Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2008-04-29
2008-04-29
Safed, Kamal A. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C562S493000, C514S365000, C514S570000, C514S568000, C548S202000
Reexamination Certificate
active
07365225
ABSTRACT:
The present invention is related to aryl dicarboxamides of formula (I) and use thereof for the treatment and/or prevention of obesity and/or metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type I and/or II, inadequate glucose tolerance, insulin resistance, hyperlipidemia, hypertriglyceridemia, hypercholes-terolemia, polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of aryl dicarboxamides of formula (I) to modulate, notably to inhibit the activity of PTPs. A is an aminocarbonyl moiety; Cy is an aryl, heteroaryl, aryl-heteroaryl, heteroaryl-aryl, aryl-aryl, cycloalkyl or heterocycle group; n is either 0 or 1; R1and R2are independently from each other is selected from the group consisting of hydrogen or C1-C6-alkyl; R4and R5are each independently from each other selected from the group consisting of H, hydroxy, C1-C6alkyl, carboxy, C1-C6alkoxy, C1-C3alkyl carboxy, C2-C3alkenyl carboxy, C2-C3alkynyl carboxy, amino or R4and R5may form an unsaturated or saturated heterocyclic ring, whereby at least one of R4or R5is not a hydrogen or C1-C6alkyl
REFERENCES:
patent: 00/69810 (2000-11-01), None
patent: 03/024955 (2003-03-01), None
patent: 03/064376 (2003-08-01), None
Ganguly et al., Tetrahedron Letters (2002), 43, abstract.
Watanabe et al., “Structure-Activity Relationship and Rational Design of 3,4-Dephostatin Derivatives as Protein Tyrosine Phosphatase Inhibitors”, Tetrahedron, 56 (2000), 741-752.
Swinnen et al. “Methylene amides, particularly [(arylmethyl)amino](oxo)acetic acids, useful as modulators, and especially inhibitors, of protein tyrosine phosphatases (PTPs), and their preparation, uses, e.g., as antidiabetics, and pharmaceutical compositions”, CAPLUS AN 2003:610410, (abstract only).
http://health.yahoo.com/topic/diabetes/overview/article/healthwise/hw34305.
http://en.wikipedia.org/wiki/Hyperlipidemia.
(http://www.healthscout.com/ency/68/366/ main.html.
http://diabetes.webmd. com/guide/preventing-type-2-diabetes.
http://www.webmd.com/diet/tc/Obesity-Overview.
Asante Appiah et al., Am J Physiol. Endocrinol Metab, 2003, 284, E663-E670.
Elchebly et al., Science 283, 1544 (1999); p. 1544-1548.
http://www.centerwatch.com/patient
mtresults
mt030929.html.
Choong, Ingrid C. et al., “Identification of Potent and Selective Small-Molecule Inhibitors of Caspase-3 through the Use of Extended Tethering and Structure-Based Drug Design”, Journal of Medicinal Chemistry, vol. 45, No. 23, pp. 5005-5022, 2002.
Ahima, Rexford S. et al., “Leptin”, Annu. Rev. Physiol., vol. 62, pp. 413-437, 2000.
Bergnes, Gustave et al., “Generation of an Ugi Library of phosphate mimic-containing compounds and identification of novel dual specific phosphatase inhibitors”, Bioorganic & Medicinal Chemistry Letters, vol. 9, pp. 2849-2854, 1999.
Bjorge, Jeffrey D. et al., “Identification of protein-tyrosine phosphatase 1B as the major tyrosine phosphatase activity Capable of dephosphorylating and activating c-src in several human breast cancer cell lines”, The Journal of Biological Chemistry, vol. 275, No. 52, pp. 41439-41446, 2000.
Cheng, Alan et al., “Attenuation of leptin action and regulation of obesity by protein tyrosine phosphatase 1B”, Developmental cell, vol. 2, pp. 497-503, 2002.
Defronzo, Ralph A. et al., “Insulin Resistance: A Multifaceted syndrome responsible for NIDDM, Obesity, Hypertension, Dyslipidemia, and atherosclerotic cardiovascular disease”, Diabetes Care, vol. 14, No. 3, pp. 173-194, 1991.
Diamanti-Kandarakis, Evanthia et al., “Therapeutic effects of metformin on insulin resistance and hyperandrogenism in polycystic ovary syndrome”, European Journal of Endocrinology, vol. 138, pp. 269-274, 1998.
Dunaif, “Insulin resistance and the polycystic ovary syndrome: mechanism and implications for pathogenesis”, Endocrine Reviews, vol. 18, No. 6, pp. 774-800, 1997.
Elchebly, Mounib et al., “Modulation of insulin signaling by protein tyrosine phosphatases”, J. Mol. Med., vol. 78, pp. 473-482, 2000.
Jarrett, R. J., “Cardiovascular disease and hypertension in diabetes mellitus”, Diabetes/Metabolism Reviews, vol. 5, No. 7, pp. 547-558, 1989.
Kennedy, Brian P. et al., “Protein tyrosine phosphatase- 1b in diabetes”, Biochemical Pharmacology, vol. 60, pp. 877-883, 2000.
Klaman, Lori D. et al., “Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1B-deficient mice”, Molecular and Cellular Biology, vol. 20, No. 15, pp. 5479-5489, 2000.
McGuire, Mary C. et al., “Abnormal regulation of protein tyrosine phosphatase activities in skeletal muscle of insulin-resistant humans”, Diabetes, vol. 40, pp. 939-942, 1991.
Meyerovitch, Joseph, et al., “Hepatic phosphotyrosine phosphatase activity and its alterations in diabetic rats”, J. Clinical Invest, vol. 84, pp. 976-983, 1989.
Moller, et al., “Protein tyrosine phosphatases (PTPs) as drug targets: Inhibitors of PTP-1B for the treatment of diabetes”, Current Opinion in Drug Discovery & Development, vol. 3, No. 5, pp. 527-540, 2000.
Pathre, Purnima et al., “PTP1B regulates neurite extension mediated by cell-cell and cell-matrix adhesion molecules”, Journal of Neuroscience Research, vol. 63, No. 2, pp. 143-150, 2001.
Reaven, Gerald M. et al., “Nonketotic diabetes mellitus: insulin deficiency or insulin resistance?”, The American Journal of Medicine, vol. 60, pp. 80-88, 1976.
Shock, Lisa P. et al., “Protein tyrosine phosphatases expressed in developing brain and retinal Mueller glia”, Molecular Brain Research, vol. 28, No. 1, pp. 110-116, 1995.
Sredy, Janet et al., “Insulin resistance is associated with abnormal dephosphorylation of a synthetic phosphopeptide corresponding to the major autophosphorylation sites of the insulin receptor”, Metabolism, vol. 44, No. 8, pp. 1074-1081, 1995.
Stout, Robert W. , “Overview of the association between insulin and atherosclerosis”, Metabolism, vol. 34, No. 12, pp. 7-12, 1985.
Zhang, Zhong-Yin, “Protein tyrosine phosphatases: prospects for therapeutics”, Curr. Opin., Chem, Biol., vol. 5, No. 4, pp. 416-423, 2001.
Bombrun Agnes
Pons Jean-Francois
Swinnen Dominique
Thomas Russel J.
Laboratoires Serono SA
Loewe Sun Jae Y
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Safed Kamal A.
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