(R)-chiral halogenated substituted fused heterocyclic amino...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C564S336000

Reexamination Certificate

active

11373770

ABSTRACT:
The invention relates to substituted aryl and heteroaryl (R)-Chiral Halogenated 1-Substitutedamino-(n+1)-Alkanol compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Novel high yield, stereoselective processes for the preparation of the chiral substituted alkanol compounds from chiral and achiral intermediates are described.

REFERENCES:
patent: 2700686 (1955-01-01), Dickey et al.
patent: 3334017 (1967-08-01), Biel
patent: 3359316 (1967-12-01), Biel
patent: 3534100 (1970-10-01), Bollag et al.
patent: 5306718 (1994-04-01), Lauffer et al.
patent: 5932587 (1999-08-01), Schmeck et al.
patent: 6063788 (2000-05-01), Brandes et al.
patent: 6069148 (2000-05-01), Schmidt et al.
patent: 6127383 (2000-10-01), Schmidt et al.
patent: 6448295 (2002-09-01), Sikorski et al.
patent: 6451823 (2002-09-01), Sikorski et al.
patent: 6451830 (2002-09-01), Sikorski et al.
patent: 6455519 (2002-09-01), Sikorski et al.
patent: 6458803 (2002-10-01), Sikorski et al.
patent: 6458852 (2002-10-01), Sikorski et al.
patent: 6462092 (2002-10-01), Sikorski et al.
patent: 6476057 (2002-11-01), Sikorski et al.
patent: 6476075 (2002-11-01), Sikorski et al.
patent: 6479552 (2002-11-01), Sikorski et al.
patent: 6482862 (2002-11-01), Sikorski et al.
patent: 6521607 (2003-02-01), Sikorski et al.
patent: 6544974 (2003-04-01), Sikorski et al.
patent: 6583183 (2003-06-01), Sikorski et al.
patent: 6586433 (2003-07-01), Sikorski et al.
patent: 6605624 (2003-08-01), Lee et al.
patent: 6677341 (2004-01-01), Sikorski et al.
patent: 6677353 (2004-01-01), Sikorski et al.
patent: 6677375 (2004-01-01), Sikorski et al.
patent: 6677379 (2004-01-01), Vernier et al.
patent: 6677380 (2004-01-01), Sikorski et al.
patent: 6677382 (2004-01-01), Sikorski et al.
patent: 6683099 (2004-01-01), Sikorski et al.
patent: 6683113 (2004-01-01), Sikorski et al.
patent: 6696472 (2004-02-01), Sikorski et al.
patent: 6699898 (2004-03-01), Sikorski et al.
patent: 6710089 (2004-03-01), Sikorski et al.
patent: 6723522 (2004-04-01), Kimura et al.
patent: 6723752 (2004-04-01), Sikorski et al.
patent: 6723753 (2004-04-01), Sikorski et al.
patent: 6765023 (2004-07-01), Sikorski et al.
patent: 6787570 (2004-09-01), Sikorski et al.
patent: 6794396 (2004-09-01), Lee et al.
patent: 6803388 (2004-10-01), Sikorski et al.
patent: 6924313 (2005-08-01), Sikorski et al.
patent: 441366 (1968-01-01), None
patent: 19627430 (1998-01-01), None
patent: 0442172 (1991-08-01), None
patent: 0314435 (1993-09-01), None
patent: 0801060 (1997-10-01), None
patent: 0796846 (2000-07-01), None
patent: 0818197 (2003-11-01), None
patent: 0818448 (2003-11-01), None
patent: 2305665 (1997-04-01), None
patent: 5320117 (1993-12-01), None
patent: 0978277 (1997-03-01), None
patent: 10287662 (1998-10-01), None
patent: WO 9001874 (1990-03-01), None
patent: WO 9002113 (1990-03-01), None
patent: WO 9738973 (1997-10-01), None
patent: WO 9839299 (1998-09-01), None
Abrale, F., et al.,Synthesis and Reactions of Enantiomerically Pure Chloromethyl Oxiranes, Tetrahedron; Asymmetry, vol. 7, No. 2, pp. 581-594, (1996).
Barrett, A. G. M., et al.,Total Synthesis and Stereochemical Assignment of the Quinquecyclopropane-Containing Cholesteryl Ester Transfer Protein Inhibitor U-106305, J. Am. Chem. Soc., vol. 118, pp. 7863-7864 (1996).
Barter, P. J., et al.High density lipoproteins and coronary heart disease, Atherosclerosis, vol. 121, pp. 1-12 (1996).
Bisgaler, C. L., et al.,Cholesteryl Ester Transfer Protein Inhibition by PD 140195, Lipids, vol. 29, No. 12, pp. 811-818, (1994).
Bonin, P. D., et al.,A peptide inhibitor of cholesteryl ester transfer protein identified by screening a beteriophage display library, J. Peptide Res., vol. 51, pp. 216-225, (1998).
Bravo, P., et al.,New Fluorinated Chiral Synthons, Tetrahedron: Asymmetry, vol. 5, No. 6, pp. 987-1004, (1994).
Busch, S. J., et al.,Cholesteryl Ester Analogs Inhibit Cholesteryl Ester but not Triglyceride Transfer Catalyzed by the Plasma Cholesteryl Ester-Triglyceride Transfer Protein, Lipids, vol. 25, No. 4, pp. 216-220 (1990).
Cho, Kyung-Hyun, et al.,A peptide from hog plasma that inhibits human cholesteryl ester transfer protein, Biochimica et Biophysica Acta, vol. 1391, pp. 133-144 (1998).
Connolly, D. T., et al.,Inactivation of Cholesteryl Ester Transfer Protein by Cysteine Modification, Biochemical&Biophysical Research Communications, vol. 223, pp. 42-47 (1996).
Coval, S. J., et al.,Wiedendiol-A and -B Cholesteryl Ester Transfer Protein Inhibitors from the Marin Sponge Xestospongia Wiedenmayeri, Bioorganic&Medicinal Chemistry Letters, vol. 5, No. 6, pp. 605-610 (1995).
DesMarteau, D. D., et al.,The first fluoroalkylation of amino acids and peptides in water utilizing the novel iodonium salt (CF3SO2)2NI(Ph)CH2CF3, Chem. Commun., pp. 2241-2242 (1998).
Dunn, C., et al.,The Synthesis of Fluorine-containing Pterins, Tetrahedron, vol. 52, No. 40, pp. 13017-13026, (1996).
Hegde, V. R., et al.,A depsipeptide fungal metabolite inhibitor of cholesteryl ester transfer protein, Biorganic&Medicinal Chemistry Letters, vol. 8, pp. 1277-1280, (1998).
House's Modern Synthetic Reactions, W. A. Benjamin, Inc., Chapter 7, pp. 353-421, 1972.
House's Modern Synthetic Reactions, W. A. Benjamin, Inc., pp. 163-215, 1965.
Katagiri, T.,Intramolecular SN2 reaction at α-carbon of trifluoromethyl group: preparation of optically active 2-trifluormethylaziridine, Tetrahedron:Assymetry, vol. 8, No. 17, pp. 2933-2937, (1997).
Kuo, M. S.; et al.,Discovery, Isolation, Structure Elucidation, and Biosynthesis of U-106305, a Cholesteryl Ester Transfer Protein Inhibitor from UC 11136, J. Am. Chem. Soc., vol. 117, pp. 10829-10634, (1995).
Lee, J. C., et al.,A Cholesteryl Ester Transfer Protein Inhibitor from an Insect-associated Fungus, The Journal of Antibiotics, vol. 49, No. 7, pp. 693-696, (1996).
March's Advanced Organic Chemistry, 4thEdition, John Wiley & Sons, pp. 293-412 and pp. 649-658.
Marcoux, J. F., et al.,A General Copper-Catalyzed Synthesis of Diaryl Ethers, J. Am. Chem. Soc., vol. 119, pp. 10539-10540, (1997).
McBee, E. T., et al.,The Preparation and Properties of 3,3,3-Trifluoro-1,2-epoxypropane, J. Am. Chem. Soc., vol. 74, pp. 3022-3023 (1952).
McCarthy, P. A., et al.,New Approaches to Atherosclerosis: An Overview, Medicinal Research Reviews, vol. 13, No. 2, pp. 139-159, (1993).
Morton, R. E., et al.,Regulation of lipid transfer between lipoproteins by an endogenous plasma protein: selective inhibition among lipoprotein classes, Journal of Lipid Research, vol. 35, pp. 836-847, (1994).
Patent Abstracts of Japan, vol. 1997, No. 7, Jul. 31, 1997.
Pietzonka, T., et al.,Phosphonate-containing Analogs of Cholesteryl Ester as Novel Inhibitors of Cholesteryl Ester Transfer Protein, Bioorganic&Medicinal Chemistry Letters, vol. 6, No. 16, pp. 1951-9154 (1996).
Ramachandran, P. V., et al.,Chiral Synthesis via Organoboranes. 40. Selective Reductions. 55. A Simple One-Pot Synthesis of the Enantiomers of(Trifluoromethyl)oxirane. A General Synthesis in High Optical Purities of α-Trifluoromethyl Secondary Alcohols via the Ring-Cleavage Reactions of the Epoxide, J. Org. Chem., vol. 60, pp. 41-46, (1995).
Reagents for Organic Synthesis, Feiser & Feiser, vol. 1, copyright 1967, John Wiley & Sons, Inc.
Sheradsky, T., et al.,Studies on the Preparation of N-Alkyl-O-phenylhydroxylamines, J. Chem. Soc. Perkin Trans., vol. 12, pp. 2781-2761, (1980).
Sirtori, C. R.,New Targets for Lipid Lowering and Atherosclerosis Prevention, Pharmac. Ther., vol. 67, No. 3, pp. 433-447 (1995).
Son, Y. C., et a.,Purification and Characterization of Human Plasma Proteins that Inhibit Lipid Transfer Activities, Biochimica et Biophysica, Acta, vol. 795, pp. 473-480, (1984).
Sternbach, D. D., et al.,Reduction of O-Acyl Oximes, Tetrahedron Letters, vol. 22, No. 35, pp. 3331-3334, (1981).
Swenson, T.L., et al.,Mechanism of Cholesteryl Ester Transfer Protein Inhibition by a Neutralizing Monoclonal Antibody and Mapping of

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

(R)-chiral halogenated substituted fused heterocyclic amino... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with (R)-chiral halogenated substituted fused heterocyclic amino..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and (R)-chiral halogenated substituted fused heterocyclic amino... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3875466

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.