NO326404B1 - Mikroemulsjoner, fremgangsmate for fremstilling derav, samt slike mikroemulsjoner for bruk som et medikament - Google Patents
Mikroemulsjoner, fremgangsmate for fremstilling derav, samt slike mikroemulsjoner for bruk som et medikament Download PDFInfo
- Publication number
- NO326404B1 NO326404B1 NO19981021A NO981021A NO326404B1 NO 326404 B1 NO326404 B1 NO 326404B1 NO 19981021 A NO19981021 A NO 19981021A NO 981021 A NO981021 A NO 981021A NO 326404 B1 NO326404 B1 NO 326404B1
- Authority
- NO
- Norway
- Prior art keywords
- microemulsion
- microemulsion according
- surfactant
- polar phase
- carbon atoms
- Prior art date
Links
- 239000004530 micro-emulsion Substances 0.000 title claims abstract description 76
- 239000003814 drug Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 3
- 239000004094 surface-active agent Substances 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000003981 vehicle Substances 0.000 claims abstract description 15
- 239000003607 modifier Substances 0.000 claims abstract description 14
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 9
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 6
- 230000003000 nontoxic effect Effects 0.000 claims abstract 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 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 239000000787 lecithin Substances 0.000 claims abstract description 5
- 229940067606 lecithin Drugs 0.000 claims abstract description 5
- 235000010445 lecithin Nutrition 0.000 claims abstract description 5
- 150000003408 sphingolipids Chemical class 0.000 claims abstract description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 33
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000004665 fatty acids Chemical class 0.000 claims description 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 11
- 239000003921 oil Substances 0.000 claims description 11
- -1 hydroxyethyl lactamide Chemical compound 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000005690 diesters Chemical class 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 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 6
- 239000000600 sorbitol Substances 0.000 claims description 6
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 5
- 239000003833 bile salt Substances 0.000 claims description 5
- 229940093761 bile salts Drugs 0.000 claims description 5
- 238000007911 parenteral administration Methods 0.000 claims description 5
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 5
- 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
- 229930195725 Mannitol Natural products 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 150000002016 disaccharides Chemical class 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000002772 monosaccharides Chemical class 0.000 claims description 4
- 229940113115 polyethylene glycol 200 Drugs 0.000 claims description 4
- 229940068886 polyethylene glycol 300 Drugs 0.000 claims description 4
- 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 3
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229940083466 soybean lecithin Drugs 0.000 claims description 3
- 150000005691 triesters Chemical class 0.000 claims description 3
- RSBHKNDSJJBCMN-UHFFFAOYSA-N 1-(1-hydroxyethyl)pyrrolidin-2-one Chemical compound CC(O)N1CCCC1=O RSBHKNDSJJBCMN-UHFFFAOYSA-N 0.000 claims description 2
- 229940114069 12-hydroxystearate Drugs 0.000 claims description 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical class CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 claims description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 239000003741 agents affecting lipid metabolism Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000003444 anaesthetic effect Effects 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 239000003146 anticoagulant agent Substances 0.000 claims description 2
- 229940127219 anticoagulant drug Drugs 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 239000000480 calcium channel blocker Substances 0.000 claims description 2
- 239000000824 cytostatic agent Substances 0.000 claims description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
- 229940093471 ethyl oleate Drugs 0.000 claims description 2
- 150000002194 fatty esters Chemical class 0.000 claims description 2
- 229930182478 glucoside Natural products 0.000 claims description 2
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 2
- 230000001861 immunosuppressant effect Effects 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003176 neuroleptic agent Substances 0.000 claims description 2
- 230000000701 neuroleptic effect Effects 0.000 claims description 2
- 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 claims description 2
- 229940126409 proton pump inhibitor Drugs 0.000 claims description 2
- 239000000612 proton pump inhibitor Substances 0.000 claims description 2
- 239000002461 renin inhibitor Substances 0.000 claims description 2
- 229940086526 renin-inhibitors Drugs 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 239000002876 beta blocker Substances 0.000 claims 1
- 229940097320 beta blocking agent Drugs 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 230000004872 arterial blood pressure Effects 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 238000005191 phase separation Methods 0.000 description 7
- 238000001802 infusion Methods 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 3
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 3
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 210000001367 artery Anatomy 0.000 description 3
- 229960003580 felodipine Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- VBCKYDVWOPZOBA-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxymethyl)oxolane Chemical compound C1CCOC1COCC1CCCO1 VBCKYDVWOPZOBA-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- NZXKDOXHBHYTKP-UHFFFAOYSA-N Metohexital Chemical compound CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O NZXKDOXHBHYTKP-UHFFFAOYSA-N 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000000059 bradycardiac effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000008344 egg yolk phospholipid Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical compound C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- 229940075495 isopropyl palmitate Drugs 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 210000004705 lumbosacral region Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229960001620 methohexital sodium Drugs 0.000 description 1
- KDXZREBVGAGZHS-UHFFFAOYSA-M methohexital sodium Chemical compound [Na+].CCC#CC(C)C1(CC=C)C(=O)N=C([O-])N(C)C1=O KDXZREBVGAGZHS-UHFFFAOYSA-M 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 210000002254 renal artery Anatomy 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000005549 size reduction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000009736 wetting Methods 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9503143A SE9503143D0 (sv) | 1995-09-12 | 1995-09-12 | New preparation |
PCT/SE1996/001097 WO1997009964A1 (en) | 1995-09-12 | 1996-09-04 | Microemulsions for use as vehicles for administration of active compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
NO981021D0 NO981021D0 (no) | 1998-03-09 |
NO981021L NO981021L (no) | 1998-03-09 |
NO326404B1 true NO326404B1 (no) | 2008-11-24 |
Family
ID=20399446
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19981021A NO326404B1 (no) | 1995-09-12 | 1998-03-09 | Mikroemulsjoner, fremgangsmate for fremstilling derav, samt slike mikroemulsjoner for bruk som et medikament |
Country Status (27)
Country | Link |
---|---|
US (1) | US6602511B2 (pt) |
EP (1) | EP0850046B1 (pt) |
JP (1) | JP4203123B2 (pt) |
KR (1) | KR100448953B1 (pt) |
CN (1) | CN1160057C (pt) |
AT (1) | ATE228822T1 (pt) |
AU (1) | AU702366B2 (pt) |
BR (1) | BR9610089A (pt) |
CA (1) | CA2230730C (pt) |
CZ (1) | CZ64398A3 (pt) |
DE (1) | DE69625213T2 (pt) |
DK (1) | DK0850046T3 (pt) |
EE (1) | EE9800070A (pt) |
ES (1) | ES2186802T3 (pt) |
HU (1) | HUP9901215A3 (pt) |
IL (1) | IL123638A (pt) |
IS (1) | IS4675A (pt) |
MX (1) | MX9801755A (pt) |
NO (1) | NO326404B1 (pt) |
NZ (1) | NZ318530A (pt) |
PL (1) | PL325825A1 (pt) |
PT (1) | PT850046E (pt) |
RU (1) | RU2164134C2 (pt) |
SE (1) | SE9503143D0 (pt) |
SK (1) | SK282390B6 (pt) |
TR (1) | TR199800437T1 (pt) |
WO (1) | WO1997009964A1 (pt) |
Families Citing this family (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE9503143D0 (sv) | 1995-09-12 | 1995-09-12 | Astra Ab | New preparation |
US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
US6458373B1 (en) | 1997-01-07 | 2002-10-01 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
US7030155B2 (en) | 1998-06-05 | 2006-04-18 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
DE69942205D1 (de) * | 1998-08-13 | 2010-05-12 | Cima Labs Inc | Microemulsionen als feste dosisformen zur oralen verabreichung |
DE19859427A1 (de) * | 1998-12-22 | 2000-06-29 | Beiersdorf Ag | Kosmetische oder pharmazeutische lecithinhaltige Gele oder niedrigviskose, lecithinhaltige O/W-Mikroemulsionen |
GB9912476D0 (en) | 1999-05-28 | 1999-07-28 | Novartis Ag | Organic compounds |
FR2795960B1 (fr) * | 1999-07-05 | 2001-10-19 | Sanofi Elf | Microemulsions stables pour l'administration d'acides gras a l'homme ou a l'animal, et utilisation de ces microemulsions |
KR100441167B1 (ko) * | 2001-12-27 | 2004-07-21 | 씨제이 주식회사 | 마이크로에멀젼 예비 농축액 조성물 |
US7380606B2 (en) * | 2002-03-01 | 2008-06-03 | Cesi Chemical, A Flotek Company | Composition and process for well cleaning |
US20050124705A1 (en) * | 2002-03-28 | 2005-06-09 | Beiersdorf Ag | Cosmetic or pharmaceutical, low-viscosity oil-in-water emulsions containing phospholipids |
US7811594B2 (en) | 2002-03-28 | 2010-10-12 | Beiersdorf Ag | Crosslinked oil droplet-based cosmetic or pharmaceutical emulsions |
DE10213957A1 (de) * | 2002-03-28 | 2003-10-09 | Beiersdorf Ag | Vernetzte kosmetische oder pharmazeutische phospholipidhaltige Gele und Emulsionen auf der Basis von ethylenoxidhaltigen oder propylenoxidhaltigen Emulgatoren |
DE10213955A1 (de) * | 2002-03-28 | 2003-10-09 | Beiersdorf Ag | Kosmetische oder pharmazeutische phospholipidhaltige, niedrigviskose (versprühbare) O/W-Emulsionen |
DK1517682T3 (da) * | 2002-06-28 | 2007-02-26 | Speedel Pharma Ag | Farmaceutisk formulering indeholdende en ikke-peptidisk renininhibitor og et overfladeaktivt stof |
US20040136943A1 (en) * | 2002-12-27 | 2004-07-15 | Kao Corporation | Skin cleansing composition |
US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
PE20050596A1 (es) * | 2003-12-19 | 2005-10-18 | Novartis Ag | Microemulsion que comprende un inhibidor renina |
KR20070005617A (ko) | 2004-02-13 | 2007-01-10 | 바이오어베일러빌리티, 아이엔씨. | 마취용 고농도 프로포폴 마이크로에멀젼 조제물 |
US7727576B2 (en) * | 2004-04-16 | 2010-06-01 | Hewlett-Packard Development Company, L.P. | System and a method for producing layered oral dosage forms |
US20050232974A1 (en) * | 2004-04-19 | 2005-10-20 | Gore Makarand P | System and a method for pharmaceutical dosage preparation using jettable microemulsions |
US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
US20060222692A1 (en) * | 2005-03-31 | 2006-10-05 | Fairfield Clinical Trials Llc | Method and compositions for transdermal administration of antimicrobial medications |
US10137083B2 (en) * | 2006-03-07 | 2018-11-27 | SGN Nanopharma Inc | Ophthalmic preparations |
US11311477B2 (en) * | 2006-03-07 | 2022-04-26 | Sgn Nanopharma Inc. | Ophthalmic preparations |
US9918934B2 (en) * | 2006-12-12 | 2018-03-20 | Edgar Joel Acosta-Zara | Linker-based lecithin microemulsion delivery vehicles |
EP1938801A1 (en) * | 2006-12-22 | 2008-07-02 | Biofrontera Bioscience GmbH | Nanoemulsion |
US20080199589A1 (en) * | 2007-02-20 | 2008-08-21 | Cargill, Incorporated | Lipid Microemulsions |
EP1985298A1 (en) | 2007-04-24 | 2008-10-29 | Azad Pharma AG | Ophtalmic oil-in-water emulsions containing prostaglandins |
US9222013B1 (en) | 2008-11-13 | 2015-12-29 | Cesi Chemical, Inc. | Water-in-oil microemulsions for oilfield applications |
KR101834577B1 (ko) | 2009-08-14 | 2018-03-05 | 옵코 헬스, 인크. | 뉴로키닌-1 길항제의 정맥내 제형 |
JP4834775B2 (ja) | 2010-03-04 | 2011-12-14 | 株式会社 資生堂 | 日焼け止め用組成物 |
NL2005365C2 (en) * | 2010-09-17 | 2012-03-20 | Univ Delft Tech | Carbon nanostructures and networks produced by chemical vapor deposition. |
WO2013158567A1 (en) | 2012-04-15 | 2013-10-24 | Cesi Chemical, Inc. | Surfactant formulations for foam flooding |
US11407930B2 (en) | 2012-05-08 | 2022-08-09 | Flotek Chemistry, Llc | Compositions and methods for enhancement of production of liquid and gaseous hydrocarbons |
US9200192B2 (en) | 2012-05-08 | 2015-12-01 | Cesi Chemical, Inc. | Compositions and methods for enhancement of production of liquid and gaseous hydrocarbons |
US9801819B2 (en) * | 2012-06-28 | 2017-10-31 | Johnson & Johnson Consumer Inc. | Racecadotril compositions |
CN104411299B (zh) * | 2012-06-28 | 2017-11-10 | 麦克内尔-Ppc股份有限公司 | 消旋卡多曲类脂组合物 |
US10941106B2 (en) | 2013-03-14 | 2021-03-09 | Flotek Chemistry, Llc | Methods and compositions incorporating alkyl polyglycoside surfactant for use in oil and/or gas wells |
US9068108B2 (en) | 2013-03-14 | 2015-06-30 | Cesi Chemical, Inc. | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
US9321955B2 (en) | 2013-06-14 | 2016-04-26 | Flotek Chemistry, Llc | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
US9884988B2 (en) | 2013-03-14 | 2018-02-06 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
US9464223B2 (en) | 2013-03-14 | 2016-10-11 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
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US10577531B2 (en) | 2013-03-14 | 2020-03-03 | Flotek Chemistry, Llc | Polymers and emulsions for use in oil and/or gas wells |
US10053619B2 (en) | 2013-03-14 | 2018-08-21 | Flotek Chemistry, Llc | Siloxane surfactant additives for oil and gas applications |
US10421707B2 (en) | 2013-03-14 | 2019-09-24 | Flotek Chemistry, Llc | Methods and compositions incorporating alkyl polyglycoside surfactant for use in oil and/or gas wells |
US10000693B2 (en) | 2013-03-14 | 2018-06-19 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
US11254856B2 (en) | 2013-03-14 | 2022-02-22 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
US10287483B2 (en) | 2013-03-14 | 2019-05-14 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells comprising a terpene alcohol |
US10590332B2 (en) | 2013-03-14 | 2020-03-17 | Flotek Chemistry, Llc | Siloxane surfactant additives for oil and gas applications |
US10717919B2 (en) | 2013-03-14 | 2020-07-21 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
US11180690B2 (en) | 2013-03-14 | 2021-11-23 | Flotek Chemistry, Llc | Diluted microemulsions with low surface tensions |
US9890625B2 (en) | 2014-02-28 | 2018-02-13 | Eclipse Ior Services, Llc | Systems and methods for the treatment of oil and/or gas wells with an obstruction material |
US9890624B2 (en) | 2014-02-28 | 2018-02-13 | Eclipse Ior Services, Llc | Systems and methods for the treatment of oil and/or gas wells with a polymeric material |
CA2891278C (en) | 2014-05-14 | 2018-11-06 | Cesi Chemical, Inc. | Methods and compositions for use in oil and / or gas wells |
US9957779B2 (en) | 2014-07-28 | 2018-05-01 | Flotek Chemistry, Llc | Methods and compositions related to gelled layers in oil and/or gas wells |
JP2017181387A (ja) * | 2016-03-31 | 2017-10-05 | 株式会社ポーラファルマ | 医薬組成物の形成する膜の評価方法 |
US10934472B2 (en) | 2017-08-18 | 2021-03-02 | Flotek Chemistry, Llc | Compositions comprising non-halogenated solvents for use in oil and/or gas wells and related methods |
US11053433B2 (en) | 2017-12-01 | 2021-07-06 | Flotek Chemistry, Llc | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
CN109401745B (zh) * | 2018-11-21 | 2021-03-12 | 西南石油大学 | 一种自适应流度控制体系及其在高温高盐油藏的应用 |
US11104843B2 (en) | 2019-10-10 | 2021-08-31 | Flotek Chemistry, Llc | Well treatment compositions and methods comprising certain microemulsions and certain clay control additives exhibiting synergistic effect of enhancing clay swelling protection and persistency |
US11512243B2 (en) | 2020-10-23 | 2022-11-29 | Flotek Chemistry, Llc | Microemulsions comprising an alkyl propoxylated sulfate surfactant, and related methods |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2553666B1 (fr) | 1983-10-21 | 1986-10-31 | Correia Gabriel | Dispositif permettant de sentir individuellement odeurs et parfums en liaison avec des images et des sons |
DE3406497A1 (de) | 1984-02-23 | 1985-09-05 | Mueller Bernhard Willi Werner | Hochdisperse pharmazeutische mehrkomponentensysteme und verfahren zu ihrer herstellung |
IL78929A0 (en) | 1985-07-29 | 1986-09-30 | Abbott Lab | Microemulsion compositions for parenteral administration |
FR2628632B1 (fr) * | 1988-03-18 | 1992-04-03 | Gattefosse Ets Sa | Microemulsions a usage cosmetique ou pharmaceutique |
AU614465B2 (en) * | 1989-04-05 | 1991-08-29 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Medicinal emulsions |
US5364632A (en) * | 1989-04-05 | 1994-11-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Medicinal emulsions |
DE69229779T2 (de) | 1991-04-19 | 1999-12-23 | Lds Technologies, Inc. | Konvertierbare mikroemulsionsverbindungen |
DK0597007T3 (da) | 1991-07-26 | 1996-11-18 | Smithkline Beecham Corp | V/O mikroemulsioner |
FR2709666B1 (fr) | 1993-09-07 | 1995-10-13 | Oreal | Composition cosmétique ou dermatologique constituée d'une émulsion huile dans eau à base de globules huileux pourvus d'un enrobage cristal liquide lamellaire. |
DE4338046A1 (de) | 1993-11-08 | 1995-05-11 | Dietl Hans | Fettlösliche Arzneimittel erhaltende flüssige pharmazeutische Zubereitung zur oralen Anwendung |
FR2730932B1 (fr) | 1995-02-27 | 1997-04-04 | Oreal | Nanoemulsion transparente a base de lipides amphiphiles non-ioniques fluides et utilisation en cosmetique ou en dermopharmacie |
SE9503143D0 (sv) | 1995-09-12 | 1995-09-12 | Astra Ab | New preparation |
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