Conjugate addition reactions for the controlled delivery of pharmaceutical active compounds
First Claim
Patent Images
1. A biomaterial comprising a pharmaceutically active moiety, wherein said biomaterial has an ester or amide bond onto said pharmaceutically active moiety, said bond having a half-life of between 1 hour and 1 year in an aqueous solution at pH 7.4 and 37°
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Abstract
The invention features polymeric biomaterials formed by nucleophilic addition reactions to conjugated unsaturated groups. These biomaterials may be used for medical treatments.
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Citations
52 Claims
- 1. A biomaterial comprising a pharmaceutically active moiety, wherein said biomaterial has an ester or amide bond onto said pharmaceutically active moiety, said bond having a half-life of between 1 hour and 1 year in an aqueous solution at pH 7.4 and 37°
- 6. A biomaterial comprising a binding moiety, wherein said binding moiety has affinity for a pharmaceutically active compound, and wherein said biomaterial has an ester or amide bond onto said binding moiety, said bond having a half-life of between 1 hour and 1 year in an aqueous solution at pH 7.4 and 37°
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17. A biomaterial formed from the cross-linking of two or more precursor components, wherein at least one of said precursor components has the formula:
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D-Y—
C(O)—
(CH2)n—
S—
(CH2)2—
COX—
P, D-Y—
C(O)—
(CH2)n—
NH—
(CH2)2—
COX—
P, D-Y—
C(O)—
(CH2)n—
NH—
U—
P, D-Y—
C(O)—
(CH2)n—
S—
U—
P, D-Y—
C(O)—
(CH2)n—
S-L-S—
CH2—
CH2—
CO—
X—
P, D-Y—
C(O)—
(CH2)n—
S-L-S—
U—
P, D-Y—
C(O)—
(CH2)n—
NH-L-S—
CH2—
CH2—
CO—
X—
P, D-Y—
C(O)—
(CH2)n—
NH-L-S—
U—
P, D-Y—
C(O)—
(CH2)n—
S-L-NH—
CH2—
CH2—
CO—
X—
P, D-Y—
C(O)—
(CH2)n—
S-L-NH—
U—
P, D-Y—
C(O)—
(CH2)n—
NH-L-NH—
CH2—
CH2—
CO—
X—
P, or D-Y—
C(O)—
(CH2)n—
NH-L-NH—
U—
Pwherein D is a pharmaceutically active moiety or a binding moiety;
n is 1, 2, or 3;
Y is O, NH, or N;
L is a linear or branched linker;
X is O or N;
P is a water-soluble polymer or a water-swellable polymer comprising one or more conjugated unsaturated groups; and
U is the product of the addition of a nucleophile to an electrophilic group that is attached to said polymer.- View Dependent Claims (18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 36, 37, 38, 51, 52)
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31. A method of forming a biomaterial, said method comprising the steps of:
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(a) attaching a pharmaceutically active compound or a binding compound to a linker molecule or incorporating a nucleophilic amine or thiol into a pharmaceutically active compound or a binding compound, (b) removing any thiol-or amine-protecting groups in said linker, (c) coupling a thiol, amine, or alkene group in said linker or incorporated into said pharmaceutically active compound or said binding compound to a water-soluble polymer or a water-swellable polymer comprising two or more conjugated unsaturated groups by a conjugate addition reaction to form a precursor component, and (d) cross-linking the uncoupled conjugated unsaturated groups in one or more said precursor components. - View Dependent Claims (32, 39, 40, 41, 50)
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- 33. A method of treating or preventing a disease, disorder, or infection in a mammal by administering to said mammal a biomaterial comprising a pharmaceutically active moiety, wherein said biomaterial has an ester or amide bond onto said pharmaceutically active moiety, said bond having a half-life of between 1 hour and 1 year in an aqueous solution at pH 7.4 and 37°
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34. A method of treating or preventing a disease, disorder, or infection in a mammal by administering to said mammal a biomaterial comprising a binding moiety, wherein said biomaterial has an ester or amide bond onto said binding moiety, said bond having a half-life of between 1 hour and 1 year in an aqueous solution at pH 7.4 and 37°
- C., and wherein a pharmaceutically active moiety or compound is bound to said binding moiety.
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45. A pharmaceutically active compound of the formula D-O2C—
- (CH2)n—
SH or D-N(O)C—
(CH2)n—
SH, wherein n is 1 or 2 and D is a pharmaceutically active moiety. - View Dependent Claims (46)
- (CH2)n—
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47. A method of forming a biomaterial, said method comprising the steps of:
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(a) attaching a pharmaceutically active compound to a linker molecule or incorporating a nucleophilic amine or thiol into a pharmaceutically active compound, (b) coupling the thiol or amine in said linker or incorporated into said pharmaceutically active compound to at least a first polymer comprising two or more conjugated unsaturated groups by a conjugate addition reaction to form a precursor component;
(c) providing at least a second precursor comprising nucleophilic groups; and
(d) cross-linking the conjugated unsaturated groups of the precursor of step b) to the nucleophilic groups of the precursor of step c) by a conjugated addition reaction. - View Dependent Claims (48, 49)
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Specification