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US 6,056,938 AGranted
Cationic lipids and the use thereof
AssigneeImarx Pharaceutical Corp.
InventorsEvan C. Unger, Dekang Shen, Guanli Wu
Life of this patent
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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.
Claims146
A cationic lipid composition comprising a compound of the formula:
- ##STR22## wherein:
- each of x, y and z is independently an integer from 0 to about 100;
- each X.sub.1 is independently --O--, --S--, --NR.sub.5 --, --C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--N(R.sub.5)--, --N(R.sub.5)--C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--O--, --O--C(.dbd.X.sub.2)-- or --X.sub.2 --(R.sub.5 X.sub.2)P(.dbd.X.sub.2)--X.sub.2 --;
- each X.sub.2 is independently O or S;
- each Y.sub.1 is independently a phosphate residue, N(R.sub.6).sub.a --, S(R.sub.6).sub.a --, P(R.sub.6).sub.a -- or --CO.sub.2 R.sub.6, wherein a is an integer from 1 to 3;
- each Y.sub.2 is independently --N(R.sub.6).sub.b --, --S(R.sub.6).sub.b -- or --P(R.sub.6).sub.b --, wherein b is an integer from 0 to 2;
- each Y.sub.3 is independently a phosphate residue, N(R.sub.6).sub.a --, S(R.sub.6).sub.a --, P(R.sub.6).sub.a -- or --CO.sub.2 R.sub.6, wherein a is an integer from 1 to 3;
- each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently alkylene of 1 to about 20 carbons;
- each R.sub.5 is independently hydrogen or alkyl of 1 to about 10 carbons;
- and
- each R.sub.6 is independently --[R.sub.7 --X.sub.3 ].sub.c --R.sub.8 or --R.sub.9 --[X.sub.4 --R.sub.10 ].sub.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.sub.11).sub.q, --S(R.sub.11).sub.q, --P(R.sub.11).sub.q or --CO.sub.2 R.sub.11, wherein q is an integer from 1 to 3;
- each of X.sub.3 and X.sub.4 is independently --O--, --S--, --NR.sub.5 --, --C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--N(R.sub.5)--, --N(R.sub.5)--C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--O--, --O--C(.dbd.X.sub.2)-- or --X.sub.2 --(R.sub.5 X.sub.2)P(.dbd.X.sub.2)--X.sub.2 --,
- each R.sub.7 is independently alkylene of 1 to about 20 carbons;
- each R.sub.8 is independently hydrogen or alkyl of 1 to about 60 carbons;
- each of R.sub.9 and R.sub.10 is independently alkylene of 1 to about 20 carbons;
- and
- each R.sub.11 is independently --[R.sub.7 --X.sub.3 ].sub.c --R.sub.8 or --R.sub.9 --[X.sub.4 --R.sub.10 ].sub.d --W, wherein:
- each W is indepentdntly a phosphate residue, --N(R.sub.12).sub.w, --S(R.sub.12).sub.w, --P(R.sub.12).sub.w or --CO.sub.2 R.sub.12, wherein w is an integer from 1 to 3;
- and
- R.sub.12 is --[R.sub.7 --X.sub.3 ].sub.c --R.sub.8 ;
- and a liquid perfluorocarbon;
- with the proviso that the compound of formula (1) comprises at least two quaternary salts.
21 more elements
A cationic lipid composition comprising a compound of the formula ##STR23## wherein:
- each of x, y and z is independently an integer from 0 to about 100;
- each X.sub.1 is independently --O--, --S--, --NR.sub.5 --, --C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--N(R.sub.5)--, --N(R.sub.5)--C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--O--, --O--C(.dbd.X.sub.2)-- or --X.sub.2 --(R.sub.5 X.sub.2)P(.dbd.X.sub.2)--X.sub.2 --;
- each X.sub.2 is independently O or S;
- each Y.sub.1 is independently a phosphate residue, N(R.sub.6).sub.a --, S(R.sub.6).sub.a --, P(R.sub.6).sub.a -- or --CO.sub.2 R.sub.6, wherein a is an integer from 1 to 3;
- each Y.sub.2 is independently --N(R.sub.6).sub.b --, --S(R.sub.6).sub.b -- or --P(R.sub.6).sub.b --, wherein b is an integer from 0 to 2;
- each Y.sub.3 is independently a phosphate residue, N(R.sub.6).sub.a --, S(R.sub.6).sub.a --, P(R.sub.6).sub.a -- or --CO.sub.2 R.sub.6, wherein a is an integer from 1 to 3;
- each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently alkylene of 1 to about 20 carbons;
- each R.sub.5 is independently hydrogen or alkyl of 1 to about 10 carbons;
- and
- each R.sub.6 is independently --[R.sub.7 --X.sub.3 ].sub.c --R.sub.8 or --R.sub.9 --[X.sub.4 --R.sub.10 ].sub.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.sub.11).sub.q, --S(R.sub.11).sub.q, --P(R.sub.11).sub.q or --CO.sub.2 R.sub.6, wherein q is an integer from 1 to 3;
- each of X.sub.3 and X.sub.4 is independently --O--, --S--, --NR.sub.5 --, --C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--N(R.sub.5)--, --N(R.sub.5)--C(.dbd.X.sub.2)--, --C(.dbd.X.sub.2)--O--, --O--C(.dbd.X.sub.2)-- or --X.sub.2 --(R.sub.5 X.sub.2)P(.dbd.X.sub.2)--X.sub.2 --;
- each R.sub.7 is independently alkylene of 1 to about 20 carbons;
- each R.sub.8 is independently hydrogen or alkyl of 1 to about 40 carbons;
- each of R.sub.9 and R.sub.10 is independently alkylene of 1 to about 20 carbons;
- and
- each R.sub.11 is independently --[R.sub.7 --X.sub.3 ].sub.c --R.sub.8 or --R.sub.9 --[X.sub.4 --R.sub.10 ].sub.d --W, wherein:
- each W is independently a phosphate residue, --N(R.sub.12).sub.w, --S(R.sub.12).sub.w, --P(R.sub.12).sub.w or --CO.sub.2 R.sub.6, wherein w is an integer from 1 to 3;
- and
- R.sub.12 is --[R.sub.7 --X.sub.3 ].sub.c --R.sub.8 ;
- and a liquid perfluorocarbon;
- with the proviso that the compound of formula (I) comprises at least one quaternary salt.
20 more elements
Dependencies are inferred from the claim text.