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Expert Opinion on Therapeutic Patents Volume 13, 2003 - Issue 6
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Review

Recent advances in histamine H3/H4 receptor ligands

Holger Stark Institut für Pharmazeutische Chemie, Johann Wolfgang Goethe-Universität, Biozentrum, Marie-Curie-Strasse 9, 60439 Frankfurt am Main, Germany. [email protected]
Pages 851-865 | Published online: 02 Mar 2005

Bibliography

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  • •First description of the histamine H3 receptor.
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  • •Recommendable view on heteroreceptor function of H3 receptors.
  • WATANABE T, TIMMERMAN H, YANAI K (Eds). Histamine research in the new millenium. Elsevier Science Publishers, Amsterdam, The Netherlands (2001).
  • ••Important collection of the latest findings inhistamine research.
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  • ••Cloning of hH3 receptor.
  • SCHWARTZ JC, MORISSET S, ROULEAU A et al.: Application of genomics to drug design: the example of the histamine H3 receptor. Eur. Neuropsychopharmacol (2001) 11(6):441–448.
  • •Recommendable review on a variety of H3 receptor aspects.
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  • ••Paper showing detailed pharmacology of H3receptor isoforms and screening of numerous neuropsychiatric drugs.
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  • •Differences in H3 receptor isoforms.
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  • ••First paper describing high constitutive activity of H3 receptors in vivo and of a neutral antagonist and inverse agonists.
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  • •Constitutive activity and inverse agonism.
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  • ••Cloning of hH4 receptor.
  • HOUGH LB: Genomics meets histamine receptors: new subtypes, new receptors. Pharmacol Exp. The]: (2001) 59(3):415–419.
  • •Short summary of actual genomic investigation on H3 and H4 receptors.
  • STARK H, SCHLEGEL B, SIPPL W: News on old histamine I. A new member in the receptor family. Pharm. Unsere Zeit(2003) 32:92–93.
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  • ••Recommendable discussion on H3 and H4receptor aspects in immune system and haematopoisis.
  • TOZER MJ, KALINDJIAN B: Histamine H3 receptor antagonists. Expert Opin. Ther. Patents (2000) 10(7):1045–1055.
  • •Recommendable review on the H3 receptor antagonist and patent situation.
  • STARK H, ARRANGJM, LIGNEAU X et al.: The histamine H3 receptor and its ligands. Frog. Med. Chem. (2001) 38:279–308.
  • ••Recommendable review on histamine H3receptor ligands.
  • BROWN RE, STEVENS DR, HAAS HL: The physiology of brain histamine. Frog. Neurobiol (2001) 63(6):637–672.
  • ••Recommendable review on physiologicalaspects of brain histamine.
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  • ••Recommendable short review ontherapeutic aspects of H3 receptor ligands.
  • HAAS H, PANULA P: The role of histamine and the tuberomamillary nucleus in the nervous system. Nat. Rev Neurosci. (2003) 4:121–130.
  • ••Recommendable review on histarninergicinnervation within the tuberomarnillary nucleus.
  • LIPP R, STARK H, SCHUNACK W: Pharmacochemistry of H3-receptors. In: Biochemistry and Methology (Volume 16). The Histamine Receptor. Schwartz JC, Haas HL (Eds), Wiley-Liss, New York (1992):57–72.
  • SASSE A, SADEK B, LIGNEAU X et al.: New histamine H3-receptor ligands of the proxifan series: imoproxifan and other selective antagonists with high oral in vivo potency. [Med. Chem. (2000) 43(17):3335–3343.
  • ARRANG JM, GARBARG M, LANCELOT JC et al.: Highly potent and selective ligands for histamine H3-receptors. Nature (1987) 327(6118):117–123.
  • ••First paper describing selective ligands forH3 receptors.
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  • STARK H, SADEK B, KRAUSE M et al.: Novel histamine H3-receptor antagonists with carbonyl-substituted 4-(3-(phenoxy)propy1)-1H-imidazole structures like ciproxifan and related compounds. J. Med. Chem. (2000) 43(21):3987–3994.
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  • STARK H. Convenient procedures for synthesis of ciproxifan, a histamine H3-receptor antagonist. Arch. Pharm. (Weinheim) (2000) 333(9):315–316.
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  • LEVI R, SMITH NCE: Histamine H3-receptors: a new frontier in myocardial ischemia. Pharmacol Exp. Ther. (2000) 292:825–830.
  • •Recommendable paper describing cardiac functions of H3 receptors.
  • MACKINS CL, LEVI R: Therapeutic potential of H3-receptor agonists in myocardial infarction. Expert Opin. Investig. Drugs (2000) 9(11):2537–2542.
  • MORINI G, TIMMERMAN H, SCHUNACK W, GRANDI D: Agonists for the histamine H3-receptor differ in their gastroprotective activity in the rat. Inflamm. Res. (2002) 51\(Supp1.1):S75–S76.
  • MORINI G, GRANDI D, STARK H, SCHUNACK W: Histamine H3-receptor antagonists inhibit gastroprotection by N-a-methylhistamine in the rat. Br. J. Pharmacol (2000) 129(8):1597–1600.
  • PANULA P, LINTUNEN M, KARLSTEDT K: Histamine in brain development and tumors. Semin. Cancer Biol. (2000) 10(1):11–14.
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  • POLI E, POZZOLI C, CORUZZI G: Role of histamine H3 receptors in the control of gastrointestinal motility. An overview. .1. Physiol Paris (2001) 95(1–6):67–74.
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  • ••Recommendable paper on neuropsychiatric functions of H3 receptor ligands.
  • ROULEAU A, STARK H, SCHUNACK W, SCHWARTZ JC: Anti-inflammatory and antinociceptive properties of BP 2-94, a histamine H3-receptor agonist prodrug. Pharmacol. Exp. Ther. (2000) 295(1):219–225.
  • •First paper on H3 receptor agonist pro-drugs.
  • CANNON KE, NALWALK JW, STADEL R et al.: Spinal H3-receptor activation induces mechanical but not thermal antinociception. Program No. 54.1 2002 Abstract Viewer/Itinerary Planner. Society for Neuroscience, Washington, DC, USA (2002) CD-ROM.
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  • •Description of histarninergic functions in waking and sleep control.
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  • •Recommendable paper on H3 receptor agonists in migraine.
  • GUERRERO RO, CARDENAS MA, OCAMPO AA, PACHECO MF: Histamine as a therapeutic alternative in migraine prophylaxis: a randomized, placebo-controlled, double-blind study. Headache (1999) 39(8):576–580.
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  • RUBIO S, BEGEGA A, SANTIN LJ, ARIAS JL: Improvement of spatial memory by W-a-methylhistamine, a histamine H3-receptor agonist, on the Morris water-maze in rat. Behav. Brain Res. (2002) 129(1-2):77–82.
  • FOZARD JR: BP-294 Ste Clyne Bioprojet. Curr. Opin. Investig. Drugs(2000)1(1):86–89.
  • KRAUSE M, STARK H, SCHUNACK W: Azomethine prodrugs of (h) -a-methylhistamine, a highly potent and selective histamine H3-receptor agonist. Curi: Med. Chem. (2001) 8:1329–1340.
  • •Review on H3 receptor azomethine pro-drugs.
  • STARK H, KRAUSE M, ROULEAU A, GARBARG M, SCHWARTZ JC, SCHUNACK W: Enzyme-catalyzed pro-drug approaches for the histamine H3-receptor agonist (M-a-methylhistamine. Bioorg. Med. Chem. (2001) 9:191–198.
  • SASSE A, STARK H, REIDEMEISTER S et al.: Novel partial agonists for the histamine H3 receptor with high M vitro and in vivo activity.' Med. Chem. (1999) 42.4269–4274.
  • •First paper on lipophilic non-arninergic agonists for the H3 receptor.
  • SASSE A, LIGNEAU X, ROULEAU A et at Influence of bulky substituents on histamine H3 receptor agonist/antagonist properties. I Med. Chem (2002) 45:4000–4010.
  • PELLOUX-LEON N, FKYERAT A, TERTIUK W et al.: Potent partial agonists for the histamine H3 receptor lacking a nitrogen atom in the side chain. 29th Meeting of the European Histamine Research Society Nemi (Rome), Italy (2000) Abstract 31.
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  • ANICHTCHIK OV, HUOTARI M, PEITSARO N, HAYCOCK JW, MANNISTO PT, PANULA P: Modulation of histamine H3 receptors in the brain of 6-hydroxydopamine-lesioned rats. Ear. .1. Neurosci. (2000) 12(11):3823–3832.
  • PASSANI MB, BLANDINA P: The neuronal histaminergic system in cognition. Curr. Med. Chem. Cen. Nerv. Syst. Agents [In press].
  • •Recommendable review on histaminergic system in cognition.
  • HALPERN MT: GT-2331 (Gliatech., Inc.). CLIFF. Opin. Centr. Peripher. Nerv. Syst. Invest. Drugs (1999) 1:524–527.
  • FLETCHER L: Guilford halts Gliatech deal. Nat. Biotech. (2000) 18(10):1023.
  • PILLOT C, ORTIZ J, HERON A, RIDRAY S, SCHWARTZ JC, ARRANG JM: Ciproxifan, a histamine H3-receptor antagonist/inverse agonist, potentiates neurochemical and behavioral effects of haloperidol in the rat. J. Neurosci. (2002) 22(16):7272–7280.
  • •H3 receptor antagonists as potential neuroleptics or additives to them.
  • PILLOT C, HERON A, SCHWARTZ JC, ARRANG JM: Ciproxifan, a histamine H3-receptor antagonist/inverse agonist, modulates the effects of methamphetamine on neuropeptide mRNA expression in rat striatum. Eur. Neurosci (2003) 17(2):307–314.
  • LINTUNEN M, HYYTIA P, SALLMEN T et al.: Increased brain histamine in an alcohol-preferring rat line and modulation of ethanol consumption by H3 receptor mechanisms. FASEB (2001)15(6):1074–1076.
  • MORI T, NARITA M, ONODERA K, SUZUKI T: Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system. Nihon Shinkei Seishin Yakurigaku Zasshi (2002) 22(3):73–78.
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  • ••First paper describing H3I- mice.
  • TAKAHASHI K, SUWA H, ISHIKAWA T, KOTANI H: Targeted disruption of H3 receptors results in change in brain histamine tone leading to an obese phenotype. " Clin. Invest. (2002) 110:1791–1799.
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  • FOX GB, PAN JB, RADEK RJ et al: Twonovel and selective non-imidazole H3 receptor antagonists A-304121 and A-317920: II. in vivo behavioral and neurophysiological characterization. Pharmacol Exp. Ther. (2003) [In press].
  • •Paper describing numerous in vivo effects of non-imidazole H3 receptor antagonists.
  • VOHORA D, PAL SN, PILLAI KK: Histamine and selective H3-receptor ligands: a possible role in the mechanism and management of epilepsy. Phannacol. Biochem. Behav. (2001) 68(4):735–741.
  • YOSHIDA M, NOGUCHI E, TSURU N: Lack of substantial effect of the H3-antagonist thioperamide and of the non-selective mixed H3-antagonist/H1-agonist betahistine on amygdaloid kindled seizures. Epilepsy Res. (2000) 40(2-3):141–145.
  • ESCHUN G, BAUTISTA E, DUKE K et al.: Effect of histamine H3 receptor blockade on venous return and splanchnic hemodynamics in experimental bacteremia. Grit. Care Med. (2002) 30(3):628–636.
  • TOZER MJ, BUCK IM, COOKE T, KALINDJIAN SB, PETHER MJ, STEEL KI: w-amidaz01-4-yBalkane-1-sulfonamides: a new series of potent histamine H3 receptor antagonists. Bioorg. Med. Chem. (2002) 10(2):425–432.
  • GRASSMANN S, SADEK B, LIGNEAU X et al.: Progress in the proxifan class: heterocyclic congeners as novel potent and selective histamine H3-receptor antagonists. Eur. I Pharm. ScL (2002) 15(4):367–378.
  • ASLANIAN R, MUTAHI MW, SHIH NY: Identification of an novel, orally bioavailable histamine H3 receptor antagonist based on the 4-benzyl-(1H-imidazol-4-34) template. Bioorg. Med. Chem. Lett. (2002) 12:937–941.
  • •Novel chain replacement in H3 receptor antagonists.
  • BERTINARIA M, DI STILO A, TOSCO P et al.: [3-(1H-Imidazol-4-yl)propylguanidines containing furoxan moieties: a new class of H3-antagonists endowed with NO-donor properties. Bioorg. Med. Chem. (2003) 11:1197–1205.
  • GRABMANN S, APELT J, SIPPL W et al.: Imidazole derivatives as a novel class of hybrid compounds with inhibitory N-methyltransferase potencies and histamine hH3 receptor affinities. Bioorg. Med. Chem. (2003) 11:2163–2174.
  • YANG R, HEY JA, ASLANIAN R, RIZZO CA: Coordination of histamine H3 receptor antagonists with human adrenal cytochrome P450 enzymes. Pharmacology (2002) 66(3):128–135.
  • ARRANG JM, GARBARG M, QUACH TT, DAM TRUNG TUONG M, YERAMIANE, SCHWARTZ JC: Actions of betahistine at histamine receptors in the brain. Eur. Pharmacol (1985) 111(1):73–84.
  • TIGHILET B, TROTTIER S, MOURRE C, CHOTARD C, LACOUR M: Betahistine dihydrochloride interaction with the histaminergic system in the cat: neurochemical and molecular mechanisms. Eur.j Pharmacol (2002) 446(1-3):63–73.
  • KATHMANN M, SCHLICKER E, GOTHERT M: Intermediate affinity and potency of clozapine and low affinity of other neuroleptics and of antidepressants at H3 receptors. Psychopharmacology (Ben) (1994) 116(4):464–468.
  • AZUMA H, SAWADA S,TAKEUCHI S, HIGASHIYAMA K, KAKIGI A, TAKEDA T: Expression of mRNA encoding the H1, H2 and H3 histamine receptors in the rat cochlea. NemoReport (2003) 14(3):423–425.
  • GANELLIN CR, LEURQUIN F, PIRIPITSI A et al.: Synthesis of potent non-imidazole histamine H3-receptor antagonists. Arch. Pharm. (Weinheim) (1998) 331(12):395–404.
  • •First paper on potent non-imidazole H3 receptor antagonists.
  • WALCZYNSKI K, GURYN R, ZUIDERVELD OP, TIMMERMAN H: Non-imidazole histamine H3 ligands. Part I. Synthesis of 2-(1-piperaziny1)- and 2- (hexahydro-1H-1,4-diazepin-1- yl)benzothiazole derivatives as H3-antagonists with H1 blocking activities. Farmaco (1999) 54(10):684–694.
  • WALCZYNSKI K, GURYN R, ZUIDERVELD OP, TIMMERMAN H: Non-imidazole histamine H3 ligands. Part 2. New 2-substituted benzothiazoles as histamine H3 antagonists. Arch. Pharm. ffeinheiml (1999) 332(11):389–398.
  • LINNEY ID, BUCK IM, HARPER EA et at.: Design, synthesis and structure-activity relationships of novel non-imidazole histamine H3 receptor antagonists. Med. Chem. (2000) 43(12):2362–2370.
  • LAZEWSKA D, KIEC- KONONOWICZ K, PERTZ HH, STARK H, SCHUNACK W, ELZ S: Piperidine-containing histamine H3-receptor antagonists of the carbamate series: variation of the spacer length. Pharmazie (2001) 56(12):927–932.
  • METER G, LIGNEAU X, PERTZ HH et al.: Piperidino-hydrocarbon compounds as novel non-imidazole histamine H3-receptor antagonists. Bioorg. Med. Chem. (2002) 10(8):2535–2542.
  • LAZEWSKA D, KIEC- KONONOWICZ K, PERTZ HH, ELZ S, STARK H, SCHUNACK W: Piperidine-containing histamine H3 receptor antagonists of the carbamate series: the influence of the additional ether functionality. Pharmazie (2002) 57(12):791–795.
  • METER G, APELT J, REICHERT U et al: Influence of imidazole replacement in different structural classes of histamine H3-receptor antagonists. Eur. .1 Pharm. Sci. (2001) 13(3):249–259.
  • •Imidazole replacement in different classes of H3 receptor antagonists.
  • LIEDTKE S, FLAU K, KATHMANNM et al.: Replacement of imidazole by a piperidine moiety differentially affects the potency of histamine H3-receptor antagonists. Naunyn Schmiedeberg 's Arch. Pharmacol (2003) 367(1):43–50.
  • SHAH C, MCATEE L, BREITENBUCHER JG et al.: Novel human histamine H3 receptor antagonists. Bioorg. Med. Chem. Lett. (2002) 12:3309–3312.
  • FAGHIH R, DWIGHT W, VASUDEVAN A et al: Aminoalkylbiphenylnitrils as histamine-3 receptor ligands. Bioorg. Med. Chem. Lett. (2002) 12:3077–3079.
  • FAGHIH R, DWIGHT W, GENTLES R et al.: Structure-activity relationships of non-imidazole H3 receptor ligands. Part 1. Bioorg. Med. Chem. Lett (2002) 12(15):2031–2034.
  • FAGHIH R, DWIGHT W, BLACK Let al.: Structure-activity relationships of non-imidazole H3 receptor ligands. Part 2: binding preference for D-amino acids motifs. Bioorg. Med. Chem. Lett. (2002) 12(15):2035–2037.
  • ESBENSHADE TA, KRUEGER KM, MILLER TR et al.: Two novel and selective non-imidazole histamine H3 receptor antagonists A-304121 and A-317920: I. In vitropharmacological effects.' Pharmacol Exp. Ther. (2003) [In press].
  • •Different efficacies of inverse agonism for H3 receptor antagonists.
  • LIGNEAU X, MORISSET S,TARDIVEL-LACOMBE J et al.: Distinct pharmacology of rat and human histamine H3 receptors: role of two amino acids in the third transmembrane domain. Br. J. Pharmacol (2000) 131(7):1247–1250.
  • STARK H, SIPPLW, LIGNEAU X et al.: Different antagonist binding properties of human and rat histamine H3 receptors. Bioorg. Med. Chem. Lett. (2001) 11(7):951–954.
  • UVEGES AJ, KOWAL D, ZHANG Yet al.: The role of transmembrane helix 5 in agonist binding to the human H3 receptor. Pharmacol. Exp. Ther: (2002) 301(2):451–458.
  • TING P, LEE J, ALBANESE M et al: The synthesis of substituted fluorenes as novel non-imidazole histamine H3 inhibitors. Bioorg. Med. Chem. Lett. (2002) 12(18):2643–2646.
  • MIKO T, LIGNEAU X, PERTZ HH et al.: Novel nonimidazole histamine H3 receptor antagonists: 1- (4- (phenoxymethyl)benzyl) piperidines and related compounds. I Med. Chem. (2003) 46:1523–1530.
  • CANGIOLI I, BALDI E, MANNAIONI PF et al.: Activation of histaminergic H3 receptors in the rat basolateral amygdala improves expression of fear memory and enhances acetylcholine release. Eat Neurosci. (2002) 16(3):521–528.
  • APELT J, LIGNEAU X, PERTZ HH et al.: Development of a new class of non-imidazole histamine H3 receptor ligands with combined inhibitory histamine N-methyltransferase activity.J Med. Chem. (2002) 45(5):1128–1141.
  • •Paper describing extremely potent H3 receptor antagonist and HMT inhibitors.
  • LEURS R, TLTLP MT, MENGE WM, ADOLFS MJ, ZUIDERVELD OP, TIMMERMAN H: Evaluation of the receptor selectivity of the H3 receptor antagonists, iodophenpropit and thioperamide: an interaction with the 5-HT3 receptor revealed. Br:J. Pharmacol (1995) 116(4):2315–2321.
  • ALLEN MC: Agonist and antagonist effects of histamine H3 receptor ligands on 5-HT3 receptor-mediated ion current in NG 108-15 cells. Eur.j Pharmacol (1998) 361(2-3):261–268.
  • VOROBJEV VS, SHARONOVA IN, WALSH IB, HAAS HL: Histamine potentiates N-methyl-D-aspartate responses in acutely isolated hippocampal neurons. Neuron (1993) 11:837–844.
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Website

  • http://www.gper.org/7tm/htm1s/entries.htm1 GPCR database.
  • http://www.gper.org/7tm/seq/a11/ HH3R_HUMAN.SW.html GPCR database for histamine H3 receptor.
  • http://www.4adi.com/data/histamine/ hr14seq. html Sequence alignment of histamine subreceptors.
  • http://bioinf.man.ac.uk/dbbrowser/ gperPRINTS/PRO1471.html Protein fingerprint database for histamine H3 receptor.
  • http://www.gper.org/7tm/seq/a11/ HH4R_HUMAN.SW.html GPCR data base for histamine H4 receptor.
  • http://www.genmapp.org/IVIAPPSet-Human/GPCRDB_MAPPs/_Support/ Hs_GPCRs_Other/HRH4_Q9H3N8.htm Gene mapping of histamine H4 receptors.

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