Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
2008-02-04
2009-06-02
Aulakh, Charanjit S (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C514S280000, C514S287000
Reexamination Certificate
active
07541346
ABSTRACT:
Selective phosphorylation of phenpanstatin (3a) with tetrabutylammonium dihydrogen phosphate and dicyclohexylcarbodiimide in pyridine followed by cation exchange chromatographic procedures was found to provide an efficient route to a new series (3b-3d) of promising 3,4-O-cyclic phosphate prodrugs designated phenpanstatin phosphates. Application of analogous reaction conditions to pancratistatin (1a) led to a mixture of monophosphate derivatives where sodium pancratistatin 4-O-phosphate (4a) was isolated and the structure confirmed by x-ray crystallography. Modification of the reaction conditions allowed direct phosphorylation of pancratistatin followed by cation exchange chromatography to afford sodium pancratistatin 3,4-O-cyclic phosphate (5b) which was selected for preclinical development.
REFERENCES:
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patent: WO 02/50023 (2002-06-01), None
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Mamber et al., “Tubulin Polymerization by Paclitaxel (Taxol) Phosphate Prodrugs After Metabolic Activation with Alkaline Phosphatase”,The Journal of Pharmacology and Experimental Therapeutics, 274(2):877-883 (1995).
Shnyder et al., “Sodium Pancratistatin 3,4-O-Cyclic Phosphate, a Water-Soluble Synthetic Derivative of Pancratistatin, is Highly Effective in a Human Colon Tumor Model”,J. Nat. Prod., 71:321-324 (2008).
Melody Noeleen
Pettit George R.
Arizona Board of Regents, a body corporate of the State of Arizo
Aulakh Charanjit S
McAndrews Held & Malloy Ltd.
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