Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-03-15
2011-03-15
Andres, Janet L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S511000
Reexamination Certificate
active
07906661
ABSTRACT:
A process is provided for the semi-synthesis of taxane derivatives useful in the preparation of docetaxel, in particular, the semi-synthesis of protected taxane derivatives in a one pot reaction of protecting the C-2′, C-7 and C-10 positions and introducing a t-Boc group at the nitrogen of the amide group at the C-3′ position in paclitaxel and subsequently conversion to docetaxel, and derivatives used therein.
REFERENCES:
patent: 5319112 (1994-06-01), Kingston et al.
patent: 5380916 (1995-01-01), Rao
patent: 5530020 (1996-06-01), Gunawardana et al.
patent: 5703247 (1997-12-01), Kingston et al.
patent: 5808113 (1998-09-01), Murray et al.
patent: 6136989 (2000-10-01), Foo et al.
patent: 6197981 (2001-03-01), Liu
patent: 6222053 (2001-04-01), Zamir et al.
patent: 6576777 (2003-06-01), Zamir et al.
patent: 7202370 (2007-04-01), Naidu
patent: 2001/0014746 (2001-08-01), Holton
patent: 2001/0037020 (2001-11-01), Holton
patent: 2001/0041803 (2001-11-01), Kasitu et al.
patent: 2008/0033189 (2008-02-01), Naidu
patent: 2008/0146824 (2008-06-01), Naidu et al.
patent: 2008/0262250 (2008-10-01), Naidu
patent: 1403261 (2004-03-01), None
patent: WO98/50378 (1998-11-01), None
patent: WO99/54322 (1999-10-01), None
patent: WO 2004/033442 (2004-04-01), None
patent: WO2005/082875 (2005-09-01), None
patent: WO2005/105767 (2005-11-01), None
patent: WO2005/118563 (2005-12-01), None
patent: WO2006/004708 (2006-01-01), None
Nicolaou et al., “Chemistry and Biology of Taxol,”Angew. Chem. Int. Ed. Engl. 33:15-44, 1994.
International Search Report dated Sep. 28, 2005 from PCT/US2005/019697.
International Search Report dated Nov. 28, 2005 from PCT/US2005/023224, filed on Jun. 29, 2005.
Beckvermit et al., “An Improved Method for Separating Paclitaxel and Cephalomannine Using Ozone and Girard Reagents,”J. Org. Chem., vol. 61, No. 25, pp. 9038-9040 (1996).
Chen et al., “Synthesis and Biological Evaluation of Novel C-4 Aziridine-Bearing Paclitaxel (Taxol) Analogs,” CAPLUS 123:112445, Abstract Only,Journal of Medicinal Chemistry, vol. 38, No. 12, pp. 2263-2267 (1995).
Commerçon et al., “Improved Protection and Esterification of a Precursor of the TAXOTERE® and Taxol Side Chains,”Tetrahedron Letters, vol. 33, No. 36, pp. 5185-5188 (1992).
Final Office action from the U.S. Patent and Trademark Office in U.S. Appl. No. 11/587,407, dated Apr. 16, 2009.
Gennari et al., “Computer-Assisted Design and Synthetic Applications of Chiral Enol Borinates: Novel, Highly Enantioselective Aldol Reagents,”J. Braz. Chem. Soc., vol. 9, No. 4, pp. 319-326 (1998).
Gennari et al., “Rationally designed chiral enol Borinates: Powerful reagents for the stereoselective synthesis of natural products,”Pure&Appl. Chem., vol. 69, No. 3, pp. 507-512 (1997).
International Search Report for PCT/US2005/014080 (mailed Aug. 3, 2005).
International Search Report for PCT/US2005/005953 (mailed Sep. 14, 2005).
Kanazawa et al., “Highly Stereocontrolled and Efficient Preparation of the Protected, Esterification-Ready Docetaxel (Taxotere) Side Chain,”Journal of Organic Chemistry, vol. 59, pp. 1238-1240 (1994).
Klein, L., “Synthesis of 9-Dihydrotaxol: A Novel Bioactive Taxane,”Tetrahedron Letters, vol. 34, No. 13, pp. 2047-2050 (Mar. 26, 1993).
Notice of Allowance from the U.S. Patent and Trademark Office in U.S. Appl. No. 11/587,407, dated Jul. 22, 2010.
Office Action from European Patent Office in European Patent Application No. 05760288.0, dated Jul. 23, 2009.
Office action from the U.S. Patent and Trademark Office in U.S. Appl. No. 10/590,647, dated Sep. 19, 2008.
Office action from the U.S. Patent and Trademark Office in U.S. Appl. No. 11/587,407, dated Sep. 25, 2008.
Office action from the U.S. Patent and Trademark Office in U.S. Appl. No. 11/587,407, dated Nov. 27, 2009.
Office action from the U.S. Patent and Trademark Office in U.S. Appl. No. 11/628,428, dated Sep. 4, 2009.
Office action from the U.S. Patent and Trademark Office in U.S. Appl. No. 11/628,428, dated Feb. 3, 2010.
Pines et al., “The Stereochemistry of 2,3-Diphenyl-1-methylpropylamine,”Journal of Medical Chemistry, vol. 10, No. 4, pp. 725-728 (1967).
Rimoldi et al., “An Improved Method for the Separation of Paclitaxel and Cephalomannine,”Journal of Natural Products, vol. 59, No. 2, pp. 167-168 (1996).
Fan Bo
Foo Samuel Siang Kiang
Naidu Ragina
Xue BaoYu
Andres Janet L.
Chatham Biotec, Limited
Covington Raymond
Klarquist & Sparkman, LLP
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