DE10207178A1 - Komponenten für die Herstellung amphoterer Liposomen - Google Patents
Komponenten für die Herstellung amphoterer LiposomenInfo
- Publication number
- DE10207178A1 DE10207178A1 DE10207178A DE10207178A DE10207178A1 DE 10207178 A1 DE10207178 A1 DE 10207178A1 DE 10207178 A DE10207178 A DE 10207178A DE 10207178 A DE10207178 A DE 10207178A DE 10207178 A1 DE10207178 A1 DE 10207178A1
- Authority
- DE
- Germany
- Prior art keywords
- liposomes
- lipid
- amphoteric
- acid
- active ingredient
- 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- Withdrawn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 97
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000002632 lipids Chemical class 0.000 claims abstract description 40
- 239000004480 active ingredient Substances 0.000 claims description 27
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- 235000018102 proteins Nutrition 0.000 claims description 14
- 102000004169 proteins and genes Human genes 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000129 anionic group Chemical group 0.000 claims description 10
- 150000001982 diacylglycerols Chemical class 0.000 claims description 10
- 125000006850 spacer group Chemical group 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 9
- 125000002091 cationic group Chemical group 0.000 claims description 9
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 8
- 239000013598 vector Substances 0.000 claims description 8
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 7
- 235000001014 amino acid Nutrition 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-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
- 239000002088 nanocapsule Substances 0.000 claims description 5
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 230000027455 binding Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- AWUCVROLDVIAJX-UHFFFAOYSA-N glycerol 1-phosphate Chemical class OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 238000011068 loading 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
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 238000001890 transfection Methods 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
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- 235000003704 aspartic acid Nutrition 0.000 claims description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 150000001985 dialkylglycerols Chemical class 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 238000001727 in vivo Methods 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 230000000692 anti-sense effect Effects 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 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
- 238000000926 separation method Methods 0.000 claims description 2
- 238000003745 diagnosis Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 239000012528 membrane Substances 0.000 description 26
- 210000004027 cell Anatomy 0.000 description 21
- -1 alkyl radical Chemical class 0.000 description 18
- 230000032258 transport Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 210000002966 serum Anatomy 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 235000014304 histidine Nutrition 0.000 description 7
- 230000008859 change Effects 0.000 description 6
- 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 6
- 230000035699 permeability Effects 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000000170 cell membrane Anatomy 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000009435 amidation Effects 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001768 cations Chemical class 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
- 238000010276 construction Methods 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000001419 dependent effect Effects 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
- 238000005538 encapsulation Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 150000002892 organic cations Chemical group 0.000 description 3
- 230000004962 physiological condition Effects 0.000 description 3
- 229920000867 polyelectrolyte Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-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
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CUTLLJSSJRJSJP-JPXXJBEJSA-N C(CCC(=O)O)(=O)O.N[C@@H](CC1=CNC=N1)C(=O)C(O)(C(O)C(O)C(CCCCCCCCCCCCCCC)=O)C(CCCCCCCCCCCCCCC)=O Chemical compound C(CCC(=O)O)(=O)O.N[C@@H](CC1=CNC=N1)C(=O)C(O)(C(O)C(O)C(CCCCCCCCCCCCCCC)=O)C(CCCCCCCCCCCCCCC)=O CUTLLJSSJRJSJP-JPXXJBEJSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical class O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 210000001519 tissue Anatomy 0.000 description 2
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- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-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
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- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10207178A DE10207178A1 (de) | 2002-02-19 | 2002-02-19 | Komponenten für die Herstellung amphoterer Liposomen |
| JP2003569642A JP2005517739A (ja) | 2002-02-19 | 2003-02-19 | 両性リポソームを製造するための成分 |
| DE50307127T DE50307127D1 (de) | 2002-02-19 | 2003-02-19 | Komponenten fur die herstellung amphoterer liposomen |
| US10/505,093 US20050164963A1 (en) | 2002-02-19 | 2003-02-19 | Components for producing amphoteric liposomes |
| AT03742541T ATE360635T1 (de) | 2002-02-19 | 2003-02-19 | Komponenten fur die herstellung amphoterer liposomen |
| EP03742541A EP1478652B1 (de) | 2002-02-19 | 2003-02-19 | Komponenten fur die herstellung amphoterer liposomen |
| PCT/EP2003/001662 WO2003070735A2 (de) | 2002-02-19 | 2003-02-19 | Komponenten für die herstellung amphoterer liposomen |
| AU2003215567A AU2003215567A1 (en) | 2002-02-19 | 2003-02-19 | Components for producing amphoteric liposomes |
| US13/291,650 US8580297B2 (en) | 2002-02-19 | 2011-11-08 | Components for producing amphoteric liposomes |
| US14/052,215 US9668973B2 (en) | 2002-02-19 | 2013-10-11 | Components for producing amphoteric liposomes |
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| DE10207178A DE10207178A1 (de) | 2002-02-19 | 2002-02-19 | Komponenten für die Herstellung amphoterer Liposomen |
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| DE10207178A Withdrawn DE10207178A1 (de) | 2002-02-19 | 2002-02-19 | Komponenten für die Herstellung amphoterer Liposomen |
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Families Citing this family (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10207178A1 (de) * | 2002-02-19 | 2003-09-04 | Novosom Ag | Komponenten für die Herstellung amphoterer Liposomen |
| EP1549352A4 (en) * | 2002-05-06 | 2005-07-27 | Nucleonics Inc | METHOD OF DISTRIBUTING NUCLEIC ACIDS |
| DE102004054730A1 (de) * | 2004-03-28 | 2006-05-11 | Novosom Ag | Serumstabile amphotere Liposomen |
| DE102004056659A1 (de) * | 2004-11-19 | 2006-06-01 | Novosom Ag | Abgabe von Oligonucleotiden an entzündete Schleimhaut |
| EP1764090A1 (en) * | 2005-09-15 | 2007-03-21 | Novosom AG | Amphoteric liposomes for local drug applications |
| JP5777846B2 (ja) * | 2005-06-15 | 2015-09-09 | マサチューセッツ インスティテュート オブ テクノロジー | アミン含有脂質およびその使用 |
| JP5571308B2 (ja) | 2005-09-15 | 2014-08-13 | マリーナ バイオテック,インコーポレイテッド | 両性リポソームにおけるまたはそれに関する改善 |
| JP5623016B2 (ja) | 2005-12-01 | 2014-11-12 | プロネイ・セラピューティクス・インコーポレイテッドPronaitherapeutics, Inc. | 癌治療法およびそれに用いる医薬組成物 |
| US20080138393A1 (en) * | 2006-12-11 | 2008-06-12 | Access To Business Group International Llc | Water soluble extract of spinach for prevention and repair of DNA damage |
| WO2008074487A2 (en) * | 2006-12-19 | 2008-06-26 | Novosom Ag | Lipids and lipid assemblies comprising transfection enhancer elements |
| EP1935434A1 (en) * | 2006-12-19 | 2008-06-25 | Novosom AG | Construction and use of transfection enhancer elements |
| WO2008151034A1 (en) * | 2007-05-31 | 2008-12-11 | The University Of Alabama | Improved process for purification of aryl carboxylic acids |
| WO2008154700A1 (en) | 2007-06-20 | 2008-12-24 | Phylogica Limited | Compositions and uses thereof for the treatment of acute respiratory distress syndrome (ards) and clinical disorders associated with therewith |
| GB0720486D0 (en) * | 2007-10-19 | 2007-11-28 | Univ Edinburgh | Cationic lipids |
| US8969353B2 (en) | 2008-11-07 | 2015-03-03 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| EA037404B1 (ru) | 2008-11-10 | 2021-03-24 | Арбутус Биофарма Корпорэйшн | Липиды и композиции для доставки лекарственных средств |
| DK3338765T3 (en) | 2009-12-01 | 2019-03-04 | Translate Bio Inc | STEROID DERIVATIVE FOR THE SUPPLY OF MRNA IN HUMANGENETIC DISEASES |
| CN102207678B (zh) * | 2010-01-25 | 2015-05-20 | 罗门哈斯电子材料有限公司 | 包含含氮化合物的光致抗蚀剂 |
| EP3578205A1 (en) | 2010-08-06 | 2019-12-11 | ModernaTX, Inc. | A pharmaceutical formulation comprising engineered nucleic acids and medical use thereof |
| EP2609135A4 (en) | 2010-08-26 | 2015-05-20 | Massachusetts Inst Technology | POLY (BETA AMINO ALCOHOLS), THEIR PREPARATION AND USES THEREOF |
| CN103429606A (zh) | 2010-10-01 | 2013-12-04 | 现代治疗公司 | 设计核酸及其使用方法 |
| WO2012109495A1 (en) | 2011-02-09 | 2012-08-16 | Metabolic Solutions Development Company, Llc | Cellular targets of thiazolidinediones |
| US9238716B2 (en) | 2011-03-28 | 2016-01-19 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| CA2831613A1 (en) | 2011-03-31 | 2012-10-04 | Moderna Therapeutics, Inc. | Delivery and formulation of engineered nucleic acids |
| EP2714971A4 (en) | 2011-05-23 | 2015-01-21 | Phylogica Ltd | METHOD FOR DETERMINING, IDENTIFYING AND INSULATING CELL-PENETRATING PEPTIDES |
| EP2532649B1 (en) * | 2011-06-07 | 2015-04-08 | Incella GmbH | Amino lipids, their synthesis and uses thereof |
| JP6184945B2 (ja) | 2011-06-08 | 2017-08-23 | シャイアー ヒューマン ジェネティック セラピーズ インコーポレイテッド | mRNA送達のための脂質ナノ粒子組成物および方法 |
| JP2013043885A (ja) * | 2011-08-26 | 2013-03-04 | Kansai Bunri Sogo Gakuen | デヒドロアミノ酸含有グリセロール誘導体 |
| US9464124B2 (en) | 2011-09-12 | 2016-10-11 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
| SG11201401102VA (en) * | 2011-09-30 | 2014-09-26 | Chugai Pharmaceutical Co Ltd | Ion concentration-dependent binding molecule library |
| KR20190099538A (ko) | 2011-10-03 | 2019-08-27 | 모더나 세라퓨틱스, 인코포레이티드 | 변형된 뉴클레오사이드, 뉴클레오타이드, 및 핵산, 및 이들의 용도 |
| US8759464B2 (en) | 2011-10-05 | 2014-06-24 | Arkema France | Polar, multi-hydroxyl functional amino compounds, compositions, process for preparation, their uses and applications |
| EA032088B1 (ru) | 2011-10-27 | 2019-04-30 | Массачусетс Инститьют Оф Текнолоджи | Аминокислотные производные, функционализованные на n-конце, способные образовывать микросферы, инкапсулирующие лекарственное средство |
| EP4144378A1 (en) | 2011-12-16 | 2023-03-08 | ModernaTX, Inc. | Modified nucleoside, nucleotide, and nucleic acid compositions |
| US9283287B2 (en) | 2012-04-02 | 2016-03-15 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of nuclear proteins |
| AU2013243954A1 (en) | 2012-04-02 | 2014-10-30 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of cosmetic proteins and peptides |
| US9254311B2 (en) | 2012-04-02 | 2016-02-09 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of proteins |
| US9572897B2 (en) | 2012-04-02 | 2017-02-21 | Modernatx, Inc. | Modified polynucleotides for the production of cytoplasmic and cytoskeletal proteins |
| EP3536787A1 (en) | 2012-06-08 | 2019-09-11 | Translate Bio, Inc. | Nuclease resistant polynucleotides and uses thereof |
| EP2882706A1 (en) | 2012-08-13 | 2015-06-17 | Massachusetts Institute of Technology | Amine-containing lipidoids and uses thereof |
| 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 |
| DK2922554T3 (en) | 2012-11-26 | 2022-05-23 | Modernatx Inc | Terminalt modificeret rna |
| US20150315154A1 (en) * | 2012-12-07 | 2015-11-05 | Council Of Scientific & Industrial Research | Histidinylated cationic amphiphiles, process for preparation therof and their liposomal formulation |
| EP2971010B1 (en) | 2013-03-14 | 2020-06-10 | ModernaTX, Inc. | Formulation and delivery of modified nucleoside, nucleotide, and nucleic acid compositions |
| IL305374A (en) | 2013-03-14 | 2023-10-01 | Ethris Gmbh | Cftr mrna compositions and related methods and uses |
| JP6586075B2 (ja) | 2013-03-14 | 2019-10-02 | トランスレイト バイオ, インコーポレイテッド | メッセンジャーrnaの精製方法 |
| US8980864B2 (en) | 2013-03-15 | 2015-03-17 | Moderna Therapeutics, Inc. | Compositions and methods of altering cholesterol levels |
| WO2014179562A1 (en) | 2013-05-01 | 2014-11-06 | Massachusetts Institute Of Technology | 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof |
| JP5914418B2 (ja) | 2013-06-26 | 2016-05-11 | 富士フイルム株式会社 | 脂質粒子、核酸送達キャリア、核酸送達キャリア製造用組成物、脂質粒子の製造方法及び遺伝子導入方法 |
| US10023626B2 (en) | 2013-09-30 | 2018-07-17 | Modernatx, Inc. | Polynucleotides encoding immune modulating polypeptides |
| BR112016007255A2 (pt) | 2013-10-03 | 2017-09-12 | Moderna Therapeutics Inc | polinucleotídeos que codificam receptor de lipoproteína de baixa densidade |
| EA034103B1 (ru) | 2013-10-22 | 2019-12-27 | Транслейт Био, Инк. | СПОСОБ ЛЕЧЕНИЯ ФЕНИЛКЕТОНУРИИ С ПРИМЕНЕНИЕМ мРНК |
| BR112016009014B1 (pt) | 2013-10-22 | 2024-02-06 | Translate Bio, Inc | USO DE COMPOSIÇÃO COMPREENDENDO mRNA PARA DEFICIÊNCIA DE ARGININOSSUCINATO SINTETASE |
| AU2014340155B2 (en) | 2013-10-22 | 2018-11-01 | Massachusetts Institute Of Technology | Lipid formulations for delivery of messenger RNA |
| AU2014351482B2 (en) | 2013-11-22 | 2020-08-20 | Mina Therapeutics Limited | C/EBP alpha short activating RNA compositions and methods of use |
| MX373952B (es) | 2014-04-25 | 2020-07-13 | Shire Human Genetic Therapies | Métodos de purificación de arn mensajero. |
| MA48050A (fr) | 2014-05-30 | 2020-02-12 | Translate Bio Inc | Lipides biodégradables pour l'administration d'acides nucléiques |
| EA033966B1 (ru) | 2014-06-24 | 2019-12-13 | Транслейт Био, Инк. | Стереохимически обогащенные композиции для доставки нуклеиновых кислот |
| US9840479B2 (en) | 2014-07-02 | 2017-12-12 | Massachusetts Institute Of Technology | Polyamine-fatty acid derived lipidoids and uses thereof |
| JP6240570B2 (ja) | 2014-07-17 | 2017-11-29 | 富士フイルム株式会社 | 脂質粒子および核酸送達キャリア |
| 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 |
| WO2016125163A1 (en) * | 2015-02-04 | 2016-08-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | LIPID ASSEMBLIES AND USES THEREOF AND SOME pH AND ELECTROSTATIC MODULATING LIPIDS TO BE USED IN SAID ASSEMBLIES |
| CN107848988B (zh) | 2015-06-19 | 2021-10-22 | 麻省理工学院 | 烯基取代的2,5-哌嗪二酮和其在组合物中用于向个体或细胞递送药剂的用途 |
| US11564893B2 (en) | 2015-08-17 | 2023-01-31 | Modernatx, Inc. | Methods for preparing particles and related compositions |
| SMT202200178T1 (it) | 2015-09-17 | 2022-05-12 | Modernatx Inc | Composti e composizioni per il rilascio intracellulare di agenti terapeutici |
| PL3386484T3 (pl) | 2015-12-10 | 2022-07-25 | Modernatx, Inc. | Kompozycje i sposoby dostarczania środków terapeutycznych |
| PL3394030T3 (pl) | 2015-12-22 | 2022-04-11 | Modernatx, Inc. | Związki i kompozycje do wewnątrzkomórkowego dostarczania środków |
| US11583504B2 (en) | 2016-11-08 | 2023-02-21 | Modernatx, Inc. | Stabilized formulations of lipid nanoparticles |
| EP3585417B1 (en) | 2017-02-27 | 2023-02-22 | Translate Bio, Inc. | Method of making a codon-optimized cftr mrna |
| AU2018234828A1 (en) | 2017-03-15 | 2019-09-19 | Modernatx, Inc. | Lipid nanoparticle formulation |
| LT3596041T (lt) | 2017-03-15 | 2023-01-25 | Modernatx, Inc. | Terapinių medžiagų, skirtų intraląsteliniam tiekimui, junginys ir sudėtys |
| AU2018234814B2 (en) | 2017-03-15 | 2022-06-30 | Modernatx, Inc. | Crystal forms of amino lipids |
| JOP20190260A1 (ar) | 2017-05-02 | 2019-10-31 | Merck Sharp & Dohme | صيغ ثابتة لأجسام مضادة لمستقبل الموت المبرمج 1 (pd-1) وطرق استخدامها |
| CA3060581A1 (en) | 2017-05-02 | 2018-11-08 | Merck Sharp & Dohme Corp. | Formulations of anti-lag3 antibodies and co-formulations of anti-lag3 antibodies and anti-pd-1 antibodies |
| EP3624824B1 (en) | 2017-05-16 | 2024-07-10 | Translate Bio, Inc. | Codon-optimized mrna encoding cftr for use in treating cystic fibrosis |
| EP3638678B1 (en) | 2017-06-14 | 2025-12-03 | ModernaTX, Inc. | Compounds and compositions for intracellular delivery of agents |
| AU2018330495A1 (en) | 2017-09-08 | 2020-03-26 | Mina Therapeutics Limited | Stabilized hnf4a sarna compositions and methods of use |
| EP3679140B1 (en) | 2017-09-08 | 2022-11-16 | MiNA Therapeutics Limited | Stabilized cebpa sarna compositions and methods of use |
| WO2019197845A1 (en) | 2018-04-12 | 2019-10-17 | Mina Therapeutics Limited | Sirt1-sarna compositions and methods of use |
| CA3108544A1 (en) | 2018-08-24 | 2020-02-27 | Translate Bio, Inc. | Methods for purification of messenger rna |
| EP3852732A1 (en) | 2018-09-19 | 2021-07-28 | ModernaTX, Inc. | Peg lipids and uses thereof |
| CA3113436A1 (en) | 2018-09-19 | 2020-03-26 | Modernatx, Inc. | Compounds and compositions for intracellular delivery of therapeutic agents |
| AU2019345067A1 (en) | 2018-09-19 | 2021-04-08 | Modernatx, Inc. | High-purity peg lipids and uses thereof |
| BR112021008873A8 (pt) | 2018-11-07 | 2023-04-11 | Merck Sharp & Dohme | Formulação |
| AU2019384557B2 (en) | 2018-11-21 | 2025-07-17 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
| WO2020208361A1 (en) | 2019-04-12 | 2020-10-15 | Mina Therapeutics Limited | Sirt1-sarna compositions and methods of use |
| BR112022004759A2 (pt) | 2019-09-19 | 2022-06-21 | Modernatx Inc | Composições e compostos lipídicos com cauda ramificada para entrega intracelular de agentes terapêuticos |
| JP2023538144A (ja) * | 2020-08-21 | 2023-09-06 | ザ ボード オブ リージェンツ オブ ザ ユニヴァーシティー オブ テキサス システム | 機能性のイオン化可能なリン脂質 |
| GB2603454A (en) | 2020-12-09 | 2022-08-10 | Ucl Business Ltd | Novel therapeutics for the treatment of neurodegenerative disorders |
| CN114685778B (zh) * | 2020-12-30 | 2023-10-17 | 苏州艾博生物科技有限公司 | 长循环阳离子脂质体的合成方法 |
| US11524023B2 (en) | 2021-02-19 | 2022-12-13 | Modernatx, Inc. | Lipid nanoparticle compositions and methods of formulating the same |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPH04364195A (ja) * | 1990-11-29 | 1992-12-16 | Fuji Photo Film Co Ltd | リン脂質誘導体およびそれを用いたリポソーム |
| US5206027A (en) * | 1990-09-13 | 1993-04-27 | Fuji Photo Film Co., Ltd. | Amphipathic compound and liposome comprising the same |
| DE69324367T2 (de) * | 1992-08-28 | 1999-09-23 | Life Technologies Inc., Gaithersburg | Kationische lipide |
| DE10109898A1 (de) * | 2001-02-21 | 2002-09-05 | Novosom Gmbh | Lipide mit veränderlicher Ladung |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6599887B2 (en) * | 1988-07-07 | 2003-07-29 | Chimerix, Inc. | Methods of treating viral infections using antiviral liponucleotides |
| JP2886748B2 (ja) | 1992-09-17 | 1999-04-26 | 富士写真フイルム株式会社 | 写真用処理組成物及び処理方法 |
| US6180134B1 (en) * | 1993-03-23 | 2001-01-30 | Sequus Pharmaceuticals, Inc. | Enhanced ciruclation effector composition and method |
| CA2194221C (en) * | 1994-06-22 | 2001-01-02 | Timothy D. Heath | Cationic amphiphiles |
| EP0932390A1 (en) * | 1996-10-11 | 1999-08-04 | Sequus Pharmaceuticals, Inc. | Therapeutic liposome composition and method |
| US6090800A (en) * | 1997-05-06 | 2000-07-18 | Imarx Pharmaceutical Corp. | Lipid soluble steroid prodrugs |
| US6022720A (en) * | 1997-07-17 | 2000-02-08 | Glaxo Wellcome Inc. | Bax protein channel formation |
| US6379698B1 (en) * | 1999-04-06 | 2002-04-30 | Isis Pharmaceuticals, Inc. | Fusogenic lipids and vesicles |
| ES1045340Y (es) * | 2000-02-11 | 2001-02-16 | Luque Fernandez Antonio De | Cuña elevadora para camas de accionamiento neumatico. |
| GB0106041D0 (en) * | 2001-03-12 | 2001-05-02 | Cancer Res Ventures Ltd | Lipids and liposomes |
| DE10207178A1 (de) * | 2002-02-19 | 2003-09-04 | Novosom Ag | Komponenten für die Herstellung amphoterer Liposomen |
-
2002
- 2002-02-19 DE DE10207178A patent/DE10207178A1/de not_active Withdrawn
-
2003
- 2003-02-19 EP EP03742541A patent/EP1478652B1/de not_active Expired - Lifetime
- 2003-02-19 AU AU2003215567A patent/AU2003215567A1/en not_active Abandoned
- 2003-02-19 AT AT03742541T patent/ATE360635T1/de active
- 2003-02-19 WO PCT/EP2003/001662 patent/WO2003070735A2/de not_active Ceased
- 2003-02-19 US US10/505,093 patent/US20050164963A1/en not_active Abandoned
- 2003-02-19 DE DE50307127T patent/DE50307127D1/de not_active Expired - Lifetime
- 2003-02-19 JP JP2003569642A patent/JP2005517739A/ja not_active Abandoned
-
2011
- 2011-11-08 US US13/291,650 patent/US8580297B2/en not_active Expired - Fee Related
-
2013
- 2013-10-11 US US14/052,215 patent/US9668973B2/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5206027A (en) * | 1990-09-13 | 1993-04-27 | Fuji Photo Film Co., Ltd. | Amphipathic compound and liposome comprising the same |
| JPH04364195A (ja) * | 1990-11-29 | 1992-12-16 | Fuji Photo Film Co Ltd | リン脂質誘導体およびそれを用いたリポソーム |
| DE69324367T2 (de) * | 1992-08-28 | 1999-09-23 | Life Technologies Inc., Gaithersburg | Kationische lipide |
| DE10109898A1 (de) * | 2001-02-21 | 2002-09-05 | Novosom Gmbh | Lipide mit veränderlicher Ladung |
Also Published As
| Publication number | Publication date |
|---|---|
| US9668973B2 (en) | 2017-06-06 |
| DE50307127D1 (de) | 2007-06-06 |
| WO2003070735A2 (de) | 2003-08-28 |
| JP2005517739A (ja) | 2005-06-16 |
| WO2003070735A3 (de) | 2004-03-25 |
| US8580297B2 (en) | 2013-11-12 |
| US20140227345A1 (en) | 2014-08-14 |
| US20050164963A1 (en) | 2005-07-28 |
| US20120100205A1 (en) | 2012-04-26 |
| AU2003215567A1 (en) | 2003-09-09 |
| EP1478652B1 (de) | 2007-04-25 |
| EP1478652A2 (de) | 2004-11-24 |
| ATE360635T1 (de) | 2007-05-15 |
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