CA2227373A1 - Novel amide-based cationic lipids - Google Patents
Novel amide-based cationic lipids Download PDFInfo
- Publication number
- CA2227373A1 CA2227373A1 CA002227373A CA2227373A CA2227373A1 CA 2227373 A1 CA2227373 A1 CA 2227373A1 CA 002227373 A CA002227373 A CA 002227373A CA 2227373 A CA2227373 A CA 2227373A CA 2227373 A1 CA2227373 A1 CA 2227373A1
- Authority
- CA
- Canada
- Prior art keywords
- moiety
- carbon atoms
- lipid
- group
- amide
- 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.)
- Abandoned
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 23
- 125000002091 cationic group Chemical group 0.000 title abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 120
- 150000002632 lipids Chemical class 0.000 claims abstract description 101
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 29
- 229920002521 macromolecule Polymers 0.000 claims abstract description 28
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 230000014509 gene expression Effects 0.000 claims abstract description 10
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 229920000447 polyanionic polymer Polymers 0.000 claims abstract description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- -1 phenylanaline Chemical compound 0.000 claims description 69
- 108091034117 Oligonucleotide Proteins 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 108020004414 DNA Proteins 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229960003104 ornithine Drugs 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 150000003973 alkyl amines Chemical group 0.000 claims description 9
- 125000000539 amino acid group Chemical group 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 239000013604 expression vector Substances 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000003277 amino group Chemical class 0.000 claims description 7
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 7
- 125000005264 aryl amine group Chemical group 0.000 claims description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
- 229920001184 polypeptide Polymers 0.000 claims description 5
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Chemical class NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 4
- 150000003974 aralkylamines Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 239000004475 Arginine Chemical class 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical class NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical class OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Chemical class OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000006035 Tryptophane Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001409 amidines Chemical group 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Chemical class OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Chemical class OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N isothiourea group Chemical group NC(S)=N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 229960004799 tryptophan Drugs 0.000 claims description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 150000002081 enamines Chemical group 0.000 claims 1
- 125000003588 lysine group Chemical class [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 129
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 103
- 150000001875 compounds Chemical class 0.000 description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 35
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 33
- 239000002585 base Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- 238000001890 transfection Methods 0.000 description 24
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 22
- 238000000746 purification Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 20
- 239000002502 liposome Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- 239000013612 plasmid Substances 0.000 description 18
- 239000002777 nucleoside Substances 0.000 description 17
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 15
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- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 8
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- LDGWQMRUWMSZIU-LQDDAWAPSA-M 2,3-bis[(z)-octadec-9-enoxy]propyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCCOCC(C[N+](C)(C)C)OCCCCCCCC\C=C/CCCCCCCC LDGWQMRUWMSZIU-LQDDAWAPSA-M 0.000 description 6
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
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- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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- C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Nanotechnology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dispersion Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50580295A | 1995-07-21 | 1995-07-21 | |
| US08/505,802 | 1995-07-21 | ||
| PCT/US1996/012087 WO1997003939A1 (en) | 1995-07-21 | 1996-07-22 | Novel amide-based cationic lipids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2227373A1 true CA2227373A1 (en) | 1997-02-06 |
Family
ID=24011908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002227373A Abandoned CA2227373A1 (en) | 1995-07-21 | 1996-07-22 | Novel amide-based cationic lipids |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6020526A (enExample) |
| EP (1) | EP0869937A4 (enExample) |
| JP (1) | JPH11510489A (enExample) |
| AU (1) | AU707947B2 (enExample) |
| CA (1) | CA2227373A1 (enExample) |
| NZ (1) | NZ313839A (enExample) |
| WO (1) | WO1997003939A1 (enExample) |
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| US5877220A (en) * | 1997-03-06 | 1999-03-02 | Genta, Incorporated | Amide-based oligomeric cationic lipids |
| US6034135A (en) * | 1997-03-06 | 2000-03-07 | Promega Biosciences, Inc. | Dimeric cationic lipids |
| US6395713B1 (en) * | 1997-07-23 | 2002-05-28 | Ribozyme Pharmaceuticals, Inc. | Compositions for the delivery of negatively charged molecules |
| WO1999008997A1 (de) * | 1997-08-13 | 1999-02-25 | Biontex Laboratories Gmbh | Neue lipopolyamine, deren darstellung und anwendung |
| GB9914045D0 (en) | 1999-06-16 | 1999-08-18 | Smithkline Beecham Plc | Novel compounds |
| EP1242609A2 (en) * | 1999-12-30 | 2002-09-25 | Novartis AG | Novel colloid synthetic vectors for gene therapy |
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| BRPI0519468A2 (pt) | 2004-12-27 | 2009-01-27 | Silence Therapeutics Ag | complexos de lipÍdeos revestido e seu uso |
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| BRPI0714875A2 (pt) | 2006-07-21 | 2013-05-28 | Silence Therapeutics Ag | meios para inibir a expressço da proteÍna cinase 3 |
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| EP3100718B1 (en) * | 2008-01-02 | 2019-11-27 | Arbutus Biopharma Corporation | Improved compositions and methods for the delivery of nucleic acids |
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| AU2009303345B2 (en) | 2008-10-09 | 2015-08-20 | Arbutus Biopharma Corporation | Improved amino lipids and methods for the delivery of nucleic acids |
| EP2405921A4 (en) | 2009-01-26 | 2013-05-22 | Protiva Biotherapeutics Inc | COMPOSITIONS AND METHODS FOR VAPORING APOLIPOPROTIEN C-III EXPRESSION |
| EP2660247A3 (en) | 2009-05-08 | 2014-09-03 | Chongxi Yu | High penetration prodrug compositions of peptides and peptide-related compounds |
| US9018187B2 (en) | 2009-07-01 | 2015-04-28 | Protiva Biotherapeutics, Inc. | Cationic lipids and methods for the delivery of therapeutic agents |
| ES2613498T3 (es) | 2009-07-01 | 2017-05-24 | Protiva Biotherapeutics Inc. | Nuevas formulaciones de lípidos para el suministro de agentes terapéuticos a tumores sólidos |
| US8569256B2 (en) | 2009-07-01 | 2013-10-29 | Protiva Biotherapeutics, Inc. | Cationic lipids and methods for the delivery of therapeutic agents |
| WO2011011447A1 (en) | 2009-07-20 | 2011-01-27 | Protiva Biotherapeutics, Inc. | Compositions and methods for silencing ebola virus gene expression |
| US8455455B1 (en) | 2010-03-31 | 2013-06-04 | Protiva Biotherapeutics, Inc. | Compositions and methods for silencing genes involved in hemorrhagic fever |
| US9006417B2 (en) | 2010-06-30 | 2015-04-14 | Protiva Biotherapeutics, Inc. | Non-liposomal systems for nucleic acid delivery |
| US8466122B2 (en) | 2010-09-17 | 2013-06-18 | Protiva Biotherapeutics, Inc. | Trialkyl cationic lipids and methods of use thereof |
| ES2702428T3 (es) * | 2010-11-15 | 2019-02-28 | Life Technologies Corp | Reactivos de transfección que contienen amina y métodos para prepararlos y usarlos |
| AU2012325997C1 (en) * | 2011-10-18 | 2018-07-05 | Dicerna Pharmaceuticals, Inc. | Amine cationic lipids and uses thereof |
| US9035039B2 (en) | 2011-12-22 | 2015-05-19 | Protiva Biotherapeutics, Inc. | Compositions and methods for silencing SMAD4 |
| JP5970439B2 (ja) * | 2013-09-20 | 2016-08-17 | チョンシー ユー | ペプチド及び関連化合物の経皮送達システム |
| CA2953341C (en) | 2014-06-25 | 2023-01-24 | Acuitas Therapeutics Inc. | Lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| WO2016176330A1 (en) | 2015-04-27 | 2016-11-03 | The Trustees Of The University Of Pennsylvania | Nucleoside-modified rna for inducing an adaptive immune response |
| HUE067372T2 (hu) | 2015-06-29 | 2024-10-28 | Acuitas Therapeutics Inc | Lipidek és nanoszemcsés lipid formulázások nukleinsavak beadására |
| CN108368028B (zh) | 2015-10-28 | 2021-09-03 | 爱康泰生治疗公司 | 用于递送核酸的新型脂质和脂质纳米颗粒制剂 |
| US12678515B2 (en) | 2015-12-30 | 2026-07-14 | Acuitas Therapeutics, Inc. | Lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| CN108699096B (zh) * | 2016-02-22 | 2021-11-26 | 赢创运营有限公司 | 用于头发香味保留的鼠李糖脂酰胺 |
| US12491261B2 (en) | 2016-10-26 | 2025-12-09 | Acuitas Therapeutics, Inc. | Lipid nanoparticle formulations |
| EP3568155A4 (en) | 2017-01-11 | 2020-09-23 | The Trustees Of The University Of Pennsylvania | RNA MODIFIED BY NUCLEOSIDE TO INDUCE AN IMMUNE RESPONSE AGAINST ZIKA VIRUS |
| US11357856B2 (en) | 2017-04-13 | 2022-06-14 | Acuitas Therapeutics, Inc. | Lipids for delivery of active agents |
| US11820728B2 (en) | 2017-04-28 | 2023-11-21 | Acuitas Therapeutics, Inc. | Carbonyl lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| WO2018209130A1 (en) | 2017-05-11 | 2018-11-15 | Tc1 Llc | Thermal interconnect for implantable blood pump |
| JP7355731B2 (ja) | 2017-08-16 | 2023-10-03 | アクイタス セラピューティクス インコーポレイテッド | 脂質ナノ粒子製剤における使用のための脂質 |
| JP7461872B2 (ja) | 2017-08-17 | 2024-04-04 | アクイタス セラピューティクス インコーポレイテッド | 脂質ナノ粒子製剤における使用のための脂質 |
| WO2019036028A1 (en) | 2017-08-17 | 2019-02-21 | Acuitas Therapeutics, Inc. | LIPIDS FOR USE IN LIPID NANOPARTICULAR FORMULATIONS |
| US11524932B2 (en) | 2017-08-17 | 2022-12-13 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| EP3852911B1 (en) | 2018-09-21 | 2025-01-22 | Acuitas Therapeutics, Inc. | Systems and methods for manufacturing lipid nanoparticles and liposomes |
| CA3116576A1 (en) * | 2018-10-18 | 2020-04-23 | Acuitas Therapeutics, Inc. | Lipids for lipid nanoparticle delivery of active agents |
| PL3908568T3 (pl) | 2019-01-11 | 2024-12-02 | Acuitas Therapeutics, Inc. | Lipidy do dostarczania środków czynnych w nanocząstkach lipidowych |
| CA3178344A1 (en) | 2020-03-31 | 2021-10-07 | The Trustees Of The University Of Pennsylvania | Universal influenza vaccine using nucleoside-modified mrna |
| EP4178544A4 (en) | 2020-07-08 | 2024-09-25 | The Trustees of the University of Pennsylvania | NUCLEOSIDE-MODIFIED RNA TO INDUCE AN IMMUNE RESPONSE AGAINST SARS-COV-2 VIRUS |
| KR20230051172A (ko) | 2020-07-16 | 2023-04-17 | 아퀴타스 테라퓨틱스 인크. | 지질 나노 입자에 사용하기 위한 양이온성 지질 |
| CN117098541A (zh) | 2020-11-25 | 2023-11-21 | 阿卡格拉医药公司 | 用于递送核酸的脂质纳米粒及相关使用方法 |
| WO2023114943A2 (en) | 2021-12-16 | 2023-06-22 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| WO2023230587A2 (en) | 2022-05-25 | 2023-11-30 | Akagera Medicines, Inc. | Lipid nanoparticles for delivery of nucleic acids and methods of use thereof |
| EP4534525A4 (en) * | 2022-06-02 | 2025-08-20 | Xiamen Sinopeg Biotech Co Ltd | CATIONIC LIPID BASED ON AMINO ACIDS CONTAINING UNSATURATED BONDS |
| CN120737002A (zh) * | 2022-06-02 | 2025-10-03 | 厦门赛诺邦格生物科技股份有限公司 | 一种氨基酸阳离子脂质 |
| WO2024034178A1 (ja) * | 2022-08-12 | 2024-02-15 | Tdk株式会社 | 溶媒中抗原回収システム及び溶媒中抗原回収方法 |
| US12691068B2 (en) * | 2022-12-27 | 2026-07-28 | Sun Vax mRNA Therapeutics Inc. | Modular lipid compounds and two- to three-component lipid nanoparticle compositions |
| CN119562942A (zh) * | 2023-06-30 | 2025-03-04 | 厦门赛诺邦格生物科技股份有限公司 | 一种含有两个叔胺基团的阳离子脂质及其应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426891A (en) * | 1945-09-14 | 1947-09-02 | American Cyanamid Co | N, n'-dioctadecyl-beta-amino-propionamide |
| US4897355A (en) * | 1985-01-07 | 1990-01-30 | Syntex (U.S.A.) Inc. | N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor |
| US4548955A (en) * | 1985-02-25 | 1985-10-22 | Sogo Pharmaceutical Company Limited | Nylon capsule responding to pH |
| FR2645866B1 (fr) * | 1989-04-17 | 1991-07-05 | Centre Nat Rech Scient | Nouvelles lipopolyamines, leur preparation et leur emploi |
| US5264618A (en) * | 1990-04-19 | 1993-11-23 | Vical, Inc. | Cationic lipids for intracellular delivery of biologically active molecules |
| KR20030097604A (ko) * | 1992-07-13 | 2003-12-31 | 유카리언, 인코포레이티드 | 세포의 세포내 구획으로 지질화된 면역글로불린을전달하기 위한 조성물, 지질화된 단백질 및 지질화된 항체 |
| US5334761A (en) * | 1992-08-28 | 1994-08-02 | Life Technologies, Inc. | Cationic lipids |
| US5777153A (en) * | 1994-07-08 | 1998-07-07 | Gilead Sciences, Inc. | Cationic lipids |
-
1996
- 1996-07-22 US US08/681,297 patent/US6020526A/en not_active Expired - Lifetime
- 1996-07-22 NZ NZ313839A patent/NZ313839A/xx unknown
- 1996-07-22 EP EP96926111A patent/EP0869937A4/en not_active Withdrawn
- 1996-07-22 CA CA002227373A patent/CA2227373A1/en not_active Abandoned
- 1996-07-22 JP JP9506945A patent/JPH11510489A/ja not_active Withdrawn
- 1996-07-22 AU AU66494/96A patent/AU707947B2/en not_active Ceased
- 1996-07-22 WO PCT/US1996/012087 patent/WO1997003939A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO1997003939A1 (en) | 1997-02-06 |
| AU707947B2 (en) | 1999-07-22 |
| EP0869937A1 (en) | 1998-10-14 |
| JPH11510489A (ja) | 1999-09-14 |
| AU6649496A (en) | 1997-02-18 |
| US6020526A (en) | 2000-02-01 |
| NZ313839A (en) | 1998-12-23 |
| EP0869937A4 (en) | 2004-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |