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US5830430A Expired / Lapsed US ⏱️ 0.0 years remaining

Cationic lipids and the use thereof

Assignee: ImaRx Therapeutics Inc
•
Filing: 1995-02-21
•
Granted: 1998-11-03
•
Expires: 2015-02-21
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Abstract

Abstract Cationic lipid compounds which comprise at least two cationic groups. The cationic lipid compounds are particularly suitable for use as carriers in the intracellular delivery of bioactive agents, including pharmaceuticals and genetic material. Compositions of the present cationic lipid compounds include suspensions, emulsions, micelles and liposomes.

Inventors

  • 👤 Evan C. Unger
  • 👤 DeKang Shen
  • 👤 Guanli Wu

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-22 23:53
CPC Classifications
C; C07; C07K; C07K14/00; C07K14/005; A; A61; A61K; A61K9/00; A61K9/10; A61K9/127; A61K9/1271; A61K9/1272; A61P; A61P37/00; A61P37/02; A61P37/04; C07C; C07C237/00; C07C237/02; C07C237/04; C07C237/10; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/10; C07K14/435; C07K14/475; C07K14/50; C07K14/501; C12; C12N; C12N15/00; C12N15/09; C12N15/87; C12N15/88; A61K38/00; A61K48/00; C07C2601/00; C07C2601/12; C07C2601/14; C12N2760/00; C12N2760/00011; C12N2760/18011; C12N2760/18511; C12N2760/18522; Y; Y10; Y10S; Y10S436/00; Y10S436/829; Y10S977/00; Y10S977/70; Y10S977/788; Y10S977/797; Y10S977/798; Y10S977/799; Y10S977/80; Y10S977/801; Y10S977/902; Y10S977/904; Y10S977/906; Y10S977/907

Claims Analysis

Total Claims: 145
Claim 1
Independent Claim 471 words
A cationic lipid compound of the formula: ##STR22## wherein: each of x, y and z is independently an integer from 0 to about 100; each X 1 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each X 2 is independently O or S; each Y 1 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each Y 2 is independently --N(R 6 ) b --, --S(R 6 ) b -- or --P(R 6 ) b --, wherein b is an integer from 0 to 2; each Y 3 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each of R 1 , R 2 , R 3 and R 4 is independently alkylene of 2 to about 20 carbons; each R 5 is independently hydrogen or alkyl of 1 to about 10 carbons; and each R 6 is independently -- R 7 --X 3 ! c --R 8 or --R 9 -- X 4 --R 10 ! d --Q, wherein: each of c and d is independently an integer from 0 to about 100; each Q is independently a phosphate residue, --N(R 11 ) q , --S(R 11 ) q , --P(R 11 ) q or --CO 2 R 11 , wherein q is an integer from 1 to 3; each of X 3 and X 4 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each R 7 is independently alkylene of 2 to about 20 carbons; each R 8 is independently hydrogen or alkyl of 1 to about 60 carbons; each of R 9 and R 10 is independently alkylene of 2 to about 20 carbons; and each R 11 is independently -- R 7 --X 3 ! c --R 8 or --R 9 -- X 4 --R 10 ! d --W, wherein: each W is independently a phosphate residue, --N(R 12 ) w , --S(R 12 ) w , --P(R 12 ) w or --CO 2 R 12 , wherein w is an integer from 1 to 3; and R 12 is -- R 7 --X 3 ! c --R 8 ; with the proviso that the compound of formula (I) comprises at least two quaternary salts.
Claim 2
Dependent Claim 471 words
A cationic lipid compound of the formula: ##STR22## wherein: each of x, y and z is independently an integer from 0 to about 100; each X 1 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each X 2 is independently O or S; each Y 1 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each Y 2 is independently --N(R 6 ) b --, --S(R 6 ) b -- or --P(R 6 ) b --, wherein b is an integer from 0 to 2; each Y 3 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each of R 1 , R 2 , R 3 and R 4 is independently alkylene of 2 to about 20 carbons; each R 5 is independently hydrogen or alkyl of 1 to about 10 carbons; and each R 6 is independently -- R 7 --X 3 ! c --R 8 or --R 9 -- X 4 --R 10 ! d --Q, wherein: each of c and d is independently an integer from 0 to about 100; each Q is independently a phosphate residue, --N(R 11 ) q , --S(R 11 ) q , --P(R 11 ) q or --CO 2 R 11 , wherein q is an integer from 1 to 3; each of X 3 and X 4 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each R 7 is independently alkylene of 2 to about 20 carbons; each R 8 is independently hydrogen or alkyl of 1 to about 60 carbons; each of R 9 and R 10 is independently alkylene of 2 to about 20 carbons; and each R 11 is independently -- R 7 --X 3 ! c --R 8 or --R 9 -- X 4 --R 10 ! d --W, wherein: each W is independently a phosphate residue, --N(R 12 ) w , --S(R 12 ) w , --P(R 12 ) w or --CO 2 R 12 , wherein w is an integer from 1 to 3; and R 12 is -- R 7 --X 3 ! c --R 8 ; with the proviso that the compound of formula (I) comprises at least two quaternary salts.
Claim 3
Dependent Claim 15 words
The compound according to claim 1 wherein said quaternary salt comprises a pharmaceutically-acceptable counter ion.
Claim 4
Dependent Claim 60 words
The compound according to claim 2 wherein said counter ion is selected from the group consisting of halide, R 13 SO 3 - , R 13 CO 2 - , phosphate, sulfite, nitrate, gluconate, guluronate, galacturonate, estolate and mesylate, wherein R 13 is hydrogen, alkyl of 1 to about 20 carbons or aryl of about 6 to about 10 carbons.
Claim 5
Dependent Claim 13 words
The compound according to claim 1 wherein said compound is in lyophilized form.
Claim 6
Dependent Claim 71 words
The compound according to claim 1 wherein: each of c, d, x, y and z is independently an integer from 0 to about 50; each Q is independently a phosphate residue, --CO 2 R 11 or --N(R 11 ) q , wherein q is 2 or 3; and each W is independently a phosphate residue, --CO 2 R 12 or --N(R 12 ) w , wherein w is 2 or 3.
Claim 7
Dependent Claim 14 words
The compound according to claim 5 wherein: each of q and w is 3.
Claim 8
Dependent Claim 29 words
The compound according to claim 6 wherein: each of c, d, x, y and z is independently an integer from 0 to about 20; and X 2 is O.
Claim 9
Dependent Claim 46 words
The compound according to claim 7 wherein: each of c, d, x, y and z is independently an integer from 0 to about 10; and each of X 1 , X 3 and X 4 is independently --C(═O)--NR 5 --, --NR 5 --C(═O)--, --C(═O)--O-- or --O--C(═O)--.
Claim 10
Dependent Claim 23 words
The compound according to claim 8 wherein: each of c, d, x, y and z is an integer from 0 to about 5.
Claim 11
Dependent Claim 97 words
The compound according to claim 9 wherein: each of R 1 , R 2 , R 3 and R 4 is independently straight chain alkylene of 2 to about 10 carbons or cycloalkylene of about 4 to about 10 carbons; each R 5 is independently hydrogen or alkyl of 1 to about 4 carbons; each R 7 is independently alkylene of 2 to about 10 carbons; each R 8 is independently hydrogen or alkyl of 1 to about 40 carbons; and each of R 9 and R 10 is independently alkylene of 2 to about 10 carbons.
Claim 12
Dependent Claim 87 words
The compound according to claim 10 wherein: each of R 1 , R 2 , R 3 and R 4 is independently straight chain alkylene of 2 to about 4 carbons or cycloalkylene of about 5 to about 7 carbons; R 5 is hydrogen; each R 7 is independently alkylene of 2 to about 4 carbons; each R 8 is independently hydrogen or alkyl of 1 to about 20 carbons; and each of R 9 and R 10 is independently alkylene of 2 to about 4 carbons.
Claim 13
Dependent Claim 54 words
The compound according to claim 11 wherein: each Y 1 is independently a phosphate residue, N(R 6 ) a -- or --CO 2 R 6 ; Y 2 is --N--(R 6 ) b --; and each Y 3 is independently a phosphate residue, N(R 6 ) a -- or --CO 2 R 6 .
Claim 14
Dependent Claim 10 words
The compound according to claim 12 wherein: x is 1.
Claim 15
Dependent Claim 14 words
The compound according to claim 13 wherein: y is 2 and z is 0.
Claim 16
Dependent Claim 37 words
The compound according to claim 14 wherein: each Y 1 is independently N(R 6 ) a -- or --CO 2 R 6 ; and R 6 is -- R 7 --X 3 ! c --R 8 .
Claim 17
Dependent Claim 45 words
The compound according to claim 15 wherein: each of R 1 , R 2 , R 3 , R 4 and R 7 is independently methylene, ethylene or cyclohexylene; and each R 8 is independently hydrogen or alkyl of about 1 to about 16 carbons.
Claim 18
Dependent Claim 18 words
The compound according to claim 16 wherein: a is 3; and each c is independently 0 or 1.
Claim 19
Dependent Claim 10 words
The compound according to claim 17 wherein: b is 1.
Claim 20
Dependent Claim 10 words
The compound according to claim 18 which is N,N'-bis(dodecyloxycarbonylmethylene)-N,N'-bis(β-N,N,N-trimethylammoniumethylaminocarbonylmethylene)ethylenediamine dihalide.
Claim 21
Dependent Claim 14 words
The compound according to claim 19 wherein said halide is chloride, bromide or iodide.
Claim 22
Dependent Claim 9 words
The compound according to claim 18 which is N,N'-bis(hexadecylaminocarbonylmethylene-N,N'-bis(trimethylammoniumethylaminocarbonylmethylene)ethylenediaminedihalide.
Claim 23
Dependent Claim 14 words
The compound according to claim 21 wherein said halide is chloride, bromide or iodide.
Claim 24
Dependent Claim 10 words
The compound according to claim 17 wherein: b is 2.
Claim 25
Dependent Claim 11 words
The compound according to claim 23 which is N,N'-bis(dodecylaminocarbonylmethylene)-N,N'-bis(β-N,N, N-trimethylammoniumethylaminocarbonylmethylene)-N,N'-dimethylethylenediamine tetrahalide.
Claim 26
Dependent Claim 14 words
The compound according to claim 24 wherein said halide is chloride, bromide or iodide.
Claim 27
Dependent Claim 11 words
The compound according to claim 23 which is N,N'-bis(dodecylaminocarbonylmethylene)-N,N'-bis(β-N,N, N-trimethylammoniumethylaminocarbonylmethylene)-N,N'-dimethylcyclohexylene-1,4-diamine tetrahalide.
Claim 28
Dependent Claim 14 words
The compound according to claim 26 wherein said halide is chloride, bromide or iodide.
Claim 29
Dependent Claim 11 words
The compound according to claim 23 which is N,N'-bis(hexadecylaminocarbonylmethylene)-N,N'-bis(β-N,N, N-trimethylaxmmoniumethylaminocarbonylmethylene)-N,N'-dimethylethylenediamine tetrahalide.
Claim 30
Dependent Claim 14 words
The compound according to claim 28 wherein said halide is chloride, bromide or iodide.
Claim 31
Dependent Claim 14 words
The compound according to claim 17 wherein: each b is independently 1 or 2.
Claim 32
Dependent Claim 11 words
The compound according to claim 30 which is N,N'-bis(hexadecyloxycarbonylmethylene)-N-(β-N,N, N-trimethylammoniumethylaminocarbonylmethylene)-N-methyl-N'-(carboxymethylene)ethylenediamine dihalide.
Claim 33
Dependent Claim 14 words
The compound according to claim 31 wherein said halide is chloride, bromide or iodide.
Claim 34
Dependent Claim 16 words
The compound according to claim 13 wherein: y is 2 and z is 0 or 1.
Claim 35
Dependent Claim 24 words
The compound according to claim 33 wherein: a is 3; b is 2; each c is independently 0 or 1; and d is 1.
Claim 36
Dependent Claim 20 words
The compound according to claim 34 wherein: R 11 is -- R 7 --X 3 ! c --R 8 .
Claim 37
Dependent Claim 43 words
The compound according to claim 35 wherein: each of R 1 , R 2 , R 3 , R 4 and R 7 is independently methylene or ethylene; and each R 8 is independently hydrogen or alkyl of 1 to about 16 carbons.
Claim 38
Dependent Claim 11 words
The compound according to claim 36 which is N,N"-bis(hexadecylaminocarbonylmethylene)-N,N',N"-tris(β-N,N, N-trimethylammoniumethylaminocarbonylmethylene)-N,N',N"-trimethyldiethylenetriamine hexahalide.
Claim 39
Dependent Claim 14 words
The compound according to claim 37 wherein said halide is chloride, bromide or iodide.
Claim 40
Dependent Claim 14 words
The compound according to claim 13 wherein: y is 3 and z is 0.
Claim 41
Dependent Claim 24 words
The compound according to claim 39 wherein: a is 3; b is 2; each c is independently 0 or 1; and d is 1.
Claim 42
Dependent Claim 59 words
The compound according to claim 40 wherein: each of R 1 , R 2 , R 3 , R 4 and R 7 is independently methylene or ethylene; each R 8 is independently hydrogen or alkyl of 1 to about 16 carbons; each of R 9 and R 10 is independently methylene or ethylene; and R 11 is methyl.
Claim 43
Dependent Claim 10 words
The compound according to claim 41 which is 1,1,7,7-tetra(β-N,N,N,N-tetramethylammoniumethylaminocarbonylmethylene)-4-hexadecylaminocarbonylmethylene-N,N',N'-trimethyl-1,4,7-triazaheptane heptahalide.
Claim 44
Dependent Claim 14 words
The compound according to claim 42 wherein said halide is chloride, bromide or iodide.
Claim 45
Dependent Claim 14 words
The compound according to claim 13 wherein: y is 3 and z is 0.
Claim 46
Dependent Claim 20 words
The compound according to claim 44 wherein: a is 3; b is 1; c is 0; and d is 1.
Claim 47
Dependent Claim 47 words
The compound according to claim 45 wherein: each of R 1 , R 2 and R 3 is independently methylene or ethylene; each R 8 is independently hydrogen or methyl; each of R 9 and R 10 is independently methylene or ethylene; and R 11 is methyl.
Claim 48
Dependent Claim 10 words
The compound according to claim 46 which is N,N,N",N"-tetra(β-N,N,N-trimethylammoniumethylaminocarbonyl-methylene)-N'-(1,2-dioleoylglycero-3-phosphoethanolaminocarbonylmethylene)diethylenetriamine tetrahalide.
Claim 49
Dependent Claim 14 words
The compound according to claim 47 wherein said halide is chloride, bromide or iodide.
Claim 50
Dependent Claim 13 words
A cationic lipid composition comprising the cationic lipid compound according to claim 1.
Claim 51
Dependent Claim 13 words
The cationic lipid composition according to claim 49 wherein said composition is lyophilized.
Claim 52
Dependent Claim 21 words
The cationic lipid composition according to claim 49 which is selected from the group consisting of micelles, liposomes and mixtures thereof.
Claim 53
Dependent Claim 17 words
The cationic lipid composition according to claim 51 further comprising an amphipathic compound for stabilizing the composition.
Claim 54
Dependent Claim 21 words
The cationic lipid composition according to claim 52 further comprising a gas, a precursor to a gas or a mixture thereof.
Claim 55
Dependent Claim 34 words
The cationic lipid composition according to claim 53 wherein said gas or said precursor to a gas is selected from the group consisting of perfluoromethane, perfluoroethane, perfluoropropane, perfluorobutane, perfluorocyclobutane, perfluoropentane, perfluorohexane, and mixtures thereof.
Claim 56
Dependent Claim 21 words
The cationic lipid composition according to claim 53 which comprises a mixture of a gas and a precursor to a gas.
Claim 57
Dependent Claim 17 words
The cationic lipid composition according to claim 54 wherein said gas or gaseous precursor further comprises nitrogen.
Claim 58
Dependent Claim 29 words
The cationic lipid composition according to claim 49 further comprising a gas, a precursor to a gas, or a mixture thereof, and an amphipathic compound for stabilizing the composition.
Claim 59
Dependent Claim 15 words
The cationic lipid composition according to claim 57 wherein said amphipathic compound comprises a lipid.
Claim 60
Dependent Claim 21 words
The cationic lipid composition according to claim 58 which is selected from the group consisting of suspensions, emulsions, and vesicle compositions.
Claim 61
Dependent Claim 14 words
The cationic lipid composition according to claim 59 which comprises a cationic vesicle composition.
Claim 62
Dependent Claim 25 words
The cationic vesicle composition according to claim 60 wherein said vesicles are selected from the group consisting of unilamellar vesicles, oligolamellar vesicles and multilamellar vesicles.
Claim 63
Dependent Claim 15 words
The cationic vesicle composition according to claim 61 wherein said lipid is a polyrnerizable lipid.
Claim 64
Dependent Claim 11 words
The cationic vesicle composition according to claim 61 further comprising polyethyleneglycol.
Claim 65
Dependent Claim 14 words
The cationic vesicle composition according to claim 61 wherein said vesicles comprise unilamellar vesicles.
Claim 66
Dependent Claim 14 words
The cationic vesicle composition according to claim 64 wherein said vesicles comprise a monolayer.
Claim 67
Dependent Claim 26 words
The cationic vesicle composition according to claim 65 wherein said lipid is a phospholipid and said gas or said precursor to a gas is sulfur hexafluoride.
Claim 68
Dependent Claim 22 words
The cationic vesicle composition according to claim 65 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropentane.
Claim 69
Dependent Claim 22 words
The cationic vesicle composition according to claim 65 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropropane.
Claim 70
Dependent Claim 14 words
The cationic vesicle composition according to claim 64 wherein said vesicles comprise a bilayer.
Claim 71
Dependent Claim 23 words
The cationic vesicle composition according to claim 69 wherein said lipid is a phospholipid and said gas or gaseous precursor is sulfur hexafluoride.
Claim 72
Dependent Claim 22 words
The cationic vesicle composition according to claim 69 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropentane.
Claim 73
Dependent Claim 22 words
The cationic vesicle composition according to claim 69 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropropane.
Claim 74
Dependent Claim 22 words
The cationic vesicle composition according to claim 59 wherein said vesicles are selected from the group consisting of oligolamellar and multilamellar vesicles.
Claim 75
Dependent Claim 13 words
The cationic vesicle composition according to claim 73 wherein said vesicles comprise monolayers.
Claim 76
Dependent Claim 23 words
The cationic vesicle composition according to claim 74 wherein said lipid is a phospholipid and said gas or gaseous precursor is sulfur hexafluoride.
Claim 77
Dependent Claim 25 words
The cationic vesicle composition according to claim 74 wherein said lipid is a phospholipid and said gas or said precursor to a gas is perfluoropentane.
Claim 78
Dependent Claim 22 words
The cationic vesicle composition according to claim 74 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropropane.
Claim 79
Dependent Claim 13 words
The cationic vesicle composition according to claim 73 wherein said vesicles comprise bilayers.
Claim 80
Dependent Claim 23 words
The cationic vesicle composition according to claim 78 wherein said lipid is a phospholipid and said gas or gaseous precursor is sulfur hexafluoride.
Claim 81
Dependent Claim 22 words
The cationic vesicle composition according to claim 78 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropentane.
Claim 82
Dependent Claim 22 words
The cationic vesicle composition according to claim 78 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropropane.
Claim 83
Dependent Claim 19 words
The cationic lipid composition according to claim 58 wherein said lipids comprise unilamellar lipids, oligolamellar lipids or multilamellar lipids.
Claim 84
Dependent Claim 14 words
The cationic lipid composition according to claim 82 wherein said lipids are polymerizable lipids.
Claim 85
Dependent Claim 11 words
The cationic lipid composition according to claim 82 further comprising polyethyleneglycol.
Claim 86
Dependent Claim 14 words
The cationic lipid composition according to claim 82 wherein said lipids comprise unilamellar lipids.
Claim 87
Dependent Claim 18 words
The cationic lipid composition according to claim 85 wherein said lipids are in the form of a monolayer.
Claim 88
Dependent Claim 22 words
The cationic lipid composition according to claim 86 wherein said lipids are phospholipids and said gas or gaseous precursor is sulfur hexafluoride.
Claim 89
Dependent Claim 21 words
The cationic lipid composition according to claim 86 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropentane.
Claim 90
Dependent Claim 21 words
The cationic lipid composition according to claim 86 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropropane.
Claim 91
Dependent Claim 18 words
The cationic lipid composition according to claim 85 wherein said lipids are in the form of a bilayer.
Claim 92
Dependent Claim 22 words
The cationic lipid composition according to claim 90 wherein said lipids are phospholipids and said gas or gaseous precursor is sulfur hexafluoride.
Claim 93
Dependent Claim 21 words
The cationic lipid composition according to claim 90 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropentane.
Claim 94
Dependent Claim 21 words
The cationic lipid composition according to claim 90 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropropane.
Claim 95
Dependent Claim 17 words
The cationic lipid composition according to claim 82 wherein said lipids comprise oligolamellar lipids or multilamellar lipids.
Claim 96
Dependent Claim 17 words
The cationic lipid composition according to claim 94 wherein said lipids are in the form of monolayers.
Claim 97
Dependent Claim 22 words
The cationic lipid composition according to claim 95 wherein said lipids are phospholipids and said gas or gaseous precursor is sulfur hexafluoride.
Claim 98
Dependent Claim 21 words
The cationic lipid composition according to claim 95 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropentane.
Claim 99
Dependent Claim 21 words
The cationic lipid composition according to claim 95 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropropane.
Claim 100
Dependent Claim 17 words
The cationic lipid composition according to claim 94 wherein said lipids are in the form of bilayers.
Claim 101
Dependent Claim 22 words
The cationic lipid composition according to claim 99 wherein said lipids are phospholipids and said gas or gaseous precursor is sulfur hexafluoride.
Claim 102
Dependent Claim 21 words
The cationic lipid composition according to claim 99 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropentane.
Claim 103
Dependent Claim 21 words
The cationic lipid composition according to claim 99 wherein said lipids are phospholipids and said gas or gaseous precursor is perfluoropropane.
Claim 104
Dependent Claim 33 words
A cationic lipid formulation for the intracellular delivery of a bioactive agent comprising, in combination with a bioactive agent, a cationic lipid composition which comprises the cationic lipid compound according to claim 1.
Claim 105
Dependent Claim 14 words
The lipis formulation according to claim 103 wherein said bioactive agent comprises genetic material.
Claim 106
Dependent Claim 20 words
The lipid formulation according to claim 103 which is selected from the group consisting of micelles, liposomes and mixtures thereof.
Claim 107
Dependent Claim 17 words
The lipid formulation according to claim 105 comprising said bioactive agent entrapped within said micelles or liposomes.
Claim 108
Dependent Claim 18 words
The lipid formulation according to claim 103 further comprising a gas, a gaseous precursor or a mixture thereof.
Claim 109
Dependent Claim 32 words
The lipid formulation according to claim 107 wherein said gas, gaseous precursor or mixture thereof is selected from the group consisting of perfluoromethane, perfluoroethane, perfluoropropane, perfluorobutane, perfluorocyclobutane, perfluoropentane, perfluorohexane and mixtures thereof.
Claim 110
Dependent Claim 18 words
The lipid formulation according to claim 108 wherein said gas, gaseous precursor or mixture thereof further comprises nitrogen.
Claim 111
Dependent Claim 39 words
The process for the preparation of a cationic lipid formulation for the intracellular delivery of a bioactive agent comprising combining together a bioactive agent and a cationic lipid composition which comprises the cationic lipid compound according to claim 1.
Claim 112
Dependent Claim 13 words
The process according to claim 110 wherein said bioactive agent comprises genetic material.
Claim 113
Dependent Claim 11 words
The process according to claim 110 wherein said formulation is lyophilized.
Claim 114
Dependent Claim 21 words
The process according to claim 110 wherein said composition is selected from the group consisting of micelles, liposomes and mixtures thereof.
Claim 115
Dependent Claim 16 words
The process according to claim 113 comprising entrapping said bioactive agent within said micelles or liposomes.
Claim 116
Dependent Claim 20 words
The process according to claim 110 wherein said composition further comprises a gas, a gaseous precursor or a mixture thereof.
Claim 117
Dependent Claim 31 words
The process according to claim 115 wherein said gas, gaseous precursor or mixture thereof is selected from the group consisting of perfluoromethane, perfluoroethane, perfluoropropane, perfluorobutane, perfluorocyclobutane, perfluoropentane, perfluorohexane and mixtures thereof.
Claim 118
Dependent Claim 17 words
The process according to claim 116 wherein said gas, gaseous precursor or mixture thereof further comprises nitrogen.
Claim 119
Dependent Claim 31 words
A method for delivering intracellularly a bioactive agent comprising contacting a cell with a cationic lipid composition which comprises the cationic lipid compound according to claim 1 and the bioactive agent.
Claim 120
Dependent Claim 15 words
The method according to claim 118 wherein said composition is reconstituted from a lyophilized composition.
Claim 121
Dependent Claim 20 words
The method of claim 118 wherein said composition is selected from the group consisting of micelles, liposomes and mixtures thereof.
Claim 122
Dependent Claim 15 words
The method of claim 120 comprising said bioactive agent entrapped within said micelles or liposomes.
Claim 123
Dependent Claim 12 words
The method of claim 118 wherein said bioactive agent comprises genetic material.
Claim 124
Dependent Claim 23 words
The method of claim 122 wherein said genetic material is selected from the group consisting of polynucleotide, DNA, RNA, polypeptide and mixtures thereof.
Claim 125
Dependent Claim 20 words
The method according to claim 118 wherein said composition further comprises a gas, a gaseous precursor or a mixture thereof.
Claim 126
Dependent Claim 31 words
The method according to claim 124 wherein said gas, gaseous precursor or mixture thereof is selected from the group consisting of perfluoromethane, perfluoroethane, perfluoropropane, perfluorobutane, perfluorocyclobutane, perfluoropentane, perfluorohexane and mixtures thereof.
Claim 127
Dependent Claim 17 words
The method according to claim 125 wherein said gas, gaseous precursor or mixture thereof further comprises nitrogen.
Claim 128
Dependent Claim 18 words
The cationic vesicle comprising a cationic lipid compound according to claim 1 and a gas or gaseous precursor.
Claim 129
Dependent Claim 22 words
The cationic vesicle according to claim 127 which is selected from the group consisting of unilamellar vesicles, oligolamellar vesicles and multilamellar vesicles.
Claim 130
Dependent Claim 11 words
The cationic vesicle according to claim 128 which comprises unilamellar vesicles.
Claim 131
Dependent Claim 11 words
The cationic vesicle according to claim 129 which comprises a monolayer.
Claim 132
Dependent Claim 11 words
The cationic vesicle according to claim 129 which comprises a bilayer.
Claim 133
Dependent Claim 20 words
The cationic vesicle according to claim 128 which is selected from the group consisting of oligolamellar vesicles and multilamellar vesicles.
Claim 134
Dependent Claim 10 words
The cationic vesicle according to claim 132 which comprises monolayers.
Claim 135
Dependent Claim 10 words
The cationic vesicle according to claim 132 which comprises bilayers.
Claim 136
Dependent Claim 16 words
The cationic vesicle according to claim 132 further comprising an amphipathic compound for stabilizing the vesicle.
Claim 137
Dependent Claim 14 words
The cationic vesicle according to claim 135 wherein said amphipathic compound comprises a lipid.
Claim 138
Dependent Claim 22 words
The cationic vesicle according to claim 136 wherein said lipid is a phospholipid and said gas or gaseous precursor is sulfur hexafluoride.
Claim 139
Dependent Claim 21 words
The cationic vesicle according to claim 136 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropentane.
Claim 140
Dependent Claim 21 words
The cationic vesicle according to claim 136 wherein said lipid is a phospholipid and said gas or gaseous precursor is perfluoropropane.
Claim 141
Dependent Claim 14 words
The cationic vesicle according to claim 136 wherein said lipid is a polymerizable lipid.
Claim 142
Dependent Claim 10 words
The cationic vesicle according to claim 136 further comprising polyethyleneglycol.
Claim 143
Dependent Claim 472 words
A cationic lipid compound of the formula ##STR23## wherein: each of x, y and z is independently an integer from 0 to about 100; each X 1 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each X 2 is independently O or S; each Y 1 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each Y 2 is independently --N(R 6 ) b --, --S(R 6 ) b -- or --P(R 6 ) b --, wherein b is an integer from 0 to 2; each Y 3 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each of R 1 , R 2 , R 3 and R 4 is independently alkylene of 1 to about 20 carbons; each R 5 is independently hydrogen or alkyl of 1 to about 10 carbons; and each R 6 is independently -- R 7 --X 3 ! c --R 8 or --R 9 -- X 4 --R 10 ! d --Q, wherein: each of c and d is independently an integer from 0 to about 100; each Q is independently a phosphate residue, --N(R 11 ) q , --S(R 11 ) q , --P(R 11 ) q or --CO 2 R 6 , wherein q is an integer from 1 to 3; each of X 3 and X 4 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each R 7 is independently alkylene of 1 to about 20 carbons; each R 8 is independently hydrogen or alkyl of 1 to about 40 carbons; each of R 9 and R 10 is independently alkylene of 1 to about 20 carbons; and each R 11 is independently -- R 7 --X 3 ! c ----R 8 or --R 9 -- X 4 --R 10 ! d --W, wherein: each W is independently a phosphate residue, --N(R 12 ) w , --S(R 12 ) w , --P(R 12 ) w , or --CO 2 R 6 , wherein w is an integer from 1 to 3; and R 12 is -- R 7 --X 3 ! c --R 8 ; with the proviso that the compound of formula (I) comprises at least one quaternary salt.
Claim 144
Dependent Claim 472 words
A cationic lipid compound of the formula ##STR23## wherein: each of x, y and z is independently an integer from 0 to about 100; each X 1 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each X 2 is independently O or S; each Y 1 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each Y 2 is independently --N(R 6 ) b --, --S(R 6 ) b -- or --P(R 6 ) b --, wherein b is an integer from 0 to 2; each Y 3 is independently a phosphate residue, N(R 6 ) a --, S(R 6 ) a --, P(R 6 ) a -- or --CO 2 R 6 , wherein a is an integer from 1 to 3; each of R 1 , R 2 , R 3 and R 4 is independently alkylene of 1 to about 20 carbons; each R 5 is independently hydrogen or alkyl of 1 to about 10 carbons; and each R 6 is independently -- R 7 --X 3 ! c --R 8 or --R 9 -- X 4 --R 10 ! d --Q, wherein: each of c and d is independently an integer from 0 to about 100; each Q is independently a phosphate residue, --N(R 11 ) q , --S(R 11 ) q , --P(R 11 ) q or --CO 2 R 6 , wherein q is an integer from 1 to 3; each of X 3 and X 4 is independently --O--, --S--, --NR 5 --, --C(═X 2 )--, --C(═X 2 )--N(R 5 )--, --N(R 5 )--C(═X 2 )--, --C(═X 2 )--O--, --O--C(═X 2 )-- or --X 2 --(R 5 X 2 )P(═X 2 )--X 2 --; each R 7 is independently alkylene of 1 to about 20 carbons; each R 8 is independently hydrogen or alkyl of 1 to about 40 carbons; each of R 9 and R 10 is independently alkylene of 1 to about 20 carbons; and each R 11 is independently -- R 7 --X 3 ! c ----R 8 or --R 9 -- X 4 --R 10 ! d --W, wherein: each W is independently a phosphate residue, --N(R 12 ) w , --S(R 12 ) w , --P(R 12 ) w , or --CO 2 R 6 , wherein w is an integer from 1 to 3; and R 12 is -- R 7 --X 3 ! c --R 8 ; with the proviso that the compound of formula (I) comprises at least one quaternary salt.
Claim 145
Dependent Claim 13 words
The compound according to claim 142 wherein said compound is in lyophilized form.

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