JP5835717B2 - 医薬組成物およびその製造方法 - Google Patents
医薬組成物およびその製造方法 Download PDFInfo
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- JP5835717B2 JP5835717B2 JP2013509268A JP2013509268A JP5835717B2 JP 5835717 B2 JP5835717 B2 JP 5835717B2 JP 2013509268 A JP2013509268 A JP 2013509268A JP 2013509268 A JP2013509268 A JP 2013509268A JP 5835717 B2 JP5835717 B2 JP 5835717B2
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- Prior art keywords
- pharmaceutical composition
- cyclodextrin
- pazopanib
- composition according
- water
- 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.)
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 107
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000003798 L01XE11 - Pazopanib Substances 0.000 claims description 113
- 229960000639 pazopanib Drugs 0.000 claims description 113
- CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 claims description 113
- 239000000203 mixture Substances 0.000 claims description 94
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 80
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 66
- 229920000858 Cyclodextrin Polymers 0.000 claims description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
- 238000009472 formulation Methods 0.000 claims description 37
- PVPBHKCSQBLDEW-ZQOBQRRWSA-N (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol 4-hydroxybutane-1-sulfonic acid Chemical compound OCCCCS(O)(=O)=O.OC[C@H]1O[C@@H]2O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@@H]6[C@@H](CO)O[C@H](O[C@@H]7[C@@H](CO)O[C@H](O[C@@H]8[C@@H](CO)O[C@H](O[C@H]1[C@H](O)[C@H]2O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O PVPBHKCSQBLDEW-ZQOBQRRWSA-N 0.000 claims description 33
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- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 8
- 241000282412 Homo Species 0.000 claims description 6
- 239000001488 sodium phosphate Substances 0.000 claims description 5
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 3
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 3
- NZAQRZWBQUIBSF-UHFFFAOYSA-N 4-(4-sulfobutoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCOCCCCS(O)(=O)=O NZAQRZWBQUIBSF-UHFFFAOYSA-N 0.000 claims 1
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- 229960004853 betadex Drugs 0.000 description 35
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- 235000002639 sodium chloride Nutrition 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 24
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 23
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
- 239000003814 drug Substances 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 229940079593 drug Drugs 0.000 description 18
- 239000000523 sample Substances 0.000 description 17
- MQHIQUBXFFAOMK-UHFFFAOYSA-N pazopanib hydrochloride Chemical group Cl.C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 MQHIQUBXFFAOMK-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
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- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 6
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
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- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- Inorganic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
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| US33171510P | 2010-05-05 | 2010-05-05 | |
| US61/331,715 | 2010-05-05 | ||
| PCT/US2011/035363 WO2011140343A1 (en) | 2010-05-05 | 2011-05-05 | Pharmaceutical compositions and methods of making same |
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| JP2013525501A JP2013525501A (ja) | 2013-06-20 |
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| JP5835717B2 true JP5835717B2 (ja) | 2015-12-24 |
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| US20070020299A1 (en) | 2003-12-31 | 2007-01-25 | Pipkin James D | Inhalant formulation containing sulfoalkyl ether cyclodextrin and corticosteroid |
| ES2493641T3 (es) * | 2007-06-28 | 2014-09-12 | Cydex Pharmaceuticals, Inc. | Administración nasal de soluciones acuosas de corticosteroides |
| US12370352B2 (en) | 2007-06-28 | 2025-07-29 | Cydex Pharmaceuticals, Inc. | Nasal and ophthalmic delivery of aqueous corticosteroid solutions |
| US8623395B2 (en) | 2010-01-29 | 2014-01-07 | Forsight Vision4, Inc. | Implantable therapeutic device |
| US10166142B2 (en) | 2010-01-29 | 2019-01-01 | Forsight Vision4, Inc. | Small molecule delivery with implantable therapeutic device |
| UY33367A (es) * | 2010-05-05 | 2011-10-31 | Glaxo Wellcome Mfg Pte Ltd | Composiciones farmacéuticas y métodos para su elaboración |
| LT2600930T (lt) | 2010-08-05 | 2021-04-12 | Forsight Vision4, Inc. | Injekcinis aparatas, skirtas vaisto tiekimui |
| US20140031769A1 (en) | 2010-11-19 | 2014-01-30 | Forsight Vision4, Inc. | Therapeutic agent formulations for implanted devices |
| ES2864203T3 (es) | 2011-09-16 | 2021-10-13 | Forsight Vision4 Inc | Aparato de intercambio de fluido |
| CA2864736A1 (en) * | 2012-02-17 | 2013-08-22 | Pharmacyclics, Inc. | Combinations of histone deacetylase inhibitor and pazopanib and uses thereof |
| AU2013228148B2 (en) * | 2012-03-08 | 2016-07-14 | Samsung Electronics Co., Ltd. | Method for controlling service in radio communication system |
| AU2014236455B2 (en) | 2013-03-14 | 2018-07-12 | Forsight Vision4, Inc. | Systems for sustained intraocular delivery of low solubility compounds from a port delivery system implant |
| CN105246438B (zh) | 2013-03-28 | 2018-01-26 | 弗赛特影像4股份有限公司 | 用于输送治疗物质的眼科植入物 |
| US11136625B2 (en) | 2013-08-28 | 2021-10-05 | Crown Bioscience, Inc. (Taicang) | Gene expression signatures predictive of subject response to a multi-kinase inhibitor and methods of using the same |
| CA2957548A1 (en) | 2014-08-08 | 2016-02-11 | Forsight Vision4, Inc. | Stable and soluble formulations of receptor tyrosine kinase inhibitors, and methods of preparation thereof |
| US10500091B2 (en) | 2014-11-10 | 2019-12-10 | Forsight Vision4, Inc. | Expandable drug delivery devices and methods of use |
| WO2016104690A1 (ja) | 2014-12-25 | 2016-06-30 | 国立大学法人京都大学 | 高密度リポタンパク質およびその細胞親和性ペプチドを融合した高密度リポタンパク質の点眼による後眼部薬物デリバリー |
| EP3439591B1 (en) | 2016-04-05 | 2020-09-23 | ForSight Vision4, Inc. | Implantable ocular drug delivery devices |
| WO2018192416A1 (en) * | 2017-04-17 | 2018-10-25 | National Institute Of Biological Sciences, Beijing | Treating Male Senescence |
| TWI770246B (zh) * | 2017-08-02 | 2022-07-11 | 昊運股份有限公司 | 新穎化合物及包含其之醫藥組成物 |
| EP4249069B1 (en) * | 2018-06-07 | 2025-11-19 | Pfizer Inc. | Aqueous formulation comprising 1-(4-{[4-(dimethylamino)piperidin-1-yl]carbonyl}phenyl)-3-[4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)phenyl]urea |
| CN113350351A (zh) * | 2020-03-13 | 2021-09-07 | 青晓制药公司 | 帕唑帕尼的应用、药物组合物、注射液及制备方法和应用 |
| USD1033637S1 (en) | 2022-01-24 | 2024-07-02 | Forsight Vision4, Inc. | Fluid exchange device |
| US20240050429A1 (en) * | 2022-08-10 | 2024-02-15 | Qx Therapeutics, Inc. | Pazopanib pharmaceutical composition, injection and preparation method and use thereof |
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| SE8904296D0 (sv) * | 1989-12-21 | 1989-12-21 | Pharmacia Ab | Transdermal system |
| US7893040B2 (en) * | 2005-07-22 | 2011-02-22 | Oculis Ehf | Cyclodextrin nanotechnology for ophthalmic drug delivery |
| SI1968594T1 (sl) * | 2005-11-29 | 2011-01-31 | Glaxosmithkline Llc | Tretma okularnih neovaskularnih motenj, kot makularne degeneracije, angiodnih prog. uveitisa in makularnega edema |
| AR059066A1 (es) * | 2006-01-27 | 2008-03-12 | Amgen Inc | Combinaciones del inhibidor de la angiopoyetina -2 (ang2) y el inhibidor del factor de crecimiento endotelial vascular (vegf) |
| WO2007121483A2 (en) * | 2006-04-18 | 2007-10-25 | Ekr Therapeutics, Inc. | Pre-mixed, ready-to-use iv bolus compositions and methods of use |
| ES2630406T3 (es) * | 2007-10-19 | 2017-08-21 | Sarcode Bioscience Inc. | Composición y procedimientos para el tratamiento de la retinopatía diabética |
| ES2494365T3 (es) * | 2008-01-30 | 2014-09-15 | Genentech, Inc. | Compuestos de pirazolopirimidina que inhiben PI3K y métodos de uso |
| JP2012533562A (ja) * | 2009-07-16 | 2012-12-27 | グラクソ ウェルカム マニュファクチュアリング ピーティーイー リミテッド | 治療法 |
| WO2011039648A1 (en) * | 2009-09-30 | 2011-04-07 | Glaxo Wellcome Manufacturing Pte Ltd. | Methods of administration and treatment |
| UY33164A (es) * | 2010-01-06 | 2011-08-31 | Glaxo Wellcome Mfg Pte Ltd | Metodo de tratamiento |
| UY33367A (es) * | 2010-05-05 | 2011-10-31 | Glaxo Wellcome Mfg Pte Ltd | Composiciones farmacéuticas y métodos para su elaboración |
| US20130023550A1 (en) * | 2010-05-05 | 2013-01-24 | Glaxo Wellcome Manufacturing Pte, Ltd | Pharmaceutical compositions and methods of making same |
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2011
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| UY33367A (es) | 2011-10-31 |
| KR20130071434A (ko) | 2013-06-28 |
| DOP2012000281A (es) | 2013-05-31 |
| CO6640262A2 (es) | 2013-03-22 |
| CA2798386A1 (en) | 2011-11-10 |
| BR112012028291A2 (pt) | 2015-09-15 |
| WO2011140343A1 (en) | 2011-11-10 |
| JP2013525501A (ja) | 2013-06-20 |
| EP2566331A4 (en) | 2013-09-18 |
| CR20120556A (es) | 2013-02-20 |
| PE20130217A1 (es) | 2013-03-21 |
| EA201291168A1 (ru) | 2013-06-28 |
| EP2566331B1 (en) | 2014-09-03 |
| PH12012502159A1 (en) | 2013-02-04 |
| HK1175947A1 (en) | 2013-07-19 |
| CN102970871A (zh) | 2013-03-13 |
| AR081364A1 (es) | 2012-08-29 |
| NZ603411A (en) | 2014-10-31 |
| US20110281901A1 (en) | 2011-11-17 |
| MX2012012837A (es) | 2013-01-24 |
| ZA201208265B (en) | 2013-07-31 |
| US20120028918A1 (en) | 2012-02-02 |
| SG185087A1 (en) | 2012-12-28 |
| TW201206908A (en) | 2012-02-16 |
| IL222751A0 (en) | 2012-12-31 |
| AU2011247995A1 (en) | 2012-12-13 |
| CL2012003075A1 (es) | 2013-03-08 |
| AU2011247995B2 (en) | 2014-07-31 |
| US20150231265A1 (en) | 2015-08-20 |
| EP2566331A1 (en) | 2013-03-13 |
| ES2519615T3 (es) | 2014-11-07 |
| MA34286B1 (fr) | 2013-06-01 |
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