AU707947B2 - Novel amide-based cationic lipids - Google Patents
Novel amide-based cationic lipids Download PDFInfo
- Publication number
- AU707947B2 AU707947B2 AU66494/96A AU6649496A AU707947B2 AU 707947 B2 AU707947 B2 AU 707947B2 AU 66494/96 A AU66494/96 A AU 66494/96A AU 6649496 A AU6649496 A AU 6649496A AU 707947 B2 AU707947 B2 AU 707947B2
- Authority
- AU
- Australia
- 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.)
- Ceased
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- 150000001408 amides Chemical class 0.000 title claims description 21
- 125000002091 cationic group Chemical group 0.000 title description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 115
- 150000002632 lipids Chemical class 0.000 claims description 92
- -1 cationic lipid Chemical class 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 46
- 108091034117 Oligonucleotide Proteins 0.000 claims description 40
- 108090000623 proteins and genes Proteins 0.000 claims description 31
- 229920002521 macromolecule Polymers 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 108020004414 DNA Proteins 0.000 claims description 23
- 102000004169 proteins and genes Human genes 0.000 claims description 19
- 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
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 9
- 150000003973 alkyl amines Chemical group 0.000 claims description 9
- 230000014509 gene expression Effects 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000000539 amino acid group Chemical group 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- 239000013604 expression vector Substances 0.000 claims description 8
- 229920000447 polyanionic polymer Polymers 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 7
- 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
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 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 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000005264 aryl amine group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 229920001184 polypeptide Polymers 0.000 claims description 5
- 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 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
- UMGDCJDMYOKAJW-UHFFFAOYSA-N isothiourea group Chemical group NC(S)=N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000012453 solvate Substances 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
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical group 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
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- 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
- 125000002947 alkylene 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
- 150000002081 enamines Chemical class 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 229960004799 tryptophan Drugs 0.000 claims description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical group OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
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- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical group OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- 230000002452 interceptive effect Effects 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
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical group OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 128
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 106
- 150000001875 compounds Chemical class 0.000 description 85
- 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 39
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 37
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
- 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
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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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- 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
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- C07K5/06086—Dipeptides with the first amino acid being basic
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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
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
Landscapes
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- 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)
- Pharmacology & Pharmacy (AREA)
- Nanotechnology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medical Informatics (AREA)
- Veterinary Medicine (AREA)
- Dispersion Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Crystallography & Structural Chemistry (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 | |
| US08/505802 | 1995-07-21 | ||
| PCT/US1996/012087 WO1997003939A1 (en) | 1995-07-21 | 1996-07-22 | Novel amide-based cationic lipids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6649496A AU6649496A (en) | 1997-02-18 |
| AU707947B2 true AU707947B2 (en) | 1999-07-22 |
Family
ID=24011908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU66494/96A Ceased AU707947B2 (en) | 1995-07-21 | 1996-07-22 | Novel amide-based cationic lipids |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6020526A (https=) |
| EP (1) | EP0869937A4 (https=) |
| JP (1) | JPH11510489A (https=) |
| AU (1) | AU707947B2 (https=) |
| CA (1) | CA2227373A1 (https=) |
| NZ (1) | NZ313839A (https=) |
| WO (1) | WO1997003939A1 (https=) |
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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 |
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| CN104119242B (zh) | 2008-10-09 | 2017-07-07 | 泰米拉制药公司 | 改善的氨基脂质和递送核酸的方法 |
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| JP6294229B2 (ja) | 2011-10-18 | 2018-03-14 | ダイセルナ ファーマシューティカルズ， インコーポレイテッドＤｉｃｅｒｎａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | アミン陽イオン性脂質およびその使用 |
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| 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 |
| SMT202200502T1 (it) | 2014-06-25 | 2023-01-13 | Acuitas Therapeutics Inc | Nuovi lipidi e formulazioni di nanoparticelle lipidiche per l'erogazione di acidi nucleici |
| US20180303925A1 (en) | 2015-04-27 | 2018-10-25 | The Trustees Of The University Of Pennsylvania | Nucleoside-Modified RNA For Inducing an Adaptive Immune Response |
| LT3313829T (lt) | 2015-06-29 | 2024-08-12 | Acuitas Therapeutics Inc. | Lipidai ir lipidų nanodalelių sudėtys, skirtos nukleorūgščių tiekimui |
| IL307179A (en) | 2015-10-28 | 2023-11-01 | Acuitas Therapeutics Inc | Novel lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| US10941173B2 (en) * | 2016-02-22 | 2021-03-09 | Evonik Operations Gmbh | Rhamnolipid amides for hair scent retention |
| US12491261B2 (en) | 2016-10-26 | 2025-12-09 | Acuitas Therapeutics, Inc. | Lipid nanoparticle formulations |
| WO2018132537A1 (en) | 2017-01-11 | 2018-07-19 | The Trustees Of The University Of Pennsylvania | Nucleoside-modified rna for inducing an immune response against zika virus |
| WO2018191657A1 (en) | 2017-04-13 | 2018-10-18 | Acuitas Therapeutics, Inc. | Lipids for delivery of active agents |
| WO2018200943A1 (en) | 2017-04-28 | 2018-11-01 | Acuitas Therapeutics, Inc. | Novel 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 |
| CA3073020A1 (en) | 2017-08-16 | 2019-02-21 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| 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 |
| EP3668834B1 (en) | 2017-08-17 | 2024-10-02 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| IL281615B2 (en) | 2018-09-21 | 2026-01-01 | Acuitas Therapeutics Inc | Systems and methods for producing lipid nanoparticles and liposomes |
| JP7543259B2 (ja) * | 2018-10-18 | 2024-09-02 | アクイタス セラピューティクス インコーポレイテッド | 活性剤の脂質ナノ粒子送達のための脂質 |
| MY202837A (en) | 2019-01-11 | 2024-05-24 | Acuitas Therapeutics Inc | Lipids for lipid nanoparticle delivery of active agents |
| WO2022016070A1 (en) | 2020-07-16 | 2022-01-20 | Acuitas Therapeutics, Inc. | Cationic lipids for use in lipid nanoparticles |
| IL303195A (en) | 2020-11-25 | 2023-07-01 | Akagera Medicines Inc | Lipid nanoparticles for delivery of nucleic acids and related methods of use |
| CA3242402A1 (en) | 2021-12-16 | 2023-06-22 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| EP4531819A2 (en) | 2022-05-25 | 2025-04-09 | Akagera Medicines, Inc. | Lipid nanoparticles for delivery of nucleic acids and methods of use thereof |
| 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 |
| US20250288531A1 (en) * | 2022-06-02 | 2025-09-18 | Xiamen Sinopeg Biotech Co., Ltd. | Amino acid-based cationic lipid containing unsaturated bonds |
| CN119630438A (zh) * | 2022-08-12 | 2025-03-14 | 五眼高新技术株式会社 | 溶剂中抗原回收系统及溶剂中抗原回收方法 |
| CN120677165A (zh) * | 2022-12-27 | 2025-09-19 | 尚威天成信使核糖核酸治疗公司 | 模块化脂质化合物和双组分至三组分脂质纳米颗粒组合物 |
| 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 |
| FI941169L (fi) * | 1992-07-13 | 1994-05-04 | Eukarion Inc | Lipidisoitujen proteiinien transvaskulaarinen ja intracellulaarinen antaminen |
| 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 EP EP96926111A patent/EP0869937A4/en not_active Withdrawn
- 1996-07-22 AU AU66494/96A patent/AU707947B2/en not_active Ceased
- 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 JP JP9506945A patent/JPH11510489A/ja not_active Withdrawn
- 1996-07-22 WO PCT/US1996/012087 patent/WO1997003939A1/en not_active Ceased
- 1996-07-22 CA CA002227373A patent/CA2227373A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2227373A1 (en) | 1997-02-06 |
| WO1997003939A1 (en) | 1997-02-06 |
| EP0869937A4 (en) | 2004-07-21 |
| AU6649496A (en) | 1997-02-18 |
| US6020526A (en) | 2000-02-01 |
| JPH11510489A (ja) | 1999-09-14 |
| NZ313839A (en) | 1998-12-23 |
| EP0869937A1 (en) | 1998-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Assignment registered |
Owner name: PROMEGA BIOSCIENCES, INC. Free format text: FORMER OWNER WAS: GENTA INCORPORATED |