Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2009-12-03
2011-12-13
Loewe, Sun Jae (Department: 1622)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S274000, C514S277000, C514S311000, C514S335000, C514S345000, C514S365000, C514S383000, C514S394000, C514S406000, C514S415000, C514S464000, C514S570000, C540S578000, C544S315000, C546S174000, C546S261000, C546S301000, C546S342000, C548S204000, C548S269400, C548S304400, C548S377100, C548S469000, C549S434000, C562S469000
Reexamination Certificate
active
08076324
ABSTRACT:
The present invention relates to di(hetero)arylcyclohexane derivatives of the formula I,in which Ar1, Ar2, R1and R2have the meanings indicated in the claims. The compounds of the formula I are valuable pharmaceutical active compounds which inhibit ATP-sensitive potassium channels in the heart muscle and are suitable, for example, for the treatment of disorders of the cardiovascular system such as arrhythmias or a decreased contractility of the heart, such as can occur, for example, in coronary heart disease, cardiac insufficiency or cardiomyopathies. In particular, they are suitable for the prevention of sudden cardiac death. The invention furthermore relates to processes and intermediates for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.
REFERENCES:
patent: 5476850 (1995-12-01), Englert et al.
patent: 5574069 (1996-11-01), Englert et al.
patent: 5652268 (1997-07-01), Englert et al.
patent: 5698596 (1997-12-01), Englert et al.
patent: 6410573 (2002-06-01), Heitsch et al.
patent: 6414030 (2002-07-01), Wirth et al.
patent: 1 264 829 (2002-12-01), None
patent: 1 679 069 (2006-07-01), None
patent: 1736467 (2006-12-01), None
patent: WO 93/19749 (1993-10-01), None
patent: WO 99/34797 (1999-07-01), None
patent: WO 99/34798 (1999-07-01), None
patent: WO 01/27107 (2001-04-01), None
patent: WO 01/87866 (2001-11-01), None
patent: WO 2004/014370 (2004-02-01), None
Rubin et al., caplus an 1946:20687.
Agabiti-Rosei et al., The European Cardiologist, 2000.
Bauer A. et al., “Role of KATPChannels in Repetitive Induction of Ventricular Fibrillation”,Europace9:154-161 (2007).
Sakurai N. et al., “Cooper (II)-Catalyzed O-Phenylation of Alcohols with or Ganobismuth (V) Reagents”,Arkivocpp. 254-264 (2007).
Billman G.E. et al., “Effects of a Novel Cardioselective ATP-Sensitive Potassium Channel Antagonist, 1-[[5-[2-(5- Chloro-o-Anisamido)Ethy1]-β-Methoxyethoxyphenyl]Sulfonyl]-3-Methylthiourea, Sodium Salt (HMR 1402), on Susceptibility to Ventricular Fibrillation Induced by Myocardial Ischemia: In Vitro and In Vivo Studies”,The Journal of Pharmacology and Experimental Therapeutics309(1):182-192 (2004).
Weyermann A. et al., “Inhibitors of ATP-Sensitive Potassium Channels in Guinea Pig Isolated Ischemic Hearts”,Naunyn-Schmiedeberg's Arch Pharmacol369:374-381 (2004).
Kotha S. et al., “Recent Applications of the Suzuki-Miyaura Cross-Coupling Reaction in Organic Synthesis”,Tetrahedron58:9633-9695 (2002).
Böhme T.M. et al., “Synthesis and Pharmacology of Benzoxazines as Highly Selective Antagonists at M4Muscarinic Receptors”,Journal of Medicinal Chemistry45(14):3094-3102 (2002).
Kanoh S. et al., “Unusual Cyclodimerization of Small Cyclic Ethers Via Neighboring Carbonyl-Group Participation and Cation Transfer”,Tetrahedron58:7065-7074 (2002).
Dendorfer A. et al., “HMR 1372, A Putative Inhibitor of ATP-Sensitive K+-Channels, Reduces Infarct Size by a Cholinergic Mechanism”,Naunyn-Schmiedeberg's Arch Pharmacol. 363:R74 (2001), Abstract.
Giblin J.P. et al., “The Molecular Assembly of ATP-Sensitive Potassium Channels”,The Journal of Biological Chemistry274(32):22652-22659 (1999).
Wirth K.J. et al., “HMR 1883, A CardioSelective KATPChannel Blocker, Inhibits Ischaemia- and Reperfusion-Induced Ventricular Fibrillation in Rats”,Naunyn-Schmiedeberg's Arch Pharmacol. 360:295-300 (1999).
Billman G.E. et al., “HMR 1883, A Novel Cardioselective Inhibitor of the ATP-Sensitive Potassium Channel. Part II: Effects on Susceptibility to Ventricular Fibrillation Induced by Myocardial Ischemia in Conscious Dogs”,The Journal of Pharmacology and Experimental Therapeutics289(3):1465-1473 (1998).
Gögelein H. et al., “HMR 1883, A Novel Cardioselective Inhibitor of the ATP-Sensitive Potassium Channel. Part I: Effects on Cardiomyocytes, Coronary Flow and Pancreatic β—Cells”,The Journal of Pharmacology and Experimental Therapeutics286(3):1453-1464 (1998).
Katritzky A.R. et al., “Selective Reactivity of sp3and sp2Carbanions of 1-Substituted 1,2,4-Triazoles. A Comparative Approach”,J. Org. Chem. 63(13):4323-4331 (1998).
Combes S. et al., “A Convenient Synthesis of Triarylbismuth Diacetates”,Synthetic Communications26(24):4569-4575 (1996).
Ghaffar T. et al., “A New Homogeneous Platinum Containing Catalyst for the Hydrolysis of Nitriles”,Tetrahedron Letters36(47):8657-8660 (1995).
Krause E. et al., “Adenosine Triphosphate-Dependent K Currents Activated by Metabolic Inhibition in Rat Ventricular Myocytes Differ from Those Elicited by the Channel Opener Rilmakalim”,Pflügers Arch.-Eur J. Physiol. 429:625-635 (1995).
Barton D.H.R. et al., “Bismuth(V) Reagents in Organic Synthesis”,Pure&Appl. Chem. 59(8):937-946 (1987).
Chorvat R.J. et al., “22-Hydroxycholesterol Derivatives as HMG CoA Reductase Suppressors and Serum Cholesterol Lowering Agents”,J. Med. Chem. 28:194-200 (1985).
Comins D.L. et al., “Regiospecific α—Alkylation of 4-Chloro(Bromo)Pyridine”,J. Org. Chem. 50(22):4410-4411 (1985).
Mitsunobu O., “The Use of Diethyl Azodicarboxylate and Triphenylphospine in Synthesis and Transformation of Natural Products”,Synthesispp. 1-28 (1981).
Lednicer D. et al., “Butyrophenones as Hypotensive Agents. Derivatives of 4-Ary1-4-(Hydroxymethyl)Cyclohexylamine”,Journal of Medicinal Chemistry18(6):593-599 (1975).
Petersen S. et al., “Reactions of Cyclic Lactim Ethers with Acylhydrazine Derivatives”,Chemische Berichte90:909-921 (1957), together with an English-language abstract.
Martin Rubin et al., 1-Arylcyclohexanecarboxylic Acids, Journal of the American Chemical Society, (1946, pp. 628-832, vol. 68).
Altenburger Jean-Michel
Bohme Thomas
Gerlach Uwe
Gretzke Dirk
Kleemann Heinz-Werner
Farquharson-Torres Serena
Loewe Sun Jae
Sanofi-Aventis
Scully , Scott, Murphy & Presser, P.C.
LandOfFree
Di(hetero)arylcyclohexane derivatives, their preparation,... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Di(hetero)arylcyclohexane derivatives, their preparation,..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Di(hetero)arylcyclohexane derivatives, their preparation,... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4296039