Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing nitrogen-containing organic compound
Reexamination Certificate
2005-04-12
2010-06-22
Tate, Christopher R (Department: 1651)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing nitrogen-containing organic compound
C435S041000, C435S183000, C435S191000
Reexamination Certificate
active
07741082
ABSTRACT:
A process for production of cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV is provided which employs a BOC-protected amine of the structureprepared by subjecting an acid of the structureto reduce amination by treating the acid with ammonium formate, nicotinamide adenine dinucleotide, dithiothreitol and partially purified phenylalanine dehydrogenase/formate dehydrogenase enzyme concentrate (PDH/FDH) and without isolating treating the resulting amine of the structure 2with di-tert-butyl dicarbonate to form the BOC-protected amine.
REFERENCES:
patent: 6068991 (2000-05-01), Liu et al.
patent: 6395767 (2002-05-01), Robl et al.
patent: 2005/0090539 (2005-04-01), Vu et al.
patent: 0 808 824 (1997-11-01), None
patent: WO 00/04179 (2000-01-01), None
Trager, George. (Drug Delivery Research Department Matrix Pharmaceutical, Inc.(Novartis/Chiron)) Bacteria Cell Lysis, <http://www.bio.net/bionet/mm/methods/1995-February/025062.html> Feb. 25, 1995 (accessed online Sep. 27, 2007.
Jollie, D.R. and Lipscomb, J.D., “Formate Dehydrogenease from Methylosinus trichosporium OB3b: Purification and Spectroscopic Characterization of the Cofactors”, the Journal of Biological Chemistry, 1991, 266(32), 21853-21863.
Asano, Y., Nakazawa, A., Endo, K. “NovelSporosarcina ureaeandBacillus sphaericus: Purification and Characterization” The Journal of Biological Chemistry 1987, 262(21), 10346-10354.
Armarego, W.L.F. and Perrin, D.D. “Common Physical Techniques Used in Purification: General Remarks” Purification of Laboratory Chemicals, 4th ed., 2000, Chapter 1, pp. 1-47.
Armarego, W.L.F. and Perrin, D.D. “Purification of Biochemicals and Related Products” Purification of Laboratory Chemicals, 5th ed., 2003, Chapter 6, pp. 500-547.
U.S. Appl. No. 11/091,183, filed Mar. 28, 2005, Sharma et al.
Hanessian, S. et al., “Probing the Importance of Spacial and Conformational Domains in Captopril Analogs'for Angiotensin Converting Enzyme Activity”, Bioorganic & Medicinal Chemistry Letters, vol. 8, pp. 2123-2128 (1998).
Hanson, R.L. et al., Synthesis of allysine ethylene acetal using phenylalanine dehydrogenase fromThermoactinomyces intermedius, Enzyme and Microbial Technology, vol. 26, pp. 348-358 (2000).
Imashiro, R. et al., “Asymmetric synthesis of methyl (2R,3S)-3-(4-methoxyphenyl) glycidate, a key intermediate of diltiazem, via Mukaiyama aldol reaction”, Tetrahedron Letters, vol. 42, pp. 1313-1315 (2001).
Reetz, M.T. et al., “General Synthesis of Potentially Antiviral α-Adamantyl Carbonyl Compounds”, Angew. Chem. Int. Ed. Engl., vol. 18, No. 1, p. 72 (1979).
Reetz, M.T. et al., “Lewis-Säure-bedingte α-tert-Alkylierung von Carbonsäuren und Carbonsäureestern”, Chem. Ber., vol. 116, pp. 3708-3724 (1983).
Reetz, M.T. et al., “Regioselektive Lewis-Säure-bedingte α-tert-Alkylierung von Acyloinen und Glycolsäure”, Chem. Ber., vol. 116, pp. 3702-3707 (1983).
Sagnard, I. et al., “Enantioselective Synthesis of Cyclopropane α-Amino Acids: Synthesis of N-Boc-cis-(2S,3R,4S)-3,4-Methanoproline and N-Boc-(2S,3R,4S)-3,4-Methanoglutamic Acid”, Tetrahedron Letters, vol. 36, No. 18, pp. 3148-3152 (1995).
Takada, H. et al., “Thermostable Phenylalanine Dehydrogenase ofThermoactinomyces intermedius: Cloning, Expression, and Sequencing of Its Gene”, J. Biochem., vol. 109, pp. 371-376 (1991).
Tverezovsky, V.V. et al., “Synthesis of (2S, 3R, 4S)-3,4-Methanoproline and Analogues by Cyclopropylidene Insertion”, Tetrahedron, vol. 53, No. 43, pp. 14773-14792 (1997).
U.S. Appl. No. 11/119,552, filed May 2, 2005, Patel et al.
U.S. Appl. No. 11/135,217, filed May 23, 2005, Sharma.
Cadin Matthew M.
Chen Jason G.
Politino Michael
Skonezny Paul M.
Bristol--Myers Squibb Company
Burton Rodney
Gibbsons Maureen S.
Kosar Aaron J
Tate Christopher R
LandOfFree
Process for preparing dipeptidyl peptidase IV inhibitors and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for preparing dipeptidyl peptidase IV inhibitors and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing dipeptidyl peptidase IV inhibitors and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4244326