US11844859B2 (en) | 2017-08-20 | 2023-12-19 | Nasus Pharma Ltd. | Dry powder compositions for intranasal delivery |
| ES3038913T3 (en) | 2018-03-20 | 2025-10-15 | Icahn School Med Mount Sinai | Beta-carboline derivatives as dyrk1a inhibitors for the treatment of e.g. diabetes |
| US11786460B2 (en) * | 2018-04-16 | 2023-10-17 | Ioulia Tseti | Pharmaceutical dry powder composition for inhalation comprising a thyroid hormone |
| US10966943B2 (en) | 2018-09-06 | 2021-04-06 | Innopharmascreen Inc. | Methods and compositions for treatment of asthma or parkinson's disease |
| EP3906233B1 (en) | 2018-12-31 | 2024-01-31 | Icahn School of Medicine at Mount Sinai | Kinase inhibitor compounds and compositions and methods of use |
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| GB9024366D0 (en) * | 1990-11-09 | 1991-01-02 | Glaxo Group Ltd | Medicaments |
| GB9026025D0 (en) * | 1990-11-29 | 1991-01-16 | Boehringer Ingelheim Kg | Inhalation device |
| US5354934A (en) * | 1993-02-04 | 1994-10-11 | Amgen Inc. | Pulmonary administration of erythropoietin |
| US5612053A (en) * | 1995-04-07 | 1997-03-18 | Edward Mendell Co., Inc. | Controlled release insufflation carrier for medicaments |
| US6645644B1 (en) * | 1996-10-17 | 2003-11-11 | The Trustees Of Princeton University | Enhanced bonding of phosphoric and phosphoric acids to oxidized substrates |
| US5874111A (en) * | 1997-01-07 | 1999-02-23 | Maitra; Amarnath | Process for the preparation of highly monodispersed polymeric hydrophilic nanoparticles |
| CA2277801C (en) * | 1997-01-16 | 2002-10-15 | Massachusetts Institute Of Technology | Preparation of particles for inhalation |
| US6309623B1 (en) * | 1997-09-29 | 2001-10-30 | Inhale Therapeutic Systems, Inc. | Stabilized preparations for use in metered dose inhalers |
| JP2001517692A (ja) * | 1997-09-29 | 2001-10-09 | インヘール セラピューティック システムズ， インコーポレイテッド | ネブライザにおける使用のための安定化調製物 |
| US7521068B2 (en) * | 1998-11-12 | 2009-04-21 | Elan Pharma International Ltd. | Dry powder aerosols of nanoparticulate drugs |
| ES2192866T3 (es) * | 1998-11-13 | 2003-10-16 | Jago Res Ag | Polvo seco para inhalacion. |
| EG23951A (en) * | 1999-03-25 | 2008-01-29 | Otsuka Pharma Co Ltd | Cilostazol preparation |
-
2001
- 2001-03-21 GB GBGB0107106.7A patent/GB0107106D0/en not_active Ceased
-
2002
- 2002-02-28 US US10/085,972 patent/US20030007932A1/en not_active Abandoned
- 2002-03-16 AT AT02745193T patent/ATE556704T1/de active
- 2002-03-16 JP JP2002578923A patent/JP2004523594A/ja active Pending
- 2002-03-16 CA CA2440010A patent/CA2440010C/en not_active Expired - Fee Related
- 2002-03-16 AU AU2002316820A patent/AU2002316820A1/en not_active Abandoned
- 2002-03-16 MX MXPA03008398A patent/MXPA03008398A/es active IP Right Grant
- 2002-03-16 EP EP02745193A patent/EP1372610B1/en not_active Expired - Lifetime
- 2002-03-16 WO PCT/EP2002/002948 patent/WO2002080884A2/en not_active Ceased
- 2002-03-20 UY UY27218A patent/UY27218A1/es not_active Application Discontinuation
-
2005
- 2005-03-30 US US11/093,491 patent/US20050196346A1/en not_active Abandoned
-
2007
- 2007-01-17 US US11/653,887 patent/US20080057003A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20080057003A1 (en) | 2008-03-06 |
| JP2004523594A (ja) | 2004-08-05 |
| EP1372610B1 (en) | 2012-05-09 |
| CA2440010A1 (en) | 2002-10-17 |
| US20030007932A1 (en) | 2003-01-09 |
| ATE556704T1 (de) | 2012-05-15 |
| EP1372610A2 (en) | 2004-01-02 |
| WO2002080884A2 (en) | 2002-10-17 |
| GB0107106D0 (en) | 2001-05-09 |
| UY27218A1 (es) | 2002-10-31 |
| AU2002316820A1 (en) | 2002-10-21 |
| MXPA03008398A (es) | 2004-01-29 |
| US20050196346A1 (en) | 2005-09-08 |
| WO2002080884A3 (en) | 2003-10-16 |
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