WO2002072068A3 - Lipids, lipid compositions, liposomes, and lipoplexes - Google Patents

Lipids, lipid compositions, liposomes, and lipoplexes Download PDF

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Publication number
WO2002072068A3
WO2002072068A3 PCT/GB2002/000972 GB0200972W WO02072068A3 WO 2002072068 A3 WO2002072068 A3 WO 2002072068A3 GB 0200972 W GB0200972 W GB 0200972W WO 02072068 A3 WO02072068 A3 WO 02072068A3
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WO
WIPO (PCT)
Prior art keywords
lipid
mixture
amine
amino acid
diether
Prior art date
Application number
PCT/GB2002/000972
Other languages
French (fr)
Other versions
WO2002072068A2 (en
Inventor
Caroline Joy Springer
James Anthony Heyes
Robert Geoffrey Cooper
Original Assignee
Cancer Rec Tech Ltd
Caroline Joy Springer
James Anthony Heyes
Robert Geoffrey Cooper
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cancer Rec Tech Ltd, Caroline Joy Springer, James Anthony Heyes, Robert Geoffrey Cooper filed Critical Cancer Rec Tech Ltd
Priority to AU2002236062A priority Critical patent/AU2002236062A1/en
Publication of WO2002072068A2 publication Critical patent/WO2002072068A2/en
Publication of WO2002072068A3 publication Critical patent/WO2002072068A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
    • 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
    • C07C237/04—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
    • C07C237/08—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 singly-bound oxygen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/47—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Abstract

This invention pertains to certain lipids and lipid compositions, liposomes and lipoplexes formed therefrom, methods for their synthesis and preparation, compositions and medicaments comprising such liposomes and lipoplexes, and methods of cellular delivery, transfection, and medical treatment employing such liposomes and lipoplexes. Preferred lipid compositions comprise: (a) a cationic lipid fraction; and, (b) a non-ionic lipid fraction; wherein said cationic lipid fraction comprises one of the following: (A) a mixture of different cationic lipids, and which mixture includes: (i) 3β-[N-(N',N'-dimethylaminoethyl)carbamoyl] cholesterol (DC-Chol); and, (ii) an amine diether lipid, or an amine diester lipid, or a mixture thereof; (B) an amino acid amide of an amine diether lipid, or an amino acid amide of an amine diester lipid, or a mixture thereof; (C) a mixture of different cationic lipids, and which mixture includes: (i) DC-Chol; and, (ii) an amino acid amide of an amine diether lipid, or an amino acid amide of an amine diester lipid, or a mixture thereof; (D) a mixture of different cationic lipids, and which mixture includes: (i) one or more of: (i-a) DC-Chol; (i-b) an amine diether lipid or an amine diester lipid, or a mixture thereof; and, (i-c) an amino acid amide of an amine diether lipid, or an amino acid amide of an amine diester lipid, or a mixture thereof; and, (ii) a peptide amide of an amine diether lipid, or a peptide amide of an amine diester lipid, or a mixture thereof.
PCT/GB2002/000972 2001-03-12 2002-03-07 Lipids, lipid compositions, liposomes, and lipoplexes WO2002072068A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002236062A AU2002236062A1 (en) 2001-03-12 2002-03-07 Lipids, lipid compositions, liposomes, and lipoplexes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0106041.7A GB0106041D0 (en) 2001-03-12 2001-03-12 Lipids and liposomes
GB0106041.7 2001-03-12

Publications (2)

Publication Number Publication Date
WO2002072068A2 WO2002072068A2 (en) 2002-09-19
WO2002072068A3 true WO2002072068A3 (en) 2007-12-21

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PCT/GB2002/000972 WO2002072068A2 (en) 2001-03-12 2002-03-07 Lipids, lipid compositions, liposomes, and lipoplexes

Country Status (3)

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AU (1) AU2002236062A1 (en)
GB (1) GB0106041D0 (en)
WO (1) WO2002072068A2 (en)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10207178A1 (en) * 2002-02-19 2003-09-04 Novosom Ag Components for the production of amphoteric liposomes
US7935812B2 (en) 2002-02-20 2011-05-03 Merck Sharp & Dohme Corp. RNA interference mediated inhibition of hepatitis C virus (HCV) expression using short interfering nucleic acid (siNA)
EP1512393A1 (en) * 2003-09-08 2005-03-09 BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG Process for the production of homogeneous liposomes and lipoplexes
CN1981044B (en) * 2004-06-07 2010-05-05 普洛体维生物治疗公司 Lipid encapsulated interfering RNA
CA2569645C (en) * 2004-06-07 2014-10-28 Protiva Biotherapeutics, Inc. Cationic lipids and methods of use
WO2006002538A1 (en) 2004-07-02 2006-01-12 Protiva Biotherapeutics, Inc. Immunostimulatory sirna molecules and uses therefor
WO2007086883A2 (en) * 2005-02-14 2007-08-02 Sirna Therapeutics, Inc. Cationic lipids and formulated molecular compositions containing them
US7404969B2 (en) * 2005-02-14 2008-07-29 Sirna Therapeutics, Inc. Lipid nanoparticle based compositions and methods for the delivery of biologically active molecules
EP2395012B8 (en) 2005-11-02 2018-06-06 Arbutus Biopharma Corporation Modified siRNA molecules and uses thereof
US7915399B2 (en) 2006-06-09 2011-03-29 Protiva Biotherapeutics, Inc. Modified siRNA molecules and uses thereof
JP5475643B2 (en) 2007-05-04 2014-04-16 マリーナ バイオテック，インコーポレイテッド Amino acid lipids and uses thereof
KR20100100875A (en) * 2007-11-14 2010-09-15 더 리전트 오브 더 유니버시티 오브 캘리포니아 Sterol-modified amphiphilic lipids
FR2925491B1 (en) * 2007-12-19 2010-09-03 Oz Biosciences Sas NEW CLASSES OF CATIONIC LIPIDS FOR THE TRANSPORT OF ACTIVE AGENTS IN CELLS
DK3988537T1 (en) 2011-12-07 2022-05-23 Alnylam Pharmaceuticals Inc BIODEGRADABLE LIPIDES FOR DELIVERY OF ACTIVE AGENTS
SG11201405552VA (en) * 2012-03-16 2014-10-30 Merck Patent Gmbh Targeting aminoacid lipids
EP3265063A4 (en) * 2015-03-03 2018-11-07 Cureport, Inc. Dual loaded liposomal pharmaceutical formulations
EP3265059A4 (en) 2015-03-03 2018-08-29 Cureport Inc. Combination liposomal pharmaceutical formulations
US20180291086A1 (en) * 2015-10-05 2018-10-11 The Regents Of The University Of Colorado, A Body Corporate Lipoplexes formulated for catalytic delivery
WO2018026866A1 (en) * 2016-08-03 2018-02-08 Neuropore Therapies, Inc. Lipid-substituted amino 1,2-and 1,3-diol compounds as modulators of tlr2 dimerization
US20210023005A1 (en) 2019-07-26 2021-01-28 Landsteiner Scientific S.A. De C.V. Cannabinoid-containing compositions in the form of spheres or sphere-like particles, methods for their preparation, and therapeutic applications
CN117460711A (en) * 2022-06-02 2024-01-26 厦门赛诺邦格生物科技股份有限公司 Amino acid cationic lipid containing unsaturated bond

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4166132A (en) * 1977-08-18 1979-08-28 Pfizer Inc. Antiviral amine derivatives of glycerol and propanediols
WO1984000368A1 (en) * 1982-07-06 1984-02-02 Max Planck Gesellschaft Derivatives of n,n-bis(2-chloroethyl)-phosphoric acid amide
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
EP0685457A1 (en) * 1993-02-19 1995-12-06 Nippon Shinyaku Company, Limited Glycerol derivative, device and pharmaceutical composition
DE19521412A1 (en) * 1995-06-14 1996-12-19 Boehringer Mannheim Gmbh New cationic and polycationic amphiphiles, reagents containing them and their use
WO1998034910A1 (en) * 1997-02-10 1998-08-13 Transgene S.A. Glycerolipidic compounds used for the transfer of an active substance into a target cell
WO2000030444A1 (en) * 1998-11-25 2000-06-02 Vanderbilt University Cationic liposomes for gene transfer

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4166132A (en) * 1977-08-18 1979-08-28 Pfizer Inc. Antiviral amine derivatives of glycerol and propanediols
WO1984000368A1 (en) * 1982-07-06 1984-02-02 Max Planck Gesellschaft Derivatives of n,n-bis(2-chloroethyl)-phosphoric acid amide
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
EP0685457A1 (en) * 1993-02-19 1995-12-06 Nippon Shinyaku Company, Limited Glycerol derivative, device and pharmaceutical composition
DE19521412A1 (en) * 1995-06-14 1996-12-19 Boehringer Mannheim Gmbh New cationic and polycationic amphiphiles, reagents containing them and their use
WO1998034910A1 (en) * 1997-02-10 1998-08-13 Transgene S.A. Glycerolipidic compounds used for the transfer of an active substance into a target cell
WO2000030444A1 (en) * 1998-11-25 2000-06-02 Vanderbilt University Cationic liposomes for gene transfer

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BHATTACHARYA S ET AL: "Vesicle and Tubular Microstructure Formation from Synthetic Sugar-Linked Amphiphiles. Evidence of Vesicle Formation from Single-Chain Amphiphiles Bearing a Disaccharide Headgroup", LANGMUIR (2000), 16(1), 87-97, 2000, XP002219195 *
HEYES J A ET AL: "Synthesis of novel cationic lipids: Effect of structural modification on the efficiency of gene transfer.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 45, no. 1, 3 January 2002 (2002-01-03), pages 99 - 114, XP002219198, ISSN: 0022-2623 *
HOJO H ET AL: "Synthesis and liposome-formation of a thermostable lipid bearing cell adhesion peptide sequence.", TETRAHEDRON LETTERS, vol. 37, no. 41, 1996, pages 7391 - 7394, XP004030914, ISSN: 0040-4039 *
KOKOTOS G ET AL: "Synthesis of 2-oxo amide triacylglycerol analogues and study of their inhibition effect on pancreatic and gastric lipases", CHEMISTRY--A EUROPEAN JOURNAL (2000), 6(22), 4211-4217, 2000, XP002219196 *
LASIC DD ET AL: "Liposomes in gene therapy.", ADVANCED DRUG DELIVERY REVIEWS, vol. 20, no. 2-3, 1996, pages 221 - 266, XP002219197, ISSN: 0169-409X *

Also Published As

Publication number Publication date
AU2002236062A8 (en) 2008-02-07
GB0106041D0 (en) 2001-05-02
AU2002236062A1 (en) 2002-09-24
WO2002072068A2 (en) 2002-09-19

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