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Expert Opinion on Therapeutic Patents Volume 26, 2016 - Issue 2
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Glycogen phosphorylase inhibitors: a patent review (2013 - 2015)

Marion Donnier-MaréchalInstitut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique 2-Glycochimie, UMR 5246, CNRS and Université Claude Bernard Lyon 1, Villeurbanne, France
&
Sébastien VidalInstitut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique 2-Glycochimie, UMR 5246, CNRS and Université Claude Bernard Lyon 1, Villeurbanne, FranceCorrespondence[email protected]
Pages 199-212 | Received 26 Oct 2015, Accepted 09 Dec 2015, Published online: 11 Jan 2016

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•• An example of post-approval discussion on side effects for type 2 diabetes drugs.

• General review on the biological aspects of GP.

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• Recent review on GP inhibitors and discussing the latest inhibitor site named ‘quercetin site’.

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•• One of the few in vivo biological evaluations of glucose-based GP inhibitors.

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•• One of the few in vivo biological evaluations of glucose-based GP inhibitors.

  • Nagy L, Docsa T, Szántó M, et al. Glycogen phosphorylase inhibitor n-(3,5-dimethyl-benzoyl)-n’-(b-d-glucopyranosyl)urea improves glucose tolerance under normoglycemic and diabetic conditions and rearranges hepatic metabolism. PLoS ONE. 2013;8:e69420.

•• One of the few in vivo biological evaluations of glucose-based GP inhibitors.

  • Docsa T, Marics B, Nemeth J, et al. Insulin sensitivity is modified by a glycogen phosphorylase inhibitor: glucopyranosylidene-spiro-thiohydantoin in streptozotocin-induced diabetic rats. Curr Top Med Chem. 2015;15:2390–2394.

•• One of the few in vivo biological evaluations of glucose-based GP inhibitors.

  • Floettmann E, Gregory L, Teague J, et al. Prolonged inhibition of glycogen phosphorylase in liver of zucker diabetic fatty rats models human glycogen storage diseases. Toxicol Pathol. 2010;38:393–401.
  • Martin WH, Hoover DJ, Armento SJ, et al. Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo. Proc Natl Acad Sci U.S.A. 1998;95:1776–1781.

•• First description of indole-carboxamide GP inhibitors.

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  • Whittamore PRO, Addie MS, Bennett SNL, et al. Novel thienopyrrole glycogen phosphorylase inhibitors: synthesis, in vitro SAR and crystallographic studies. Bioorg Med Chem Lett. 2006;16:5567–5571.
  • Birch AM, Kenny PW, Oikonomakos NG, et al. Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors. Bioorg Med Chem Lett. 2007;17:394–399.
  • Onda K, Shiraki R, Ogiyama T, et al. Design, synthesis, and pharmacological evaluation of N-bicyclo-5-chloro-1H-indole-2-carboxamide derivatives as potent glycogen phosphorylase inhibitors. Bioorg Med Chem. 2008;16:10001–10012.
  • Onda K, Suzuki T, Shiraki R, et al. Synthesis of 5-chloro-N-aryl-1H-indole-2-carboxamide derivatives as inhibitors of human liver glycogen phosphorylase a. Bioorg Med Chem. 2008;16:5452–5464.
  • Cheng K, Liu J, Liu X, et al. Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase. Carbohydr Res. 2009;344:841–850.
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  • Baker DJ, Greenhaff PL, MacInnes A, et al. The experimental type 2 diabetes therapy glycogen phosphorylase inhibition can impair aerobic muscle function during prolonged contraction. Diabetes. 2006;55:1855–1861.

••Only study available to determine the influence of GP inhibition on muscle function.

  • Zhang L. Benzazepinone derivatives as glycogen phosphorylase inhibitors, their preparation and pharmaceutical use. CN103497181A. 2014.
  • Zhang L. Benzazepine ketone compounds as glycogen phosphorylase inhibitor, preparation method therefor, and medical uses. WO2015043111A1. 2015.
  • Henke BR. Inhibition of glycogen phosphorylase as a strategy for the treatment of type 2 diabetes. In: Jones RM, editor. New therapeutic strategies for type 2 diabetes: small molecule approaches. Cambridge: The Royal Society of Chemistry; 2012. p. 324–365.

• This book is a very good compilation of therapeutic targets in the context of type 2 diabetes; the editor and authors are mainly from industry and provide a very precise overview.

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