AU2009226618B2 - Lyophilized nanoemulsion - Google Patents
Lyophilized nanoemulsion Download PDFInfo
- Publication number
- AU2009226618B2 AU2009226618B2 AU2009226618A AU2009226618A AU2009226618B2 AU 2009226618 B2 AU2009226618 B2 AU 2009226618B2 AU 2009226618 A AU2009226618 A AU 2009226618A AU 2009226618 A AU2009226618 A AU 2009226618A AU 2009226618 B2 AU2009226618 B2 AU 2009226618B2
- Authority
- AU
- Australia
- Prior art keywords
- nanoemulsion
- lyophilised
- lipid
- nanoemulsion according
- acid ester
- 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.)
- Ceased
Links
- 239000007908 nanoemulsion Substances 0.000 title claims abstract description 121
- -1 saccharose fatty acid esters Chemical class 0.000 claims abstract description 40
- 229930006000 Sucrose Natural products 0.000 claims abstract description 39
- 239000000194 fatty acid Substances 0.000 claims abstract description 39
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 25
- 229930195729 fatty acid Natural products 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000000839 emulsion Substances 0.000 claims description 45
- 239000005720 sucrose Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 150000002632 lipids Chemical class 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000004108 freeze drying Methods 0.000 claims description 25
- 239000012071 phase Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 10
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 5
- 229940088594 vitamin Drugs 0.000 claims description 5
- 229930003231 vitamin Natural products 0.000 claims description 5
- 239000011782 vitamin Substances 0.000 claims description 5
- 235000013343 vitamin Nutrition 0.000 claims description 5
- 230000000052 comparative effect Effects 0.000 claims description 3
- 238000004945 emulsification Methods 0.000 claims description 3
- 150000003722 vitamin derivatives Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 235000013681 dietary sucrose Nutrition 0.000 abstract 1
- 229960004793 sucrose Drugs 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 19
- 239000002245 particle Substances 0.000 description 18
- 230000008570 general process Effects 0.000 description 17
- 229940057917 medium chain triglycerides Drugs 0.000 description 17
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
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- 239000007788 liquid Substances 0.000 description 12
- 239000003925 fat Substances 0.000 description 10
- 235000000346 sugar Nutrition 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 235000010445 lecithin Nutrition 0.000 description 7
- 239000000787 lecithin Substances 0.000 description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 229940067606 lecithin Drugs 0.000 description 6
- 238000007911 parenteral administration Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 description 3
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- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 150000005846 sugar alcohols Chemical class 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 235000019165 vitamin E Nutrition 0.000 description 3
- 229940046009 vitamin E Drugs 0.000 description 3
- 239000011709 vitamin E Substances 0.000 description 3
- JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 229920001304 Solutol HS 15 Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229930003316 Vitamin D Natural products 0.000 description 2
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000007957 coemulsifier Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
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- 238000000502 dialysis Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229960002297 fenofibrate Drugs 0.000 description 2
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- AOHAPDDBNAPPIN-UHFFFAOYSA-N myristicinic acid Natural products COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003445 sucroses Chemical class 0.000 description 2
- 235000019166 vitamin D Nutrition 0.000 description 2
- 239000011710 vitamin D Substances 0.000 description 2
- 150000003710 vitamin D derivatives Chemical class 0.000 description 2
- 229940046008 vitamin d Drugs 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- DJAHKBBSJCDSOZ-AJLBTXRUSA-N (5z,9e,13e)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one;(5e,9e,13e)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CCC(C)=O.CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CCC(C)=O DJAHKBBSJCDSOZ-AJLBTXRUSA-N 0.000 description 1
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 description 1
- 229940114069 12-hydroxystearate Drugs 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- ONAIRGOTKJCYEY-XXDXYRHBSA-N CCCCCCCCCCCCCCCCCC(O)=O.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 Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.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 ONAIRGOTKJCYEY-XXDXYRHBSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 102100021425 Monocarboxylate transporter 10 Human genes 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 1
- 108091006608 SLC16A10 Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ONAIRGOTKJCYEY-UHFFFAOYSA-N Sucrose monostearate Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(CO)O1 ONAIRGOTKJCYEY-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 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 description 1
- 229960002206 bifonazole Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
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- 229940021223 hypertonic solution Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 230000005917 in vivo anti-tumor Effects 0.000 description 1
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
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- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
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- 229920000223 polyglycerol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- 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 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/906—Drug delivery
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/906—Drug delivery
- Y10S977/907—Liposome
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Preparation (AREA)
- Colloid Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008015366.4 | 2008-03-20 | ||
| DE102008015366A DE102008015366A1 (de) | 2008-03-20 | 2008-03-20 | Lyophilisierte Nanoemulsion |
| PCT/EP2009/001355 WO2009115175A2 (de) | 2008-03-20 | 2009-02-26 | Lyophilisierte nanoemulsion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2009226618A1 AU2009226618A1 (en) | 2009-09-24 |
| AU2009226618B2 true AU2009226618B2 (en) | 2014-04-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009226618A Ceased AU2009226618B2 (en) | 2008-03-20 | 2009-02-26 | Lyophilized nanoemulsion |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8211948B2 (enExample) |
| EP (1) | EP2252267B1 (enExample) |
| JP (1) | JP5603852B2 (enExample) |
| AU (1) | AU2009226618B2 (enExample) |
| CA (1) | CA2718791C (enExample) |
| DE (1) | DE102008015366A1 (enExample) |
| ES (1) | ES2608062T3 (enExample) |
| IL (1) | IL207913A (enExample) |
| WO (1) | WO2009115175A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8357639B2 (en) * | 2007-07-03 | 2013-01-22 | Baker Hughes Incorporated | Nanoemulsions |
| WO2009117152A1 (en) | 2008-03-20 | 2009-09-24 | Virun, Inc. | Emulsions including a peg-derivative of tocopherol |
| BRPI0909185A2 (pt) | 2008-03-20 | 2015-08-25 | Virun Inc | Derivado de vitamina e e seus usos |
| CA2792330C (en) * | 2010-03-23 | 2017-01-03 | Virun, Inc | Nanoemulsion including a peg-derivative of vitamin e and a sucrose fatty acid ester |
| WO2011162802A1 (en) | 2010-06-21 | 2011-12-29 | Virun, Inc. | Compositions containing non-polar compounds |
| US8586527B2 (en) | 2011-10-20 | 2013-11-19 | Jaipal Singh | Cerivastatin to treat pulmonary disorders |
| RS59734B1 (sr) | 2012-01-23 | 2020-02-28 | Sage Therapeutics Inc | Formulacije neuroaktivnog steroida koje uključuju kompleks alopregnanolona i sulfobutil etar beta-ciklodekstrina |
| EP2811847B1 (en) | 2012-02-10 | 2017-12-13 | Virun, Inc. | Beverage compositions containing non-polar compounds |
| EP2887944B1 (en) | 2012-08-21 | 2021-10-06 | Sage Therapeutics, Inc. | Allopregnanolone for treating refractory status epilepticus |
| US9351517B2 (en) | 2013-03-15 | 2016-05-31 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and compositions containing same |
| US9693574B2 (en) | 2013-08-08 | 2017-07-04 | Virun, Inc. | Compositions containing water-soluble derivatives of vitamin E mixtures and modified food starch |
| US10016363B2 (en) | 2014-09-18 | 2018-07-10 | Virun, Inc. | Pre-spray emulsions and powders containing non-polar compounds |
| US9861611B2 (en) | 2014-09-18 | 2018-01-09 | Virun, Inc. | Formulations of water-soluble derivatives of vitamin E and soft gel compositions, concentrates and powders containing same |
| EP3890746A4 (en) * | 2018-12-06 | 2022-08-10 | Lipicare Life Sciences Ltd. | VITAMIN D MICROEMULSIONS AND THEIR USES |
| JP7756548B2 (ja) * | 2021-11-30 | 2025-10-20 | 株式会社ダイセル | ガス発生器 |
| CN116650425B (zh) * | 2023-07-13 | 2025-06-27 | 晟迪生物医药(苏州)有限公司 | 糖酯化合物或其盐在冷冻保护、冷冻干燥保护中的应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0159237A1 (en) * | 1984-03-30 | 1985-10-23 | LABORATOIRE L. LAFON Société anonyme dite: | Galenical form for oral administration and its method of preparation by lyophilization of an oil-in-water emulsion |
| US20020193830A1 (en) * | 1996-11-15 | 2002-12-19 | Bonutti Peter M. | Apparatus and method for use in positioning an anchor |
| US20030147959A1 (en) * | 1997-01-07 | 2003-08-07 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| US20070213234A1 (en) * | 2004-05-18 | 2007-09-13 | Nestec S.A. | Oil-in-water emulsion for delivery |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5296724A (en) | 1976-02-10 | 1977-08-13 | Kyowa Hakko Kogyo Co Ltd | Preparation of powdery products |
| JPH04275216A (ja) * | 1991-03-04 | 1992-09-30 | Eisai Co Ltd | 脂溶性薬物を含有した凍結乾燥組成物 |
| DE4244122C1 (de) | 1992-12-24 | 1994-06-01 | Sanol Arznei Schwarz Gmbh | Lyophilisierte, wirkstoffhaltige Emulsion zur intravenösen Applikation |
| US5646082A (en) | 1993-06-24 | 1997-07-08 | Cosmo Research Institute | Crystalline aluminosilicate, process for producing the same, and catalyst employing the same for catalytic cracking of hydrocarbon oil |
| JPH11171796A (ja) | 1997-12-08 | 1999-06-29 | Ohta Pharmaceut Co Ltd | テプレノン経口投与用製剤およびその製造方法 |
| FR2800611B1 (fr) * | 1999-11-08 | 2002-10-11 | Oreal | Composition a application topique contenant un sucre, et ses utilisations cosmetiques |
| WO2002087692A1 (en) * | 2001-04-26 | 2002-11-07 | The Procter & Gamble Company | A method and apparatus for the treatment of cosmetic skin conditioins |
| JP2004161650A (ja) | 2002-11-12 | 2004-06-10 | Taisho Pharmaceut Co Ltd | Ｗ／ｏ／ｗ型ドライエマルション |
| WO2006134970A1 (ja) * | 2005-06-15 | 2006-12-21 | Kaneka Corporation | コエンザイムｑ１０含有水溶性組成物及びその製法 |
| FR2901124B1 (fr) * | 2006-05-17 | 2008-06-27 | Oreal | Emulsion huile dans eau fine |
| JP2008142588A (ja) * | 2006-12-06 | 2008-06-26 | Fujifilm Corp | 水中油滴型エマルション及びその製造方法、並びに機能性粉末及びその製造方法 |
| CN101428002A (zh) * | 2008-11-20 | 2009-05-13 | 沈阳万爱普利德医药科技有限公司 | 注射用紫杉醇冻干微乳剂及其制备方法 |
-
2008
- 2008-03-20 DE DE102008015366A patent/DE102008015366A1/de not_active Withdrawn
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2009
- 2009-02-26 EP EP09722255.8A patent/EP2252267B1/de active Active
- 2009-02-26 CA CA2718791A patent/CA2718791C/en active Active
- 2009-02-26 ES ES09722255.8T patent/ES2608062T3/es active Active
- 2009-02-26 AU AU2009226618A patent/AU2009226618B2/en not_active Ceased
- 2009-02-26 US US12/922,787 patent/US8211948B2/en not_active Expired - Fee Related
- 2009-02-26 WO PCT/EP2009/001355 patent/WO2009115175A2/de not_active Ceased
- 2009-02-26 JP JP2011500060A patent/JP5603852B2/ja not_active Expired - Fee Related
-
2010
- 2010-08-31 IL IL207913A patent/IL207913A/en active IP Right Grant
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0159237A1 (en) * | 1984-03-30 | 1985-10-23 | LABORATOIRE L. LAFON Société anonyme dite: | Galenical form for oral administration and its method of preparation by lyophilization of an oil-in-water emulsion |
| US20020193830A1 (en) * | 1996-11-15 | 2002-12-19 | Bonutti Peter M. | Apparatus and method for use in positioning an anchor |
| US20030147959A1 (en) * | 1997-01-07 | 2003-08-07 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| US20070213234A1 (en) * | 2004-05-18 | 2007-09-13 | Nestec S.A. | Oil-in-water emulsion for delivery |
Also Published As
| Publication number | Publication date |
|---|---|
| US8211948B2 (en) | 2012-07-03 |
| JP2011519349A (ja) | 2011-07-07 |
| EP2252267B1 (de) | 2016-09-28 |
| AU2009226618A1 (en) | 2009-09-24 |
| CA2718791C (en) | 2016-03-29 |
| WO2009115175A3 (de) | 2010-01-07 |
| CA2718791A1 (en) | 2009-09-24 |
| JP5603852B2 (ja) | 2014-10-08 |
| EP2252267A2 (de) | 2010-11-24 |
| WO2009115175A2 (de) | 2009-09-24 |
| IL207913A (en) | 2015-05-31 |
| IL207913A0 (en) | 2010-12-30 |
| DE102008015366A1 (de) | 2009-09-24 |
| US20110015266A1 (en) | 2011-01-20 |
| ES2608062T3 (es) | 2017-04-05 |
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Legal Events
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |