CA2772871A1 - Pharmaceutical formulations for indibulin - Google Patents
Pharmaceutical formulations for indibulin Download PDFInfo
- Publication number
- CA2772871A1 CA2772871A1 CA2772871A CA2772871A CA2772871A1 CA 2772871 A1 CA2772871 A1 CA 2772871A1 CA 2772871 A CA2772871 A CA 2772871A CA 2772871 A CA2772871 A CA 2772871A CA 2772871 A1 CA2772871 A1 CA 2772871A1
- Authority
- CA
- Canada
- Prior art keywords
- oral formulation
- formulation
- disintegrant
- diluent
- indibulin
- 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.)
- Abandoned
Links
- SOLIIYNRSAWTSQ-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-pyridin-4-ylacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C=CN=CC=2)=C1 SOLIIYNRSAWTSQ-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229950001541 indibulin Drugs 0.000 title claims abstract description 52
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 101
- 238000009472 formulation Methods 0.000 claims abstract description 91
- 238000000034 method Methods 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 25
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- 206010028980 Neoplasm Diseases 0.000 claims description 42
- 239000007884 disintegrant Substances 0.000 claims description 40
- 239000003085 diluting agent Substances 0.000 claims description 37
- -1 fatty acid ester Chemical class 0.000 claims description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 34
- 239000003995 emulsifying agent Substances 0.000 claims description 29
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 29
- 239000002245 particle Substances 0.000 claims description 23
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 19
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 19
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 19
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 19
- 239000006186 oral dosage form Substances 0.000 claims description 18
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- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 claims description 12
- 229940045902 sodium stearyl fumarate Drugs 0.000 claims description 12
- 230000003463 hyperproliferative effect Effects 0.000 claims description 11
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 7
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 7
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- 239000008389 polyethoxylated castor oil Substances 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- 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 4
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- 229930195725 Mannitol Natural products 0.000 claims description 4
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 4
- 229930006000 Sucrose Natural products 0.000 claims description 4
- 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 4
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims description 4
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 4
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005720 sucrose Substances 0.000 claims description 4
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 claims description 3
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- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 208000030289 Lymphoproliferative disease Diseases 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- 208000002774 Paraproteinemias Diseases 0.000 claims description 3
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- 208000009359 Sezary Syndrome Diseases 0.000 claims description 3
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- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical group OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
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- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
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| US23925409P | 2009-09-02 | 2009-09-02 | |
| US61/239,254 | 2009-09-02 | ||
| PCT/US2010/047436 WO2011028743A1 (en) | 2009-09-02 | 2010-09-01 | Pharmaceutical formulations for indibulin |
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| CA2772871A1 true CA2772871A1 (en) | 2011-03-10 |
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| US (1) | US20120219597A1 (enExample) |
| EP (1) | EP2473168A4 (enExample) |
| JP (1) | JP2013503876A (enExample) |
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| CA (1) | CA2772871A1 (enExample) |
| TW (1) | TW201113266A (enExample) |
| WO (1) | WO2011028743A1 (enExample) |
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| US20140004192A1 (en) * | 2012-04-13 | 2014-01-02 | Ziopharm Oncology, Inc. | Pharmaceutical formulations of indibulin and uses thereof |
| CN116531375A (zh) * | 2023-06-06 | 2023-08-04 | 河北大学 | 一种tppp3抑制剂及其应用 |
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| GB8824392D0 (en) * | 1988-10-18 | 1988-11-23 | Ciba Geigy Ag | Dispersible formulation |
| PT96229B (pt) * | 1989-12-22 | 1998-06-30 | Syntex Pharma Int | Processo para a preparacao de composicoes farmaceuticas em po, secas por pulverizacao, directamente compressiveis em comprimidos, contendo naproxeno ou naproxeno sodico |
| US6964946B1 (en) * | 1995-10-26 | 2005-11-15 | Baker Norton Pharmaceuticals, Inc. | Oral pharmaceutical compositions containing taxanes and methods of treatment employing the same |
| US6881420B2 (en) * | 2000-06-23 | 2005-04-19 | Teva Pharmaceutical Industries Ltd. | Compositions and dosage forms for gastric delivery of irinotecan and methods of treatment that use it to inhibit cancer cell proliferation |
| US20070098797A1 (en) * | 2005-06-02 | 2007-05-03 | Biovail Laboratories International S.R.L. | Modified release composition of at least one form of venlafaxine |
| US20060280787A1 (en) * | 2005-06-14 | 2006-12-14 | Baxter International Inc. | Pharmaceutical formulation of the tubulin inhibitor indibulin for oral administration with improved pharmacokinetic properties, and process for the manufacture thereof |
| ES2277767B1 (es) * | 2005-11-04 | 2008-04-01 | Simbec Iberica, S.L. | Formas orales solidas de ebastina. |
| TW200914006A (en) * | 2007-07-12 | 2009-04-01 | Takeda Pharmaceutical | Coated preparation |
-
2010
- 2010-08-31 TW TW099129243A patent/TW201113266A/zh unknown
- 2010-09-01 AU AU2010289643A patent/AU2010289643A1/en not_active Abandoned
- 2010-09-01 US US13/392,769 patent/US20120219597A1/en not_active Abandoned
- 2010-09-01 CA CA2772871A patent/CA2772871A1/en not_active Abandoned
- 2010-09-01 EP EP10814387.6A patent/EP2473168A4/en not_active Withdrawn
- 2010-09-01 WO PCT/US2010/047436 patent/WO2011028743A1/en not_active Ceased
- 2010-09-01 JP JP2012527986A patent/JP2013503876A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2473168A4 (en) | 2013-04-10 |
| WO2011028743A1 (en) | 2011-03-10 |
| TW201113266A (en) | 2011-04-16 |
| EP2473168A1 (en) | 2012-07-11 |
| US20120219597A1 (en) | 2012-08-30 |
| AU2010289643A1 (en) | 2012-03-22 |
| JP2013503876A (ja) | 2013-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20150902 |