Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2011-03-22
2011-03-22
Saeed, Kamal A (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S360000, C514S361000, C514S364000, C514S406000, C546S208000, C548S122000, C548S132000, C548S374100
Reexamination Certificate
active
07910606
ABSTRACT:
The present invention is directed to a compound of formula I,in which R0; R1; R2; R3; R4; Q; V, G and M have the meanings indicated below. The compound of formula I is a pharmacologically active compound. It exhibits a strong anti-thrombotic effect and is suitable, for example, for the therapy and prophylaxis of a cardio-vascular disorder like a thromboembolic disease or restenosis. It is a reversible inhibitor of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is intended. The invention furthermore is directed to a process for the preparation of the compound of formula I, and pharmaceutical preparation comprising it.
REFERENCES:
patent: 5420141 (1995-05-01), Boigegrain et al.
patent: 5998424 (1999-12-01), Galemmo et al.
patent: 6020357 (2000-02-01), Pinto et al.
patent: 6339099 (2002-01-01), Lam et al.
patent: 6906084 (2005-06-01), Nazare et al.
patent: 6953857 (2005-10-01), Nazare et al.
patent: 7067665 (2006-06-01), Nazare et al.
patent: 7317027 (2008-01-01), Nazare et al.
patent: 2004/0171604 (2004-09-01), Nazare et al.
patent: 2004/0235824 (2004-11-01), Nazare et al.
patent: 2005/0009827 (2005-01-01), Nazare et al.
patent: 2005/0009829 (2005-01-01), Nazare et al.
patent: 2005/0033049 (2005-02-01), Nazare et al.
patent: 2005/0043302 (2005-02-01), Nazare et al.
patent: 2007/0049573 (2007-03-01), Bauer et al.
patent: 2007/0179122 (2007-08-01), Urmann et al.
patent: 0987274 (2000-03-01), None
patent: WO 92/06711 (1992-04-01), None
patent: WO 95/29189 (1995-11-01), None
patent: WO 96/12800 (1996-05-01), None
patent: WO 97/47651 (1997-12-01), None
patent: WO 98/28269 (1998-07-01), None
patent: WO 99/32454 (1999-07-01), None
patent: WO 99/37304 (1999-07-01), None
patent: WO 00/39131 (2000-07-01), None
patent: WO 00/69849 (2000-11-01), None
patent: WO 01/05784 (2001-01-01), None
patent: WO 01/07436 (2001-02-01), None
patent: WO 01/19798 (2001-03-01), None
patent: WO 01/29006 (2001-04-01), None
patent: WO 01/32628 (2001-05-01), None
patent: WO 02/00647 (2002-01-01), None
patent: WO 02/00651 (2002-01-01), None
patent: WO 02/085356 (2002-10-01), None
U.S. Appl. No. 09/794,214, filed Feb. 28, 2001, Zhu, et al.
Adang Anton E P et al., A New Generation Of Orally Active Antithrombotics: Comparing Strategies in The GPIIb/IIIa, Thrombin And Factor Xa Acreas, Drugs Of The Future, (2000), vol. 25, No. 4, pp. 369-383.
Articio, et al., Aromatic Hydrazides As Specific Inhibitors Of Bovine Serum Amine Oxidase, Eur. J. Med. (1992), 27, 219-228.
Ashton Wallace T. et al., A Regioselective Route To 3-Alkyl-l-aryl-1H-Pyrazole-5-carboxylates: Synthetic Studies And Structural Assignments, J. Heterocyclic Chem., (1993), vol. 30, pp. 307-311.
Auzzi, et al., Alogenazione DI Alcuni Derivati Pirazolo [1,5-a] Pirimidinici, Ed Sci (1979), 34, 743-750.
Booker-Milburn Kevin I., A Convenient Method For The Synthesis Of C-5 Substituted 1-Tosylpryazoles, SynLett; Apr. 1992; pp. 327-328.
Bravo Plerirancesco et al., An Efficient Entry To Perfluoroalkyl Substituted Azoles Starting From Beta-Perfluoroalkyl-Beta-Dicarbonyl Compounds, Tetrahedron, (1994), vol. 50, No. 29, pp. 8827-8836.
Bundgaard Hans, Novel Chemical Approaches In Prodrug Design, Drugs Of The Future, (1991), vol. 16, No. 5, pp. 443-456.
Butler, et al., New General Methods for the Substitution of 5-Chloropyrazoles. The Synthesis of 1,3-Dialkyl-5-chloropyrazol-4-yl Aryl Ketones and New 1,3-Dialkyl-2-pyrazolin-5-ones, J. Org. Chem. (1971) 36(17), 2542-2547.
Cerrada, et al., Synthesis Of p-Nitrophenylazoles By Phase Transfer Catalysis Without Solvent, Synth. Commun (1993). 23(14) 1947-1952.
Chan, et al., New N-and O-Arylations with Phenylboronic Acids and Cupric Acetate, Tetrahedron Letters 39 (1998) 2933-2936.
Cheng, et al, Relationship Between The Inhibition Constant (KI) And The Concentration Of Inhibitor Which Causes 50 Per Cent Inhibition (I50) Of An Enzymatic Reaction, Biochem. Pharmacol. (1973), 22, 3099-3106.
Collot, et al., First Combined Selective N- And C-Arylations With Boronic Acids: Application To The Synthesis Of 1,3-Diarylindazoles. Tetrahedron Letters (2000), 41, 9053-9057.
Cooper, et al., 1,4 Dihidropyridines As Antagonists Of Platelet Activating Factor. 1. Synthesis And Structure-Activity Relationships of 2-(4-Heterocyclyl) Phenyl Derivatives, J. Med. Chem. (1992), 35, 3115-3129.
Cozzi, et al., Ethyl 2- ([5,6-Dihydro-7-(1H-Imidazol-1-YL)-2-Naphthalenyl] Oxy]-2-Methylpropanonate As A New Potent Oxyisobutyrate Hypolipidaemic With Unusual Features, Farmaco (1987) 42, 205-218.
Dewar M. J. S. et al., Sulphaniliamides Of Some Aminopyrazoles And A Note On The Application Of p-phtalimidobenzenesulphonyl Chloride To The Synthesis Of Sulphanilamides, J. Chem. Soc. (1945), pp. 114-116.
Elnagdi Mohamed Hilmy et al., Recent Developments In The Synthesis Of Pyrazole Derivatives, Heterocycles, (1985), vol. 23, No. 12, pp. 3121-3153.
Erian Ayman W. et al., Phosphonium Ylides In Organic Synthesis III 1,2 A Novel Synthesis Of Alpha-Substituted Ylides And Pyrazole Systems, Synthetic Communications, (1999), vol. 29, No. 9, pp. 1527-1537.
Farina, et al., 1,3-Dipolar Cycloadditions With Methyl 4-OXO-And 4-Hydroxy-2-Butynoates. Synthesis Of Functionalized Pyrazoles And Triazoles, Heterocycles (1989) 29, 967.
Fleisher David et al., Improved Oral Drug Delivery: Solubility Limitations Overcome By The Use Of Prodrugs, Advances Drug Delivery Reviews, (1996), vol. 19, pp. 115-130.
Foti, et al., First Synthesis Of A Bromonitrilimine. Direct Formation of 3-Bromopyrazole Derivatives., Tetrahedron Letters (1999) 40, 2605-2606.
Gardner, et al., A Versatile Approach to Analogues of the Cannabinoid-like Anti-emetic Nonabine. J. Heterocyclic Chem. 21, (1984) 121-127.
Grimmett, et al., Synthesis And Reactions Of Lithiated Monocyclic Azoles Containing Two Or More Hetero-Atoms. Part III: Pyrazoles, Heterocycles, 37(3), (1994) 2087-2147.
Haque Tasir S. et al., Parallel Synthesis Of Potent, Pyrazole-Based Inhibitors Of Helicobacter pylori Dihydroorotate Dehydrogenase, J. Med. Chem., (2002), vol. 45, pp. 4669-4678.
Hartwig, J., Recent Advances in Palladium-and Nickel-catalyzed Chemistry Provide New Ways to Constryct C-N and C-O bonds, Angew. Chem. Int. Ed. (1996) 37, pp. 2046-2067.
Hartwig, et al., Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides And Chlorides And Extended Scope Of Aromatic C-N Bond Formation With a Commercial Ligand, J. Org. Chem. (1999) 64, 5575-5580.
Heinisch Gottfried et al., Pyrazole Chemistry. Part 4 Directed Lithiation Of 4-Bromo-1-phenyl-sulphonylpyrazole. A Convenient Approach To Vicinally Disubstituted Pyrazoles. J. Chem. Soc. Perkin Trans., (1990), pp. 1829-1834.
Holzer, et al., N1-Substituted 3,5-Dimethoxy-4-Halogeno-1H-Pyrazoles: Synthesis and NMR Study, J. Heterocyclic Chem. 32, 1351 (1995).
Huang, et al., Regioselective Synthesis of 1,3,5-Triaryl-4-alkylpyrazoles: Novel Ligands For The Estrogen Receptor, Organic Letters, (2000) 2, (18), 2833-2836.
Huisgen, et al., Diazocarbonyl Compounds And 1-Diethylaminopropyne, American Chemical Society, (1979), vol. 101, No. 13, pp. 3647-3648.
Jeon, et al., Synthesis Of New 4-Benzoyl-5-Hydroxy-3-Trifluoromethylpyrazole Derivatives VIA [1,3] Rearrangements Of Benzoyl Group Using tert-Butyllithium, Synth. Commun. (1998), 28(12), 2159-2166.
Jones R. G. et al., vic-Dicarboxylic Acid Derivatives Of Pyrazole, Isoxazole, And Pyrimidine, J. Org. Chem. (1955), 12, 1491.
Kang, et al., Copper-Catalyzed N-Arylation Of Aryl Iodides With Benzamides Or Nitrogen Heterocycles in the Presence Of Ethylenediamine, Synlett. (2002), 3, 427-430.
Klapars, et al., A General And Efficient Copper Catalyst For the Amidation Of Aryl Halides and The N-Arylation Of Nitrogen Heterocycles, J. Am. Chem. Soc. (2001), 123, 7727-7729.
Kudo Noriaki et al., Synthesis And Herbicidal Activity Of 1,5-Diarylpyrazole Derivatives, Chem. Pharm. Bull., (1999), vol. 47, No. 6, pp. 857-868.
Kwong, et al., Copper-Catalyzed
Matter Hans
Nazare Marc
Wehner Volkmar
Will David William
Ort Ronald G.
Saeed Kamal A
Sanofi-Aventis Deutschland GmbH
Scully, Scott, Murphy and Presser, P.C.
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