Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2008-03-25
2008-03-25
Crane, L. E. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C536S026260
Reexamination Certificate
active
07348315
ABSTRACT:
Disclosed herein are methods of using an adenosine analog or derivative for treating heart failure, increasing cardiac muscle contractility, increasing cardiac diastolic relaxation, and increasing vasodilation. Exemplary adenosine analogs/derivatives include compounds of the following formulawhereinL is CH or O, wherein when L is CH, t is 1 and when L is O, t is 0;R1is halogen or —R6—(R7)p—R8;R2is hydrogen, alkyl, cycloalkyl, cycloalkenyl, alkynyl, alkylthio, aminoalkylthio, halogen, or —R6—(R7)p—R8;R3is H, halogen or —R6—(R7)p—R8;R4is —OH or —SH;R5is —OH or —R6—(R7)p—R8;R6is NH or S;R7is CH2;R8is H, NH2, halogen, CN, CCH, cycloallkyl, having 3 to about 10 carbon atoms or aryl having 3 to about 20 carbon atoms;R9is OH or acetamido;R10and R11are independently hydrogen or halogen;X, Y, and Z are independently N or CH;m is 0, 1, or 2;n is 0 or 1;q is 0 or 1 if L is CH, or if L is O, R3is halogen or —R6—(R7)p—R8;q is 1 if L is O, R3is H, halogen, or —R6—(R7)p—R8;provided that at least one of m, n, and q is 1; andp is 0 to 10.
REFERENCES:
patent: 4657898 (1987-04-01), Bristol et al.
patent: 4843066 (1989-06-01), Yamada et al.
patent: 4902677 (1990-02-01), Imai et al.
patent: 4990498 (1991-02-01), Suhadolnik
patent: 5017564 (1991-05-01), Makino et al.
patent: 5055304 (1991-10-01), Makino et al.
patent: 5104859 (1992-04-01), Sollevi
patent: 5140015 (1992-08-01), Olsson et al.
patent: 5219841 (1993-06-01), Inaba et al.
patent: 5246922 (1993-09-01), Kataoka et al.
patent: 5415873 (1995-05-01), Trepel et al.
patent: 5430027 (1995-07-01), Knutsen et al.
patent: 5516762 (1996-05-01), Bertics et al.
patent: 5571524 (1996-11-01), Kitakaze et al.
patent: 5712258 (1998-01-01), Liang
patent: 6153647 (2000-11-01), Mallet et al.
patent: 6255292 (2001-07-01), Liang et al.
patent: 1975 (1963-08-01), None
patent: 7857 (1970-04-01), None
patent: 853232 (1957-09-01), None
Barry, W.H., et al., “Mechanisms of transmembrane calcium movement in cultured chick embryo ventricular cells,”J. Physiol., 1982, 325, 243-260.
Burnstock, G., et al., “Structure activity relationships for derivatives of adenosine-5′-triphosphate as agonists at P2purinoceptors: heterogeneity within P2xand P2ysubtypes,”Drug Development Res., 1994, 31, 206-219.
Fischer, et al., “Identification of potent, selective P2y- purinoceptor agonists: structure-activity relationships for 2-thioether derivatives of adenosine 5′-triphosphate,”J. Med. Chem., 1993, 36, 3937-3946.
Fukunaga, et al., “Hypotensive effects of adenosine and adenosine triphosphate compared with sodium nitroprusside,”Anesth. Analg., 1982, 61(3), 273-278.
Gui, J., et al., “A serine kinase regulates intracellular localization of splicing factors in the cell cycle,”Nature, 1994, 369, 678-682.
Hoffman, B., et al., “Diogitalis and allied cardiac glycosides,” in The Pharmacological Basis of Therapeutics, Gliman, A.G., et al. (Eds.),Pergamon Press, 1990, Chapter 34, 814-839.
Kelly, R.A., et al., “Endothelin enhances the contractile responsiveness of adult rat ventricular myocytes to calcium by a pertussis toxin-sensitive pathway,”J. Clin. Invest., 1990, 86, 1164-1171.
Kennedy, “P1 and P2-purinoceptor subtypes—an update,”Arch. Intl. Pharmacodynamie et de Therapie, 1990, 303, 30-50.
Kikugawa, K., et al., “Platelet aggregation inhibitors. IX. Chemical transformation of adenosine into 2-thioadenosine derivatives,”Chemical Pharm. Bull., 1977, 25, 1959-1969.
Kovacs, t., et al., “Simple synthesis of 5-vinyl-and 5-ethynyl-2′deoxyuridine-5′-triposphates,”Tetrahedron Letts., 1988, 29(36), 4525-4528.
MacFarlane, et al., “2-methylthioadenosine[beta-32P]diphosphate—an agonist and radioligand for the receptor that inhibits the accumulation of cyclic AMP in intact blood platlets,”J. Chem. Invest., 1983, 71, 420-425.
Munson, P., et al., “LIGAND: a versatile computerized approach for characterization of ligand-binding systems,”Analytical Biochem., 1980, 107, 220-239.
Murray, et al., “Adenosine 5′-phosphorothioate. A nucleotide analog that is a subtrate, competitive inhibitor, or regulator of some enzymes that interact with adenosine 5′-phosphate,”Biochem., 1968, 7(11), 4023-4029.
Nielsen, et al., “Sodium imidodiphosphatel. Synthesis, identification and hydrolytic degradation,”Synthesis and Identification of Sodium Imidodiphosphate, 1961, 83, 99-102.
Novgorodov, S., et al., “Expression of porcine leukocyte 12-lipoxygenase in a baculovirus-insect cell system and its characterization,”Arch. Biochem. Biophys., 1994, 312, 219-226.
Podrasky, E., et al., “Positive inotropic effect mediated by a novel stimulatory P2y-like purinergic receptor in cultured fetal ventricular myocyte,”FASEB J., 1994, 8(5), 3686.
Rotrosen, D., et al., “Production of recombinant cytochrome b558 allows reconstitution of the phagocyte NADPH oxidase solely from recombinant proteins,”J. Biol. Chem., 1993, 268, 14256-14260.
Sen, L., et al., “Enhanced α1-adrenergic responsiveness in cardiomypoathic hamster cardiac myocytes: relation to the expression of pertussis toxin-sensitive G protein and α1-adrenergic receptors,”Circ. Res., 1990, 67, 1182-1192.
Watson, S., et al., “The G-protein linked receptor factsbook,”Academic Press, NY, 1994, 30-31.
Williams, “Purine receptors in mammalian tissues: pharmacology and functional significance,”Ann. Rev. Pharm. Toxicol., 1987, 27, 316-318.
Xu, H., et al., “High-efficiency gene transfer into cardiac myocytes,”Nucl. Acids Res., 1992, 20(23), 6425-6426.
Xu, D., et al., “Expression and pharmacological characterization of a stimulatory subtype of adenosine receptor in ventricular myocyte,”Circ. Res., 1992, 70, 56-65.
Yount, et al., “Adenyl imidodiphosphate, an adenosine triphosphate analog containing a P-N-P linkage,”Biochem., 1971, 10(13), 2484-2489.
Zheng, J-S., et al., “Extracellular adenosine-triphosphate (ATP—inhibits cardiac myocyte hypertrophy induced by adrenergic angonists,”Circulation, 1994, 90(4), 1039.
Marumoto, et al., “A new method for synthesis of nucleoside 3′, 5′-cyclic phosphates. Cyclization of nucleoside 5′-trichloromethylphosphonates,”Chem.&Pharm. Bulletin, Oct. 1975, 23(10), 2295-2300.
Sigma Chemical Company, Biochemicals—Organic Compounds for Research and Diagnostic Reagents (Catalog), St. Louis, MO, 1992, 45-46, 48, 53-54 and 663.
Abiru, et al.,J. Med. Chem., 2000, 35, 2253-2260.
Jacobsen, et al., “Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists,”J. Med. Chem., 2000, 23, 2196-2203.
Jacobson Kenneth A
Liang Bruce T
Cantor & Colburn LLP
Crane L. E.
The University Of Connecticut
LandOfFree
Methods of treating heart failure with modified ATP, ADP and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Methods of treating heart failure with modified ATP, ADP and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods of treating heart failure with modified ATP, ADP and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2793860