DE10207177A1 - Fakultativ kationische Lipide - Google Patents
Fakultativ kationische LipideInfo
- Publication number
- DE10207177A1 DE10207177A1 DE10207177A DE10207177A DE10207177A1 DE 10207177 A1 DE10207177 A1 DE 10207177A1 DE 10207177 A DE10207177 A DE 10207177A DE 10207177 A DE10207177 A DE 10207177A DE 10207177 A1 DE10207177 A1 DE 10207177A1
- Authority
- DE
- Germany
- Prior art keywords
- liposomes
- lipid
- active ingredient
- mol
- liposomes according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 10
- 239000002502 liposome Substances 0.000 claims abstract description 83
- -1 cationic lipid Chemical class 0.000 claims abstract description 27
- 239000004480 active ingredient Substances 0.000 claims description 23
- 150000002632 lipids Chemical class 0.000 claims description 23
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 102000004169 proteins and genes Human genes 0.000 claims description 14
- 125000006850 spacer group Chemical group 0.000 claims description 11
- 150000001982 diacylglycerols Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000013598 vector Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 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 description 6
- 239000000203 mixture Substances 0.000 claims description 6
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- AWUCVROLDVIAJX-UHFFFAOYSA-N glycerol 1-phosphate Chemical class OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002088 nanocapsule Substances 0.000 claims description 5
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 5
- 235000012000 cholesterol Nutrition 0.000 claims description 4
- 238000005538 encapsulation Methods 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 238000001727 in vivo Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002773 nucleotide Substances 0.000 claims description 4
- 125000003729 nucleotide group Chemical group 0.000 claims description 4
- 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
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical class NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001985 dialkylglycerols Chemical class 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- 238000011068 loading method Methods 0.000 claims description 3
- 150000002780 morpholines Chemical class 0.000 claims description 3
- 150000003212 purines Chemical class 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- 230000000692 anti-sense effect Effects 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 150000003408 sphingolipids Chemical class 0.000 claims description 2
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims 1
- 229940106189 ceramide Drugs 0.000 claims 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims 1
- 239000012528 membrane Substances 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 210000002966 serum Anatomy 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000012634 fragment Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002892 organic cations Chemical class 0.000 description 6
- 230000032258 transport Effects 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000009435 amidation Effects 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 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
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 230000008823 permeabilization Effects 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 229920000867 polyelectrolyte Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 2
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002085 enols Chemical class 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- ZGCHLAJIRWDGFE-UHFFFAOYSA-N 1-aminopropane-1,1-diol Chemical class CCC(N)(O)O ZGCHLAJIRWDGFE-UHFFFAOYSA-N 0.000 description 1
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 1
- BVKFQEAERCHBTG-UHFFFAOYSA-N 17,18,19-trihydroxypentatriacontane-16,20-dione Chemical compound CCCCCCCCCCCCCCCC(=O)C(O)C(O)C(O)C(=O)CCCCCCCCCCCCCCC BVKFQEAERCHBTG-UHFFFAOYSA-N 0.000 description 1
- KWVJHCQQUFDPLU-YEUCEMRASA-N 2,3-bis[[(z)-octadec-9-enoyl]oxy]propyl-trimethylazanium Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC KWVJHCQQUFDPLU-YEUCEMRASA-N 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
- WQTCTMDKQPZJES-UHFFFAOYSA-N 2-aminoethyl dihydrogen phosphate;nonane Chemical compound NCCOP(O)(O)=O.CCCCCCCCC.CCCCCCCCC WQTCTMDKQPZJES-UHFFFAOYSA-N 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 1
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 1
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- AJFWREUFUPEYII-UHFFFAOYSA-N Phosphatidylserin Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC([NH3+])C([O-])=O)OC(=O)CCCCCCCC=CCCCCCCCC AJFWREUFUPEYII-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 1
- JZSWZDBPGBBRNA-UHFFFAOYSA-N [hydroxymethyl(methyl)amino]methanol Chemical compound OCN(C)CO JZSWZDBPGBBRNA-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 1
- 239000003012 bilayer membrane Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- RQNOMGKSZOGBDD-UHFFFAOYSA-N butanedioic acid 17,18,19-trihydroxypentatriacontane-16,20-dione Chemical compound OC(=O)CCC(O)=O.CCCCCCCCCCCCCCCC(=O)C(O)C(O)C(O)C(=O)CCCCCCCCCCCCCCC RQNOMGKSZOGBDD-UHFFFAOYSA-N 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000004154 complement system Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000012202 endocytosis Effects 0.000 description 1
- 230000001159 endocytotic effect Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
- 229940029575 guanosine Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- PRJKNHOMHKJCEJ-UHFFFAOYSA-N imidazol-4-ylacetic acid Chemical compound OC(=O)CC1=CN=CN1 PRJKNHOMHKJCEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037368 penetrate the skin Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GKODZWOPPOTFGA-UHFFFAOYSA-N tris(hydroxyethyl)aminomethane Chemical compound OCCC(N)(CCO)CCO GKODZWOPPOTFGA-UHFFFAOYSA-N 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
-
- A—HUMAN NECESSITIES
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- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
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- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Virology (AREA)
- Heart & Thoracic Surgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Transplantation (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10207177A DE10207177A1 (de) | 2002-02-19 | 2002-02-19 | Fakultativ kationische Lipide |
| US10/505,107 US8192753B2 (en) | 2002-02-19 | 2003-02-19 | pH-sensitive cationic lipids, and liposomes and nanocapsules containing the same |
| AU2003210303A AU2003210303A1 (en) | 2002-02-19 | 2003-02-19 | Ph-sensitive cationic lipids, and liposomes and nanocapsules containing the same |
| PCT/EP2003/001661 WO2003070220A1 (de) | 2002-02-19 | 2003-02-19 | Ph sensitiv kationische lipide, lipsomen und nanokapseln, die diese umfassen |
| JP2003569178A JP2005526727A (ja) | 2002-02-19 | 2003-02-19 | ｐＨ感受性カチオン脂質、それを含有するリポソーム及びナノカプセル |
| EP03742540A EP1480621A1 (de) | 2002-02-19 | 2003-02-19 | Ph sensitiv kationische lipide, lipsomen und nanokapseln, die diese umfassen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10207177A DE10207177A1 (de) | 2002-02-19 | 2002-02-19 | Fakultativ kationische Lipide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10207177A1 true DE10207177A1 (de) | 2003-09-04 |
Family
ID=27674784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10207177A Ceased DE10207177A1 (de) | 2002-02-19 | 2002-02-19 | Fakultativ kationische Lipide |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8192753B2 (enExample) |
| EP (1) | EP1480621A1 (enExample) |
| JP (1) | JP2005526727A (enExample) |
| AU (1) | AU2003210303A1 (enExample) |
| DE (1) | DE10207177A1 (enExample) |
| WO (1) | WO2003070220A1 (enExample) |
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|---|---|---|---|---|
| CA2487274A1 (en) * | 2002-05-06 | 2003-11-13 | Nucleonics Inc. | Spermine chemically linked to lipids and cell-specific targeting molecules as a transfection agent |
| JP2007520481A (ja) * | 2004-01-15 | 2007-07-26 | アルザ・コーポレーシヨン | 治療薬を送達するためのリポソーム組成物 |
| US20080088046A1 (en) * | 2006-10-13 | 2008-04-17 | Steffen Panzner | Amphoteric liposomes, a method of formulating an amphoteric liposome and a method of loading an amphoteric liposome |
| EP1764091B1 (en) | 2005-09-15 | 2017-08-30 | Marina Biotech, Inc. | Improvements in or relating to amphoteric liposomes |
| EP1948674A4 (en) | 2005-11-02 | 2009-02-04 | Protiva Biotherapeutics Inc | MODIFIED SIRNA MOLECULES AND APPLICATIONS THEREOF |
| JP5122474B2 (ja) * | 2005-12-01 | 2013-01-16 | プロネイ・セラピューティクス・インコーポレイテッド | 両性リポソーム製剤 |
| KR101388320B1 (ko) | 2005-12-15 | 2014-04-22 | 뽈리쁠뤼스-트랑스펙씨옹 | 양이온성 올리고뉴클레오티드, 이를 제조하기 위한 자동화방법 및 이의 용도 |
| EP1844772A1 (en) | 2006-04-06 | 2007-10-17 | Polyplus-Transfection SA | Compositions for transfection of oligonucleotides active for gene silencing and their biological and therapeutical applications |
| AU2007306556B2 (en) | 2006-10-13 | 2014-04-10 | Marina Biotech, Inc. | Improvements in or relating to amphoteric liposomes |
| JP2010513354A (ja) * | 2006-12-19 | 2010-04-30 | ノヴォソム アクチェンゲゼルシャフト | トランスフェクションエンハンサー要素を含む脂質および脂質集合体 |
| US9006191B2 (en) | 2007-12-27 | 2015-04-14 | Protiva Biotherapeutics, Inc. | Silencing of polo-like kinase expression using interfering RNA |
| FR2926818B1 (fr) * | 2008-01-30 | 2012-04-06 | Centre Nat Rech Scient | siRNA CATIONIQUES, SYNTHESE ET UTILISATION POUR L'ARN INTERFERENCE |
| WO2009129319A2 (en) | 2008-04-15 | 2009-10-22 | Protiva Biotherapeutics, Inc. | Silencing of csn5 gene expression using interfering rna |
| JP5588619B2 (ja) * | 2009-03-11 | 2014-09-10 | 一丸ファルコス株式会社 | ｐＨ応答性リポソーム |
| US20130017223A1 (en) | 2009-12-18 | 2013-01-17 | The University Of British Columbia | Methods and compositions for delivery of nucleic acids |
| JP2013530187A (ja) | 2010-06-17 | 2013-07-25 | ザ ユナイテッド ステイツ オブ アメリカ アズ リプレゼンティッド バイ ザ シークレタリー デパートメント オブ ヘルス アンド ヒューマン サービシーズ | 炎症性疾患を治療するための組成物及び方法。 |
| CN103153284B (zh) | 2010-07-06 | 2015-11-25 | 诺华股份有限公司 | 含有其pKa值有利于RNA递送的脂质的脂质体 |
| FI4005592T3 (fi) | 2010-07-06 | 2023-01-13 | Virionin kaltaisia kuljetuspartikkeleita itsereplikoituville rna-molekyyleille | |
| PT3243526T (pt) | 2010-07-06 | 2020-03-04 | Glaxosmithkline Biologicals Sa | Distribuição de arn para despoletar múltiplas vias imunitárias |
| US10487332B2 (en) | 2010-07-06 | 2019-11-26 | Glaxosmithkline Biologicals Sa | Immunisation of large mammals with low doses of RNA |
| JP5911870B2 (ja) | 2010-08-31 | 2016-04-27 | ノバルティス アーゲー | 免疫原をコードするｒｎａの送達のためのｐｅｇ化リポソーム |
| KR102266691B1 (ko) | 2010-10-11 | 2021-06-23 | 노파르티스 아게 | 항원 전달 플랫폼 |
| WO2012106490A1 (en) | 2011-02-03 | 2012-08-09 | The Government Of The U.S.A., As Represented By The Secretary, Department Of Health & Human Services | Multivalent vaccines for rabies virus and filoviruses |
| WO2012109495A1 (en) | 2011-02-09 | 2012-08-16 | Metabolic Solutions Development Company, Llc | Cellular targets of thiazolidinediones |
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| JP2014522842A (ja) | 2011-07-06 | 2014-09-08 | ノバルティス アーゲー | 免疫原性組み合わせ組成物およびその使用 |
| WO2013032643A2 (en) * | 2011-08-31 | 2013-03-07 | Dicerna Pharmaceuticals, Inc. | Lipids capable of conformational change and their use in formulations to deliver therapeutic agents to cells |
| EP2780456A1 (en) | 2011-11-17 | 2014-09-24 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Therapeutic rna switches compositions and methods of use |
| US9035039B2 (en) | 2011-12-22 | 2015-05-19 | Protiva Biotherapeutics, Inc. | Compositions and methods for silencing SMAD4 |
| MX375442B (es) | 2012-09-21 | 2025-03-06 | Intensity Therapeutics Inc | Un agente terapéutico y un agente mejorador de la permeación intracelular para usarse en el tratamiento de cáncer. |
| CN104884637A (zh) | 2012-11-05 | 2015-09-02 | 普隆奈治疗公司 | 利用生物标志物通过bcl2表达的调节治疗癌症的方法 |
| JP6339884B2 (ja) | 2014-07-17 | 2018-06-06 | 富士フイルム株式会社 | イミダゾール化合物およびそれを含有するリポソーム |
| US10415037B2 (en) | 2014-10-02 | 2019-09-17 | Arbutus Biopharma Corporation | Compositions and methods for silencing hepatitis B virus gene expression |
| WO2016197132A1 (en) | 2015-06-04 | 2016-12-08 | Protiva Biotherapeutics Inc. | Treating hepatitis b virus infection using crispr |
| CN108350455A (zh) | 2015-07-29 | 2018-07-31 | 阿布特斯生物制药公司 | 用于使b型肝炎病毒基因表达沉默的组合物和方法 |
| WO2017040702A1 (en) * | 2015-08-31 | 2017-03-09 | The Regents Of The University Of California | Bipolar tetraether lipids |
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| EP3419629A4 (en) | 2016-02-25 | 2019-10-30 | Applied Biological Laboratories, Inc. | COMPOSITIONS AND PROCEDURES FOR PROTECTION AGAINST AIRBORNE PATHOGENES AND IRRITATES |
| EP3439695B1 (en) | 2016-04-04 | 2022-05-04 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Multivalent vaccines for rabies virus and coronaviruses |
| WO2018039131A1 (en) | 2016-08-22 | 2018-03-01 | Protiva Biotherapeutics, Inc. | Anti-pd-1 antibodies, or fragments thereof, for treating hepatitis b |
| AU2017379901B2 (en) | 2016-12-21 | 2024-02-15 | Arbutus Biopharma Corporation | Methods for ameliorating infusion reactions |
| US11198831B2 (en) | 2019-01-31 | 2021-12-14 | Kvi Llc | Lubricant for a device |
| CA3174708A1 (en) | 2020-03-04 | 2021-09-10 | Verve Therapeutics, Inc. | Compositions and methods for targeted rna delivery |
| EP4132951A4 (en) | 2020-04-09 | 2025-06-11 | Verve Therapeutics, Inc. | CHEMICALLY MODIFIED GENE EDITING GUIDE RNAS WITH CAS12B |
| CN116234538A (zh) * | 2021-03-09 | 2023-06-06 | 日本精化株式会社 | 磷脂 |
| EP4380576A4 (en) | 2021-08-03 | 2026-04-29 | Verve Therapeutics Inc | RNA TARGETED COMPOSITIONS AND ADMINISTRATION METHODS |
| CN115894281B (zh) * | 2021-09-22 | 2025-07-01 | 广州谷森制药有限公司 | 阳离子脂质化合物、其制备方法、组合物及应用 |
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| EP0169812A1 (de) * | 1984-07-25 | 1986-01-29 | Ciba-Geigy Ag | Phosphatidylverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP0434365A2 (en) * | 1989-12-18 | 1991-06-26 | Merck & Co. Inc. | HIV protease inhibitors useful for the treatment of aids |
| EP0451763A2 (en) * | 1990-04-09 | 1991-10-16 | Fuji Photo Film Co., Ltd. | Peptide derivatives with amphiphatic properties, intermediates thereof and liposomes and films comprising said derivatives |
| DE69324367T2 (de) * | 1992-08-28 | 1999-09-23 | Life Technologies Inc., Gaithersburg | Kationische lipide |
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| DE69711920T2 (de) * | 1996-12-04 | 2002-08-08 | L'oreal, Paris | Neue histidinderivate, verfahren zu ihrer herstellung und ihre verwendung als mittel gegen freie radikale |
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| DE69430626T2 (de) * | 1993-03-12 | 2002-12-19 | Genzyme Corp., Cambridge | Neue phospholipid-saccharid-konjugate |
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-
2002
- 2002-02-19 DE DE10207177A patent/DE10207177A1/de not_active Ceased
-
2003
- 2003-02-19 WO PCT/EP2003/001661 patent/WO2003070220A1/de not_active Ceased
- 2003-02-19 US US10/505,107 patent/US8192753B2/en active Active
- 2003-02-19 AU AU2003210303A patent/AU2003210303A1/en not_active Abandoned
- 2003-02-19 EP EP03742540A patent/EP1480621A1/de not_active Ceased
- 2003-02-19 JP JP2003569178A patent/JP2005526727A/ja not_active Abandoned
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| EP0169812A1 (de) * | 1984-07-25 | 1986-01-29 | Ciba-Geigy Ag | Phosphatidylverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP0434365A2 (en) * | 1989-12-18 | 1991-06-26 | Merck & Co. Inc. | HIV protease inhibitors useful for the treatment of aids |
| EP0451763A2 (en) * | 1990-04-09 | 1991-10-16 | Fuji Photo Film Co., Ltd. | Peptide derivatives with amphiphatic properties, intermediates thereof and liposomes and films comprising said derivatives |
| DE69131347T2 (de) * | 1990-04-19 | 2000-03-30 | Vical, Inc. | Kationische lipide für die intrazelluläre abgabe von biologisch aktiven molekülen |
| DE69324367T2 (de) * | 1992-08-28 | 1999-09-23 | Life Technologies Inc., Gaithersburg | Kationische lipide |
| DE69427498T2 (de) * | 1993-02-12 | 2001-10-18 | Oreal | Verfahren zur Stabilisierung von Vesikeln aus amphiphilen Lipiden und diese stabilisierte Vesikeln enthaltende Zusammensetzung für die topische Anwendung |
| DE69424406T2 (de) * | 1993-02-19 | 2000-10-26 | Nippon Shinyaku Co., Ltd. | Arzneistoffzusammensetzung, die ein nukleinsäurecopolymer enthält |
| DE69430626T2 (de) * | 1993-03-12 | 2002-12-19 | Genzyme Corp., Cambridge | Neue phospholipid-saccharid-konjugate |
| DE69711920T2 (de) * | 1996-12-04 | 2002-08-08 | L'oreal, Paris | Neue histidinderivate, verfahren zu ihrer herstellung und ihre verwendung als mittel gegen freie radikale |
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| DE10109897A1 (de) * | 2001-02-21 | 2002-11-07 | Novosom Ag | Fakultativ kationische Liposomen und Verwendung dieser |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005526727A (ja) | 2005-09-08 |
| AU2003210303A1 (en) | 2003-09-09 |
| US8192753B2 (en) | 2012-06-05 |
| WO2003070220A1 (de) | 2003-08-28 |
| US20060002991A1 (en) | 2006-01-05 |
| EP1480621A1 (de) | 2004-12-01 |
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