CA2223088A1 - Novel carbamate-based cationic lipids - Google Patents
Novel carbamate-based cationic lipids Download PDFInfo
- Publication number
- CA2223088A1 CA2223088A1 CA002223088A CA2223088A CA2223088A1 CA 2223088 A1 CA2223088 A1 CA 2223088A1 CA 002223088 A CA002223088 A CA 002223088A CA 2223088 A CA2223088 A CA 2223088A CA 2223088 A1 CA2223088 A1 CA 2223088A1
- Authority
- CA
- Canada
- Prior art keywords
- moiety
- carbon atoms
- lipid
- cell
- group
- 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
- 125000002091 cationic group Chemical group 0.000 title abstract description 32
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title abstract description 9
- 150000002632 lipids Chemical class 0.000 claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 229920002521 macromolecule Polymers 0.000 claims abstract description 30
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 21
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 230000014509 gene expression Effects 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
- 230000002452 interceptive effect Effects 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 108091034117 Oligonucleotide Proteins 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 27
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- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 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
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- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 6
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 5
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- 229920001184 polypeptide Polymers 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000003974 aralkylamines Chemical group 0.000 claims description 4
- 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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
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- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical class OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-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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- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Chemical class NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 3
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Chemical class OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003973 alkyl amines 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
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
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- 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 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
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- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 4
- 125000000320 amidine group Chemical group 0.000 claims 1
- 125000001240 enamine group Chemical group 0.000 claims 1
- 229940012017 ethylenediamine Drugs 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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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- -1 cationic lipid compounds Chemical class 0.000 description 48
- 239000002585 base Substances 0.000 description 34
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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)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dispersion Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biochemistry (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48346595A | 1995-06-07 | 1995-06-07 | |
| US08/483,465 | 1995-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2223088A1 true CA2223088A1 (en) | 1996-12-19 |
Family
ID=23920143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002223088A Abandoned CA2223088A1 (en) | 1995-06-07 | 1996-06-05 | Novel carbamate-based cationic lipids |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6251939B1 (OSRAM) |
| EP (1) | EP0830368A1 (OSRAM) |
| JP (1) | JPH11507352A (OSRAM) |
| AU (1) | AU701106B2 (OSRAM) |
| CA (1) | CA2223088A1 (OSRAM) |
| WO (1) | WO1996040726A1 (OSRAM) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU705549B2 (en) * | 1995-06-07 | 1999-05-27 | Promega Biosciences, Inc. | Phosphonic acid-based cationic lipids |
| US6756054B1 (en) * | 1996-05-24 | 2004-06-29 | Ic-Vec Limited | Polycationic sterol derivatives as transfection agents |
| 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 |
| US5948925A (en) * | 1997-05-06 | 1999-09-07 | Genzyme Corporation | Cationic amphiphiles containing linkers derived from neutral or positively charged amino acids |
| US5952516A (en) * | 1997-05-08 | 1999-09-14 | Genzyme Corporation | Cationic amphiphiles containing multiplesteroid lipophilic groups |
| US5942634A (en) * | 1997-05-09 | 1999-08-24 | Genzyme Corporation | Cationic amphiphiles for cell transfections |
| EP1003711B1 (de) | 1997-08-13 | 2001-11-07 | Biontex Laboratories GmbH | Neue lipopolyamine, deren darstellung und anwendung |
| EP1242609A2 (en) * | 1999-12-30 | 2002-09-25 | Novartis AG | Novel colloid synthetic vectors for gene therapy |
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- 1996-06-05 JP JP9501850A patent/JPH11507352A/ja not_active Withdrawn
- 1996-06-05 WO PCT/US1996/009553 patent/WO1996040726A1/en not_active Ceased
- 1996-06-05 EP EP96919222A patent/EP0830368A1/en not_active Withdrawn
- 1996-06-05 US US08/665,057 patent/US6251939B1/en not_active Expired - Fee Related
- 1996-06-05 CA CA002223088A patent/CA2223088A1/en not_active Abandoned
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2001
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|---|---|
| JPH11507352A (ja) | 1999-06-29 |
| US6251939B1 (en) | 2001-06-26 |
| AU701106B2 (en) | 1999-01-21 |
| US6670393B2 (en) | 2003-12-30 |
| EP0830368A1 (en) | 1998-03-25 |
| US20030097011A1 (en) | 2003-05-22 |
| WO1996040726A1 (en) | 1996-12-19 |
| AU6161796A (en) | 1996-12-30 |
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