Claims
- 1. A method of preparing a dicarboxylated phenoxy containing compound from a phenoxy containing compound, the method comprising the step of (a) alkylating the phenoxy containing compound with a dicarboxylate alkylating agent to form the dicarboxylated phenoxy containing compound.
- 2. A method of preparing an alkylated phenoxy containing compound from a phenoxy containing compound, the method comprises the steps of (a) alkylating the phenoxy containing compound with a dicarboxylate alkylating agent to form a dicarboxylated phenoxy containing compound, and (b) decarboxylating the dicarboxylated phenoxy containing compound to form the alkylated phenoxy containing compound.
- 3. The method of claim 2, wherein the phenoxy containing compound has the formula
- 4. The method of claim 2, wherein the dicarboxylate alkylating agent has the formula
- 5. The method of claim 2, wherein the molar ratio of phenoxy containing compound to dicarboxylate alkylating agent is from about 1:1 to about 1:0.5.
- 6. The method of claim 2, wherein the alkylating step is performed in the presence of a base.
- 7. The method of claim 6, wherein the molar ratio of base to phenoxy containing compound is greater than 1.
- 8. The method of claim 7, wherein the base is pyridine, picoline, tetramethylguanidine, triethylamine, diisopropylethylamine, sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, or any combination of any of the foregoing.
- 9. The method of claim 8, wherein the base is sodium carbonate.
- 10. The method of claim 2, wherein the alkylating step is performed at a temperature of from about 40 to about 80° C.
- 11. The method of claim 10, wherein the alkylating step is performed at a temperature of from about 60 to about 80° C.
- 12. The method of claim 2, wherein the dicarboxylate phenoxy containing compound has the formula
- 13. The method of claim 2, further comprising hydrolyzing one or more carboxyl moieties of the alkylated phenoxy carboxylic acid compound after step (a) to form the free acid of the alkylated phenoxy carboxylic acid compound.
- 14. The method of claim 13, wherein the decarboxylating step is performed after the hydrolyzing step.
- 15. The method of claim 2, wherein decarboxylating comprises heating the dicarboxylated phenoxy containing compound in an organic solvent to a temperature ranging from about 140 to about 200° C.
- 16. The method of claim 15, wherein the organic solvent has a boiling point of at least about 110° C.
- 17. The method of claim 15, wherein the organic solvent is selected from xylenes, toluene, heptane, dimethyl acetamide, dimethyl formamide, methyl sulfoxide, isoparaffins, and any combination of any of the foregoing.
- 18. The method of claim 2, wherein the alkylated phenoxy containing compound has the formula
- 19. A method of preparing an alkylated phenoxy containing compound from a dicarboxylated phenoxy containing compound comprising the step of decarboxylating and hydrolyzing the dicarboxylated phenoxy containing compound to form the alkylated phenoxy containing compound.
- 20. A compound having the formula
- 21. A composition comprising:
(A) an active agent; and (B) at least one compound of claim 20.
- 22. A dosage unit form comprising:
(A) the composition of claim 21; and (B) (i) an excipient,
(ii) a dilutent, (iii) a disintegrant, (iv) a lubricant, (v) a plasticizer, (vi) a colorant, (vi) a dosing vehicle, or (vii) any combination thereof.
- 23. A method for administering a biologically-active agent to an animal in need of the agent, the method comprising administering orally to the animal the composition of claim 21.
- 24. A method for preparing a composition comprising mixing:
(A) at least one active agent; (B) the compound of claim 20; and (C) optionally, a dosing vehicle.
Parent Case Info
[0001] This application claims the benefit of U.S. Provisional Application No. 60/325,657, filed Sep. 26, 2001, which is hereby incorporated by reference.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/US02/30671 |
9/26/2002 |
WO |
|
Provisional Applications (1)
|
Number |
Date |
Country |
|
60325657 |
Sep 2001 |
US |