Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2008-01-08
2008-01-08
Shiao, Rei-tsang (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S277100, C546S277400, C548S469000
Reexamination Certificate
active
07317027
ABSTRACT:
The present invention relates to compounds of the formula Iwherein R0, R1, R2, R3, Q, V, G and M are as defined herein. The compounds of the formula I are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors 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 relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.
REFERENCES:
patent: 6140351 (2000-10-01), Arnaiz et al.
patent: 6337344 (2002-01-01), Defossa
patent: 6436965 (2002-08-01), Labelle et al.
patent: 6790853 (2004-09-01), Jacobson et al.
patent: 6906084 (2005-06-01), Nazare et al.
patent: 6953857 (2005-10-01), Nazaré et al.
patent: 7067665 (2006-06-01), Nazaréet al.
patent: 7135469 (2006-11-01), Pinto
patent: 2004/0171604 (2004-09-01), Nazaréet al.
patent: 2004/0204406 (2004-10-01), Nazaréet al.
patent: 2004/0235824 (2004-11-01), Nazaréet al.
patent: 2005/0009827 (2005-01-01), Nazaréet al.
patent: 2005/0009829 (2005-01-01), Nazaréet al.
patent: 2005/0033049 (2005-02-01), Nazaréet al.
patent: 2005/0043302 (2005-02-01), Nazaréet al.
patent: 0987274 (2000-03-01), None
patent: 2004203791 (2004-07-01), None
patent: 2004210716 (2004-07-01), None
patent: WO92/06711 (1992-04-01), None
patent: WO95/29189 (1995-11-01), None
patent: WO96/12800 (1996-05-01), None
patent: WO97/47651 (1997-12-01), None
patent: WO01/07436 (2001-02-01), None
patent: WO 01/19788 (2001-03-01), None
patent: WO 01/64639 (2001-09-01), None
patent: WO 02/00651 (2002-01-01), None
patent: WO 02/070523 (2002-09-01), None
Wang et al., 2002, CAS:137169502.
U.S. Appl. No. 09/794,214, filed Feb. 28, 2001, Zhu et al.
U.S. Appl. No. 10/326,005, filed Dec. 20, 2002, Castelhano et al.
U.S. Appl. No. 10/510,046, filed Oct. 01, 2004, Cezanne et al.
U.S. Appl. No. 10/301,397, filed Nov. 21, 2002, Nazaré.
Adang, Anton E. P. et al., A New Generation of Orally Active Antithrombotics: Comparing Strategies in the GPII/IIIa, Thrombin and Factor Xa Areas, Drugs of the Future, (2000), vol. 24, No. 4, pp. 369-383.
Ball, et al., The Mechanism of Lithiation and Nitrile Insertion Reactions of beta-methylazines: evidence from the structure of 3-C5H4NCH=C(Ph)N(H)C(Ph)=NLi PMDETA, J. Organomet. Chem.; 550; 1998; pp. 457-461.
Beswick, et al., The Synthesis of 4-Substituted Indoles via Arenetricarbonylchromium(0) Complexes, Tetrahedron; 44; 1988; pp. 7325-7334.
Bornstein Joseph et al., Facile Hydrolysis of the Trifluoromethyl Group in the Presence of Base. Some Trifluoromethylated Indoles, J. Amer. Chem. Society, vol. 79, 1957, pp. 1745-1748.
Brennan Mary R et al., The Preparation and Spectral Characterization of 2-Haloindoles, 3-Haloindoles, and 2,3-Dihaloindoles, Heterocycles, 1986, vol. 24, No. 10, pp. 2879-2885.
Buchwald, 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.
Bundgaard, Hans, Novel Chemical Approaches in Prodrug Design, Drugs of the Future, (1991), vol. 16, No. 5, pp. 443-458.
Burton Harold et al., The Synthesis of 5- and 6-Benzyloxyindoles and Attempts to prepare 5- and 6-Hydroxyindoles therefrom, J. Chem. Society, 1937, pp. 1726-1728.
Caddick, et al., Microwave Assisted Organic Reactions, Tetrahedron; 51; 1995; pp. 10403-10432.
Chan, et al., New N- and O-Arylations With Phenylboronic Acids And Cupric Acetate, Tetrahedron Letters 39 (1998) 2933-2936.
Chen, Cheng-yi et al., Syntheses of Indoles via a Palladium-Catalyzed Annulation between Iodoanilines and Ketones, J. Org. Chem., 1997, vol. 62, pp. 2676-2677.
Cheng, et al, Relationship Between The Inhibition Constant (KI) And The Concentation Of Inhibitor Which Causes 50 Per Cent Inhibition (I50) Of An Enzymatic Reaction, Biochem. Pharmacol. (1973), 22, 3099-3108.
Chikvaidze J Sh et al, Indole Derivatives , Khim. Geterotsikl, Soedin, 1991, Bol. 11, pp. 1508-1511 (English Abstract attached; full text English translation will be provided when and if obtained.).
Clemo, et al., A Contribution to the Study of Nicotine and the Synthesis of 7-Azaindole and Derivatives, J. Chem. Soc.; 1945; pp. 603-607.
Collot, et al., Regiospecific Functionalization of Indole-2-Carboxylates and Diastereoselective Preparation of the Corresponding Indolines, Heterocycles; 51; 12; 1999; pp. 2823-2846.
Comins Daniel L et al., N-Methyl Lithiation of N-Methylindoles Directed by a-Amino Alkoxides, Tetrahedron Letters, 1989, vol. 30, No. 33, pp. 4337-4340.
Davis, Michael L. et al., Reactions of beta-(Lithiomethyl)azines with Nitriles as a Route to Pyrrolo-pyridines, -quinolines, -pyrazines, -quinoxalines and -pyrimidines, Tetrahedron, vol. 48, No. 5, pp. 939-952, 1992.
Desarbre Eric et al., Synthesis of 2-Substituted-1H-Pyrrolo[2,3-b]Pyridines: Preparation of 7-Azaolivacine Analogue and 7-Azaindolopyridopyrimidine Derivatives, Tetrehedron, 1997, vol. 53, No. 10, pp. 3637-3648.
Dormoy Jean-Robert et al., Elaboration d'une nouvelle voie d'accés aux 6H-pyrido[4,3:b]carbazoles et analogues: A. Synthése et étude des précurseurs, Tetrahedron, 1993, vol. 49, No. 14, pp. 2885-2914.
Estel, et al., Metalation/S RN 1 Coupling in Heterocyclic Synthesis. A Convient Methodology for Ring Functionalization., J. Org. Chem.; 53; 1988; pp. 2740-2744.
Ezquerra Jesús et al., Efficient Reagents for the Synthesis of 5-, 7-, and 5,7-Substituted Indoles Starting from Aromatic Amines; Scope and Limitations, J. Org. Chem., 1996, vol. 61, pp. 5804-5812.
Fleisher, David et al., Improved Oral Drug Delivery: Solubility Limitations Overcome by the Use of Prodrugs, Advanced Drug Delivery Reviews, (1996), vol. 19, pp. 115-130.
Gray Nancy M et al., Novel Indole-2-Carboxylates as Ligands for the Strychnine-Insensitive N-Methyl-D-aspartate-Linked Glycine Receptor, J. Med. Chem., 1991, vol. 34, pp. 1283-1292.
Hands, David et al., A Convenient Method for the Preparation of 5-, 6- and 7-Azaindoles and Their Derivatives, Synthesis, Jul. 1996, pp. 877-882.
Hartwig, John, Ubergangsmetall-Katalysierte Synthese Von Arylaminen Und Arylethem Aus Arylhalogeniden Und-Triflaten: Anwendungen Und Reaktionsmechanismus, Angew. Chem. 1998, 110, 2154-2177.
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.
Hasan Iltifat et al., Synthesis and Reactions of N-Protected 2-Lithiated Pyrroles and Indoles. The tert-Butoxycarbonyl Substituent as a Protecting Group, J. Org. Chem., 1981, vol. 46, pp. 157-164.
Hiremath Shivayogi P et al., Synthesis & Reaction of Indole-1,2-Dicarboxaldehydes with Hydrazine & Hydroxylamine, Indian J. of Chemistry, 1980, vol. 19B, pp. 770-774.
Hughes, David L., Progress in the Fischer Indole Reaction, A Review, Org. Prep.Proc Int.; 25; 1993; pp. 607-632.
Khanna Ish K et al., 1,2-Diarylimidazoles as Potent, Cyclooxygenase-2 Selective, and Orally Active Antiinflammatory Agents, J. Med. Chem., 1997, vol. 40, pp. 1634-1647.
Kline Toni, Preparation of 2-Iodotryptamine and 2-Iodo-5-methoxytryptamine, J. Heterocycl. Chem., 1985, vol. 22, pp. 505-509.
Krstenansky, et al., Recent Advances in Microwave-assisted Organic Synthesis, Current Opinion in Drug Discovery & Development; 3(4); 2000; pp. 454-461.
Kuneri, Masao, Indole-related Compounds, Chem Abst.; 1962, pp. 3441i-3442b.
Kwong, et al., Copper-Catalyzed Coupling Of Alkylamines And Aryl Iodides: An Efficient System Even In An Air Atmosphere, Organic Lett. 2002, 4 (4), 581-584.
Lam, et al., New Aryl/He
Matter Hans
Nazare Marc
Ritter Kurt
Urmann Matthias
Wehner Volkmar
Lin Jiang
Sanofi-Aventis Deutschland GmbH
Shiao Rei-tsang
LandOfFree
Azaindole-derivatives as factor Xa inhibitors does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Azaindole-derivatives as factor Xa inhibitors, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Azaindole-derivatives as factor Xa inhibitors will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2791118