Heterocyclic amide derivatives having glycogen phosphorylase...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C514S412000, C544S358000, C548S303700, C548S454000

Reexamination Certificate

active

07122567

ABSTRACT:
Heterocyclic amides of formula (1)wherein:Z is CH or nitrogen;R4and R5together are either —S—C(R6)═C(R7)— or —C(R7)═C(R6)—S—;R6and R7are selected from for example hydrogen, halo, C1-4alkyl, and C1-4alkanoyl;A is phenylene or heteroarylene;n is 0, 1 or 2;R1is selected from for example halo, nitro, cyano, hydroxy, carboxy;r is 1 or 2;Y is —NR2R3or —OR3;R2and R3are selected from for example hydrogen, hydroxy, aryl, heterocyclyl and C1-4alkyl(optionally substituted by 1 or 2 R8groups);R4is selected from for example hydrogen, halo, nitro, cyano, hydroxy, C1-4alkyl, and C1-4alkanoyl;R8is selected from for example hydroxy, —COCOOR9, —C(O)N(R9)(R10), —NHC(O)R9, (R9)(R10)N— and —COOR9;R9and R10are selected from for example hydrogen, hydroxy, C1-4alkyl (optionally substituted by 1 or 2 R13);R13is selected from hydroxy, halo, trihalomethyl and C1-4alkoxy;or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

REFERENCES:
patent: 3706810 (1972-12-01), Cyanamid
patent: 4599198 (1986-07-01), Hoover
patent: 4668769 (1987-05-01), Hoover
patent: 4720503 (1988-01-01), Witzel
patent: 4751231 (1988-06-01), Halczenko
patent: 4786641 (1988-11-01), Goldmann
patent: 4794120 (1988-12-01), Manoury
patent: 5863903 (1999-01-01), Lundgren
patent: 5998463 (1999-12-01), Hulin et al.
patent: 2004/0002495 (2004-01-01), Sher
patent: 2004/0142938 (2004-07-01), Sher et al.
patent: 2004/0220229 (2004-11-01), Bussolotti et al.
patent: 2004/0266768 (2004-12-01), Schoenafinger et al.
patent: 200740 (1983-06-01), None
patent: 4445968 (1996-06-01), None
patent: 697403 (1996-02-01), None
patent: 0846464 (1998-06-01), None
patent: 0884050 (1998-12-01), None
patent: 0978279 (2000-02-01), None
patent: 1149580 (2001-02-01), None
patent: 1177791 (2001-07-01), None
patent: 1125580 (2001-08-01), None
patent: 1134213 (2001-09-01), None
patent: 1136071 (2001-09-01), None
patent: 1 338 594 (2003-08-01), None
patent: 1 340 500 (2003-09-01), None
patent: 1088824 (2004-01-01), None
patent: 1145717 (2004-05-01), None
patent: 2081747 (1996-03-01), None
patent: 021247565 (1990-05-01), None
patent: 04179949 (1992-06-01), None
patent: 2001 089368 (2001-04-01), None
patent: 2001 206856 (2001-07-01), None
patent: 2001247565 (2001-09-01), None
patent: 2004196702 (2004-07-01), None
patent: WO-93/25574 (1993-12-01), None
patent: WO-95/24391 (1995-09-01), None
patent: WO-96/39384 (1996-12-01), None
patent: WO-96/39385 (1996-12-01), None
patent: WO-97/09040 (1997-03-01), None
patent: WO-97/31901 (1997-09-01), None
patent: WO-97/45425 (1997-12-01), None
patent: WO-98/27108 (1998-06-01), None
patent: WO-98/40353 (1998-09-01), None
patent: WO-98/50359 (1998-11-01), None
patent: WO-99/26659 (1999-06-01), None
patent: WO-99/36393 (1999-07-01), None
patent: WO-00/42213 (2000-07-01), None
patent: WO-00/47206 (2000-08-01), None
patent: WO-01/05954 (2001-01-01), None
patent: WO-01/23347 (2001-04-01), None
patent: 01/32622 (2001-05-01), None
patent: WO-01/32654 (2001-05-01), None
patent: WO-01/52825 (2001-07-01), None
patent: WO-01/68055 (2001-09-01), None
patent: WO-01/68092 (2001-09-01), None
patent: WO-01/68603 (2001-09-01), None
patent: WO-01/94300 (2001-12-01), None
patent: WO-01/96311 (2001-12-01), None
patent: WO-01/96347 (2001-12-01), None
patent: 02/20530 (2002-03-01), None
patent: WO-02/26714 (2002-04-01), None
patent: WO-02/34718 (2002-05-01), None
patent: WO-02/080844 (2002-10-01), None
patent: WO-02/096864 (2002-12-01), None
patent: WO-02/098348 (2002-12-01), None
patent: WO-03/037864 (2003-05-01), None
patent: 03/045920 (2003-06-01), None
patent: 03/072570 (2003-09-01), None
patent: 03/074484 (2003-09-01), None
patent: 03/074485 (2003-09-01), None
patent: 03/074513 (2003-09-01), None
patent: 03/074517 (2003-09-01), None
patent: 03/074532 (2003-09-01), None
patent: 03/091213 (2003-11-01), None
patent: 2004/031193 (2004-04-01), None
patent: 2004/031194 (2004-04-01), None
patent: 2004/041780 (2004-05-01), None
patent: 2004/092158 (2004-10-01), None
patent: 2004/113345 (2004-12-01), None
patent: 2005/013975 (2005-02-01), None
patent: 2005/013981 (2005-02-01), None
patent: 2005/018637 (2005-03-01), None
patent: 2005/019172 (2005-03-01), None
patent: 2005/020985 (2005-03-01), None
patent: 2005/020986 (2005-03-01), None
patent: 2005/020987 (2005-03-01), None
U.S. Appl. No. 10/344,506, by Whittamore et al.
Clore & Blackgard (1994), Diabetes 43: 256-262.
DeFronzo, R.A. et al, (1992) Diabetes Care 15; 318-355.
Reaven, G.M. (1995) Diabetologia 38:3-13.
Birch, A., et al., “Novel Thienopyrrole Glycogen Phosphorylase inhibitors: In Vitro SAR and Crystallographic Studies,” Poster, AstraZeneca UK, CVGI Research, Mereside, Alderley Park, Macclesfield, Cheshire.
Crochet, R.A., et al., “Synthesis of Substituted Thieno[2,3-b] pyrroles,” vol. 11, 143-150 (Apr. 1974).
Freeman, S., et al., “Effect of Glucose on Rat and Human Liver Glycogen Phosphorylasea Activity and Potency of a Glycogen Phosphoylase Inhibitor,” Diabetes, 52, Supp., 1470-P, A340.
Hartman, G.D., et al., “The Synthesis of 5-Alkylaminomethylthieno[2,3-b]Pyrrole-5-Sulfonamides,” Heterocycles, 29(10):1943-1949 (1989).
Hoover, D.J., et al., “Indole-2-carboxamide Inhibitors of Human Liver Glycogen Phosphorylase,” J. Med. Chem., 41:2934-2938 (1998).
Hudson, S., et al., “The effect of a glycogen phosphorylase inhibitor upon muscle fatigue in anaesthetised rats,” J. Physiol., 539:52-53 (2002).
Jakobsen, P., et al., “Iminosugars: Potential Inhibitors of Liver Glycogen Phosphorylase., ” Bioorganic Med. Chem., 9:733-744 (2001).
Martin, W.H., et al., “Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo,” PNAS, 95:1776-1781 (Feb. 1998).
McCormack, J.G., et al., “Pharmacological Approaches to Inhibit Endogenous Glucose Production as a Means of Anti-diabetic Therapy,” Curr. Pharmaceutical Design, 7:1451-1474 (2001).
Oikonomakos, N.G., et al., “Allosteric inhibition of glycogen phosphorylase alpha by the potential antidiabetic drug 3-isopropyl 4-(2-chlorophenyl)-1,4-dihydro-1-ethyl-2-methyl-pyridine-3,5,6-tricarboxylate,” Protein Sci., 8:1930-1945 (1999).
Rath, V.L. et al., “Activation of Human Liver Glycogen Phosphorylase by Alteration of the Secondary Structure and Packing of the Catalytic Core,” Mol. Cell, 6:139-148 (Jul. 2000).
Rosauer, K.G., et al., “Novel, 3,4-Dihydroquinolin-2(1H)-one Inhibitors of Human Glycogen Phosphorylase a,” Bioorganic & Medicinal Chemistry Letters, 13:4385-4388 (2003).
Soman, G., et al. “Aromatic Compounds as Allosteric Inhibitors of Glycogen Phosphorylase beta,” biochimica et Biophysica Acta, 358:359-362 (1974).
Soman, G., et al., “The Nature of the Binding Site for Aromatic Compounds in Glycogen Phosphorylase beta,” Biochem. J., 147:369-371 (1975).
Teague, J., “Mobilisation of Tissue Glycogen Following Inhibition of Glycogen Phosphorylase in fa/fa Rat,” Diabetes, 53, Supp. 1, A365, 1521-P.
Treadway, J.L., et al., “Glycogen phosphorlase inhibitors for treatment of type 2 diabetes mellitus,” Exp. Opin. Invest. Drugs, 10(2):439-454 (2001).
Turnbull, A., et al., “Pharmacological Inhibition of Glycogen Phosphorylase (GP) Lowers Plasma Glucose in Rat Models of Type 2 Diabetes,” Dibetes, 52, Supp., 1485-P, A343.
Venkatarangan, P., et al., “Prediction of Ligand-REceptor Binding Thermodynamics by Free Energy Force Field Three-Dimensional Quantitative Structure-Activity Relationship Analysis: Applications to a Set of Glucose Analogue Inhibitors of Glycogen Phosphorylase,” J. Med. Chem.,

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