DE10109897A1 - Fakultativ kationische Liposomen und Verwendung dieser - Google Patents
Fakultativ kationische Liposomen und Verwendung dieserInfo
- Publication number
- DE10109897A1 DE10109897A1 DE10109897A DE10109897A DE10109897A1 DE 10109897 A1 DE10109897 A1 DE 10109897A1 DE 10109897 A DE10109897 A DE 10109897A DE 10109897 A DE10109897 A DE 10109897A DE 10109897 A1 DE10109897 A1 DE 10109897A1
- Authority
- DE
- Germany
- Prior art keywords
- liposomes
- positive
- membrane
- negative
- charge
- 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.)
- Withdrawn
Links
- 239000002502 liposome Substances 0.000 title claims abstract description 101
- 125000002091 cationic group Chemical group 0.000 title description 17
- 239000002800 charge carrier Substances 0.000 claims abstract description 27
- 239000012528 membrane Substances 0.000 claims abstract description 20
- 150000002632 lipids Chemical class 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000003636 chemical group Chemical group 0.000 claims description 6
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 2
- 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 17
- 102000039446 nucleic acids Human genes 0.000 description 12
- 108020004707 nucleic acids Proteins 0.000 description 12
- 150000007523 nucleic acids Chemical class 0.000 description 12
- 239000000872 buffer Substances 0.000 description 11
- 230000027455 binding Effects 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 230000007935 neutral effect Effects 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000004927 fusion Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 150000003904 phospholipids Chemical class 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 108010067770 Endopeptidase K Proteins 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 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 4
- 230000004568 DNA-binding Effects 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 239000007995 HEPES buffer Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 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 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- -1 alkyl homocysteines Chemical class 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- BIABMEZBCHDPBV-UHFFFAOYSA-N dipalmitoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 3
- 230000004962 physiological condition Effects 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000032258 transport 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
- 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
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 2
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Chemical class 0.000 description 2
- 229920004890 Triton X-100 Polymers 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 108010041102 azocasein Proteins 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 210000001163 endosome Anatomy 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- 230000016615 flocculation Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 230000008823 permeabilization Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YEDNBEGNKOANMB-REOHCLBHSA-N (2r)-2-amino-3-sulfanylpropanamide Chemical compound SC[C@H](N)C(N)=O YEDNBEGNKOANMB-REOHCLBHSA-N 0.000 description 1
- KSXTUUUQYQYKCR-LQDDAWAPSA-M 2,3-bis[[(z)-octadec-9-enoyl]oxy]propyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC KSXTUUUQYQYKCR-LQDDAWAPSA-M 0.000 description 1
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 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
- 238000005188 flotation Methods 0.000 description 1
- 230000000799 fusogenic effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000010196 hermaphroditism Effects 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940067605 phosphatidylethanolamines Drugs 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 125000002328 sterol group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002885 thrombogenetic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/7105—Natural ribonucleic acids, i.e. containing only riboses attached to adenine, guanine, cytosine or uracil and having 3'-5' phosphodiester links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/711—Natural deoxyribonucleic acids, i.e. containing only 2'-deoxyriboses attached to adenine, guanine, cytosine or thymine and having 3'-5' phosphodiester links
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10109897A DE10109897A1 (de) | 2001-02-21 | 2001-02-21 | Fakultativ kationische Liposomen und Verwendung dieser |
| AT02701290T ATE363893T1 (de) | 2001-02-21 | 2002-02-21 | Amphotere liposomen und verwendung dieser |
| BRPI0207775A BRPI0207775B1 (pt) | 2001-02-21 | 2002-02-21 | lipossomos anfotéricos, método para carregamento dos mesmos com ingredientes ativos e sua utilização |
| AU2002234643A AU2002234643B2 (en) | 2001-02-21 | 2002-02-21 | Amphoteric liposomes and the use thereof |
| PCT/EP2002/001880 WO2002066012A2 (de) | 2001-02-21 | 2002-02-21 | Amphotere liposomen und verwendung dieser |
| JP2002565572A JP2004525898A (ja) | 2001-02-21 | 2002-02-21 | 両性リポソーム及びその使用 |
| DE50210271T DE50210271D1 (de) | 2001-02-21 | 2002-02-21 | Amphotere liposomen und verwendung dieser |
| CA2438116A CA2438116C (en) | 2001-02-21 | 2002-02-21 | Amphoteric liposomes and the use thereof |
| ES02701290T ES2289079T3 (es) | 2001-02-21 | 2002-02-21 | Liposomas anfotericos y su utilizacion. |
| CNB028052137A CN1241549C (zh) | 2001-02-21 | 2002-02-21 | 两性脂质体及其应用 |
| EP02701290A EP1363601B1 (de) | 2001-02-21 | 2002-02-21 | Amphotere liposomen und verwendung dieser |
| US10/081,617 US7371404B2 (en) | 2001-02-21 | 2002-02-21 | Amphoteric liposomes and their use |
| US11/590,143 US20070269504A1 (en) | 2001-02-21 | 2006-10-31 | Amphoteric liposomes |
| US11/590,357 US7780983B2 (en) | 2001-02-21 | 2006-10-31 | Amphoteric liposomes |
| US12/806,342 US20110293695A1 (en) | 2001-02-21 | 2010-08-09 | Amphoteric liposomes |
| JP2010211089A JP5480764B2 (ja) | 2001-02-21 | 2010-09-21 | 両性リポソーム及びその使用 |
| JP2013237869A JP2014031383A (ja) | 2001-02-21 | 2013-11-18 | 両性リポソーム及びその使用 |
| JP2014165961A JP2014218520A (ja) | 2001-02-21 | 2014-08-18 | 両性リポソーム及びその使用 |
| JP2016001813A JP2016104786A (ja) | 2001-02-21 | 2016-01-07 | 両性リポソーム及びその使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10109897A DE10109897A1 (de) | 2001-02-21 | 2001-02-21 | Fakultativ kationische Liposomen und Verwendung dieser |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10109897A1 true DE10109897A1 (de) | 2002-11-07 |
Family
ID=7675950
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10109897A Withdrawn DE10109897A1 (de) | 2001-02-21 | 2001-02-21 | Fakultativ kationische Liposomen und Verwendung dieser |
| DE50210271T Expired - Lifetime DE50210271D1 (de) | 2001-02-21 | 2002-02-21 | Amphotere liposomen und verwendung dieser |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50210271T Expired - Lifetime DE50210271D1 (de) | 2001-02-21 | 2002-02-21 | Amphotere liposomen und verwendung dieser |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US7371404B2 (https=) |
| EP (1) | EP1363601B1 (https=) |
| JP (5) | JP2004525898A (https=) |
| CN (1) | CN1241549C (https=) |
| AT (1) | ATE363893T1 (https=) |
| AU (1) | AU2002234643B2 (https=) |
| BR (1) | BRPI0207775B1 (https=) |
| CA (1) | CA2438116C (https=) |
| DE (2) | DE10109897A1 (https=) |
| ES (1) | ES2289079T3 (https=) |
| WO (1) | WO2002066012A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10207177A1 (de) * | 2002-02-19 | 2003-09-04 | Novosom Ag | Fakultativ kationische Lipide |
Families Citing this family (135)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10109897A1 (de) * | 2001-02-21 | 2002-11-07 | Novosom Ag | Fakultativ kationische Liposomen und Verwendung dieser |
| US7858117B2 (en) * | 2002-02-21 | 2010-12-28 | Novosom Ag | Amphoteric liposomes and their use |
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| AU2006291429B2 (en) * | 2005-09-15 | 2013-04-04 | Biontech Delivery Technologies Gmbh | Improvements in or relating to amphoteric liposomes |
-
2001
- 2001-02-21 DE DE10109897A patent/DE10109897A1/de not_active Withdrawn
-
2002
- 2002-02-21 US US10/081,617 patent/US7371404B2/en not_active Expired - Lifetime
- 2002-02-21 DE DE50210271T patent/DE50210271D1/de not_active Expired - Lifetime
- 2002-02-21 AU AU2002234643A patent/AU2002234643B2/en not_active Ceased
- 2002-02-21 WO PCT/EP2002/001880 patent/WO2002066012A2/de not_active Ceased
- 2002-02-21 ES ES02701290T patent/ES2289079T3/es not_active Expired - Lifetime
- 2002-02-21 EP EP02701290A patent/EP1363601B1/de not_active Expired - Lifetime
- 2002-02-21 CN CNB028052137A patent/CN1241549C/zh not_active Expired - Fee Related
- 2002-02-21 CA CA2438116A patent/CA2438116C/en not_active Expired - Lifetime
- 2002-02-21 JP JP2002565572A patent/JP2004525898A/ja active Pending
- 2002-02-21 AT AT02701290T patent/ATE363893T1/de active
- 2002-02-21 BR BRPI0207775A patent/BRPI0207775B1/pt not_active IP Right Cessation
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2006
- 2006-10-31 US US11/590,357 patent/US7780983B2/en not_active Expired - Lifetime
- 2006-10-31 US US11/590,143 patent/US20070269504A1/en not_active Abandoned
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2010
- 2010-08-09 US US12/806,342 patent/US20110293695A1/en not_active Abandoned
- 2010-09-21 JP JP2010211089A patent/JP5480764B2/ja not_active Expired - Fee Related
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- 2013-11-18 JP JP2013237869A patent/JP2014031383A/ja active Pending
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2014
- 2014-08-18 JP JP2014165961A patent/JP2014218520A/ja active Pending
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2016
- 2016-01-07 JP JP2016001813A patent/JP2016104786A/ja active Pending
Non-Patent Citations (6)
| Title |
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| Budker et al.: Nat. Biotechnol. (1996) 14(6), S. 760-64 * |
| Chu et al.: J. of Liposome Research 4(1), S. 361-395 (1994) * |
| Couvreur et al,: J. of Liposome Research 7(1), S. 1-18 (1997) * |
| Hafez et al.: Biochim. Biophys. Acta 1463, S. 107-114 (2000), Abstr. * |
| Hafez et al.: Biophys. J. 79, S. 1438-46 (2000) Abstr. * |
| Ropert et al.: Delivery Strategies Antisense Oligonucleotide Ther. (1995), S. 233-45 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10207177A1 (de) * | 2002-02-19 | 2003-09-04 | Novosom Ag | Fakultativ kationische Lipide |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2289079T3 (es) | 2008-02-01 |
| US7371404B2 (en) | 2008-05-13 |
| BRPI0207775B1 (pt) | 2015-10-20 |
| BR0207775A (pt) | 2004-03-30 |
| US20070269504A1 (en) | 2007-11-22 |
| EP1363601B1 (de) | 2007-06-06 |
| JP2011021026A (ja) | 2011-02-03 |
| EP1363601A2 (de) | 2003-11-26 |
| ATE363893T1 (de) | 2007-06-15 |
| US7780983B2 (en) | 2010-08-24 |
| AU2002234643B2 (en) | 2007-06-21 |
| CA2438116C (en) | 2011-10-11 |
| US20070252295A1 (en) | 2007-11-01 |
| JP2004525898A (ja) | 2004-08-26 |
| JP2014218520A (ja) | 2014-11-20 |
| JP2014031383A (ja) | 2014-02-20 |
| US20110293695A1 (en) | 2011-12-01 |
| JP2016104786A (ja) | 2016-06-09 |
| WO2002066012A2 (de) | 2002-08-29 |
| DE50210271D1 (de) | 2007-07-19 |
| WO2002066012A3 (de) | 2002-12-19 |
| CN1492756A (zh) | 2004-04-28 |
| CN1241549C (zh) | 2006-02-15 |
| US20030099697A1 (en) | 2003-05-29 |
| CA2438116A1 (en) | 2002-08-29 |
| JP5480764B2 (ja) | 2014-04-23 |
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