JP2004525902A5 - - Google Patents
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- JP2004525902A5 JP2004525902A5 JP2002566203A JP2002566203A JP2004525902A5 JP 2004525902 A5 JP2004525902 A5 JP 2004525902A5 JP 2002566203 A JP2002566203 A JP 2002566203A JP 2002566203 A JP2002566203 A JP 2002566203A JP 2004525902 A5 JP2004525902 A5 JP 2004525902A5
- Authority
- JP
- Japan
- Prior art keywords
- liposome
- group
- liposome according
- sterol
- active substance
- 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.)
- Granted
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- 239000002502 liposome Substances 0.000 claims description 59
- 239000013543 active substance Substances 0.000 claims description 16
- 108090000623 proteins and genes Proteins 0.000 claims description 12
- 102000004169 proteins and genes Human genes 0.000 claims description 12
- 229930182558 Sterol Natural products 0.000 claims description 9
- 150000003432 sterols Chemical class 0.000 claims description 9
- 235000003702 sterols Nutrition 0.000 claims description 9
- 239000002088 nanocapsule Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 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 4
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 3
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 3
- 238000002405 diagnostic procedure Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000013598 vector Substances 0.000 claims description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 239000002773 nucleotide Substances 0.000 claims 2
- 125000003729 nucleotide group Chemical group 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 125000006850 spacer group Chemical group 0.000 claims 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims 1
- OSELKOCHBMDKEJ-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4c)-yl)-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 OSELKOCHBMDKEJ-UHFFFAOYSA-N 0.000 claims 1
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 claims 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 claims 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims 1
- IZVFFXVYBHFIHY-UHFFFAOYSA-N (3alpha, 5alpha)-Cholest-7-en-3-ol, 9CI Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCCC(C)C)CCC33)C)C3=CCC21 IZVFFXVYBHFIHY-UHFFFAOYSA-N 0.000 claims 1
- PKEPPDGGTSZLBL-UHFFFAOYSA-N (3beta, 5alpha, 22E)-Cholesta-7, 22-dien-3-ol, 9CI Natural products C1C(O)CCC2(C)C(CCC3(C(C(CCC=C(C)C)C)CCC33)C)C3=CCC21 PKEPPDGGTSZLBL-UHFFFAOYSA-N 0.000 claims 1
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 claims 1
- HVYWMOMLDIMFJA-VEIPTCAHSA-N (3r,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical compound C1C=C2C[C@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-VEIPTCAHSA-N 0.000 claims 1
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 claims 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 1
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 claims 1
- YRWIUNJQYGATHV-FTLVODPJSA-N 19-Hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(CO)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 YRWIUNJQYGATHV-FTLVODPJSA-N 0.000 claims 1
- YRWIUNJQYGATHV-UHFFFAOYSA-N 19-hydroxycholesterol Natural products C1C=C2CC(O)CCC2(CO)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 YRWIUNJQYGATHV-UHFFFAOYSA-N 0.000 claims 1
- RZPAXNJLEKLXNO-UKNNTIGFSA-N 22-Hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)C(O)CCC(C)C)[C@@]1(C)CC2 RZPAXNJLEKLXNO-UKNNTIGFSA-N 0.000 claims 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 claims 1
- INBGSXNNRGWLJU-ZHHJOTBYSA-N 25-hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)(C)O)C)[C@@]1(C)CC2 INBGSXNNRGWLJU-ZHHJOTBYSA-N 0.000 claims 1
- INBGSXNNRGWLJU-UHFFFAOYSA-N 25epsilon-Hydroxycholesterin Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(CCCC(C)(C)O)C)C1(C)CC2 INBGSXNNRGWLJU-UHFFFAOYSA-N 0.000 claims 1
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 claims 1
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 claims 1
- IZVFFXVYBHFIHY-SKCNUYALSA-N 5alpha-cholest-7-en-3beta-ol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)CCCC(C)C)CC[C@H]33)C)C3=CC[C@H]21 IZVFFXVYBHFIHY-SKCNUYALSA-N 0.000 claims 1
- CQSRUKJFZKVYCY-UHFFFAOYSA-N 5alpha-isofucostan-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(=CC)C(C)C)C1(C)CC2 CQSRUKJFZKVYCY-UHFFFAOYSA-N 0.000 claims 1
- OYXZMSRRJOYLLO-UHFFFAOYSA-N 7alpha-Hydroxycholesterol Natural products OC1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 OYXZMSRRJOYLLO-UHFFFAOYSA-N 0.000 claims 1
- OYXZMSRRJOYLLO-KGZHIOMZSA-N 7beta-hydroxycholesterol Chemical compound C([C@@H]1O)=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 OYXZMSRRJOYLLO-KGZHIOMZSA-N 0.000 claims 1
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 claims 1
- 108020004414 DNA Proteins 0.000 claims 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 claims 1
- UCTLRSWJYQTBFZ-UHFFFAOYSA-N Dehydrocholesterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCCC(C)C)CCC33)C)C3=CC=C21 UCTLRSWJYQTBFZ-UHFFFAOYSA-N 0.000 claims 1
- BDCFUHIWJODVNG-UHFFFAOYSA-N Desmosterol Natural products C1C=C2CC(O)C=CC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 BDCFUHIWJODVNG-UHFFFAOYSA-N 0.000 claims 1
- QSVJYFLQYMVBDR-UHFFFAOYSA-N Ergosterin Natural products C1C(O)CCC2(C)C3=CCC4(C)C(C(C)C=CC(C)C(C)C)CCC4C3=CC=C21 QSVJYFLQYMVBDR-UHFFFAOYSA-N 0.000 claims 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 claims 1
- GBBBJSKVBYJMBG-QTWVXCTBSA-N Fucosterol Natural products CC=C(CC[C@@H](C)[C@@H]1CC[C@@H]2[C@H]3C=C[C@@H]4C[C@H](O)CC[C@@]4(C)[C@@H]3CC[C@@]12C)C(C)C GBBBJSKVBYJMBG-QTWVXCTBSA-N 0.000 claims 1
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 claims 1
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims 1
- OSELKOCHBMDKEJ-VRUYXKNBSA-N Isofucosterol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C OSELKOCHBMDKEJ-VRUYXKNBSA-N 0.000 claims 1
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 claims 1
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 claims 1
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims 1
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims 1
- 230000000692 anti-sense effect Effects 0.000 claims 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 claims 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims 1
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims 1
- 235000000431 campesterol Nutrition 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- QSVJYFLQYMVBDR-CMNOFMQQSA-N dehydroergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)C3=CC[C@]4(C)[C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]4C3=CC=C21 QSVJYFLQYMVBDR-CMNOFMQQSA-N 0.000 claims 1
- 239000003405 delayed action preparation Substances 0.000 claims 1
- AVSXSVCZWQODGV-DPAQBDIFSA-N desmosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC=C(C)C)C)[C@@]1(C)CC2 AVSXSVCZWQODGV-DPAQBDIFSA-N 0.000 claims 1
- 150000001982 diacylglycerols Chemical class 0.000 claims 1
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 claims 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 claims 1
- OSELKOCHBMDKEJ-JUGJNGJRSA-N fucosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC\C(=C/C)C(C)C)[C@@]1(C)CC2 OSELKOCHBMDKEJ-JUGJNGJRSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 claims 1
- 229940058690 lanosterol Drugs 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims 1
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- 229950005143 sitosterol Drugs 0.000 claims 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 claims 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims 1
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- 239000012528 membrane Substances 0.000 description 10
- 150000002632 lipids Chemical class 0.000 description 9
- 230000035699 permeability Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- WLNARFZDISHUGS-MIXBDBMTSA-N cholesteryl hemisuccinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 WLNARFZDISHUGS-MIXBDBMTSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 150000003573 thiols Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 238000005538 encapsulation Methods 0.000 description 3
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- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 230000008901 benefit Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
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- -1 europium ions Chemical class 0.000 description 2
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
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| DE10207177A1 (de) * | 2002-02-19 | 2003-09-04 | Novosom Ag | Fakultativ kationische Lipide |
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| EP1393719A1 (en) * | 2002-08-23 | 2004-03-03 | Munich Biotech AG | Camptothecin-carboxylate formulations |
| AU2004238076A1 (en) * | 2003-05-09 | 2004-11-25 | Novosom Ag | Injectable liposomal depots for delivering active ingredients |
| CN1849112B (zh) * | 2003-09-09 | 2012-06-13 | 吉里德科学公司 | 治疗性脂质体 |
| EP1547580A1 (en) * | 2003-12-23 | 2005-06-29 | MediGene Oncology GmbH | Loading of a camptothecin drug into colloidal nanoparticles |
| WO2005063212A1 (en) * | 2003-12-31 | 2005-07-14 | Amorepacific Corporation | Cholesteryl hemisuccinate incorporated lipid-based nano-carriers and skin-care compositions for external application containing the same |
| US20050191344A1 (en) * | 2004-01-15 | 2005-09-01 | Samuel Zalipsky | Liposome composition for delivery of therapeutic agents |
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| WO2006048329A1 (en) * | 2004-11-05 | 2006-05-11 | Novosom Ag | Improvements in or relating to pharmaceutical compositions comprising an oligonucleotide as an active agent |
| JP2008520600A (ja) * | 2004-11-19 | 2008-06-19 | ノヴォソム アクチェンゲゼルシャフト | 局所投与のための医薬組成物におけるまたはそれに関する改善 |
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| EP1911443A1 (en) * | 2006-10-13 | 2008-04-16 | Novosom AG | Amphoteric liposomes, method of formulating an amphoteric liposome and a method of loading an amphoteric liposome |
| AU2006291429B2 (en) | 2005-09-15 | 2013-04-04 | Biontech Delivery Technologies Gmbh | Improvements in or relating to amphoteric liposomes |
| PL1957044T3 (pl) * | 2005-12-01 | 2013-11-29 | Pronai Therapeutics Inc | Amfoteryczny preparat liposomowy |
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| CA2665783C (en) | 2006-10-13 | 2015-12-15 | Novosom Ag | Improvements in or relating to amphoteric liposomes, a method of formulating an amphoteric liposome and a method of loading an amphoteric liposome |
| WO2008074487A2 (en) * | 2006-12-19 | 2008-06-26 | Novosom Ag | Lipids and lipid assemblies comprising transfection enhancer elements |
| HUE040417T2 (hu) | 2007-05-04 | 2019-03-28 | Marina Biotech Inc | Aminosavlipidek és alkalmazásuk |
| US8822409B2 (en) | 2007-06-20 | 2014-09-02 | Phylogica Limited | Compositions and uses thereof for the treatment of acute respiratory distress syndrome (ARDS) and clinical disorders associated with therewith |
| JP2009203228A (ja) * | 2008-01-29 | 2009-09-10 | Kochi Univ | キレーター化合物含有薬物輸送剤 |
| US8765171B2 (en) | 2009-03-09 | 2014-07-01 | The Regents Of The University Of California | Methods and compositions for liposomal formulation of antigens and uses thereof |
| WO2010135714A2 (en) | 2009-05-22 | 2010-11-25 | The Methodist Hospital Research Institute | Methods for modulating adipocyte expression using microrna compositions |
| EP3318248B1 (en) * | 2009-12-01 | 2019-04-10 | Translate Bio, Inc. | Delivery of mrna for the augmentation of proteins and enzymes in human genetic diseases |
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| CZ201181A3 (cs) * | 2011-02-15 | 2012-09-12 | Ústav organické chemie a biochemie Akademie ved CR, v.v.i. | Deriváty pregnanolonu substituované v poloze 3alfa kationickou skupinou, zpusob jejich výroby, jejich použití a prostredek je obsahující |
| WO2012159164A1 (en) | 2011-05-23 | 2012-11-29 | Phylogica Limited | Method of determining, identifying or isolating cell-penetrating peptides |
| GB201116248D0 (en) * | 2011-09-20 | 2011-11-02 | Glaxosmithkline Biolog Sa | Liposome production using isopropanol |
| US20150297725A1 (en) | 2012-07-30 | 2015-10-22 | Rutgers, The State University Of New Jersey | Cochleates made with soy phosphatidylserine |
| US10942184B2 (en) | 2012-10-23 | 2021-03-09 | Caris Science, Inc. | Aptamers and uses thereof |
| EP4170031A1 (en) | 2012-10-23 | 2023-04-26 | Caris Science, Inc. | Aptamers and uses thereof |
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| AU2013361323B2 (en) | 2012-12-19 | 2018-09-06 | Caris Science, Inc. | Compositions and methods for aptamer screening |
| US20170000715A1 (en) * | 2014-01-29 | 2017-01-05 | Humedix Co., Ltd. | Pegylated 7-dehydrocholesterol derivatives |
| JP6399530B1 (ja) * | 2017-09-04 | 2018-10-03 | 一丸ファルコス株式会社 | ｐＨ感受性リポソーム |
| US20200208152A1 (en) | 2017-09-08 | 2020-07-02 | Mina Therapeutics Limited | Stabilized sarna compositions and methods of use |
| EP3775211B1 (en) | 2018-04-12 | 2023-04-05 | MiNA Therapeutics Limited | Sirt1-sarna compositions and methods of use |
| US12240824B2 (en) * | 2018-05-30 | 2025-03-04 | Translate Bio, Inc. | Vitamin cationic lipids |
| EP3953473A1 (en) | 2019-04-12 | 2022-02-16 | MiNA Therapeutics Limited | Sirt1-sarna compositions and methods of use |
| GB2603454A (en) | 2020-12-09 | 2022-08-10 | Ucl Business Ltd | Novel therapeutics for the treatment of neurodegenerative disorders |
| TW202305133A (zh) | 2021-03-26 | 2023-02-01 | 英商米納治療有限公司 | Tmem173 sarna組合物及其使用方法 |
| WO2023099884A1 (en) | 2021-12-01 | 2023-06-08 | Mina Therapeutics Limited | Pax6 sarna compositions and methods of use |
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-
2001
- 2001-02-21 DE DE10109898A patent/DE10109898A1/de not_active Withdrawn
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2002
- 2002-02-21 US US10/468,652 patent/US7312206B2/en not_active Expired - Lifetime
- 2002-02-21 JP JP2002566202A patent/JP2004521917A/ja active Pending
- 2002-02-21 CA CA002438910A patent/CA2438910C/en not_active Expired - Fee Related
- 2002-02-21 EP EP02712923A patent/EP1363933B1/de not_active Expired - Lifetime
- 2002-02-21 CN CNB028053206A patent/CN1231493C/zh not_active Expired - Fee Related
- 2002-02-21 DE DE50210313T patent/DE50210313D1/de not_active Expired - Lifetime
- 2002-02-21 WO PCT/EP2002/001879 patent/WO2002066490A2/de not_active Ceased
- 2002-02-21 EP EP07106269A patent/EP1806354A2/de not_active Withdrawn
- 2002-02-21 WO PCT/EP2002/001878 patent/WO2002066489A2/de not_active Ceased
- 2002-02-21 US US10/468,654 patent/US7407947B2/en not_active Expired - Lifetime
- 2002-02-21 JP JP2002566203A patent/JP4470197B2/ja not_active Expired - Fee Related
- 2002-02-21 EP EP02729931A patent/EP1363932B1/de not_active Expired - Lifetime
- 2002-02-21 BR BR0207776-0A patent/BR0207776A/pt not_active IP Right Cessation
- 2002-02-21 AT AT02712923T patent/ATE430759T1/de active
- 2002-02-21 DE DE50213524T patent/DE50213524D1/de not_active Expired - Lifetime
- 2002-02-21 AT AT02729931T patent/ATE364620T1/de active
- 2002-02-21 AU AU2002244726A patent/AU2002244726A1/en not_active Abandoned
- 2002-02-21 AU AU2002302364A patent/AU2002302364B2/en not_active Ceased
-
2007
- 2007-11-02 US US11/934,147 patent/US20080113017A1/en not_active Abandoned
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