Indolamid derivatives which possess glycogenphosphorylase...

Details Indolamid derivatives which possess glycogenphosphorylase... Indolamid derivatives which possess glycogenphosphorylase...

2006-11-21

2006-11-21

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...

C514S381000, C514S414000, C514S419000, C546S201000, C548S254000, C548S467000, C548S492000

Reexamination Certificate

active

07138415

ABSTRACT:
Heterocyclic amides of formula (1)wherein:is a single or double bond;A is phenylene or heteroarylene;m is 0, 1 or 2;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 andC1-4alkyl(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)(R9), —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), Brabander et al.
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: 4791112 (1988-12-01), Bagley et al.
patent: 4794120 (1988-12-01), Manoury
patent: 5521155 (1996-05-01), Malabarba et al.
patent: 5863903 (1999-01-01), Lundgren
patent: 5998463 (1999-12-01), Hulin
patent: 6660742 (2003-12-01), Lee
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: 116360 (1984-08-01), 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: 03/074485 (2003-09-01), None
patent: 03/074513 (2003-09-01), None
patent: 03/074517 (2003-09-01), None
patent: 03/074531 (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: 2004092158 (2004-10-01), None
patent: 2004113345 (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
Crochel, R.A., et al., “Synthesis of Substituted Thieno[2,3-b] pyrroles,” vol. 11, 143-150 (Apr. 1974).
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 anaestetised 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).
Treadway, J.L., et al., “Glycogen phosphorlase inhibitors for treatment of type 2 diabetes mellitus,” Exp. Opin. Invest. Drugs, 10(3):439-454 (2001).
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., 42:2169-2179 (1999).
Crochet, R.A., et al., J. Het. Chem., “Synthesis of Substituted Thieno[2,3-b] pyrroles,” vol. 11, 143-150 (Apr. 1974).
Vertigan, H., “Impact of cell glycogen content on modulation of hepatocyte glucose metabolism by pharmacological agents,” Diabetologia, 47, Supp. 1, 589, A214 (2004).
Teague, J., “Mobilisation of Tissue Glycogen Following Inhibition of Glycogen Phosphorylase in fa/fa Rat.” Diabetes, 52, Supp. 2, A365, 1521-P (2003).
Font, M. et al. “Indoles and pyridazino[4,5-b] indoles as nonnucleoside analog inhibitors of HIV-1 reverse transcripptase”, European Journal Med Chem (1985), 30(12), 963-71.
Vertigan, H. et al. “Impact of cell glycogen content on modulation of hepatocyte glucose metabolism by pharmacological agents”, EASD Munich (2004).
Barlett, J. et al. “In Vitro and In Vivo Profile of Gpi688m a novel, Potent Inhibitor of Glycogen Phosphorylase”, ADA S

Affiliated with

Also associated with

Rating

Indolamid derivatives which possess glycogenphosphorylase... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Indolamid derivatives which possess glycogenphosphorylase..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Indolamid derivatives which possess glycogenphosphorylase... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3657685