Sugar containing, amphiphilic copolymers
Disclosed herein are polymers made from at least one monomer of formulae (I), (II), (III), and (IV), in combination with a monomer of formula (V) that may be used in pharmaceutical formulations. These polymers comprise a hydrocarbon backbone and are made from monomers that contain at least one carbon-carbon double bond. Methods of making these polymers are also disclosed.
1. A polymer having an acrylate-derived backbone, where the polymer is derived from at least a first monomer, a second monomer and a third monomer, wherein i) the first monomer is selected from the group consisting of a compound of formula (I), (II), and (III); ii) the second monomer is a compound of formula (IV) and iii) the third monomer is a compound of formula (V),
wherein at each occurrence, R 1 , R 2 and R 3 are independently H or methyl;—
R 4 is H or C1-C 6 alkyl;
R 6 is C1-C 6 alkyl; and
at each occurrence, R 10 is independently H, C1-C4 alkyl, C2-C4 alkanoyl, C2-C5 alkenoyl, —C1-C4 alkyl-aryl, or -alkanoylaryl;
wherein the C 2 -C 6 hydroxyalkyl group has one or two OH groups.
2. A polymer according to claim 1 , wherein at least one occurrence of R 1 is H.
3. A polymer according to claim 1 , wherein at least one occurrence of R 2 is H.
4. A polymer according to claim 1 , wherein at least one occurrence of R 3 is H.
5. A polymer according to claim 1 , wherein R 6 is C1-C4 alkyl.
6. A polymer according to claim 1 , wherein R 10 is —C(O)CH 3 or benzoyl.
7. A polymer according to claim 1 , further comprising a fourth monomer selected from the group consisting of a compound of formula (I), (II), and (III), with the proviso that the first and fourth monomers are of different formulas.
8. A polymer according to claim 1 , further comprising a fourth and fifth monomer, wherein the first monomer is a compound of formula (I), the fourth monomer is a compound of formula (II) and the fifth monomer is a compound of formula (III).
9. A polymer according to claim 1 , wherein the compound of formula (I) has the formula:
10. A polymer according to claim 1 , wherein the compound of formula (II) has the formula:
11. A polymer according to claim 1 , wherein the compound of formula (III) has the formula:
or combinations thereof.
12. A polymer according to claim 1 , wherein the compound of formula (IV) has the formula:
or combinations thereof.
13. A polymer according to claim 1 , wherein the compound of formula (V) has the formula:
wherein each R 10 is —C(O)CH 3 .
14. A polymer according to claim 1 , wherein the polymer is a statistical polymer.
15. A method of making a polymer according to claim 1 , comprising treating the monomers, with a free radical initiator in the presence of a chain transfer agent.
16. A pharmaceutical formulation comprising at least one polymer according to claim 1 , and an active pharmaceutical ingredient.
17. A method of increasing the solubility of a drug, the method comprising formulating the drug at least one polymer according to claim 1 .
18. A pharmaceutical formulation according to claim 16 , wherein the formulation is in spray-dried form.