AU701106B2 - Novel carbamate-based cationic lipids - Google Patents
Novel carbamate-based cationic lipids Download PDFInfo
- Publication number
- AU701106B2 AU701106B2 AU61617/96A AU6161796A AU701106B2 AU 701106 B2 AU701106 B2 AU 701106B2 AU 61617/96 A AU61617/96 A AU 61617/96A AU 6161796 A AU6161796 A AU 6161796A AU 701106 B2 AU701106 B2 AU 701106B2
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- Australia
- Prior art keywords
- moiety
- carbon atoms
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- lipid
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- 125000002091 cationic group Chemical group 0.000 title claims description 32
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title claims description 9
- 150000002632 lipids Chemical class 0.000 claims description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 108091034117 Oligonucleotide Proteins 0.000 claims description 54
- -1 cationic lipid Chemical class 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 27
- 108090000623 proteins and genes Proteins 0.000 claims description 27
- 229920002521 macromolecule Polymers 0.000 claims description 26
- 108020004414 DNA Proteins 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
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- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 230000014509 gene expression Effects 0.000 claims description 10
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- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 9
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- 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 5
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
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- VHQQPFLOGSTQPC-UHFFFAOYSA-N n-Pentatriacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC VHQQPFLOGSTQPC-UHFFFAOYSA-N 0.000 claims 1
- YTINXVKJSCWFHF-UHFFFAOYSA-N pentatriacontan-18-yl n-(2-hydroxyethyl)carbamate Chemical compound CCCCCCCCCCCCCCCCCC(OC(=O)NCCO)CCCCCCCCCCCCCCCCC YTINXVKJSCWFHF-UHFFFAOYSA-N 0.000 claims 1
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48346595A | 1995-06-07 | 1995-06-07 | |
| US08483465 | 1995-06-07 | ||
| PCT/US1996/009553 WO1996040726A1 (en) | 1995-06-07 | 1996-06-05 | Novel carbamate-based cationic lipids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6161796A AU6161796A (en) | 1996-12-30 |
| AU701106B2 true AU701106B2 (en) | 1999-01-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU61617/96A Ceased AU701106B2 (en) | 1995-06-07 | 1996-06-05 | Novel carbamate-based cationic lipids |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6251939B1 (enExample) |
| EP (1) | EP0830368A1 (enExample) |
| JP (1) | JPH11507352A (enExample) |
| AU (1) | AU701106B2 (enExample) |
| CA (1) | CA2223088A1 (enExample) |
| WO (1) | WO1996040726A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0840744A4 (en) * | 1995-06-07 | 1999-03-10 | Genta Inc | CATIONIC LIPIDS BASED ON PHOSPHONIC ACID |
| DE69727384T2 (de) * | 1996-05-24 | 2004-11-04 | IC-VEC Ltd. | Polykatonische sterin-derivate zur transfektion |
| WO2004089973A2 (en) * | 1997-01-23 | 2004-10-21 | Epimmune Inc. | Peptides, polypeptides, and proteins of reduced immunogenicity and methods for their production |
| FR2760193B1 (fr) * | 1997-02-28 | 1999-05-28 | Transgene Sa | Lipides et complexes de lipides cationiques et de substances actives, notamment pour la transfection de cellules |
| 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 |
| US5925628A (en) * | 1997-03-31 | 1999-07-20 | Genzyme Corporation | Cationic amphiphiles for intracellular delivery of therapeutic molecules |
| US5912239A (en) * | 1997-04-04 | 1999-06-15 | Genzyme Corporation | Imidazole-containing cationic amphiphiles for intracellular delivery of therapeutic molecules |
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Also Published As
| Publication number | Publication date |
|---|---|
| JPH11507352A (ja) | 1999-06-29 |
| AU6161796A (en) | 1996-12-30 |
| CA2223088A1 (en) | 1996-12-19 |
| US6670393B2 (en) | 2003-12-30 |
| US20030097011A1 (en) | 2003-05-22 |
| EP0830368A1 (en) | 1998-03-25 |
| US6251939B1 (en) | 2001-06-26 |
| WO1996040726A1 (en) | 1996-12-19 |
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