JP2006500437A - 薬物送達 - Google Patents
薬物送達 Download PDFInfo
- Publication number
- JP2006500437A JP2006500437A JP2004537295A JP2004537295A JP2006500437A JP 2006500437 A JP2006500437 A JP 2006500437A JP 2004537295 A JP2004537295 A JP 2004537295A JP 2004537295 A JP2004537295 A JP 2004537295A JP 2006500437 A JP2006500437 A JP 2006500437A
- Authority
- JP
- Japan
- Prior art keywords
- polyethyleneimine polymer
- polyethyleneimine
- polymer according
- linear
- halide
- 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.)
- Pending
Links
- 238000012377 drug delivery Methods 0.000 title abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 96
- 229920002873 Polyethylenimine Polymers 0.000 claims description 109
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 73
- 108010036949 Cyclosporine Proteins 0.000 claims description 73
- 229960001265 ciclosporin Drugs 0.000 claims description 64
- 229930182912 cyclosporin Natural products 0.000 claims description 51
- 229940079593 drug Drugs 0.000 claims description 47
- 239000003814 drug Substances 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 45
- 238000009472 formulation Methods 0.000 claims description 35
- 150000004820 halides Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- 230000002209 hydrophobic effect Effects 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims description 15
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical group CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 claims description 8
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 235000009518 sodium iodide Nutrition 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 4
- 229930012538 Paclitaxel Natural products 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- 229930182833 estradiol Natural products 0.000 claims description 4
- 229960005309 estradiol Drugs 0.000 claims description 4
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 4
- 229960005420 etoposide Drugs 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229960001592 paclitaxel Drugs 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 4
- 229960005205 prednisolone Drugs 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 4
- 229960003604 testosterone Drugs 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000001165 hydrophobic group Chemical group 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000002685 pulmonary effect Effects 0.000 claims description 2
- 238000005063 solubilization Methods 0.000 abstract description 3
- 230000007928 solubilization Effects 0.000 abstract description 3
- 229930105110 Cyclosporin A Natural products 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 239000000693 micelle Substances 0.000 description 12
- 229940063121 neoral Drugs 0.000 description 11
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000002105 nanoparticle Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 238000012552 review Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 238000003127 radioimmunoassay Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 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 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000036267 drug metabolism Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BHTRKEVKTKCXOH-LBSADWJPSA-N tauroursodeoxycholic acid Chemical compound 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)CC1 BHTRKEVKTKCXOH-LBSADWJPSA-N 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 239000001116 FEMA 4028 Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 238000012382 advanced drug delivery Methods 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000011557 critical solution Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 2
- 229940012189 methyl orange Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004627 transmission electron microscopy Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000012565 NMR experiment Methods 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- BPKIGYQJPYCAOW-FFJTTWKXSA-I calcium;potassium;disodium;(2s)-2-hydroxypropanoate;dichloride;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].C[C@H](O)C([O-])=O BPKIGYQJPYCAOW-FFJTTWKXSA-I 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000005100 correlation spectroscopy Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000550 preparative sample Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/0226—Quaternisation of polyalkylene(poly)amines
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0221942.6A GB0221942D0 (en) | 2002-09-20 | 2002-09-20 | Drug delivery |
| PCT/GB2003/004036 WO2004026941A1 (en) | 2002-09-20 | 2003-09-22 | Drug delivery |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006500437A true JP2006500437A (ja) | 2006-01-05 |
| JP2006500437A5 JP2006500437A5 (enExample) | 2006-11-02 |
Family
ID=9944516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004537295A Pending JP2006500437A (ja) | 2002-09-20 | 2003-09-22 | 薬物送達 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20060148982A1 (enExample) |
| EP (1) | EP1543063B1 (enExample) |
| JP (1) | JP2006500437A (enExample) |
| AT (1) | ATE426635T1 (enExample) |
| AU (1) | AU2003267581A1 (enExample) |
| CA (1) | CA2499681A1 (enExample) |
| DE (1) | DE60326859D1 (enExample) |
| DK (1) | DK1543063T3 (enExample) |
| GB (1) | GB0221942D0 (enExample) |
| SI (1) | SI1543063T1 (enExample) |
| WO (1) | WO2004026941A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008519128A (ja) * | 2004-11-03 | 2008-06-05 | エクスプレッション・ジェネティックス・インコーポレーテッド | 遺伝子送達用の生分解性架橋カチオン性マルチブロックコポリマーおよびそれを製造する方法 |
| JP2009524719A (ja) * | 2006-01-27 | 2009-07-02 | チバ ホールディング インコーポレーテッド | ポリマー状抗菌剤 |
| JP2010513644A (ja) * | 2006-12-22 | 2010-04-30 | ビーエーエスエフ ソシエタス・ヨーロピア | 移染防止剤としての疎水性に変性されたポリアルキレンイミン |
| JP2010533710A (ja) * | 2007-07-19 | 2010-10-28 | オールエクセル,インコーポレイティド | 抗癌剤としての自己集合性の両親媒性ポリマー |
| JP2015535292A (ja) * | 2012-11-05 | 2015-12-10 | サーモディクス,インコーポレイテッド | 疎水性生理活性物質を送達するための組成物および方法 |
| US10213528B2 (en) | 2011-05-20 | 2019-02-26 | Surmodics, Inc. | Delivery of hydrophobic active agent particles |
| US12226552B2 (en) | 2019-09-30 | 2025-02-18 | Surmodics, Inc. | Active agent depots formed in situ |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0422877D0 (en) * | 2004-10-14 | 2004-11-17 | Univ Glasgow | Bioactive polymers |
| WO2007084126A1 (en) | 2006-01-19 | 2007-07-26 | Allexcel, Inc. | Solubilization and targeted delivery of drugs with self-assembling amphiphilic polymers |
| EP2500015A1 (en) * | 2006-12-05 | 2012-09-19 | Landec Corporation | Delivery of drugs |
| US20090263346A1 (en) * | 2006-12-05 | 2009-10-22 | David Taft | Systems and methods for delivery of drugs |
| US20090246155A1 (en) * | 2006-12-05 | 2009-10-01 | Landec Corporation | Compositions and methods for personal care |
| US20100004124A1 (en) * | 2006-12-05 | 2010-01-07 | David Taft | Systems and methods for delivery of materials for agriculture and aquaculture |
| US8399007B2 (en) * | 2006-12-05 | 2013-03-19 | Landec Corporation | Method for formulating a controlled-release pharmaceutical formulation |
| US8114883B2 (en) * | 2007-12-04 | 2012-02-14 | Landec Corporation | Polymer formulations for delivery of bioactive materials |
| FR2928373B1 (fr) | 2008-03-05 | 2010-12-31 | Centre Nat Rech Scient | Polymere derive de la polyethylenimine lineaire pour le transfert de gene. |
| GB0903559D0 (en) | 2009-03-02 | 2009-04-08 | Univ London Pharmacy | Oral delivery of hydrophilic drugs to the brain |
| MX342897B (es) | 2009-04-28 | 2016-10-18 | Surmodics Inc | Dispositivos y metodos para suministrar agentes bioactivos. |
| GB0915449D0 (en) | 2009-09-04 | 2009-10-07 | Univ Robert Gordon | Composition |
| CA2797709C (en) | 2010-04-28 | 2018-07-31 | Jason J. Locklin | Photochemical cross-linkable polymers, methods of making photochemical cross-linkable polymers, methods of using photochemical cross-linkable polymers, and methods of making articles containing photochemical cross-linkable polymers |
| US8721936B2 (en) | 2011-04-21 | 2014-05-13 | University Of Georgia Research Foundation, Inc. | Devices and methods for forming non-spherical particles |
| US10213529B2 (en) | 2011-05-20 | 2019-02-26 | Surmodics, Inc. | Delivery of coated hydrophobic active agent particles |
| WO2013012664A2 (en) | 2011-07-15 | 2013-01-24 | The University Of Georgia Research Foundation, Inc | Permanent attachment of agents to surfaces containing c-h functionality |
| WO2013019918A2 (en) | 2011-08-04 | 2013-02-07 | The University Of Georgia Research Foundation, Inc. | Permanent attachment of ammonium and guanidine-based antimicrobials to surfaces containing-oh functionality |
| US9839213B2 (en) | 2011-10-14 | 2017-12-12 | The University Of Georgia Research Foundation, Inc. | Photochemical cross-linkable polymers, methods of making photochemical cross-linkable polymers, methods of using photochemical cross-linkable polymers, and methods of making articles containing photochemical cross-linkable polymers |
| US11246963B2 (en) | 2012-11-05 | 2022-02-15 | Surmodics, Inc. | Compositions and methods for delivery of hydrophobic active agents |
| US10898446B2 (en) | 2016-12-20 | 2021-01-26 | Surmodics, Inc. | Delivery of hydrophobic active agents from hydrophilic polyether block amide copolymer surfaces |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01236240A (ja) * | 1989-01-14 | 1989-09-21 | Miyoshi Oil & Fat Co Ltd | 新規な高分子化合物 |
| JPH02232229A (ja) * | 1989-01-20 | 1990-09-14 | Hoechst Ag | アルキル化ポリエチレンイミン誘導体 |
| JPH07188698A (ja) * | 1993-12-27 | 1995-07-25 | Miyoshi Oil & Fat Co Ltd | 両性界面活性剤 |
| JPH0912717A (ja) * | 1995-06-23 | 1997-01-14 | Miyoshi Oil & Fat Co Ltd | 抗菌剤、抗菌性樹脂及び抗菌性塗料 |
| JPH11514024A (ja) * | 1996-06-19 | 1999-11-30 | ザ、プロクター、エンド、ギャンブル、カンパニー | 変性ポリアミンから悪臭を除去する方法 |
| JP2004520328A (ja) * | 2000-12-29 | 2004-07-08 | バイエル アクチェンゲゼルシャフト | 活性物質としてポリアミンを含む医薬 |
| JP2004522809A (ja) * | 2000-09-14 | 2004-07-29 | エクスプレッション・ジェネティックス・インコーポレーテッド | 生物学的適合遺伝子送達剤としての新規カチオンリポポリマー |
| JP2006503933A (ja) * | 2002-09-20 | 2006-02-02 | ザ・ユニバーシティ・オブ・ストラスクライド | 親水性基および疎水性基で置換された可溶化多糖類 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5879022A (ja) * | 1981-11-04 | 1983-05-12 | Bitamin Kenkyusho:Kk | 第四級窒素原子を含有する新規な金属架橋高分子化合物、その製法及び該高分子化合物を有効成分とする高脂血症治療剤 |
| US5338532A (en) * | 1986-08-18 | 1994-08-16 | The Dow Chemical Company | Starburst conjugates |
| US5681543A (en) * | 1988-02-29 | 1997-10-28 | Shering Aktiengesellschaft | Polymer-bonded complexing agents and pharmaceutical agents containing them for MRI |
| WO1999043752A1 (fr) * | 1998-02-27 | 1999-09-02 | Dnavec Research Inc. | Compositions pour transporter des substances chargees negativement |
| JP3523821B2 (ja) * | 2000-02-09 | 2004-04-26 | ナノキャリア株式会社 | 薬物が封入されたポリマーミセルの製造方法および該ポリマーミセル組成物 |
| JP2004510829A (ja) * | 2000-10-09 | 2004-04-08 | バイエル アクチェンゲゼルシャフト | 核酸を細胞内に転移させるための複合体 |
-
2002
- 2002-09-20 GB GBGB0221942.6A patent/GB0221942D0/en not_active Ceased
-
2003
- 2003-09-22 DE DE60326859T patent/DE60326859D1/de not_active Expired - Lifetime
- 2003-09-22 WO PCT/GB2003/004036 patent/WO2004026941A1/en not_active Ceased
- 2003-09-22 JP JP2004537295A patent/JP2006500437A/ja active Pending
- 2003-09-22 AT AT03748273T patent/ATE426635T1/de not_active IP Right Cessation
- 2003-09-22 US US10/528,602 patent/US20060148982A1/en not_active Abandoned
- 2003-09-22 AU AU2003267581A patent/AU2003267581A1/en not_active Abandoned
- 2003-09-22 SI SI200331599T patent/SI1543063T1/sl unknown
- 2003-09-22 CA CA002499681A patent/CA2499681A1/en not_active Abandoned
- 2003-09-22 EP EP03748273A patent/EP1543063B1/en not_active Expired - Lifetime
- 2003-09-22 DK DK03748273T patent/DK1543063T3/da active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01236240A (ja) * | 1989-01-14 | 1989-09-21 | Miyoshi Oil & Fat Co Ltd | 新規な高分子化合物 |
| JPH02232229A (ja) * | 1989-01-20 | 1990-09-14 | Hoechst Ag | アルキル化ポリエチレンイミン誘導体 |
| JPH07188698A (ja) * | 1993-12-27 | 1995-07-25 | Miyoshi Oil & Fat Co Ltd | 両性界面活性剤 |
| JPH0912717A (ja) * | 1995-06-23 | 1997-01-14 | Miyoshi Oil & Fat Co Ltd | 抗菌剤、抗菌性樹脂及び抗菌性塗料 |
| JPH11514024A (ja) * | 1996-06-19 | 1999-11-30 | ザ、プロクター、エンド、ギャンブル、カンパニー | 変性ポリアミンから悪臭を除去する方法 |
| JP2004522809A (ja) * | 2000-09-14 | 2004-07-29 | エクスプレッション・ジェネティックス・インコーポレーテッド | 生物学的適合遺伝子送達剤としての新規カチオンリポポリマー |
| JP2004520328A (ja) * | 2000-12-29 | 2004-07-08 | バイエル アクチェンゲゼルシャフト | 活性物質としてポリアミンを含む医薬 |
| JP2006503933A (ja) * | 2002-09-20 | 2006-02-02 | ザ・ユニバーシティ・オブ・ストラスクライド | 親水性基および疎水性基で置換された可溶化多糖類 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008519128A (ja) * | 2004-11-03 | 2008-06-05 | エクスプレッション・ジェネティックス・インコーポレーテッド | 遺伝子送達用の生分解性架橋カチオン性マルチブロックコポリマーおよびそれを製造する方法 |
| JP2009524719A (ja) * | 2006-01-27 | 2009-07-02 | チバ ホールディング インコーポレーテッド | ポリマー状抗菌剤 |
| JP2010513644A (ja) * | 2006-12-22 | 2010-04-30 | ビーエーエスエフ ソシエタス・ヨーロピア | 移染防止剤としての疎水性に変性されたポリアルキレンイミン |
| JP2010533710A (ja) * | 2007-07-19 | 2010-10-28 | オールエクセル,インコーポレイティド | 抗癌剤としての自己集合性の両親媒性ポリマー |
| KR101470679B1 (ko) * | 2007-07-19 | 2014-12-08 | 올엑셀, 인크. | 항암제로서의 자기 조립형 양친매성 중합체 |
| US10213528B2 (en) | 2011-05-20 | 2019-02-26 | Surmodics, Inc. | Delivery of hydrophobic active agent particles |
| US11529440B2 (en) | 2011-05-20 | 2022-12-20 | Surmodics, Inc. | Delivery of hydrophobic active agent particles |
| US12083249B2 (en) | 2011-05-20 | 2024-09-10 | Surmodics, Inc. | Delivery of hydrophobic active agent particles |
| JP2015535292A (ja) * | 2012-11-05 | 2015-12-10 | サーモディクス,インコーポレイテッド | 疎水性生理活性物質を送達するための組成物および方法 |
| US12226552B2 (en) | 2019-09-30 | 2025-02-18 | Surmodics, Inc. | Active agent depots formed in situ |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1543063A1 (en) | 2005-06-22 |
| AU2003267581A1 (en) | 2004-04-08 |
| DE60326859D1 (de) | 2009-05-07 |
| GB0221942D0 (en) | 2002-10-30 |
| CA2499681A1 (en) | 2004-04-01 |
| AU2003267581A8 (en) | 2004-04-08 |
| SI1543063T1 (sl) | 2009-08-31 |
| DK1543063T3 (da) | 2009-05-18 |
| WO2004026941A1 (en) | 2004-04-01 |
| US20060148982A1 (en) | 2006-07-06 |
| ATE426635T1 (de) | 2009-04-15 |
| EP1543063B1 (en) | 2009-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006500437A (ja) | 薬物送達 | |
| Shen et al. | Mucoadhesive effect of thiolated PEG stearate and its modified NLC for ocular drug delivery | |
| Dora et al. | Potential of erlotinib cyclodextrin nanosponge complex to enhance solubility, dissolution rate, in vitro cytotoxicity and oral bioavailability | |
| Al-Quadeib et al. | Stealth Amphotericin B nanoparticles for oral drug delivery: In vitro optimization | |
| Gref et al. | New self-assembled nanogels based on host–guest interactions: characterization and drug loading | |
| Yao et al. | A series of novel chitosan derivatives: synthesis, characterization and micellar solubilization of paclitaxel | |
| Yu et al. | Supersaturated polymeric micelles for oral cyclosporine A delivery | |
| JP4865228B2 (ja) | 親水性基および疎水性基で置換された可溶化多糖類 | |
| Jones et al. | Reverse polymeric micelles for pharmaceutical applications | |
| Gabr et al. | Carboxylate cross-linked cyclodextrin: A nanoporous scaffold for enhancement of rosuvastatin oral bioavailability | |
| Cavallaro et al. | Tamoxifen‐loaded polymeric micelles: preparation, physico‐chemical characterization and in vitro evaluation studies | |
| EP2051998B1 (en) | Polymeric micellar clusters and their uses in formulating drugs | |
| EP2216015A1 (en) | Poorly soluble substance-surfactant complex product, and process for production thereof | |
| KR20080104928A (ko) | 암의 진단과 치료를 동시에 수행하는 항암제 | |
| Luengo-Alonso et al. | A novel performing PEG-cholane nanoformulation for amphotericin B delivery | |
| EP1434567B1 (fr) | Procede de preparation d'un compose d'interaction de substances actives avec un support poreux par fluide supercritique | |
| Lemos-Senna et al. | Evaluation of the hydrophobic drug loading characteristics in nanoprecipitated amphiphilic cyclodextrin nanospheres | |
| CN106883404B (zh) | 聚乙二醇维生素e琥珀酸酯衍生物及其制备方法和应用 | |
| Bajaj et al. | Spray dried mebendazole–loaded Soluplus-based polymeric micelles for improved biopharmaceutical attributes: In vitro and in vivo studies | |
| US8796234B2 (en) | Crosslinking branched molecule through thiol-disulfide exchange to form hydrogel | |
| CN108309936B (zh) | 载番茄红素自组装纳米胶束及其制备方法 | |
| Patel et al. | Patent review on cyclodextrin based nanosponges prepared by different methods: physicochemical characterization, factors influencing formation and applications | |
| US8372933B2 (en) | Hyperbranched polymers based on cyclodextrins and poly (amidoamines) for the controlled release of insoluble drugs | |
| Zhang et al. | Synthesis of β‐Cyclodextrin Containing Copolymer via “Click” Chemistry and Its Self‐Assembly in the Presence of Guest Compounds | |
| CN113698589B (zh) | 一种维生素e琥珀酸酯磷脂化合物及其应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060913 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060913 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20090304 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090616 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090827 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090903 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20091016 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20091023 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091112 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091215 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100312 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100319 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20100817 |