Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-11-14
2008-11-18
Davis, Zinna N (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S143000, C546S152000, C546S159000
Reexamination Certificate
active
07452994
ABSTRACT:
This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.
REFERENCES:
patent: 5563151 (1996-10-01), Bowles
patent: 5583131 (1996-12-01), Bridger
patent: 5698546 (1997-12-01), Bridger
patent: 5817807 (1998-10-01), Bridger
patent: 5932749 (1999-08-01), Li
patent: 6365583 (2002-04-01), MacFarland
patent: WO-99/31264 (1999-06-01), None
patent: WO-99/32100 (1999-07-01), None
patent: WO-00/45814 (2000-08-01), None
patent: WO-00/56729 (2000-09-01), None
Abernethy et al, Journal of Organic Chemistry, vol. 25, pp. 1924-1928, 1960.
Alreja et al., Heterocycles (1986) 24:1637.
Ami and Horui, Biosci. Biotechnol. Biochem. (1999) 63:2150-2156.
Balkenkohl et al., J. Prakt. Chem. (1997) 339:381-384.
Biard-Piechaczyk et al., Immunology Letters (1999) 701-3.
Blanco et al., The CXCR4 Antagonist AMD3100 Efficiently Inhibits Cell-Surface-Expressed Human Immunodeficiency Virus Type 1 Envelop-Induced Apoptosis American Society for Microbiology, Jan. 2000, pp. 51-56.
Bosch et al., Bioorganic & Medicinal Chemistry Letters (2000) 10:563-566.
Campos et al., Tetrahedron:Asymmetry (2000) 11:2705-2717.
Carrea and Riva, Angew. Chem. Int. Ed. Engl. (1999) 39-2226.
Cliffe et al., Tetrahedron Letters (1991) 32(46):6789-6792.
Crossley et al., journal? 977-982.
De Castro et al., Tetrahedron (2000) 56:1387-1391.
Fedyk et al., Journal of Leukocyic Biology 66:667.
Glase et al., J. Med. Chem. (1995) 38:3132-3137.
Gotor, Biocat. Biotrans. (2000) 18:87.
Greene and Wuts, Protective Groups in Organic Synthesis, 3rd edition, Wiley-Interscience, New York (1999) pp. 552-564.
Gupta et al., J. Biol. Chem. (1998) 7:4282-4287.
Gutman et al., Tetrahedron:Asymmetry (1998) 9:4369.
Hacking et al., Mol. Catalysis B:Enzymatic (2000) 9:201-208.
Herbein et al., Nature (1998) 395:189-193.
Hesselgesser et al., Current Biology, (1997) 7(2):112-121.
Hesselgesser et al. Current Biology (1998) 8(10):595-598.
Honel and Vierhapper, J. Chem. Soc. Perkin. I. (1980) 1933-1939.
Honel and Vierhapper, Monatshefte für Chemie (1984) 115:1219-1228.
Iglesias et al., Tet. Asym. (1997) 8:2675-2677.
International Search Report for PCT/US02/29372, mailed on Aug. 10, 2004, 4 pages.
Kato et al., Enantiomer (2000) 5:521-524.
Kazlauskas and Weissfloch, J. of Molecular Catalysis B:Enzymatic (1997) 3:65-72.
Kitaguchi et al., Am. Chem. Soc. (1989) 111:3094-3095.
Koeller and Wong, Nature (2001) 409:232.
Koltunov and Repinskaya, Russ. J. Org. Chem. (2000) 36:446-447.
Lardenois et al., Synth. Comm. (1996) 26:2305.
Lee et al., Blood (1999) 93(4):1145-1156.
Luna et al., Tet. Asym. (1998) 9:4483-4487.
Maestro et al., Tetrahedron:Assymetry (1997) 8:3153-3159.
Messina et al., J. Org. Chem. (1999) 64:3767-3769.
Morgan et al., J. Org. Chem. (2000) 65:5451-5459.
Nikolic et al., Nature (1998) 395:194.
Ohagen et al., Journal of Virology (1999) 73(2):897-906.
Okazaki et al., Bull. Chem. Soc. Jpn. (1990) 63:3167.
Orsat et al., J. Am. Chem. Soc. (1996) 118:712-713.
Ponath, Exp. Opin. Invest. Drugs (1998) 7:1-18.
Pozo and Gotor, Tetrahedron (1993) 49:4321-4326.
Reetz and Dreisbach, Chimia (1994) 48:570.
Rylander, Catalytic Hydrogenation over Platinum Metals, Academic Press, New York (1967) p. 385.
Sanchez et al., Tet. Asym. (1997) 8:37-40.
Schoffers et al., Tetrahedron (1996) 52:3769-3826.
Schramm et al., Journal of Virology (2000) volume?:184-192.
Sharma et al., Synthesis (1981) 316-318.
Shiotani et al., Yakagaku Zasshi (1967) 87:547-549.
Smidt et al., Biotechnology Techniques (1996) 10:335-338.
Sucheck et al., Angew. Chem. Int. Ed. (2000) 39(6):1080-1084.
Supplementary European Search Report for EP 02 77 5823, mailed on Dec. 23, 2004, 3 pages.
Tagawa et al., Heterocycles (1989) 29:1741.
Tagawa et al., Heterocycles (1989) 29:1781.
Tagawa et al., Heterocycles (1992) 33:327.
Tagawa et al., Heterocycles (1992) 34:1605.
Takayama et al., Chem. Soc. Chem. Commun. (1999) 2:127-128.
Takayama et al., Tet. Lett. (1996) 37:6287-6290.
Tanida et al., J. of Heterocyclic Chemistry (1986) 23:177-181.
Van Langen et al., Tetrahedron:Asymmetry (2000) 11:4593-4600.
Van Rantwijk et al., Monat. Chem. (2000) 131:549.
Vierhapper and Eliel, J. Am. Chem. Soc. (1974) 96:2256-2257.
Vierhapper and Eliel, J. Org. Chem. (1975) 40:2729-2734.
Vierhapper and Honel, Monat. Chem. (1984) 115:1219-1228.
Wagegg et al., Journal of Biotechnology (1998) 61:75-78.
Wang et al., J. Org. Chem. (1997) 62:3488-3495.
Crossley et al., J Chem Soc. 1976.
Fedyk et al., Journal of Leukocyic Biology 66:667, 1999.
Greene and Wuts, Protective Groups in Organic Synthesis, 3rd edition, Wiley-Interscience.
Juaristi et al., Tetrahedron: Asymmetry (1999) 10:2441-2495.
Office Action for European Application No. 02 775 823.4, mailed on Mar. 26, 2008, 3 pages.
Bridger Gary J.
McEachern Ernest J.
Skerlj Renato T.
Skupinska Krystyna A.
Yang Wen
Anormed Inc.
Davis Zinna N
Morrison & Foerster / LLP
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