Process for preparing a dipeptidyl peptidase IV inhibitor...

Details Process for preparing a dipeptidyl peptidase IV inhibitor... Process for preparing a dipeptidyl peptidase IV inhibitor...

2007-03-06

2007-03-06

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C560S227000

Reexamination Certificate

active

11091183

ABSTRACT:
A process is provided for preparing a dipeptidyl peptidase IV inhibitor of the structurewhereinis treated with TFAA in isopropyl acetate to protect the tertiary hydroxyl group as a trifluoroacetate group to form 4(which is a novel intermediate)which is converted to acid chloride compound 5(which is a novel compound)using Vilsmeier reagent or other chloro reagent and coupled with compound 6 in a heterogeneous mixture of ethyl acetate and aqueous bicarbonate to give compound 7The N,O-bis(trifluoroacetyl) groups of compound 7 are deprotected to give free base compound 10.

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
U.S. Appl. No. 11/104,015, filed Apr. 12, 2005, Politino, 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 Carbonsäureestem”, 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.

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