FUNCTIONALIZED DIPHENOLICS AND ABSORBABLE POLYMERS THEREFROM
First Claim
Patent Images
1. A functionalized diphenolic compound selected from:
- wherein;
Amino Acid is independently a phenol-containing amino acid;
X is independently selected from;
—
CH2COO—
;
—
CH(CH3)COO—
;
—
CH2CH2OCH2COO—
;
—
CH2CH2CH2CH2CH2COO—
;
—
(CH2)yCOO—
; and
, —
(CH2CH2O)zCH2COO—
, where y is independently selected from 2-4 and 6-24 and z is selected from 2-24, Y is independently selected from;
—
COCH2O—
;
—
COCH(CH3)O—
;
—
COCH2OCH2CH2O—
;
—
COCH2CH2CH2CH2CH2O—
;
—
CO(CH2)mO—
; and
, —
COCH2O(CH2CH2O)n—
, where m is selected from 2-4 and 6-24 and n is selected from 2-24;
R′
is independently selected from hydrogen, benzyl, and C1-6 alkyl; and
, a, b, and c, are independently selected from 0-4, provided that a+b+c total from 1-6.
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Abstract
The present invention relates to dephenolic compounds, an example of which is shown below, which are functionalized, and polymers formed from the same.
-
Citations
40 Claims
-
1. A functionalized diphenolic compound selected from:
-
wherein;
Amino Acid is independently a phenol-containing amino acid;
X is independently selected from;
—
CH2COO—
;
—
CH(CH3)COO—
;
—
CH2CH2OCH2COO—
;
—
CH2CH2CH2CH2CH2COO—
;
—
(CH2)yCOO—
; and
, —
(CH2CH2O)zCH2COO—
, where y is independently selected from 2-4 and 6-24 and z is selected from 2-24,Y is independently selected from;
—
COCH2O—
;
—
COCH(CH3)O—
;
—
COCH2OCH2CH2O—
;
—
COCH2CH2CH2CH2CH2O—
;
—
CO(CH2)mO—
; and
, —
COCH2O(CH2CH2O)n—
, where m is selected from 2-4 and 6-24 and n is selected from 2-24;
R′
is independently selected from hydrogen, benzyl, and C1-6 alkyl; and
,a, b, and c, are independently selected from 0-4, provided that a+b+c total from 1-6. - View Dependent Claims (2, 3)
-
-
4. A functionalized diphenolic compound of formula I, II, or III:
-
R1 is a bond or is selected from OCH2, OCH2CO2CH2, CO2CH2CO2CH2, CH2CHR1a, CH2CHR1aCO2CH2, CH2CHR1aCO2CH2CO2CH2, CH═
CH or (CH2)d;
R1a is selected from H and NC(O)R′
;
X is independently selected from;
—
CH2COO—
;
—
CH(CH3)COO—
;
—
CH2CH2OCH2COO—
;
—
CH2CH2CH2CH2CH2COO—
;
—
(CH2)yCOO—
; and
, —
(CH2CH2O)zCH2COO—
, where y is independently selected from 2-4 and 6-24 and z is selected from 2-24,Y is independently selected from;
—
COCH2O—
;
—
COCH(CH3)O—
;
—
COCH2OCH2CH2O—
;
—
COCH2CH2CH2CH2CH2O—
;
—
CO(CH2)mO—
; and
, —
COCH2O(CH2CH2O)n—
, where m is selected from 2-4 and 6-24 and n is selected from 2-24;
R′
is independently selected from hydrogen, benzyl, and C1-6 alkyl;
a, b, and c, are independently selected from 0-4, provided that a+b+c total from 1-6;
d is selected from 1-8; and
,e is selected from 0, 1, and 2. - View Dependent Claims (5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
-
-
6. A compound according to claim 5, wherein:
-
y is independently selected from 2, 3, and 4;
z is independently selected from 2, 3, and 4;
m is independently selected from 2, 3, and 4; and
n is independently selected from 2, 3, and 4.
-
-
7. A compound according to claim 5, wherein:
-
X is independently selected from;
—
CH2COO—
;
—
CH(CH3)COO—
;
—
CH2CH2OCH2COO—
; and
,—
CH2CH2CH2CH2CH2COO—
;
Y is independently selected from;
—
COCH2O—
;
—
COCH(CH3)O—
;
—
COCH2OCH2CH2O—
;
—
COCH2CH2CH2CH2CH2O—
;
a, b, and c, are independently selected from 0-2, provided that a+b+c total from 2-4; and
,d is selected from 1, 2, 3, and 4.
-
-
8. A compound according to claim 7, wherein:
-
R′
is independently selected from hydrogen, benzyl, and C1-4 alkyl;
a, b, and c, are independently selected from 0-2, provided that a+b+c total from 2-3; and
,d is selected from 1, 2, and 3.
-
-
9. A compound according to claim 8, wherein:
-
R′
is independently selected from hydrogen, benzyl, and CH3;
a, b, and c, are independently selected from 0-1, provided that a+b+c total from 2-3; and
,d is selected from 1 and 2.
-
-
10. A compound according to claim 5, wherein:
-
X is —
CH2COO—
;
Y is —
COCH2O—
;
R′
is independently selected from hydrogen, benzyl, and C1-4 alkyl;
a, b, and c, are independently selected from 0-2, provided that a+b+c total from 2-4; and
,d is selected from 1, 2, 3, and 4.
-
-
11. A compound according to claim 10, wherein:
-
R′
is independently selected from hydrogen, benzyl, and CH3; and
,a, b, and c, are independently selected from 0-1, provided that a+b+c total from 2-3; and
,d is selected from 1 and 2.
-
-
12. A compound according to claim 4, wherein the compound is selected from:
-
13. A composition, comprising:
- two or more different compounds of claim 4.
-
14. A solvent for a drug, comprising:
- at least one compound of claim 4.
-
15. A nutritional composition, comprising at least one compound of claim 4.
-
16. A cosmetic composition, comprising at least one compound of claim 4 and a cosmetic ingredient.
-
17. A pharmaceutical composition, comprising at least one compound of claim 4 and a pharmaceutically acceptable excipient.
-
18. A polymer, comprising:
- a functionalized diphenolic compound of formula I, II, or III;
III wherein;
R1 is a bond or is selected from OCH2, OCH2CO2CH2, CO2CH2CO2CH2, CH2CHR1a, CH2CHR1aCO2CH2, CH2CHR1aCO2CH2CO2CH2, CH═
CH or (CH2)d;
R1a is selected from H and NR′
R′
;
X is independently selected from;
—
CH2COO—
;
—
CH(CH3)COO—
;
—
CH2CH2OCH2COO—
;
—
CH2CH2CH2CH2CH2COO—
;
—
(CH2)yCOO—
; and
, —
(CH2CH2O)zCH2COO—
, where y is independently selected from 2-4 and 6-24 and z is selected from 2-24,Y is independently selected from;
—
COCH2O—
;
—
COCH(CH3)O—
;
—
COCH2OCH2CH2O—
;
—
COCH2CH2CH2CH2CH2O—
;
—
CO(CH2)mO—
; and
, —
COCH2O(CH2CH2O)n—
, where m is selected from 2-4 and 6-24 and n is selected from 2-24;
R′
is independently selected from hydrogen, benzyl, and C1-6 alkyl;
a, b, and c, are independently selected from 0-4, provided that a+b+c total from 1-6;
d is selected from 1-8; and
,e is selected from 0, 1, and 2. - View Dependent Claims (19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40)
- a functionalized diphenolic compound of formula I, II, or III;
-
20. The polymer of claim 19, wherein:
-
y is independently selected from 2, 3, and 4;
z is independently selected from 2, 3, and 4;
m is independently selected from 2, 3, and 4; and
n is independently selected from 2, 3, and 4.
-
-
21. The polymer of claim 19, wherein:
-
X is independently selected from;
—
CH2COO—
;
—
CH(CH3)COO—
;
+P2 —
CH2CH2OCH2COO—
; and
,—
CH2CH2CH2CH2CH2COO—
;
Y is independently selected from;
—
COCH2O—
;
—
COCH(CH3)O—
;
—
COCH2OCH2CH2O—
;
—
COCH2CH2CH2CH2CH2O—
;
a, b, and c, are independently selected from 0-2, provided that a+b+c total from 2-4; and
,d is selected from 1, 2, 3, and 4.
-
-
22. The polymer of claim 21, wherein:
-
R′
is independently selected from hydrogen, benzyl, and C1-4 alkyl;
a, b, and c, are independently selected from 0-2, provided that a+b+c total from 2-3; and
,d is selected from 1, 2, and 3.
-
-
23. The polymer of claim 22, wherein:
-
R′
is independently selected from hydrogen, benzyl, and CH3;
a, b, and c, are independently selected from 0-1, provided that a+b+c total from 2-3; and
,d is selected from 1 and 2.
-
-
24. The polymer of claim 19, wherein:
-
X is —
CH2COO—
;
Y is —
COCH2O—
;
R′
is independently selected from hydrogen, benzyl, and C1-4 alkyl;
a, b, and c, are independently selected from 0-2, provided that a+b+c total from 2-4; and
,d is selected from 1, 2, 3, and 4.
-
-
25. The polymer of claim 24, wherein:
-
R′
is independently selected from hydrogen, benzyl, and CH3; and
,a, b, and c, are independently selected from 0-1, provided that a+b+c total from 2-3; and
,d is selected from 1 and 2.
-
-
26. The polymer of claim 19, wherein the functionalized diphenolic is reacted with a compound selected from a dicarboxylic acid, a dialcohol, a diisocyanate, an amino-alcohol, a hydroxycarboxylic acid, and a diamine to form a polymer selected from a polyester, polyurethane, polyesteramide, polyamide, and polyanhydride.
-
27. The polymer of claim 26, wherein the polymer, further comprises:
- a second functionalized diphenolic.
-
28. The polymer of claim 26, wherein the polymer is further polymerized with a lactone monomer.
-
29. The polymer of claim 28, wherein the lactone monomer is selected from glycolide, lactide, ε
- -caprolactone, trimethylene carbonate, and p-dioxanone.
-
30. An implantable medical device, comprising:
- a polymer of claim 26.
-
31. The implantable medical device of claim 30, wherein the polymer has been further polymerized with a lactone monomer selected from glycolide, lactide, ε
- -caprolactone, trimethylene carbonate, and p-dioxanone.
-
32. The implantable medical device of claim 30, wherein the device is a stent.
-
33. The implantable medical device of claim 32, wherein the polymer has been further polymerized with a lactone monomer selected from glycolide, lactide, ε
- -caprolactone, trimethylene carbonate, and p-dioxanone.
-
34. The implantable medical device of claim 30, wherein the device is a scaffold for tissue engineer, comprising:
- a porous structure for the attachment and proliferation of cells.
-
35. The implantable medical device of claim 34, wherein the polymer has been further polymerized with a lactone monomer selected from glycolide, lactide, ε
- -caprolactone, trimethylene carbonate, and p-dioxanone.
-
36. A coating for a stent, comprising:
- a polymer of claim 26.
-
37. The stent coating of claim 36, wherein the polymer has been further polymerized with a lactone monomer selected from glycolide, lactide, ε
- -caprolactone, trimethylene carbonate, and p-dioxanone.
-
38. A drug delivery system, comprising:
- a polymer of claim 26 physically admixed with a biologically or pharmacologically active agent.
-
39. The drug delivery system of claim 38, wherein the biologically or pharmacologically active agent is physically embedded or dispersed into the polymer and the polymer is in the form of a polymeric matrix.
-
40. The drug delivery system of claim 39, wherein the polymer has been further polymerized with a lactone monomer selected from glycolide, lactide, ε
- -caprolactone, trimethylene carbonate, and p-dioxanone.
Specification