IP Library Granted Patent US 8,703,982
Granted Patent B2
US 8,703,982 · App. 12/705,247 · Granted Apr 22, 2014

Purification of taxanes

Inventors: Brian A. Bucher (Boston, MA); Edward M. Desimone, III (Indianapolis, IN); Roland R. Franke (Gloucester, MA); Rex T. Gallagher (Hampton, MA); Barry J. Hand (Acton, MA); Christopher D. Howe (Beverly, MA); James A. Johnson (Edenton, NC); John S. Juchum (Kingston, NH); Marc A. Plante (Middleton, MA); T. G. Sambandam (Uxbridge, MA); Dong S. Yang (Quincy, MA)
Assignee: Phyton Holdings LLC
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Quick Facts
Patent No.
US 8,703,982
App. No.
12/705,247
Granted
Apr 22, 2014
Kind
B2
Abstract

Disclosed is a method of crystallizing a taxane comprising combining the taxane and methylene chloride to obtain a solution and adding an anti-solvent to the solution to obtain a crystalline taxane, wherein the anti-solvent is selected from the group consisting of hexane and heptane.

Claims (19)

1. A method of crystallizing docetaxel comprising:

(a) combining docetaxel and methylene chloride to obtain a solution; and

(b) adding an anti-solvent to the solution to obtain a crystalline docetaxel, wherein the anti-solvent is selected from the group consisting of hexane and heptane.

2. The method of claim 1 , wherein the anti-solvent is hexane.

3. The method of claim 1 , wherein the anti-solvent is heptane.

4. The method of claim 1 , further comprising recrystallizing the crystalline docetaxel.

5. The method of claim 4 , wherein the recrystallization comprises:

(c) combining the crystalline docetaxel and a solubilizing solvent to obtain a second solution; and

(d) adding an anti-solvent to the second solution.

6. The method of claim 1 , wherein the docetaxel used in step (a) is isolated from a taxane material comprising docetaxel obtained from a semi-synthesis or total synthesis process, the isolation process comprising:

(i) loading or injecting the material on a column comprising a PBS resin;

(ii) eluting docetaxel from the PBS resin; and

(iii) recovering the eluted docetaxel.

7. The method of claim 6 , wherein molecules used as reactants in the semi-synthetic or total synthetic process are not derived solely from Taxus brevifolia.

8. The method of claim 6 , wherein the material loaded or injected on the column comprises less than about 8% by weight of C-2′ benzoyl primary taxanes.

9. The method of claim 6 , wherein the PBS resin is DEAM.

10. The method of claim 6 , wherein the PBS resin is PEI.

11. The method of claim 10 , wherein the amino groups of the PEI are functionalized.

12. The method of claim 6 , wherein the PBS resin has an average pore size ranging from about 60 to about 800 Angstrom Units and an average particle size ranging from about 0.25 to about 500 microns.

Assignments (4)
EMPLOYEE PROPRIETARY INFORMATION AGREEMENT ATTACHED AS APPENDIX TO ASSIGNMENT Recorded Dec 11, 2015
From: SAMBANDAM, T.G.; HOWE, CHRISTOPHER D
To: NATURAL PHARMACEUTICALS, INC.
Reel/Frame 037272/0064 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2015
From: JOHNSON, JAMES H; HAND, BARRY J; FRANKE, ROLAND R; BUCHER, BRIAN A; JUCHUM, JOHN S; GALLAGHER, REX T; PLANTE, MARC A; DESIMONE, III, EDWARD M; YANG, DONG S
To: NATURAL PHARMACEUTICALS, INC.
Reel/Frame 037272/0422 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2015
From: NATURAL PHARMA CANADA, ULC; NATURAL PHARMACEUTICALS, INC.
To: PHYTON, INC.
Reel/Frame 037273/0380 →
CHANGE OF NAME Recorded Dec 11, 2015
From: PHYTON, INC.
To: PHYTON HOLDINGS, LLC
Reel/Frame 037277/0296 →
Continuity (6)
Continuation 11764362 · Jun 18, 2007
Continuation 10549490
Continuation 10664539 · Sep 18, 2003
Provisional Application 60455377 · Mar 17, 2003
Provisional Application 60456478 · Mar 21, 2003
Related Publication 20100145080A1 · Jun 10, 2010