Organic compounds -- part of the class 532-570 series – Organic compounds – 9,10-seco-cyclopentanohydrophenanthrene ring system or...
Reexamination Certificate
2007-06-26
2007-06-26
Qazi, Sabiha N. (Department: 1616)
Organic compounds -- part of the class 532-570 series
Organic compounds
9,10-seco-cyclopentanohydrophenanthrene ring system or...
C514S167000
Reexamination Certificate
active
11390999
ABSTRACT:
Compounds of formula 1A and 1B are provided where X1and X2are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological disorders
REFERENCES:
patent: 4666634 (1987-05-01), Miyamoto et al.
patent: 5086191 (1992-02-01), DeLuca et al.
patent: 5536713 (1996-07-01), Deluca et al.
patent: 5585369 (1996-12-01), DeLuca et al.
patent: 5843928 (1998-12-01), Deluca et al.
patent: 5945410 (1999-08-01), DeLuca et al.
patent: 6127559 (2000-10-01), DeLuca et al.
patent: 6384087 (2002-05-01), Zemel et al.
patent: 6537981 (2003-03-01), DeLuca et al.
patent: 6566352 (2003-05-01), DeLuca et al.
patent: 6579861 (2003-06-01), DeLuca et al.
patent: 6627622 (2003-09-01), DeLuca et al.
patent: 2002/0091109 (2002-07-01), Takenouchi et al.
patent: 2002/0192264 (2002-12-01), Zemel et al.
patent: 2004/0220418 (2004-11-01), DeLuca et al.
patent: 2005/0004085 (2005-01-01), DeLuca et al.
patent: 2005/0065088 (2005-03-01), Thompson
patent: 2005/0065133 (2005-03-01), Lee
patent: 2005/0065180 (2005-03-01), Lee
patent: 2005/0070512 (2005-03-01), Lee
Ishizuka et al., BioChemistry, 1984, 23, 1473-1478.
Endres et al., BioChemistry, 2000, 2123-2129.
International Search Report dated Aug. 11, 2006 for PCT/US2006/011508.
Baggiolini et al., “Stereocontrolled Total Synthesis of 1α,25-Dihydroxycholecalciferol and 1α,25-Dihydroxyergocalciferol,” J. Org. Chem.,51, 3098 (1986); published by American Chemical Society.
Bury, Y. et al.., “Structure Activity Relationship of Carboxylic Ester Antagonists of the Vitamin D3Receptor,” Mol. Pharmacol., 58 (5), 1067 (2000); published by The American Society for Pharmacology and Experimental Therapeutics; published by American Chemical Society.
Daniewski et al., “A Novel Silylcopper Catalyst for the Reductive Bromination of Hajos Dione. Improved Preparation of a CD Synthon for the Synthesis of Vitamin D,” J. Org. Chem., 66, 626-628 (2001); published by American Chemical Society.
Herdick, M. et al., “Carboxylic ester antagonists of 1α,25-dihydroxyvitamin D3show cell-specific actions,” Chem. Biol., 7 (11), 885 (2000); published by Elsevier Science Ltd.
Herdick, M. et al., “Antagonistic Action of a 25-Carboxylic Ester Analogue of 1α,25-Dihydroxyvitamin D3Is Mediated by a Lack of Ligand-induced Vitamin D Receptor Interaction with Coactivators,” J. Biol. Chem., 275 (22), 16506 (2000); published by The American Society for Pharmacology and Experimental Therapeutics.
Hiroshi, H. et al., Abstract of JP 03210156, Sep. 13, 1991.
Ishizuka, S. et al., “Vitamin D antagonist, TEI-9647, inhibits osteoclast formation induced by 1α,25-hydroxyvitamin D3from pagetic bone marrow cells,” J. Steroid Biochem. Mol. Biol., 89-90 (1-5), 331 (2004); published by Elsevier Ltd.
Ishizuka, S. et al., “Antagonistic Actions in Vivo of (23S)-25-Dehydro-1α-Hydroxyvitamin D3-26,23-Lactone on Calcium Metabolism Induced by 1α,25-Dihydroxyvitamin D3,” Endocrinology, 142 (1), 59 (2001); published by The Endocrine Society.
Lythgoe, et al., “Calciferol and its Relatives. Part 22. A Direct Total Synthesis of Vitamin D2and Vitamin D3,” J. Chem. Soc. Perkin Trans. I, N6, 590 (1978).
Lythgoe, “Synthetic Approaches to Vitamin D and its Relatives,” Chem. Soc. Rev., 9, 449 (1983).
Mascarenas et al., “Studies of the Synthesis of Side-Chain Hydroxylated Metabolites of Vitamin D. 3. Synthesis of 25-Ketovitamin D3and 25-Hydroxyvitamin D3,” J. Org. Chem., 51, 1269 (1986).
Mincione et al., “Improved Conversion of Vitamin D2into the Windaus Ketone and its Regioselective Hydroxylation via Organoboranes at C26,” Synth. Commun., 19, 723 (1989).
Miura, D. et al., “Antagonistic Action of Novel 1α, 25-Dihydroxyvitamin D3-26,23-lactone Analogs on Differentiation of Human Leukemia Cells (HL-60) Induced by 1α-25-Dihydroxyvitamin D3,” J. Biol. Chem., 274 (23), 16392 (1999); published by The American Society for Biochemistry and Molecular Biology, Inc.
Nishii et al., “The Development of Vitamin D3Analogues for the Treatment of Osteoporosis,” Osteoporosis Int. Suppl. 1, 190 (1993); published by European Foundation for Osteoporosis.
Perlman, et al., “1α, 25-Dihydroxy-19-Nor-Vitamin D3, a Novel Vitamin D-related Compound with Potential Therapeutic Activity,” Tetrahedron Lett. 31(13), 1823 (1990); published by Pergamon Press plc.
Perlman et al., “Novel Synthesis of 19-Nor-Vitamin D Compounds,” Tetrahedron Lett., 32 (52), 7663 (1991);published by Pergamon Press plc.
Peterson et al., “Studies of the Ketone Obtained from the Ozonolysis of Vitamin D. Molecular Mechanics Calculations for It and Related Hydrindanones,” J. Org. Chem., 51, 1948 (1986); published by American Chemical Society.
Posner et al., “Stereocontrolled Total Synthesis of Calcitriol Derivatives: 1,25-Dihydroxy-2-(4′-hydroxybutyl)vitamin D3Analogs of an Osteoporosis Drug,” J. Org. Chem., 59, 7855 (1994); published by American Chemical Society.
Posner et al., “2-Fluoroalkyl A-Ring Analogs of 1,25-Dihydroxyvitamin D3-Stereocontrolled Total Synthesis via Intramolecular and Intermolecular Diels-Alder Cycloadditions. Preliminary Biological Testing,” J. Org. Chem., 60, 4617 (1995).
Saito et al., “Remarkable effect of 2α-modification on the VDR antagonistic activity of 1α-hydroxyvitamin D3-26,23-lactones,” Org. Biomol. Chem., 1, 4396 (2003); published by The Royal Society of Chemistry.
Sardina et al., “Studies on the Synthesis of Side-Chain Hydroxylated Metabolites of Vitamin D. 2. Stereocontrolled Synthesis of 25-Hydroxyvitamin D2,” J. Org. Chem., 51, 1264 (1986); published by American Chemical Society.
Sicinski, R. R. et al., “New 1α,25-Dihydroxy-19-norvitamin D3Compounds of High Biological Activity: Synthesis and Biological Evaluation of 2-Hydroxymethyl, 2-Methyl, and 2-Methylene Analogues,” J. Med. Chem., 41, 4662-4674 (1998); published by American Chemical Society.
Toell, A. et al., “Different Molecular Mechanisms of Vitamin D3Receptor Antagonists,” Mol. Pharmacol., 59 (6), 1478 (2001); published by The American Chemical Society for Pharmacology and Experimental Therapeutics.
Toh et al., “Studies on a Convergent Route to Side-Chain Analogues of Vitamin D: 25-Hydroxy-23-oxavitamin D3,” J. Org. Chem., 48, 1414 (1983); published by American Chemical Society.
Väisänen, S. et al., “Critical Role of Helix 12 of the Vitamin D3Receptor for the Partial Agonism of Carboxylic Ester Antagonists,” J. Mol. Biol., 315 (2), 229 (2002); published by Academic Press.
Chiellini Grazia
Clagett-Dame Margaret
DeLuca Hector F.
Grzywacz Pawel
Plum Lori A.
Qazi Sabiha N.
Wisconsin Alumni Research Foundation
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