Synthesis of 4/5-pyrimidinylimidazoles via sequential...

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

07807832

ABSTRACT:
This invention relates to methods of making pyrimidinyl-substituted imidazole compounds by sequential substitution of the 4- and 2-chloro groups of 2,4-dichloropyrimidine, nucleophilic substitution to form pyrimidinylalkyne derivatives, oxidation to the corresponding 1,2-diketones, and cyclocondensation reactions.

REFERENCES:
patent: 3778441 (1973-12-01), Burckhardt et al.
patent: 2005/0085473 (2005-04-01), Hirschheydt et al.
patent: 02072165 (1990-03-01), None
patent: WO 01/37835 (2001-05-01), None
patent: WO 01/38324 (2001-05-01), None
patent: WO 02/088108 (2002-11-01), None
patent: WO 02/088113 (2002-11-01), None
patent: WO 03/087026 (2003-10-01), None
Dorwald F. A. Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim p. IX of Preface.
Wolff et. al., “Burger's Medicinal Chemistry and Drug Discovery,” 5th Ed. Part 1, pp. 975-977 (1995).
Banker, et. al., Modern Pharmaceuticals, (1996) p. 596.
International Search Report dated Nov. 29, 2006 for corresponding Appln. No. PCT/US2006/029280.
De Dios A. et al.: “Design of Potent and Selective 2-aminobenzimidazole-based p38alpha MAP kinase inhibitors with excellent in vivo efficacy” Journal of Medicinal Chemistry vol. 48, No. 7, Apr. 7, 2005, pp. 2270-2273, XP002407719.
Adams, J.L. et al. Pyrimdinylimidazole Inhibitors of p38: Cyclic N-1 Imidazole Substituents Enhance p38 Kinas Inhibition and Oral Activity.Bioorg. Med. Chem. Lett. 2001, 11, 2867-2870.
Bulman Page, P.C.; Rosenthal, S. A Simple and General Synthesis of α-Keto Esters.Tetrahedron Lett. 1986, 27, 1947-1950.
Chi, K.-W. et al. Palladium Catalyst in DMSO for the Oxidation of Tolans to Benzils.Synth. Commun. 1994, 24, 2119-2122.
Chu-Moyer, M.Y. et al. Orally-Effective, Long-Acting Sorbitol Dehydrogenase Inhibitors: Synthesis, Structure-Activity Relationships, and in Vivo Evaluations of Novel Heretocycle-Substituted Piperazino-Pyrimidines.J. Med. Chem. 2002, 45, 511-528.
Deng, X.; Mani, N. An Efficient Route to 4-Aryl-5-pyrmidinylimidazoles via Sequential Functionalization of 2,4-Dichloropyrimidine.Org. Lett. 2006, 8(2), 269-272.
Frantz, D.E. et al. Synthesis of Substituted Imidazoles via Organocatalysis.Org. Lett. 2004, 6, 843-846.
Fullerton, T. et al. Suppression of ex Vivo Cytokine Production by SB-242235, A Selective Inhibitor of p38 MAP Kinase.Clin. Pharmacol. Ther. 2000, 67, 114, Abstract OI-B-4.
Holand, S.; Epsztein, R. Recherches sur les α-glycols acétyléniques. IV.—Etude du comportement des α-glycols α,α'-diacétyleéniques diastéréoisoméres en milieu alcalin.Bull. Chim. Soc. Fr. 1971, 5, 1694-1701.
Ito, S. et al. Synthesis and Self-Assembly of Functionalized Hexa-peri-hexabenzocoronenes.Chem.—Eur. J. 2000, 6, 4327-4342.
Kita, Y. et al. Hypervalent Iodine Oxidation of Ethynylcarbinols: A Short and Efficient Conversion of Dihydroxyacetonyl Groups from Keto Groups.Chem. Pharm. Bull. 1989, 37, 891-894.
Lee, D.G.; Chang, V.S. Oxidation of Hydrocarbons. 9. The Oxidation of Alkynes by Potassium Permanganate.J. Org. Chem. 1979, 44, 2726-2730.
Liverton, N. J. et al. Design and Synthesis of Potent, Selective, and Orally Bioavailable Tetrasubstituted Imidazole Inhibitors of p38 Mitogen-Activated Protein Kinase.J. Med. Chem. 1999, 42, 2180-2190.
Mangalagiu, I. Ethenylation and Alkynylation in Palladium-Catalyzed Carbosubstitution in Heteroazines.Acta Chem. Scand. 1996, 50, 914-917.
McIntyre, C.J. et al. Pyridazine Based Inhibitors of p38 MAPK.Bioorg. Med. Chem. Lett. 2002, 12, 689-692.
Minato, M. et al. Osmium Tetraoxide Catalyzed Vicinal Hydroxylation of Higher Olefins by Using Hexacyanoferrate(III) Ion as a Cooxidant.J. Org. Chem. 1990, 55, 766-768.
Mylari, B.L. et al. Sorbitol Dehydrogenease Inhibitors (SDIs): A New Potent, Enantiomeric SDI, 4-[2-1R-Hydroxy-ethyl)-pyrimidin-4-yl]-piperazine-1-sulfonic Acid Dimethylamide.J. Med. Chem. 2001, 44, 2695-2700.
Pattenden, G. et al. Facile Synthesis of the “Tricarbonyl” Subunit in the Immunosuppressant Rapamycin.Tetrahedron Lett. 1993, 34, 2677-2680.
Revesz, L. et al. Novel p38 Inhibitors with Potent Oral Efficacy in Several Models of Rheumatoid Arthritis.Bioorg. Med. Chem. Lett. 2004, 14(13), 3595-3599.
Sharpless, K.B. et al. Permanganate in Acetic Anhydride. α-Diketones Directly from Olefins.J. Am. Chem. Soc. 1971, 93, 3303-3304.
Sonogashira, K. et al. A Convenient Synthesis of Acetylenes: Catalytic Substitutions of Acetylenic Hydrogen with Bromoalkenes, Iodoarenes, and Bromopyridines.Tetrahedron Lett. 1975, 16(50), 4467-4470.
Srinivasan, N.S.; Lee, D.G. Preparation of 1,2-Diketones: Oxidation of Alkynes by Potassium Permanganate in Aqueous Acetone.J. Org. Chem. 1979, 44, 1574.
Tullis, J.S. et al. The Development of New Triazole Based Inhibitors of Tumor Necrosis Factor-α (TNF-α) Production.Bioorg. Med. Chem. Lett. 2003, 13, 1665-1668.
Van Leusen, A.M. et al. Base-Induced Cycloaddition of Sulfonylmethyl Isocyanides to C,N Double Bonds. Synthesis of 1,5-Disubstituted and 1,4,5-Trisubstituted Imidazoles from Aldimines and Imidoyl Chlorides.J. Org. Chem. 1977, 42, 1153-1159.
Walsh, C.J.; Mandal, B.K. Improved Synthesis of Unsymmetrical, Heteroaromatic 1,2-Diketones and the Synthesis of Carbazole Ring Substituted Tetraaryl Cyclopentadieneones.J. Org. Chem. 1999, 64, 6102-6105.
Yoshida, K; Taguchi, J. Reaction of N-Substituted Cyclic Amines with 2,4-Dichloroquinazoline, 2,4-Dichloropyrimidine, and its 5-Methyl Derivative.J. Chem. Soc., Perkin Trans. 1 1992, 7, 919-922.
Yusubov, M.S. et al. Chemoselective Oxidation of Carbon-Carbon Double or Triple Bonds to 1,2-Diketones with DMSO-Based Reagents.Synthesis1995, 10, 1234-1236.
Yusubov, M.S. et al. Synthesis of Unsymmetrical Hetaryl-1,2-diketones.Tetrahedron2002, 58, 1607-1610.
2-(2,6-Dichlorophenyl)-4,5-diarylimidazoles as c-Met Tyrosine Kinase Inhibitors.iDrugs2003, 6(12), 1202.

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

Synthesis of 4/5-pyrimidinylimidazoles via sequential... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of 4/5-pyrimidinylimidazoles via sequential..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of 4/5-pyrimidinylimidazoles via sequential... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4229843

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