Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-06-08
2009-06-23
Andres, Janet L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S511000, C549S214000
Reexamination Certificate
active
07550608
ABSTRACT:
The present invention provides processes for the production of docetaxel. Docetaxel is produced by protecting the C(7) and the C(10) hydroxy groups of 10-DAB with a bridging silicon-based protecting group. The resulting 7,10-protected 10-DAB derivative is then derivatized and deprotected to form docetaxel.
REFERENCES:
patent: 4924011 (1990-05-01), Denis et al.
patent: 5015744 (1991-05-01), Holton
patent: 5175315 (1992-12-01), Holton
patent: 5399726 (1995-03-01), Holton et al.
patent: 5430160 (1995-07-01), Holton
patent: 5466834 (1995-11-01), Holton
patent: 5539103 (1996-07-01), Holton
patent: 5668270 (1997-09-01), Bauman et al.
patent: 5723634 (1998-03-01), Holton
patent: 5760251 (1998-06-01), Gao et al.
patent: 5763477 (1998-06-01), Duvvuri et al.
patent: 6191287 (2001-02-01), Holton et al.
patent: 6225463 (2001-05-01), de Vos et al.
patent: 6265587 (2001-07-01), Chanteloup et al.
patent: 6562962 (2003-05-01), Holton
patent: 6825365 (2004-11-01), Chanteloup et al.
patent: 0 400 971 (1990-05-01), None
patent: 0 617 034 (1994-09-01), None
patent: 94/18164 (1994-08-01), None
patent: 97/07110 (1997-02-01), None
patent: 97/15562 (1997-05-01), None
patent: 02/085878 (2002-10-01), None
patent: 2004/013096 (2004-02-01), None
patent: 2006/004898 (2006-01-01), None
patent: 2006/089207 (2006-08-01), None
Office Action dated Oct. 10, 2007, U.S. Appl. No. 11/449,075, 4 pages.
Tarrant, J.G. et al., “Synthesis and Biological Activity of Macrocyclic Taxane Analogues,” Bioorganic & Medicinal Chemistry Letters, 2004, pp. 2555-2558, vol. 14.
Gelest, Inc. Catalog, Silicon-Based Blocking Agents; Reagents For: Functional Group Protection, Synthesis, Derivitization, 2004, 29 pages.
Greene, et al., “Protective Groups In Organic Synthesis,” John Wiley & Sons, New York, 2007, pp. 165-166.
Corriu, R.J.P., “Hypervalent Species of Silicon: Structure and Reactivity,” Journal of Organometallic Chemistry, 1990, pp. 81-106, vol. 400.
Denis, J.-N., et al., “A Highly Efficient, Practical Approach to Natural Taxol,” J. Am. Chem. Soc., 1988, pp. 5917-5919, vol. 110, No. 17.
Grobe, J., et al., “Atrane Analogous Compounds of Type Me2Si-Y-M′Me2(OCH2CH2)NME (-O-CH3-CH2-) (I),” Z. Naturforsch., B Anorg. Chem., Org. Chem., 1983, pp. 269-279, vol. 38B, No. 3.
Gueritte-Voegelein, F., et al., “Chemical Studies of 10-Deacetyl Baccatin III. Hemisynthesis of Taxol Derivatives,” Tetrahedron, 1986, pp. 4451-4460, vol. 42, No. 16.
Holton, R.A., et al., “Selective Protection of the C(7) and C(10) Hydroxyl Groups in 10-Deacetyl Baccatin III,” Tetrahedron Letters, 1998, pp. 2883-2886, vol. 39.
Office Action dated Feb. 16, 2007, U.S. Appl. No. 11/449,075, 13 pages.
Office Action dated Jun. 21, 2007, U.S. Appl. No. 11/449,075, 16 pages.
Uhlig, W., et al., “Synthesis and Reactivity of Triflate Substituted Siloxane Derivatives,” Z. Anorg. Allg. Chem., 1994, pp. 939-943, vol. 620.
Jagtap, P. G., et al., “A Facile N-Debenzoylation of Paclitaxel: Conversion of Paclitaxel to Docetaxel,” Tetrahedron Letters, 1999, pp. 189-192, vol. 40.
International Search Report, PCT/US2006/022335, dated Dec. 27, 2006, 4 pages.
Commercon, A., et al., “Improved Protection and Esterification of a Precursor of the Taxotere® and Taxol Side Chains”, Tetrahedron Letters, 1992, pp. 5185-5188, vol. 33, No. 36.
Denis, J-N., et al., “A Highly Efficient, Practical Approach to Natural Taxol”, J. Am. Chem. Soc., 1988, pp. 5917-5919, vol. 110, No. 17.
Farina, V., et al., “A Simple Chiral Synthesis of the Taxol Side Chain”, Synlett, Sep. 1992, pp. 761-763, vol. 9.
Hart, D. J., et al., “The Ester Enolate-Imine Condensation Route to β-Lactams”, Chem. Rev., 1989, pp. 1447-1465, vol. 89, No. 7.
Mangatal, L., et al., “Application of the Vicinal Oxyamination Reaction with Asymmetric Induction to the Hemisynthesis of Taxol and Analogues”, Tetrahedron, 1989, pp. 4177-4190, vol. 45, No. 13.
Senilh, V., et al., “Analyse Structurale et etude Biochimique de produits isoles de I'lf:Taxus baccataL. (Taxacees)”, C.R. Acad. Sci. Paris, IT, 1981, pp. 501-503, vol. 293, No. 7.
van Tilburg, E. W., et al., “Radiosynthesis of [11C]docetaxel”, Journal of Labelled Compounds and Radiopharmaceuticals, 2004, pp. 763-777, vol. 47.
Holton Robert A.
Vu Phong
Andres Janet L.
Bryan Cave LLP
Covington Raymond
Florida State University Research Foundation, Inc.
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