Highly enantiomerically pure lactam-substituted propanoic...

Details Highly enantiomerically pure lactam-substituted propanoic... Highly enantiomerically pure lactam-substituted propanoic...

2005-05-24

2005-05-24

Kifle, Bruck (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S551000

Reexamination Certificate

active

06897323

ABSTRACT:
The present invention relates to highly enantiomerically pure lactam-substituted propanoic acid derivatives and methods of making and using therefor. The invention involves a multi-step synthesis to produce the lactam compounds. In one step of the reaction sequence, asymmetric hydrogenation of a lactam-enamide was performed to produce an intermediate that can ultimately be converted to a series of pharmaceutical compounds. The invention also contemplates the in situ synthesis of an intermediate of the multi-step synthesis, which provides economic advantages to the overall synthesis of the lactam compounds.

REFERENCES:
patent: 3022293 (1962-02-01), Miller
patent: 4108992 (1978-08-01), Pearson et al.
patent: 4446146 (1984-05-01), Southgate et al.
patent: 4552889 (1985-11-01), Scott
patent: 4696943 (1987-09-01), Gobert et al.
patent: 19918420 (2000-10-01), None
patent: 0 106 988 (1984-05-01), None
patent: 0 306 266 (1989-03-01), None
patent: 0 365 992 (1990-05-01), None
patent: 1 309 692 (1973-03-01), None
patent: 2110207 (1983-06-01), None
patent: 2202075 (1988-09-01), None
patent: 10279541 (1998-10-01), None
patent: WO 92 16497 (1992-10-01), None
patent: WO 96 17862 (1996-06-01), None
patent: WO 97 40809 (1997-11-01), None
patent: WO 01 62726 (2001-08-01), None
Easton et al., Tetrahedron Letters (1990), 31 24, 3471-4.*
Ohkuma et al. “Catalytic Asymmetric Synthesis,” 2nd Ed. Wiley-VCH, Inc., pp. 1-17 (2000).
Zoller et al. “Amidoalkylation of Mercaptans With Glyoxylic Acid Derivatives” Tetrahedron, vol. 31:pp. 863-866 (1975).
Schmidt et al. Amino Acids and Peptides; XLIII, Dehydroamino Acids; XVIII, Synthesis of Dehydroamino Acids and Amino Acids from N-Acyl-2-(dialkyloxyphosphinyl)-glycin Esters; II Synthesis, pp. 53-60, Jan. 1984.
Richards et al, Tetrahedron: Asymmetry, 1998, vol. 9, pp. 2377-2407.
Fiorini et al, Journal of Molecular Catalysis, 1979, vol. 5, pp. 303-310.
Pracejus et al, Tetrahedron Letters, 1977, vol. 39, pp. 3497-3500.
Marquarding et al, Journal of the American Chemical Society, 1970, vol. 92, pp. 5389-5393.
Armstrong et al, Analytical Chemistry, 1985, vol. 57, No. 2, pp. 481-484.
Boaz, Tetrahedron Letters, 1989, vol. 30, No. 16, pp. 2061-2064.
Hayashi et al, Bull Chemical Society of Japan, 1980, vol. 53, No. 4, pp. 1138-1151.
Schmidt et al, Synthesis, 1992, pp. 487-490.
Katritzky et al, Journal of Organic Chemistry, 2000, vol. 65, pp. 4364-4369.
Lloyd et al, Tetrahedron, 1999, vol. 55, No. 33, pp. 10201-10220.
Nicolas et al, Drug Metabolism and Disposition, 1999, vol. 27, No. 2, pp. 250-254.
Wolfe et al, Journal of Organic Chemistry, 1997, vol. 62, pp. 654-663.
Kim et al., Bulletin of the Korean Chemical Society, 1996, vol. 17, No. 1, pp. 34-38.
Noyer et al, European Journal of Pharmacology, 1995, vol. 286, No. 2, pp. 137-146.
Baggaley et al, Journal of The Chemical Society, 1990, vol. 6, pp. 1521-1533.
Thaisrivongs et al, Journal of Medicinal Chemistry, 1988, vol. 31, No. 7, pp. 1369-1376.
Shipov et al, Journal of General Chemistry of the U.S.S.R., 1991, pp. 2142-2150.
Roth et al, Tetrahedron, 1995, vol. 51, No. 3, pp. 801-810.

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