Silicon amphiphilic compounds and the use thereof
First Claim
Patent Images
1. A compound of the formula:
-
wherein;
each X1 is independently —
O—
, —
S—
, —
SO—
, —
SO2—
, —
NR4—
, —
X3—
C(═
X4)—
, —
C(═
X4)—
X3—
or —
C(═
X4)—
;
X2 is —
R5—
X3—
R6—
, —
R5—
X3—
C(═
X4)—
R6—
, —
R5—
C(═
X4)—
X3—
R6—
, —
R5—
X3—
C(═
X4)—
R6—
C(═
X4)—
X5—
R7—
,
—
R5—
X3—
(YX3)P(═
X4)—
X3—
R6—
X5—
C(═
X4)—
R6—
C(═
X4)—
X3—
or a saccharide diradical;
each X3. is independently a direct bond, —
O—
, —
NR4—
or —
S—
;
each X4 is independently O or S;
each X5 is independently —
O—
, —
NR4—
or —
S—
;
Y is hydrogen or a pharmaceutically acceptable counter ion;
Z is a direct bond or a hydrophilic polymer;
Q is a silicon residue;
each R1 is independently optionally substituted alkyl of 1 to about 50 carbons;
R2 is alkylene of 1 to about 30 carbons;
each of R3 and R4 is independently hydrogen or alkyl of 1 to about 10 carbons; and
each of R5, R6 and R7 is independently a direct bond or alkylene of 1 to about 30 carbons.
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Accused Products
Abstract
Novel silicon amphiphilic compounds which comprise a silicon residue. The silicon amphiphilic compounds are particularly suitable for use in compositions for diagnostic imaging, such as ultrasound. Compositions of the silicon amphiphilic compounds comprise a gas or gaseous precursor, and may take the form of vesicle compositions, such as micelles or liposomes.
297 Citations
122 Claims
-
1. A compound of the formula:
-
wherein; each X1 is independently —
O—
, —
S—
, —
SO—
, —
SO2—
, —
NR4—
, —
X3—
C(═
X4)—
, —
C(═
X4)—
X3—
or —
C(═
X4)—
;
X2 is —
R5—
X3—
R6—
, —
R5—
X3—
C(═
X4)—
R6—
, —
R5—
C(═
X4)—
X3—
R6—
, —
R5—
X3—
C(═
X4)—
R6—
C(═
X4)—
X5—
R7—
,
—
R5—
X3—
(YX3)P(═
X4)—
X3—
R6—
X5—
C(═
X4)—
R6—
C(═
X4)—
X3—
or a saccharide diradical;
each X3. is independently a direct bond, —
O—
, —
NR4—
or —
S—
;
each X4 is independently O or S;
each X5 is independently —
O—
, —
NR4—
or —
S—
;
Y is hydrogen or a pharmaceutically acceptable counter ion;
Z is a direct bond or a hydrophilic polymer;
Q is a silicon residue;
each R1 is independently optionally substituted alkyl of 1 to about 50 carbons;
R2 is alkylene of 1 to about 30 carbons;
each of R3 and R4 is independently hydrogen or alkyl of 1 to about 10 carbons; and
each of R5, R6 and R7 is independently a direct bond or alkylene of 1 to about 30 carbons. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 110)
Q is a residue of the formula —
X6—
[Si(R8)2—
X3—
Z]n—
Si(R8)3wherein; n is an integer from 0 to about 10,000;
X6 is a direct bond, —
O—
, —
NR5—
or —
S—
; and
each R8 is independently alkyl of 1 to about 10 carbons.
-
-
3. A compound according to claim 2 wherein:
-
each X1 is independently —
O—
, —
NR4—
, —
X3—
C(═
X4)—
, —
C(═
X4)-X3—
or —
C(═
X4)—
; and
X2 is —
R5—
X3—
R6—
, —
R5—
X3—
C(═
X4)—
R6—
C(═
X4)—
X5—
R7—
or —
R5—
X3—
(YX3)P(═
X4)—
X3—
R6—
X3—
C(═
X4)—
R6—
C(═
X4)—
X3—
.
-
-
4. A compound according to claim 3 wherein:
each X1 is independently —
O—
, —
X3—
C(═
X4)—
or —
C(═
X4)—
X3—
.
-
5. A compound according to claim 4 wherein:
-
X1 is —
C(═
X4)—
X3—
;
X3 is —
O—
;
X4 is O;
X5 is —
O—
or —
NR4—
; and
X6 is a direct bond or —
O—
.
-
-
6. A compound according to claim 5 wherein:
n is an integer from 0 to about 1,000.
-
7. A compound according to claim 6 wherein:
n is an integer from 0 to about 100.
-
8. A compound according to claim 7 wherein:
-
each R1 is independently optionally substituted alkyl of 1 to about 30 carbons;
R2 is alkylene of 1 to about 15 carbons;
each of R3 and R4 is independently hydrogen or alkyl of 1 to about 4 carbons;
each of R5, R6 and R7 is independently a direct bond or alkylene of 1 to about 15 carbons; and
each R8 is independently alkyl of 1 to about 4 carbons.
-
-
9. A compound according to claim 8 wherein:
-
each R1 is independently optionally substituted alkyl of 1 to about 20 carbons;
R2 is alkylene of 1 to about 10 carbons;
R3 and R4 are hydrogen;
each of R5, R6 and R7 is independently a direct bond or alkylene of 1 to about 10 carbons; and
R8 is methyl.
-
-
10. A compound according to claim 9 wherein:
-
R2 is alkylene of 1 to about 5 carbons; and
each of R5, R6 and R7 is independently a direct bond or alkylene of 1 to about 5 carbons.
-
-
11. A compound according to claim 10 wherein:
R2 is methylene.
-
12. A compound according to claim 11 wherein:
n is an integer from 0 to about 10.
-
13. A compound according to claim 12 wherein:
n is an integer. from 1 to about 8.
-
14. A compound according to claim 13 wherein:
n is an integer from about 3 to about 6.
-
15. A compound according to claim 14 wherein:
each R1 is independently optionally substituted alkyl of 1 to about 15 carbons.
-
16. A compound according to claim 15 wherein:
Z is a direct bond.
-
17. A compound according to claim 16 wherein:
-
X2 is —
R5—
X3—
R6—
; and
X6 is —
O—
.
-
-
18. A compound according to claim 17 wherein:
-
R5 is methylene; and
R6 is a direct bond.
-
-
19. A compound according to claim 16 wherein:
X2 is —
R5—
X3—
C(═
X4)—
R6—
C(═
X4)—
X5—
R7—
.
-
20. A compound according to claim 19 wherein:
-
X5 is —
NR4—
; and
X6 is —
O—
.
-
-
21. A compound according to claim 20 wherein:
-
R5 is methylene;
R6 is ethylene; and
R7 is propylene.
-
-
22. A compound according to claim 15 wherein:
Z is a hydrophilic polymer.
-
23. A compound according to claim 22 wherein:
Z is selected from the group consisting of polyethylene glycol, polyvinyl alcohol or polyvinyl pyrrolidone.
-
24. A compound according to claim 23 wherein:
Z is polyethylene glycol.
-
25. A compound according to claim 24 wherein:
X2 is —
R5—
X3—
C(═
X4)—
R6—
C(═
X4)—
X5—
R7—
.
-
26. A compound according to claim 25 wherein:
-
R5 is methylene;
R6 is ethylene; and
R7 is a direct bond.
-
-
27. A compound according to claim 26 wherein:
X6 is —
O—
.
-
28. A compound according to claim 27 wherein:
X5 is —
NR4—
.
-
29. A compound according to claim 27 wherein:
X5is —
O—
.
-
30. A compound according to claim 12 wherein:
n is 0.
-
31. A compound according to claim 30 wherein:
Z is a hydrophilic polymer.
-
32. A compound according to claim 31 wherein:
Z is selected from the group consisting of polyethylene glycol, polyvinyl alcohol or polyvinyl pyrrolidone.
-
33. A compound according to claim 32 wherein:
Z is polyethylene glycol.
-
34. A compound according to claim 33 wherein:
X2 is —
R5—
X3—
(YX3)P(═
X4)—
X3—
R6—
X5—
C(═
X4)—
R6—
C(═
X4)—
X3—
.
-
35. A compound according to claim 34 wherein:
-
X5 is —
NR4—
; and
X6 is a direct bond.
-
-
36. A compound according to claim 35 wherein:
-
R5 is methylene; and
R6 is ethylene.
-
-
37. A compound according to claim 36 wherein:
each R1 is independently optionally substituted alkyl of 1 to about 15 carbons.
-
38. A compound according to claim 37 wherein:
each R1 is independently substituted alkyl of 1 to about 15 carbons.
-
39. A compound according to claim 38 wherein:
said substituent of said substituted alkyl is halogen.
-
40. A compound according to claim 39 wherein:
- said halogen is fluorine.
-
41. A compound according to claim 40 wherein:
- R1 comprises perfluorinated alkyl.
-
42. A compound according to claim 41 wherein:
-
said perfluorinated alkyl has the formula CaF2a+1—
(CH2)b—
wherein;
a is an integer from 1 to about 30; and
b is an integer from 0 to about 29;
provided that the sum of a and b is not greater than about 30.
-
-
43. A compound according to claim 42 wherein:
-
a is an integer from 1 to about 10; and
b is an integer from 1 to about 20.
-
-
44. A compound according to claim 43 wherein:
-
a is an integer from about 3 to about 8; and
b is an integer from about 5 to about 15.
-
-
45. A compound according to claim 44 wherein:
-
a is an integer from about 4 to about 6; and
b is an integer from about 9 to about 13.
-
-
46. A compound according to claim 45 wherein:
-
a is an integer from about 3 to about 8; and
b is an integer from about 5 to about 15.
-
-
47. A compound according to claim 46 wherein:
-
a is an integer from about 4 to about 6; and
b is an integer from about 9 to about 13.
-
-
48. A compound according to claim 47 wherein:
-
a is about 5; and
b is about 11.
-
-
110. A compound according to claim 1 which is in a lyophilized form.
- 49. A silicon amphiphilic compound which comprises a silicon residue.
- 57. A composition for diagnostic imaging comprising a silicon amphiphilic compound and a gas or gaseous precursor.
-
83. A cosmetic formulation comprising, in combination with a cosmetic agent, a composition comprising a silicon amphiphilic compound and a gas or gaseous precursor.
- 84. A method for the preparation of a composition which comprises a silicon amphiphilic compound and a gas or gaseous precursor, wherein the method comprises agitating, in the presence of a gas or gaseous precursor, an aqueous mixture of a silicon amphiphilic compound.
Specification