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7-hexanoyltaxol and methods for preparing the same

Imported: 23 Feb '17 | Published: 22 Oct '02

Christopher K. Murray, Qun Y. Zheng, Sagar R. Shakya

USPTO - Utility Patents

Abstract

An antitumor compound of formula (5):

Also provided by the present invention is a method of preparing a compound of formula (5) whereby diesterification of the alcohol groups located at the 2′and 7 positions of paclitaxel is followed by the hydrolysis of the 2′hexanoate group resulting in 7-hexanoyltaxol.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings, which are incorporated in and form a part of the specification, illustrate the preferred embodiments of the present invention, and together with the description serve to explain the principles of the invention.

FIG. 1 depicts a schematic illustrating the various synthetic routes used in the preparation of the compositions of the present invention.

FIG. 1

a depicts a schematic illustrating the preferred method of preparing the preferred composition of the present invention.

FIG. 2

a depicts the dose response curves generated by exposing various leukemia cell lines to various concentrations of the composition of the present invention.

FIG. 2

b depicts the dose response curves generated by exposing various leukemia cell lines to various concentrations of paclitaxel.

FIG. 3

a depicts the dose response curves generated by exposing various non-small cell lung cancer cell lines to various concentrations of the composition of the present invention.

FIG. 3

b depicts the dose response curves generated by exposing various non-small cell lung cancer cell lines to various concentrations of paclitaxel.

FIG. 4

a depicts the dose response curves generated by exposing various colon cancer cell lines to various concentrations of the composition of the present invention.

FIG. 4

b depicts the dose response curves generated by exposing various colon cancer cell lines to various concentrations of paclitaxel.

FIG. 5

a depicts the dose response curves generated by exposing various CNS cancer cell lines to various concentrations of the composition of the present invention.

FIG. 5

b depicts the dose response curves generated by exposing various CNS cancer cell lines to various concentrations of paclitaxel.

FIG. 6

a depicts the dose response curves generated by exposing various melanoma cell lines to various concentrations of the composition of the present invention.

FIG. 6

b depicts the dose response curves generated by exposing various melanoma cell lines to various concentrations of paclitaxel.

FIG. 7

a depicts the dose response curves generated by exposing various ovarian cancer cell lines to various concentrations of the composition of the present invention.

FIG. 7

b depicts the dose response curves generated by exposing various ovarian cancer cell lines to various concentrations of paclitaxel.

FIG. 8

a depicts the dose response curves generated by, exposing various renal cancer cell lines to various concentrations of the composition of the present invention.

FIG. 8

b depicts the dose response curves generated by exposing various renal cancer cell lines to various concentrations of paclitaxel.

FIG. 9

a depicts the dose response curves generated by exposing, various prostate cancer cell lines to various concentrations of the composition of the present invention.

FIG. 9

b depicts the dose response curves generated by exposing various prostate cancer cell lines to various concentrations of paclitaxel.

FIG. 10

a depicts the dose response curves generated by exposing various breast cancer cell lines to various concentrations of the composition of the present invention.

FIG. 10

b depicts the dose response curves generated by exposing various breast cancer cell lines to various concentrations of paclitaxel.

Claims

1. A method of treating multidrug resistant cells comprising, exposing the multidrug resistant cells to a compound having the formula

wherein R is a monovalent organic compound, a monovalent aliphatic compound, a monovalent cyclic group or a branched or unbranched alkyl, alkenyl, alkynyl group or aryl group.

2. The method of claim 1, wherein said monovalent aliphatic compound is a hydrocarbon or a hetero-acyclic group.

3. The method of claim 1, wherein said monovalent cyclic group is an alicyclic or aromatic group.

4. The method of claim 3, wherein said monovalent alicyclic group comprises monovalent carbocyclic and heterocyclic groups.

5. The method of claim 3, wherein said monovalent aromatic group comprises monovalent carboaromatic groups and monovalent hetero-aromatic groups.

6. The method of claim 1, wherein said cells proliferate in an uncontrolled manner.

7. The method of claim 6, wherein said cells are cancer cells.

8. A method of treating multidrug resistant cells comprising, exposing the multidrug resistant cells to a compound having the formula

9. The method of claim 8, wherein said cells proliferate in an uncontrolled manner.

10. The method of claim 9, wherein said cells are cancer cells.

11. A method of treating an animal having a tumor that is resistant to at least one chemotherapeutic agent comprising,

12. The method of claim 11, wherein said animal is a human.