C7 lactyloxy-substituted taxanes
View Patent ↗A taxane having the formula: wherein X 3 is furyl, X 5 is t-butoxycarbonyl, Bz is benzoyl, and Ac is acetyl.
1. A composition comprising an isolated taxane having the formula:
wherein
X 3 is furyl,
X 5 is t-butoxycarbonyl,
Bz is benzoyl, and
Ac is acetyl.
2. The composition of claim 1 wherein X 3 is 2-furyl.
3. The composition of claim 2 wherein the composition comprises a diastereomic mixture of 7-((S)-(−)-2-hydroxyloxy-propionyl)-2-furyl-docetaxel and 7-((R)-(+)-2-hydroxyloxypropionyl)-2-furyl-docetaxel.
4. The composition of claim 3 wherein the mixture is a racemic mixture of 7-((S)-(−)-2-hydroxyloxypropionyl)-2-furyl-docetaxel and 7-((R)-(+)-2-hydroxyloxy-propionyl)-2-furyl-docetaxel.
5. The composition of claim 3 wherein the molar ratio of the diastereomers in the mixture is at least 5:1.
6. The composition of claim 3 wherein the molar ratio of the diastereomers in the mixture is at least 10:1.
7. The composition of claim 3 wherein the molar ratio of the diastereomers in the mixture is at least 20:1.
8. The composition of claim 1 wherein the taxane is in crystalline form.
9. A method of preparing the composition of claim 1 , the method comprising crystallizing the taxane from a solution.
10. A pharmaceutical composition comprising a therapeutically effective amount of the composition of claim 1 and at least one pharmaceutically acceptable carrier.
11. The pharmaceutical composition of claim 10 wherein the composition is in liquid form.
12. The pharmaceutical composition of claim 10 wherein the composition is a solid.
13. The pharmaceutical composition of claim 10 wherein the composition is in a dosage unit form.
14. A method for preparing a medicament, the method comprising mixing a composition of claim 1 with a nonaqueous, pharmaceutically acceptable solvent.
15. A method of inhibiting colon tumor growth in a mammal, said method comprising administering a therapeutically effective amount of a pharmaceutical composition of claim 13 .
16. The method of claim 15 , wherein the pharmaceutical composition is administered orally.
17. The method of claim 15 , wherein the pharmaceutical composition is administered parenterally.
18. An isolated taxane having the formula:
wherein
X 3 is furyl,
X 5 is t-butoxycarbonyl,
Bz is benzoyl, and
Ac is acetyl.
19. The taxane of claim 18 wherein X 3 is 2-furyl.