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Research Article

Methylsulfonylpyrazolyl Oxadiazoles and Thiadiazoles as Potent, Orally Bioavailable Cannabinoid-1 Receptor Antagonists for the Treatment of Obesity

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Pages 947-967 | Published online: 19 Aug 2009

Bibliography

  • Bray GA . Obesity: the disease.J. Med. Chem.49, 4001–4007 (2006).
  • WHO . Report of a WHO consultation on obesity. Obesity-preventing and managing a global epidemic. Geneva, Switzerland (2000).
  • Antel J , GregoryPC, Nordheim,U. CB1 cannabinoid receptor antagonists for treatment of obesity and prevention of comorbid metabolic disorders.J. Med. Chem.49, 4008–4016 (2006).
  • Mokdad AH , MarksJS, StroupDF, GerberdingJL. Actual causes of death in the United States.J. Am. Med. Assoc.291, 1238–1245 (2004).
  • Hepworth D , CarpinoPA, BlackSC. Centrally acting anti-obesity agents.Annu. Rep. Med. Chem.41, 77–97 (2006).
  • Pagotto U , VicennatiV, Pasquali,R. The endocannabinoid system and the treatment of obesity.Ann. Med.37, 270 (2005).
  • Stella N , SchweitzerP, PiomelliD. A second endogenous cannabinoid that modulates long-term potentiation.Nature388, 773–778 (1997).
  • Muineddu G , RuiuS, MussinuJMet al. Tricyclic pyrazoles part 2: synthesis and biological evaluation of novel 4,5-dihydro-1H-benzo[g]indazole-based ligands for cannabinoid receptors. Bioorg. Med. Chem. 13, 3309–3320 (2005).
  • Matsuda LA , LolaitSJ, BrownsteinMJ, YoungAC, BonnerTI. Structure of a cannabinoid receptor and functional expression of the cloned cDNA.Nature346, 561–564 (1990).
  • Munro S , ThomasKL, Abu-ShaarM. Molecular characterization of a peripheral receptor for cannabinoids.Nature365, 61–65 (1993).
  • Lange JHM , KruseCG. Recent advances in CB1 cannabinoid receptor antagonists.Curr. Opin. Drug Discov. Dev.7, 498–506 (2004).
  • Lange JHM , KruseCG. Medicinal chemistry strategies to CB1 cannabinoid receptor antagonists.Drug Discov. Today10, 693–702 (2005).
  • Barth F . CB1 cannabinoid receptor antagonists.Annu. Rep. Med. Chem.40, 103–118 (2005).
  • Bellocchio L , ManciniG, VicennatiV, PasqualiR, PagottoU. Cannabinoid receptors as therapeutic targets for obesity and metabolic diseases.Curr. Opin. Pharmacol.6, 586–591 (2006).
  • Boström J , BerggrenK, GreasleyP, WilstermannM. Scaffold hopping, synthesis and structure–activity relationships of 5,6-diaryl-pyrazine-2-amide derivatives: a novel series of CB1 receptor antagonists.Bioorg. Med. Chem.15, 4077–4084 (2007).
  • Lee SH , SeoHJ, Lee,SHet al. Biarylpyrazolyl oxadiazole as potent, selective, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesity. J. Med. Chem. 51(22), 7216–7233 (2008).
  • Lin LS , LanzaTJ, JewellJPet al. Discovery of N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-{[5-(trifluoromethyl) pyridin-2-yl]oxy}propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. J. Med. Chem. 49, 7584–7587 (2006).
  • Chen C y, Frey LF, Shultz S et al. Catalytic, enantioselective synthesis of taranabant, a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. Org. Process Res. Dev.11, 616–623 (2007).
  • Lin LS , HaS, BallRGet al. Conformational analysis and receptor docking of N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (taranabant, MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist. J. Med. Chem. 51, 2108–2114 (2008).
  • Fong TM , GuanXM, MarshDJet al. Antiobesity efficacy of a novel cannabinoid-1 receptor inverse agonist, N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (MK-0364), in rodents. J. Pharmacol. Exp. Ther. 321, 1013–1022 (2007).
  • Lange JH , CoolenHK, van Stuivenberg HH et al. Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB1 cannabinoid receptor antagonists. J. Med. Chem.47, 627 (2004).
  • Griffith DA , HadcockJR, BalckSCet al. Discovery of 1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4-ethylaminopiperidine-4-carboxylic acid amide hydrochloride (CP-945,598), a novel, potent, and selective cannabinoid type 1 receptor antagonist. J. Med. Chem. 52(2), 234–237 (2009).
  • Jones D . End of the line for cannabinoid receptor 1 as an anti-obesity target?Nature Rev. Drug Discov.7, 961–962 (2008).
  • Lange JHM , KruseCG. Cannabinoid CB1 receptor antagonists in therapeutic and structural perspectives.Chem. Rec.8, 156–168 (2008).
  • Shim JY , WelshWJ, CartierE, EdwardsJL, HowlettAC. molecular interaction of the antagonist N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide with the CB1 cannabinoid receptor. J. Med. Chem.45, 1447–1459 (2002).
  • Kang SY , LeeSH, SeoHJet al. Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists. Bioorg. Med. Chem. italic>Lett. 18, 2384–2388 (2008).
  • Kim JY , SeoHJ, LeeSHet al. Diarylpyrazolyl oxadiazole and thiadiazole derivatives as cannabinoid CB1 receptor antagonists. Bioorg. Med. Chem. Lett. 19, 142–145 (2009).
  • Lee SH , SeoHJ, KimMJet al. Oxadiazole-diarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands. Bioorg. Med. Chem. Lett. 19, 1899–1902 (2009).
  • Lan R , LiuQ, FanPet al. Structure–activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J. Med. Chem. 42, 769–776 (1999).
  • Katoch-Rouse R , PavlovaOA, CaulderT, HoffmanAF, MukhinAG, HortiAG. Synthesis, structure–activity relationship, and evaluation of SR141716 analogues: development of central cannabinoid receptor ligands with lower lipophilicity.J. Med. Chem.46, 642–645 (2003).
  • Nimitz JS , MosherHS. A new synthesis of α-keto esters and acids.J. Org. Chem.46, 211–213 (1981).
  • Brain CT , PaulJM, LoongYet al. Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions. Tetrahedron Lett. 40, 3275–3278 (1999).
  • Brain CT , BruntonSA. Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents.Synlett40(16), 382 (2001).
  • Kiryanov AA , SampsonP, SeedAJ. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson’s reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis,J. Org. Chem.66, 7925–7929 (2001).
  • Kuster JE , StevensonJI, WardSJ, D‘AmbraTE, HaycockDA. Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids.J. Pharmacol. Exp. Ther.264, 1352–1363 (1993).
  • Hildebrandt AL , Kelly-SullivanDM, BlackSC. Antiobesity effects of chronic cannabinoid CB1 receptor antagonist treatment in diet-induced obese mice.Eur. J. Pharmacol.462(1–3), 125–132 (2003).
  • Murphy JW , KendallDA. Integrity of extracellular loop 1 of the human cannabinoid receptor 1 is critical for high-affinity binding of the ligand CP55,940 but not SR141716A.Biochem. Pharmacol.65, 1623–1631 (2003).

Patents

  • SANOFI (Paris, France): US005462960 (1995). Pyrazole-3-carboxamide derivatives, process for their preparation and pharmaceutical compositions in which they are present.
  • PFIZER, INC.: WO2006043175 (2006). Process for preparing purine compounds.
  • PFIZER, INC.: US20040077650 (2004). Cannabinoid receptor ligands and uses thereof.
  • PFIZER, INC.: US20050043327 (2005). Pharmaceutical composition for the prevention and treatment of addiction in a mammal.
  • SANOFI-AVENTIS: WO2006/087480 (2006). (1,5-diphenyl-1H-pyrazol-3-yl)oxadiazole derivatives, preparation method thereof and use of same in therapeutics.
  • TANABE SEIYAKU CO. LTD.: WO2007/046550 (2007). Pyrazole compounds having cannabinoid receptor (CB1) antagonizing activity.
  • SOLVAY: WO 2007138050 (2007). Sulfur containing pyrazole derivatives as selective cannabinoid CB1 receptor antagonists.
  • SOLVAY: WO 2005118557 (2005). Tetrasubstituted imidazole derivatives as cannabinoid CB1 receptor modulators with a high CB1/CB2 receptor subtype selectivity.

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