CA2575216A1 - Stable injectable composition of alpha tocopheryl succinate, analogues and salts thereof - Google Patents
Stable injectable composition of alpha tocopheryl succinate, analogues and salts thereof Download PDFInfo
- Publication number
- CA2575216A1 CA2575216A1 CA002575216A CA2575216A CA2575216A1 CA 2575216 A1 CA2575216 A1 CA 2575216A1 CA 002575216 A CA002575216 A CA 002575216A CA 2575216 A CA2575216 A CA 2575216A CA 2575216 A1 CA2575216 A1 CA 2575216A1
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- tocopheryl succinate
- oil
- weight
- composition according
- 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
- IELOKBJPULMYRW-NJQVLOCASA-N D-alpha-Tocopheryl Acid Succinate Chemical group OC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C IELOKBJPULMYRW-NJQVLOCASA-N 0.000 title claims abstract description 213
- 150000003839 salts Chemical class 0.000 title claims abstract description 80
- 239000007972 injectable composition Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 118
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000001246 colloidal dispersion Methods 0.000 claims description 98
- 235000002639 sodium chloride Nutrition 0.000 claims description 83
- 239000007787 solid Substances 0.000 claims description 78
- 239000003921 oil Substances 0.000 claims description 67
- 235000019198 oils Nutrition 0.000 claims description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 239000002245 particle Substances 0.000 claims description 57
- 150000003904 phospholipids Chemical class 0.000 claims description 48
- 239000006185 dispersion Substances 0.000 claims description 39
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 36
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 32
- 239000002577 cryoprotective agent Substances 0.000 claims description 31
- 239000002246 antineoplastic agent Substances 0.000 claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- 239000003963 antioxidant agent Substances 0.000 claims description 24
- 235000006708 antioxidants Nutrition 0.000 claims description 24
- 230000003078 antioxidant effect Effects 0.000 claims description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 18
- 229930012538 Paclitaxel Natural products 0.000 claims description 17
- 239000012736 aqueous medium Substances 0.000 claims description 17
- 229960001592 paclitaxel Drugs 0.000 claims description 17
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 17
- 235000012000 cholesterol Nutrition 0.000 claims description 16
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- 239000008344 egg yolk phospholipid Substances 0.000 claims description 14
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 14
- 239000008158 vegetable oil Substances 0.000 claims description 14
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 13
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000000787 lecithin Substances 0.000 claims description 12
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 claims description 8
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 229940099418 d- alpha-tocopherol succinate Drugs 0.000 claims description 8
- 229960003668 docetaxel Drugs 0.000 claims description 8
- 238000004108 freeze drying Methods 0.000 claims description 8
- 239000007962 solid dispersion Substances 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 230000006907 apoptotic process Effects 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- 238000003860 storage Methods 0.000 claims description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 239000002609 medium Substances 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- 239000007764 o/w emulsion Substances 0.000 claims description 6
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 6
- HLWRUJAIJJEZDL-UHFFFAOYSA-M sodium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical class [Na+].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC([O-])=O HLWRUJAIJJEZDL-UHFFFAOYSA-M 0.000 claims description 6
- 239000008347 soybean phospholipid Substances 0.000 claims description 6
- 238000001694 spray drying Methods 0.000 claims description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 238000007912 intraperitoneal administration Methods 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- 241000124008 Mammalia Species 0.000 claims description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
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- 239000001913 cellulose Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
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- 229940123237 Taxane Drugs 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
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- 231100000433 cytotoxic Toxicity 0.000 claims description 3
- 230000001472 cytotoxic effect Effects 0.000 claims description 3
- AWUCVROLDVIAJX-UHFFFAOYSA-N glycerol 1-phosphate Chemical class OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 230000003204 osmotic effect Effects 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 claims description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 2
- 235000019737 Animal fat Nutrition 0.000 claims description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 2
- 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 2
- 201000009030 Carcinoma Diseases 0.000 claims description 2
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- AERBNCYCJBRYDG-UHFFFAOYSA-N D-ribo-phytosphingosine Natural products CCCCCCCCCCCCCCC(O)C(O)C(N)CO AERBNCYCJBRYDG-UHFFFAOYSA-N 0.000 claims description 2
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- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 2
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical class NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 claims description 2
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- YNQYZBDRJZVSJE-UHFFFAOYSA-M sodium;2,3-dihydroxypropyl 2,3-di(octadecanoyloxy)propyl phosphate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCCC YNQYZBDRJZVSJE-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
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- A—HUMAN NECESSITIES
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- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K31/355—Tocopherols, e.g. vitamin E
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- 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
- A61K9/10—Dispersions; Emulsions
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
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| US59209704P | 2004-07-28 | 2004-07-28 | |
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| PCT/US2005/026783 WO2006015120A2 (en) | 2004-07-28 | 2005-07-28 | Stable injectable composition of alpha tocopheryl succinate, analogues and salts thereof |
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| CA2575216A1 true CA2575216A1 (en) | 2006-02-09 |
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| CA002575216A Abandoned CA2575216A1 (en) | 2004-07-28 | 2005-07-28 | Stable injectable composition of alpha tocopheryl succinate, analogues and salts thereof |
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| EP (1) | EP1778217A4 (https=) |
| JP (1) | JP2008508302A (https=) |
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| CN (1) | CN1925853B (https=) |
| AU (1) | AU2005269383A1 (https=) |
| CA (1) | CA2575216A1 (https=) |
| IL (1) | IL180741A0 (https=) |
| NO (1) | NO20070983L (https=) |
| RU (1) | RU2007107359A (https=) |
| WO (1) | WO2006015120A2 (https=) |
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| US7871632B2 (en) * | 2004-07-12 | 2011-01-18 | Adventrx Pharmaceuticals, Inc. | Compositions for delivering highly water soluble drugs |
| US8557861B2 (en) | 2004-09-28 | 2013-10-15 | Mast Therapeutics, Inc. | Low oil emulsion compositions for delivering taxoids and other insoluble drugs |
| US20080038316A1 (en) * | 2004-10-01 | 2008-02-14 | Wong Vernon G | Conveniently implantable sustained release drug compositions |
| CN101011355B (zh) * | 2006-02-01 | 2013-01-02 | 陈献 | 经维生素e琥珀酸酯稳定的医药组合物、其制备及用途 |
| TWI376239B (en) * | 2006-02-01 | 2012-11-11 | Andrew Xian Chen | Vitamin e succinate stabilized pharmaceutical compositions, methods for the preparation and the use thereof |
| US20080045589A1 (en) * | 2006-05-26 | 2008-02-21 | Susan Kelley | Drug Combinations with Substituted Diaryl Ureas for the Treatment of Cancer |
| NZ575920A (en) | 2006-09-15 | 2012-08-31 | Stephen John Ralph | Pro-oxidant anti-cancer compounds |
| NZ555163A (en) * | 2007-05-14 | 2010-05-28 | Fonterra Co Operative Group | Methods of immune or hematological enhancement, inhibiting tumour formation or growth, and treating or preventing cancer, cancer symptoms, or the symptoms of cancer treatments |
| CA2686225A1 (en) * | 2007-06-22 | 2008-12-31 | Scidose Llc | Solubilized formulation of docetaxel without tween 80 |
| NZ602579A (en) | 2008-03-14 | 2013-12-20 | Stephen John Ralph | Mitochondrially delivered anti-cancer compounds |
| US20100260830A1 (en) * | 2009-04-08 | 2010-10-14 | Brian A Salvatore | Liposomal Formulations of Tocopheryl Amides |
| WO2011004552A1 (ja) * | 2009-07-09 | 2011-01-13 | 国立大学法人九州大学 | 水溶性薬物キャリア及びその製造方法 |
| EP2464406B1 (en) * | 2009-08-10 | 2016-10-26 | Proviflo, LLC | Catheter lock solutions utilizing tocopherol and mid-chain fatty acids |
| WO2011025771A1 (en) * | 2009-08-25 | 2011-03-03 | Biogen Idec Ma Inc. | Compositions for delivery of insoluble agents |
| US8912228B2 (en) | 2009-10-19 | 2014-12-16 | Scidose Llc | Docetaxel formulations with lipoic acid |
| US20110092579A1 (en) * | 2009-10-19 | 2011-04-21 | Scidose Llc | Solubilized formulation of docetaxel |
| US7772274B1 (en) | 2009-10-19 | 2010-08-10 | Scidose, Llc | Docetaxel formulations with lipoic acid |
| US8476310B2 (en) | 2009-10-19 | 2013-07-02 | Scidose Llc | Docetaxel formulations with lipoic acid |
| US8541465B2 (en) * | 2009-10-19 | 2013-09-24 | Scidose, Llc | Docetaxel formulations with lipoic acid and/or dihydrolipoic acid |
| UA110383C2 (en) | 2011-06-08 | 2015-12-25 | Akzo Nobel Chemicals Int Bv | Deicing composition |
| EA027593B1 (ru) | 2011-06-08 | 2017-08-31 | Акцо Нобель Кемикалз Интернэшнл Б.В. | Противогололедная композиция |
| AR088524A1 (es) | 2011-11-09 | 2014-06-18 | Akzo Nobel Chemicals Int Bv | Composicion descongelante, proceso de preparacion, conjunto de parte y uso |
| EP2846773A4 (en) | 2012-05-10 | 2015-12-30 | Painreform Ltd | DEPOT FORMULATIONS OF A LOCAL ANESTHETICS AND METHOD FOR THE MANUFACTURE THEREOF |
| JP6094388B2 (ja) * | 2013-06-07 | 2017-03-15 | ニプロ株式会社 | ペメトレキセドを含む注射用組成物 |
| JP6087769B2 (ja) * | 2013-08-30 | 2017-03-01 | サントリー食品インターナショナル株式会社 | 烏龍茶抽出物を含有する容器詰飲料 |
| WO2016201269A2 (en) | 2015-06-11 | 2016-12-15 | Proviflo, Llc | Graft-port hemodialysis systems, devices and methods |
| WO2017120586A1 (en) * | 2016-01-07 | 2017-07-13 | Western University Of Health Sciences | Formulations for treating bladder cancer |
| KR101978108B1 (ko) * | 2017-07-20 | 2019-05-13 | 데루타-후라이 화마 가부시키가이샤 | 암 세포의 대사 특이성에 기초하는 신규 항 악성 종양제 |
| US12453805B2 (en) | 2020-09-24 | 2025-10-28 | Everest Medical Innovation GmbH | Cryoprotective compositions, surgical kits, and methods for protection of a surgical site during cryosurgery |
| US12426594B2 (en) | 2020-09-24 | 2025-09-30 | Everest Medical Innovation GmbH | Cryoprotective compositions and methods for protection of a surgical site during cryosurgery |
| CN120365238A (zh) * | 2025-05-29 | 2025-07-25 | 无锡知妍生物科技有限公司 | 单生育酚壬二酸酯及其应用 |
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| US3173838A (en) * | 1962-03-28 | 1965-03-16 | Eastman Kodak Co | Solid, vitamin e-active product and process for making it |
| US4783220A (en) * | 1986-12-18 | 1988-11-08 | Xerox Corporation | Vesicle ink compositions |
| CA2130357A1 (en) * | 1992-02-18 | 1993-08-19 | Doron Friedman | Dry compositions for preparing submicron emulsions |
| US5961970A (en) * | 1993-10-29 | 1999-10-05 | Pharmos Corporation | Submicron emulsions as vaccine adjuvants |
| GB9409778D0 (en) * | 1994-05-16 | 1994-07-06 | Dumex Ltd As | Compositions |
| GB9514878D0 (en) * | 1995-07-20 | 1995-09-20 | Danbiosyst Uk | Vitamin E as a solubilizer for drugs contained in lipid vehicles |
| US6458373B1 (en) * | 1997-01-07 | 2002-10-01 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| US6727280B2 (en) * | 1997-01-07 | 2004-04-27 | Sonus Pharmaceuticals, Inc. | Method for treating colorectal carcinoma using a taxane/tocopherol formulation |
| US7030155B2 (en) * | 1998-06-05 | 2006-04-18 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| US20030236236A1 (en) * | 1999-06-30 | 2003-12-25 | Feng-Jing Chen | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
| US20030005407A1 (en) * | 2000-06-23 | 2003-01-02 | Hines Kenneth J. | System and method for coordination-centric design of software systems |
| US20030099674A1 (en) * | 2001-08-11 | 2003-05-29 | Chen Andrew X. | Lyophilized injectable formulations containing paclitaxel or other taxoid drugs |
| US20040175415A1 (en) * | 2003-03-05 | 2004-09-09 | Chan Alvin C. | Formulations and methods of delivery of intact tocopheryl succinate to humans |
| US7871632B2 (en) * | 2004-07-12 | 2011-01-18 | Adventrx Pharmaceuticals, Inc. | Compositions for delivering highly water soluble drugs |
-
2005
- 2005-07-28 CN CN2005800020729A patent/CN1925853B/zh not_active Expired - Fee Related
- 2005-07-28 US US11/192,439 patent/US20060024360A1/en not_active Abandoned
- 2005-07-28 RU RU2007107359/15A patent/RU2007107359A/ru not_active Application Discontinuation
- 2005-07-28 JP JP2007523807A patent/JP2008508302A/ja not_active Withdrawn
- 2005-07-28 WO PCT/US2005/026783 patent/WO2006015120A2/en not_active Ceased
- 2005-07-28 KR KR1020077004963A patent/KR20070059072A/ko not_active Withdrawn
- 2005-07-28 CA CA002575216A patent/CA2575216A1/en not_active Abandoned
- 2005-07-28 AU AU2005269383A patent/AU2005269383A1/en not_active Abandoned
- 2005-07-28 EP EP05779446A patent/EP1778217A4/en not_active Withdrawn
-
2007
- 2007-01-16 IL IL180741A patent/IL180741A0/en unknown
- 2007-02-21 NO NO20070983A patent/NO20070983L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006015120A3 (en) | 2006-05-18 |
| JP2008508302A (ja) | 2008-03-21 |
| EP1778217A4 (en) | 2008-10-08 |
| EP1778217A2 (en) | 2007-05-02 |
| KR20070059072A (ko) | 2007-06-11 |
| RU2007107359A (ru) | 2008-09-10 |
| CN1925853B (zh) | 2011-01-26 |
| AU2005269383A1 (en) | 2006-02-09 |
| CN1925853A (zh) | 2007-03-07 |
| IL180741A0 (en) | 2007-07-04 |
| WO2006015120A2 (en) | 2006-02-09 |
| US20060024360A1 (en) | 2006-02-02 |
| NO20070983L (no) | 2007-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |