Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2007-04-24
2007-04-24
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...
Reexamination Certificate
active
09653563
ABSTRACT:
A compound of the formula (I):or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, a method of antagonizing endothelin, methods for the inhibition of bone metastases, methods for the prevention of growth of new metastases, methods for the inhibition of bone turnover, and methods for the prevention of bone loss in patients, including cancer patients, using an endothelin ET-A receptor antagonist.
REFERENCES:
patent: 3342833 (1967-09-01), Fremery et al.
patent: 3719667 (1973-03-01), Gutowski
patent: 3840556 (1974-10-01), Kukolja
patent: 4132709 (1979-01-01), Santrouch et al.
patent: 4216218 (1980-08-01), Ehrogott et al.
patent: 4279918 (1981-07-01), Eistetter et al.
patent: 4340715 (1982-07-01), Grounder et al.
patent: 5482960 (1996-01-01), Berryman et al.
patent: 5668164 (1997-09-01), Ma et al.
patent: 5767144 (1998-06-01), Winn et al.
patent: 5998468 (1999-12-01), Cheng et al.
patent: 6017951 (2000-01-01), Patt et al.
patent: 6048893 (2000-04-01), Smith et al.
patent: 0 439 444 (1991-07-01), None
patent: 2275926 (1994-09-01), None
patent: 93/08799 (1993-05-01), None
patent: 94/02474 (1994-02-01), None
patent: 94/14434 (1994-07-01), None
patent: 95/04534 (1995-02-01), None
patent: 95/05372 (1995-02-01), None
patent: 95/05376 (1995-02-01), None
patent: 95/33748 (1995-12-01), None
patent: 95/33752 (1995-12-01), None
patent: 95/35107 (1995-12-01), None
patent: 96/06095 (1996-02-01), None
patent: 97/30045 (1997-08-01), None
patent: 97/30046 (1997-08-01), None
Liu, Gang et al., “Design Synthesis and Activity of a Series of Pyrrolidine—3 carboxylic Acid—Based, Highly Specific, Orally Active ETB Antagonists Containing a Diphenylmethylamine Acetamide Side Chain” J. Med. Chem. (1999), 42 (18), 3679-3689.
Aktan et al., BQ-123, A Specific Endothelin (ETA) Receptor Antagonist, Prevents Ischemia-reperfusion injury in Kidney Transplantation ,Transplant Int,vol. 9, 1996, pp. 201-207.
Benigni et al., “A Specific Endothelin Subtype A Receptor Antagonist Protects Against Injury in Renal Disease Progression”,Kidney International, vol. 44, 1993, pp. 440-444.
Berliner et al.,Journal of the American Chemical Society, vol. 72, 1950, pp. 222-227.
Berridge et al., “Lithium Amplifies Agonist-dependent Phosphatidylinositol Responses in Brain and Salivary Glands”,Biochem. J.,vol. 206, 1982, pp. 587-595.
Bhagwat, S., “Synthesis of Enantiomerically Pure Pyrrolidinones as Endothelin Receptor Antagonists”, Tetrahedron Letters, 37(27), 1996, pp. 4627-4630.
Bobik et al., “Growth Factor Activity of Endothelin on Vascular Smooth Muscle”,American Journal of Physiology, vol. 258, 1990, pp. C408-C415.
Bonvallet et al.,American Journal of Physiology, vol. 266, 1994, pp. H1327-H1331.
Borch et al., “The Cyanohydridoborate Anion as a Selective Reducing Agent”,J. Am. Chem. Soc., vol. 93, No. 12, 1971, pp. 2897-2904.
Bourguignon et al.,Canadian Journal of Chemistry, vol. 63, 1985, pp. 2354-2361.
Bowman,J. Chem. Soc., 1950, pp. 1346-1349.
Bram et al.,Bull. Chem. Soc. France, 1964, pp. 945-951.
Bredereck et al.,Chem. Berichte, vol. 97, 1964, pp. 3397-3406.
Brintzinger et al.,Chem. Berichte, vol. 85, 1952, pp. 455-457.
Bunchman et al., “Smooth Muscle Cell Proliferation by Conditioned Media from Cyclosponne-Treated Endothelial Cells: A Role of Endothelin”,Transplantation Proceedings, vol. 23, No. 1, 1991, pp. 967-968.
Bunting et al.,J. Am. Chem. Soc., vol. 115, 1993, pp. 11705-11715.
Cahiez et al., Copper-Catalyzed Conjugate Addition of Organomagnesium Reagents to α, β-Ethylenic Esters: A Simple High Yield Procedure,Tetrahedron Letters, vol. 31, No. 51, 1990, pp. 7425-7428.
Chemical Abstract, vol. 74, No. 9, 1971, p. 304.
Chemical Abstract, vol. 119, No. 21, 1993, p. 999.
Chobanian et al., Antiatherogenic Effect of Captopril in the Watanabe Heritable Hyperlipidermic Rabbit,Hypertension, vol. 15, No. 3, 1990, pp. 327-331.
Clozel et al., Pathophysiological Role of Endothelin Revealed by the First Orally Active Endothelin Receptor Antagonist ,Nature, vol. 365, 1993, pp. 759-761.
Corey et al.,Tetrahedron Letters, vol. 36, 1972, pp. 3769-3772.
Cottrell et al.,J. Chem. Soc., Perkin Trans. 1, vol. 5, 1991, pp. 1091-1097.
Craig et al., “Modern Pharmacology, Third Edition”, Little, Brown and Company, Boston, US, p. 33, col. 2-p. 35, col. 1.
Ferro et al., The Clinical Potential of Endothelin Receptor Antagonists in Cardiovascular Medicine ,Drugs, vol. 51, No. 1, 1996, pp. 12-27.
Foegh et al., “Inhibition of Coronary Artery Transplant Atherosclerosis in Rabbits with Angiopeptin, an Octapeptide”,Atherosclerosis, vol. 78, 1989, pp. 229-236.
Fung et al., “Nonpeptide Renin Inhibitors Employing a Novel 3-Aza (or oxa)-2,4-dialkyl Glutaric Acid Moiety as a P2/P3 Amide Bona Replacement”,J. Med. Chem., vol. 35, No. 10, 1992, pp. 1722-1734.
Ge, et al., Yaoxue Xuebao, 20 427-432 (1985).
Gershon et al.,J. Heterocyclic Chem., vol. 24, 1987, pp. 205-209.
Greene et al., “Protective Groups in Organic Synthesis”, 2ndEd., 1991, pp. 152-186.
Gupton et al.,Synthetic Communications, vol. 12, No. 1, 1982, pp. 35-41.
Hara et al., Amelioration of Brain Damage after Focal Ischemia in the Rat by a Novel Inhibitor of Lipid Peroxidation ,European J. Pharmacol., vol. 197, 1991, pp. 75-82.
Hatt,Journal of the Chemical Society, vol. 132, 1929, pp. 1623-1632.
Heistad et al.,Circulation Research, vol. 54, No. 6, 1984, pp. 711-718.
Higuchi et al., “Pro-drugs as Novel Delivery Systems”, A.C.S. Symposium Series,American Chemical Society, vol. 14, (1975).
Hirata et al.,Biochem. Biophys. Res. Commun., vol. 154, No. 3, 1988, pp. 868-875.
Hogaboam et al., An Orally Active Non-selective Endothelin Receptor Antagonist, Bosentan, Markedly Reduces Injury in a Rat Model fo Colitis,European J. Pharmacol., vol. 309, 1996, pp. 261-269.
Hoshino et al., A Convenient Preparation of Certain N,N-Dialkylcarbamoyl Chlorides ,Synthetic Communications, vol. 17, No. 16, 1987, pp. 1887-1892.
Hudlicky et al.,Synthetic Communications, vol. 16, No. 2, 1986, pp 169-182.
Imbriaco et al.,Clinical Cancer Research, vol. 4, 1998, pp. 1765-1772.
Ishida et al.,Biochem. Pharmacol., vol. 44, No. 7, 1992, pp. 1431-1436.
Itoh et al.,Biochemical and Biophysical Research Communications, vol. 195, No. 2, 1993, pp. 969-975.
Itoh et al.,FEBS Letters, vol. 231, No. 2, 1988, pp. 440-444.
“IUPAC 1974 Recommendations for Section E, Fundamental Stereochemistry”,Pure Appl. Chem., vol. 45, pp. 13-30 (1976).
Jae, et al., “Pyrrolidine-3-carboxylic acids as Endothelin Antagonists. 2. Sulfonamide-Based ETA-ETB Mixed Antagonists.” Journal of Medicinal Chemistry, vol. 40, No. 20, 1997, pp. 3217-3227.
Kaldor et al., “A Mild, Osmium Tetraoxide-Catalyzed Method for the Oxidation of Sulfides to Sulfones”,Tetrahedron Letters, vol. 32, No. 38, 1991, pp. 5043-5046.
Kanemasa et al., “Nonstabilized Azomethine Ylides Generated by Decarboxylative Condensation of α-Amino Acids. Structural Variation, Reactivity, and Stereoselectivity”,Bull. Chem. Soc. Of Japan, vol. 62, No. 6, 1989, pp. 1960-1968.
Klemm et al., Endothelin 1 Mediates ex vivo Coronary Vasoconstriction Caused by Exogenous and Endogenous Cytokines ,Proc. Natl. Acad. Sci., vol. 92, 1995, pp. 2691-2695.
Kon et al., Glomerular Actions of Endothelin In Vivo ,J. Clin. Invest.,vol. 83, 1989, pp. 1762-1767.
Kon et al., Role of Endothelin in Cyclosporine-induced Glomerular Dysfunction ,Kidney International, vol. 37, 1990, pp. 1487-1491.
Krapcho et al.,Organic Syntheses, vol. 47, 1967, pp. 20-23.
Margulies et al.,Circulation, vol. 82, No. 6, 1990, pp. 2226-2230.
Matsumura et al.,European Journal of Pharmacology, vol. 185, 1990, pp. 103-106.
Matsumura et al.,Life Sciences, vol. 49, 1991, pp. 841-848.
McMurdo et al.,European Journal of Pharmacology, vol. 259, 1994, pp. 51-55.
Nakagomi et al.,J. Neurosurg., vol. 66, 1987, pp. 915-923.
Nelson et al.,Nature Medic
Boyd Steven A.
Henry Kenneth J.
Hutchins Charles W.
Jae Hwan-Soo
Janus Todd J.
Abbott Labortories
Donner B. Gregory
Saeed Kamal A.
Shiao Robert
LandOfFree
Endothelin antagonists does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Endothelin antagonists, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Endothelin antagonists will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3734830