SK282390B6 - Netoxická mikroemulzia ako nosič na podávanie účinných látok a spôsob jej prípravy - Google Patents
Netoxická mikroemulzia ako nosič na podávanie účinných látok a spôsob jej prípravy Download PDFInfo
- Publication number
- SK282390B6 SK282390B6 SK283-98A SK28398A SK282390B6 SK 282390 B6 SK282390 B6 SK 282390B6 SK 28398 A SK28398 A SK 28398A SK 282390 B6 SK282390 B6 SK 282390B6
- Authority
- SK
- Slovakia
- Prior art keywords
- microemulsion
- polar phase
- surfactant
- oil
- carbon atoms
- Prior art date
Links
- 239000004530 micro-emulsion Substances 0.000 title claims abstract description 73
- 231100000252 nontoxic Toxicity 0.000 title claims abstract description 6
- 230000003000 nontoxic effect Effects 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 239000004094 surface-active agent Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003607 modifier Substances 0.000 claims abstract description 15
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 10
- 239000013543 active substance Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 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 6
- 239000000787 lecithin Substances 0.000 claims abstract description 6
- 229940067606 lecithin Drugs 0.000 claims abstract description 6
- 235000010445 lecithin Nutrition 0.000 claims abstract description 6
- 150000003408 sphingolipids Chemical class 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 28
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 24
- -1 glucofurol Chemical compound 0.000 claims description 20
- 239000003921 oil Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 235000019198 oils Nutrition 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000004665 fatty acids Chemical class 0.000 claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 13
- 239000011780 sodium chloride Substances 0.000 claims description 9
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 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
- 238000000034 method Methods 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
- 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 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
- 239000003833 bile salt Substances 0.000 claims description 5
- 229940093761 bile salts Drugs 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 Chemical class 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
- 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
- 229940114069 12-hydroxystearate Drugs 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 239000003814 drug Substances 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
- 239000004615 ingredient Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 150000005691 triesters Chemical class 0.000 claims description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-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
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 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
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 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
- 229940005513 antidepressants Drugs 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
- 230000001085 cytostatic effect Effects 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
- 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
- 239000003112 inhibitor 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
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 239000002461 renin inhibitor Substances 0.000 claims description 2
- 229940086526 renin-inhibitors Drugs 0.000 claims description 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 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
- 125000003158 alcohol group Chemical group 0.000 claims 2
- RSBHKNDSJJBCMN-UHFFFAOYSA-N 1-(1-hydroxyethyl)pyrrolidin-2-one Chemical compound CC(O)N1CCCC1=O RSBHKNDSJJBCMN-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229920000573 polyethylene Chemical class 0.000 claims 1
- 229960004063 propylene glycol Drugs 0.000 claims 1
- 229940126409 proton pump inhibitor Drugs 0.000 claims 1
- 239000000612 proton pump inhibitor Substances 0.000 claims 1
- 239000012071 phase Substances 0.000 description 36
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 12
- 230000004872 arterial blood pressure Effects 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- JVKUCNQGESRUCL-UHFFFAOYSA-N 2-Hydroxyethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCCO JVKUCNQGESRUCL-UHFFFAOYSA-N 0.000 description 6
- 229920001304 Solutol HS 15 Polymers 0.000 description 6
- 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 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 229960003580 felodipine Drugs 0.000 description 5
- 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 5
- 239000000243 solution Substances 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 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 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 3
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000000004 hemodynamic effect Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 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 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940083466 soybean lecithin Drugs 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 description 1
- VBCKYDVWOPZOBA-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxymethyl)oxolane Chemical compound C1CCOC1COCC1CCCO1 VBCKYDVWOPZOBA-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical class CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 244000287680 Garcinia dulcis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000006270 Proton Pumps Human genes 0.000 description 1
- 108010083204 Proton Pumps Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 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
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000008344 egg yolk phospholipid Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 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
- DPBVJRXPSXTHOL-UHFFFAOYSA-N propyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCC DPBVJRXPSXTHOL-UHFFFAOYSA-N 0.000 description 1
- 210000002254 renal artery Anatomy 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
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001052 transient effect Effects 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
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 (2)
| Publication Number | Publication Date |
|---|---|
| SK28398A3 SK28398A3 (en) | 1998-11-04 |
| SK282390B6 true SK282390B6 (sk) | 2002-01-07 |
Family
ID=20399446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK283-98A SK282390B6 (sk) | 1995-09-12 | 1996-09-04 | Netoxická mikroemulzia ako nosič na podávanie účinných látok a spôsob jej prípravy |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6602511B2 (xx) |
| EP (1) | EP0850046B1 (xx) |
| JP (1) | JP4203123B2 (xx) |
| KR (1) | KR100448953B1 (xx) |
| CN (1) | CN1160057C (xx) |
| AT (1) | ATE228822T1 (xx) |
| AU (1) | AU702366B2 (xx) |
| BR (1) | BR9610089A (xx) |
| CA (1) | CA2230730C (xx) |
| CZ (1) | CZ64398A3 (xx) |
| DE (1) | DE69625213T2 (xx) |
| DK (1) | DK0850046T3 (xx) |
| EE (1) | EE9800070A (xx) |
| ES (1) | ES2186802T3 (xx) |
| HU (1) | HUP9901215A3 (xx) |
| IL (1) | IL123638A (xx) |
| IS (1) | IS4675A (xx) |
| MX (1) | MX9801755A (xx) |
| NO (1) | NO326404B1 (xx) |
| NZ (1) | NZ318530A (xx) |
| PL (1) | PL325825A1 (xx) |
| PT (1) | PT850046E (xx) |
| RU (1) | RU2164134C2 (xx) |
| SE (1) | SE9503143D0 (xx) |
| SK (1) | SK282390B6 (xx) |
| TR (1) | TR199800437T1 (xx) |
| WO (1) | WO1997009964A1 (xx) |
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| SE9503143D0 (sv) | 1995-09-12 | 1995-09-12 | Astra Ab | New preparation |
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| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
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| GB9912476D0 (en) | 1999-05-28 | 1999-07-28 | Novartis Ag | Organic compounds |
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| 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 |
| US20050124705A1 (en) * | 2002-03-28 | 2005-06-09 | Beiersdorf Ag | Cosmetic or pharmaceutical, low-viscosity oil-in-water emulsions containing phospholipids |
| US20050147629A1 (en) * | 2002-06-28 | 2005-07-07 | Jutta Riedl | Pharmaceutical formulation comprising non-peptide renin inhibitor and surfactant |
| TWI348381B (en) * | 2002-12-27 | 2011-09-11 | Kao Corp | Skin cleansing composition |
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| US7727576B2 (en) * | 2004-04-16 | 2010-06-01 | Hewlett-Packard Development Company, L.P. | System and a method for producing layered oral dosage forms |
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| US20060222692A1 (en) * | 2005-03-31 | 2006-10-05 | Fairfield Clinical Trials Llc | Method and compositions for transdermal administration of antimicrobial medications |
| US11311477B2 (en) * | 2006-03-07 | 2022-04-26 | Sgn Nanopharma Inc. | Ophthalmic preparations |
| US10137083B2 (en) * | 2006-03-07 | 2018-11-27 | SGN Nanopharma Inc | Ophthalmic preparations |
| US9918934B2 (en) * | 2006-12-12 | 2018-03-20 | Edgar Joel Acosta-Zara | Linker-based lecithin microemulsion delivery vehicles |
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| US20080199589A1 (en) * | 2007-02-20 | 2008-08-21 | Cargill, Incorporated | Lipid Microemulsions |
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| NL2005365C2 (en) * | 2010-09-17 | 2012-03-20 | Univ Delft Tech | Carbon nanostructures and networks produced by chemical vapor deposition. |
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| US11407930B2 (en) | 2012-05-08 | 2022-08-09 | Flotek Chemistry, Llc | Compositions and methods for enhancement of production of liquid and gaseous hydrocarbons |
| EP2866789B1 (en) * | 2012-06-28 | 2018-08-01 | Johnson & Johnson Consumer Inc. | Racecadotril lipid compositions |
| US9801819B2 (en) * | 2012-06-28 | 2017-10-31 | Johnson & Johnson Consumer Inc. | Racecadotril compositions |
| US10053619B2 (en) | 2013-03-14 | 2018-08-21 | Flotek Chemistry, Llc | Siloxane surfactant additives for oil and gas applications |
| US10590332B2 (en) | 2013-03-14 | 2020-03-17 | Flotek Chemistry, Llc | Siloxane surfactant additives for oil and gas applications |
| 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 |
| US10577531B2 (en) | 2013-03-14 | 2020-03-03 | Flotek Chemistry, Llc | Polymers and emulsions for use in oil and/or gas wells |
| US10717919B2 (en) | 2013-03-14 | 2020-07-21 | 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 |
| US10000693B2 (en) | 2013-03-14 | 2018-06-19 | Flotek Chemistry, Llc | Methods and compositions 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 |
| 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 |
| US9428683B2 (en) | 2013-03-14 | 2016-08-30 | Flotek Chemistry, Llc | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
| 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 |
| US9868893B2 (en) | 2013-03-14 | 2018-01-16 | Flotek Chemistry, Llc | Methods and compositions for use in oil and/or gas wells |
| US9321955B2 (en) | 2013-06-14 | 2016-04-26 | Flotek Chemistry, Llc | Methods and compositions for stimulating the production of hydrocarbons from subterranean formations |
| US11180690B2 (en) | 2013-03-14 | 2021-11-23 | Flotek Chemistry, Llc | Diluted microemulsions with low surface tensions |
| US9884988B2 (en) | 2013-03-14 | 2018-02-06 | 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 |
| 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 |
| 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 |
| CA2891278C (en) | 2014-05-14 | 2018-11-06 | Cesi Chemical, Inc. | Methods and compositions for use in oil and / or gas wells |
| CA2898770C (en) | 2014-07-28 | 2019-05-21 | Cesi Chemical, Inc. | 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 |
| US5364632A (en) * | 1989-04-05 | 1994-11-15 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Medicinal emulsions |
| CA2013755C (en) * | 1989-04-05 | 1993-11-30 | Simon Benita | Medicinal emulsions |
| EP0580778B1 (en) | 1991-04-19 | 1999-08-11 | LDS Technologies, Inc. | Convertible microemulsion formulations |
| EP0597007B1 (en) | 1991-07-26 | 1996-10-16 | Smithkline Beecham Corporation | W/o microemulsions |
| 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 |
-
1995
- 1995-09-12 SE SE9503143A patent/SE9503143D0/xx unknown
-
1996
- 1996-09-04 US US08/718,485 patent/US6602511B2/en not_active Expired - Fee Related
- 1996-09-04 IL IL12363896A patent/IL123638A/en not_active IP Right Cessation
- 1996-09-04 DE DE69625213T patent/DE69625213T2/de not_active Expired - Lifetime
- 1996-09-04 PL PL96325825A patent/PL325825A1/xx unknown
- 1996-09-04 AU AU70037/96A patent/AU702366B2/en not_active Ceased
- 1996-09-04 NZ NZ318530A patent/NZ318530A/en not_active IP Right Cessation
- 1996-09-04 KR KR10-1998-0701818A patent/KR100448953B1/ko not_active IP Right Cessation
- 1996-09-04 BR BR9610089A patent/BR9610089A/pt not_active IP Right Cessation
- 1996-09-04 SK SK283-98A patent/SK282390B6/sk unknown
- 1996-09-04 EE EE9800070A patent/EE9800070A/xx unknown
- 1996-09-04 TR TR1998/00437T patent/TR199800437T1/xx unknown
- 1996-09-04 CZ CZ98643A patent/CZ64398A3/cs unknown
- 1996-09-04 EP EP96931319A patent/EP0850046B1/en not_active Expired - Lifetime
- 1996-09-04 CA CA002230730A patent/CA2230730C/en not_active Expired - Fee Related
- 1996-09-04 RU RU98106482/14A patent/RU2164134C2/ru active
- 1996-09-04 HU HU9901215A patent/HUP9901215A3/hu unknown
- 1996-09-04 DK DK96931319T patent/DK0850046T3/da active
- 1996-09-04 CN CNB961981377A patent/CN1160057C/zh not_active Expired - Fee Related
- 1996-09-04 JP JP51187897A patent/JP4203123B2/ja not_active Expired - Fee Related
- 1996-09-04 WO PCT/SE1996/001097 patent/WO1997009964A1/en active IP Right Grant
- 1996-09-04 ES ES96931319T patent/ES2186802T3/es not_active Expired - Lifetime
- 1996-09-04 AT AT96931319T patent/ATE228822T1/de active
- 1996-09-04 PT PT96931319T patent/PT850046E/pt unknown
-
1998
- 1998-02-25 IS IS4675A patent/IS4675A/is unknown
- 1998-03-05 MX MX9801755A patent/MX9801755A/es not_active IP Right Cessation
- 1998-03-09 NO NO19981021A patent/NO326404B1/no not_active IP Right Cessation
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