5-HT1A receptor ligands and their therapeutic applications: review of new patents

References

• Jacobs BL, Azmitia EC. Structure and function of the brain serotonin system. Physiol Rev. 1992;72:165–229.
   PubMed Web of Science ®Google Scholar
• Polter AM, Li X. 5-HT1A receptor-regulated signal transduction pathways in brain. Cell Sig. 2010;22:1406–1412.
   PubMed Web of Science ®Google Scholar
• Chilmonczyk Z, Bojarski A, Pilc A, et al. Functional selectivity and antidepressant activity of serotonin 1A receptor ligands. Int J Mol Sci. 2015;16:18474–18506.
   PubMed Web of Science ®Google Scholar
• Valdizán EM, Castro E, Pazos A. Agonist-dependent modulation of G-protein coupling and transduction of 5-HT1A receptors in rat dorsal raphe nucleus. Int J Neuropsychopharmacol. 2010;13:835–843.
   PubMed Web of Science ®Google Scholar
• Azmitia EC, Gannon PJ, Kheck NM, et al. Cellular localization of the 5-HT1A receptor in primate brain neurons and glial cells. Neuropsychopharmacology. 1996;14:35–46.
   PubMed Web of Science ®Google Scholar
• Miyazaki I, Asanuma M. Serotonin 1A receptors on astrocytes as a potential target for the treatment of Parkinson’s disease. Curr Med Chem. 2016;23:686–700.
   PubMed Web of Science ®Google Scholar
• Sprouse JS, Aghajanian GK. Responses of hippocampal pyramidal cells to putative serotonin 5-HT1A and 5-HT1B agonists: a comparative study with dorsal raphe neurons Neuropharmacology. 1988;27:707–715.
   PubMed Web of Science ®Google Scholar
• Albert PR, Le François B, Millar AM. Transcriptional dysregulation of 5-HT1A autoreceptors in mental illness. Mol Brain 2011;4:21.
   PubMed Web of Science ®Google Scholar
• Albert PR. Transcriptional regulation of the 5-HT1A receptor: implications for mental illness, Philos Trans R Soc Lond B Biol Sci. 2012;367:2402–2415.
   PubMed Web of Science ®Google Scholar
• Garcia-Garcia AL, Newman-Tancredi A, Leonardo ED. P5-HT1A receptors in mood and anxiety: recent insights into autoreceptor versus heteroreceptor function. Psychopharmacology (Berl). 2014;231:623–636.
   PubMed Web of Science ®Google Scholar
• Sprouse J, Reynolds L, Li X, et al. 8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production. Neuropharmacology. 2004;46:52–62. Available from: http://www.ncbi.nlm.nih.gov/pubmed/14654097
   PubMed Web of Science ®Google Scholar
• Howland RH. Buspirone: back to the future. J Psychosoc Nurs Ment Heal Serv. 2015;53:21–24.
   PubMed Web of Science ®Google Scholar
• Boess FG, Martin IL. Molecular biology of 5-HT receptors. Neuropharmacology. 1994;33:275–317.
   PubMed Web of Science ®Google Scholar
• Bang-Andersen B, Ruhland T, Jørgensen M, et al. Discovery of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): a novel multimodal compound for the treatment of major depressive disorder. J Med Chem. 2011;54:3206–3221.
   PubMed Web of Science ®Google Scholar
• Wang S-M, Han C, Lee S-J, et al. Vilazodone for the treatment of major depressive disorder: focusing on its clinical studies and mechanism of action. Psychiatry Investig. 2015;12:155–163.
   PubMed Web of Science ®Google Scholar
• Citrome L. Cariprazine: chemistry, pharmacodynamics, pharmacokinetics, and metabolism, clinical efficacy, safety, and tolerability. Exp Op Drug Metab Tox. 2013;9:193–206.
   PubMed Web of Science ®Google Scholar
• McCreary AC, Glennon JC, Ashby CR Jr, et al. SLV313 (1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-4- [5-(4-fluoro-phenyl)-pyridin-3-ylmethyl]-piperazine monohydrochloride): a novel dopamine D2 receptor antagonist and 5-HT1A receptor agonist potential antipsychotic drug. Neuropsychopharmacology. 2006;32:78.
   PubMed Web of Science ®Google Scholar
• de Boer SF, Newman-Tancredi A. Anti-aggressive effects of the selective high-efficacy “biased” 5-HT₁A receptor agonists F15599 and F13714 in male WTG rats. Psychopharmacology (Berl). 2016;233:937–947.
   PubMed Web of Science ®Google Scholar
• Watson J, Collin L, Ho M, et al. 5-HT(1A) receptor agonist-antagonist binding affinity difference as a measure of intrinsic activity in recombinant and native tissue systems. Brit J Pharmacol. 2000;130:1108–1114.
   PubMed Web of Science ®Google Scholar
• Reinhold JA, Mandos LA, Rickels K, et al. Pharmacological treatment of generalized anxiety disorder. Expert Opin Pharmacother. 2011;12:2457–2467.
   PubMed Web of Science ®Google Scholar
• Schatzberg A, Nemeroff C. The American psychiatric publishing textbook of psychopharmacology. 4th ed. ed. Washington, D.C.: American Psychiatric Publishing Inc; 2009.
   Google Scholar
• Enkelmann R. Alprazolam versus buspirone in the treatment of outpatients with generalized anxiety disorder. Psychopharmacology (Berl). 1991;105:428–432.
   PubMed Web of Science ®Google Scholar
• Sramek JJ, Tansman M, Suri A, et al. Efficacy of buspirone in generalized anxiety disorder with coexisting mild depressive symptoms. J Clin Psychiatry. 1996;57:287–291. Available from: http://www.ncbi.nlm.nih.gov/pubmed/8666569
   PubMed Web of Science ®Google Scholar
• Pierz KA, Thase ME. A review of vilazodone, serotonin, and major depressive disorder. Prim Care Companion CNS Disord. 2014. DOI:10.4088/PCC.13r01554
   PubMedGoogle Scholar
• Dawson LA, Watson JM. Vilazodone: a 5-HT1A receptor agonist/serotonin transporter inhibitor for the treatment of affective disorders. CNS Neurosci Ther. 2009;15:107–117.
   PubMed Web of Science ®Google Scholar
• Fang Z-L, Harrison TJ, Yang J-Y, et al. Prevalence of hepatitis B virus infection in a highly endemic area of southern China after catch-up immunization. J Med Vir. 2012;84:878–884.
   PubMed Web of Science ®Google Scholar
• Sahli ZT, Banerjee P, Tarazi FI. The preclinical and clinical effects of vilazodone for the treatment of major depressive disorder. Exp Op Drug Disc. 2016;11:515–523.
   PubMed Web of Science ®Google Scholar
• Chauhan S, Singh PS. Is vilazodone really the answer to the delay associated with the onset of antidepressant action of SSRIs? – a randomised control trial. Int J Clin Psych. 2018;6:9–18.
   Google Scholar
• Sanchez C, Asin KE, Artigas F. Vortioxetine, a novel antidepressant with multimodal activity: review of preclinical and clinical data. Pharmacol Ther. 2015;145:43–57.
   PubMed Web of Science ®Google Scholar
• Garnock-Jones KP. Vortioxetine: a review of its use in major depressive disorder. CNS Drugs. 2014;28:855–874.
   PubMed Web of Science ®Google Scholar
• Westrich L, Haddjeri N, Dkhissi-Benyahya O, et al. Involvement of 5-HT₇ receptors in vortioxetine’s modulation of circadian rhythms and episodic memory in rodents. Neuropharmacology. 2015;89:382–390.
   PubMed Web of Science ®Google Scholar
• Borsini F, Evans K, Jason K, et al. Pharmacology of flibanserin. CNS Drug Rev. 2002;8:117–142.
   PubMedGoogle Scholar
• Dhanuka I, Simon JA. Flibanserin for the treatment of hypoactive sexual desire disorder in premenopausal women. Exp Op Pharmacother. 2015;16:2523–2529.
   PubMed Web of Science ®Google Scholar
• Deeks ED. Flibanserin: first global approval. Drugs. 1815–1822;75(2015). DOI:10.1007/s40265-015-0474-y
   Google Scholar
• Dooley EM, Miller MK, Clayton AH. Flibanserin: from bench to bedside. Sex Med Rev. 2017;5:461–469.
   PubMed Web of Science ®Google Scholar
• [cited 2018 June 1]. Available from: https://drugs.ncats.io/drug/37JK4STR6Z
   Google Scholar
• [cited 2018 June 1]. Available from: https://www.drugbank.ca/
   Google Scholar
• [cited 2018 June 1]. Available from: http://www.guidetopharmacology.org/GRAC/ObjectDisplayForward?objectId=1
   Google Scholar
• Newman-Tancredi A. Biased agonism at serotonin 5-HT 1A receptors: preferential postsynaptic activity for improved therapy of CNS disorders. Neuropsychiatry (London). 2011;1:149–164.
   Google Scholar
• Assié M-B, Bardin L, Auclair AL, et al. F15599, a highly selective post-synaptic 5-HT1A receptor agonist: in-vivo profile in behavioural models of antidepressant and serotonergic activity. Int J Neuropsychopharmacol. 2010;13:1285–1298.
   PubMed Web of Science ®Google Scholar
• Newman-Tancredi A, Martel J-C, Assié M-B, et al. Signal transduction and functional selectivity of F15599, a preferential post-synaptic 5-HT1A receptor agonist. Br J Pharmacol. 2009;156:338–353.
   PubMed Web of Science ®Google Scholar
• [cited 2018 June 1]. Available from: http://www.bristol.ac.uk/news/2014/april/rett-syndrome-research.html
   Google Scholar
• [cited 2018 June 1]. Available from: https://rettsyndrome.wordpress.com/2015/06/24/rsrt-awards-530000-to-neurolixis-for-clinical-development-of-nlx-101/
   Google Scholar
• [cited 2018 June 1]. Available from: http://neurolixis.com/images/stories/nlx_pf_license_23sept13.pdf
   Google Scholar
• McCreary AC, Varney MA, Newman-Tancredi A. The novel 5-HT 1A receptor agonist, NLX-112 reduces l -DOPA-induced abnormal involuntary movements in rat: A chronic administration study with microdialysis measurements. Neuropharmacology. 2016;105:651–660.
   PubMed Web of Science ®Google Scholar
• Iderberg H, McCreary AC, Varney MA, et al. NLX-112, a novel 5-HT 1A receptor agonist for the treatment of l -DOPA-induced dyskinesia: behavioral and neurochemical profile in rat. Exp Neurol. 2015;271:335–350.
   PubMed Web of Science ®Google Scholar
• [cited 2018 June 1]. Available from: http://www.neurolixis.com/en/company/therapeutic-focus/parkinsons-disease.html
   Google Scholar
• Vidal B, Fieux S, Colom M, et al. 18F-F13640 preclinical evaluation in rodent, cat and primate as a 5-HT1A receptor agonist for PET neuroimaging. Brain Struct Funct. 2018;223:2973–2988.
   PubMed Web of Science ®Google Scholar
• [cited 2018 June 1]. Available from: https://www.clinicaltrials.gov/ct2/show/NCT03347331?term=befiradol&rank=1
   Google Scholar
• Aznavour N, Zimmer L. [18F]MPPF as a tool for the in vivo imaging of 5-HT1A receptors in animal and human brain. Neuropharmacology. 2007;52:695–707.
   PubMed Web of Science ®Google Scholar
• Vuong B-K, Kiesewetter DO, Lang L, et al. An automated one-step one-pot [(18)F]FCWAY synthesis: development and minimization of chemical impurities. Nucl Med Biol. 2007;34:433–438.
   PubMed Web of Science ®Google Scholar
• Rojas PS, Fiedler JL. What do we really know about 5-HT1A receptor signaling in neuronal cells? Front Cell Neurosci. 2016;10. DOI:10.3389/fncel.2016.00272
   PubMed Web of Science ®Google Scholar
• Celada P, Bortolozzi A, Artigas F. Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research. CNS Drugs. 2013;27:703–716. .
   PubMed Web of Science ®Google Scholar
• Carhart-Harris R, Nutt D. Serotonin and brain function: a tale of two receptors, J Psychopharm. 2017;31:1091–1120.
   PubMed Web of Science ®Google Scholar
• Yohn CN, Gergues MM, Samuels BA. The role of 5-HT receptors in depression. Mol Brain. 2017;10:28.
   PubMed Web of Science ®Google Scholar
• Glikmann-Johnston Y, Saling MM, Reutens DC, et al. Hippocampal 5-HT1A receptor and spatial learning and memory, front. Pharmacol. 2015;6. DOI:10.3389/fphar.2015.00289.
   Web of Science ®Google Scholar
• Lacivita P, Di Pilato P, De Giorgio N, et al. The therapeutic potential of 5-HT1A receptors: A patent review. Expert Opin Ther Pat. 2012;22:887–902..
   PubMed Web of Science ®Google Scholar
• Martins CL, Da Silva F, Silva CD, et al., N-phenylpiperazine derivatives that are antagonists of A1A, A1D adrenoreceptors and 5-HT1A receptors for the treatment of benign prostate hyperplasia, pharmacutical compositions containing the same. US 2015/0011566. 2015.
   Google Scholar
• Martins CL, Da Silva F, Silva CD, et al., N-phenylpiperazine derivatives that are antagonists of A1A, A1D adrenoreceptors and 5-HT1A receptors for the treatment of benign prostate hyperplasia, pharmacutical compositions containing the same. WO 2013/102249. 2013.
   Google Scholar
• McNeal J. Pathology of benign prostatic hyperplasia. Insight into etiology. Ulor Clin North Am. 1990;17:477–486.
   PubMedGoogle Scholar
• Abdul M, Anezinis PE, Logothetis CJ, et al. Growth inhibition of human prostatic carcinoma cell lines by serotonin antagonists. Anticancer Res. 1994;14:1215–1220. Available from: http://www.ncbi.nlm.nih.gov/pubmed/8074475
   PubMed Web of Science ®Google Scholar
• Dizeyi N, Bjartell A, Nilsson E, et al. Expression of serotonin receptors and role of serotonin in human prostate cancer tissue and cell lines. Prostate. 2004;59:328–336.
   PubMed Web of Science ®Google Scholar
• Silva RO, de Oliveira AS, Nunes Lemes LF, et al. Synthesis and structure–activity relationships of novel arylpiperazines as potent antagonists of α1-adrenoceptor. Eur J Med Chem. 2016;122:601–610.
   PubMed Web of Science ®Google Scholar
• Ullah N, Al-Shaheri A. 4-aryl-1-(biarylmethylene)piperidine compounds. US 2014/0296528. 2013.
   Google Scholar
• Ullah N. 6-piperazinyl-3,4-dihydroquinazolin-2(1H)-ones. US 2015/0374695. 2015.
   Google Scholar
• CHEMBL database release. 2017;23.DOI:10.6019/CHEMBL.database.23. Available from: https://www.ebi.ac.uk/chembl/downloads
   Google Scholar
• Li J, Chen X, Ma Z, et al. Benzoisothiazole compounds and use in preparation of antipsychotic drugs. WO 2014/180165. 2014.
   Google Scholar
• Li J, Chen X, Ma Z, et al. Benzoisothiazole compounds and use in preparation of antipsychotic drugs. US 2016/0096811. 2016.
   Google Scholar
• Chen XW, Sun YY, Fu L, et al. Synthesis and pharmacological characterization of novel N-(trans-4-(2-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)cyclohexyl)amides as potential multireceptor atypical antipsychotics. Eur J Med Chem. 2016;123:332–353.
   PubMed Web of Science ®Google Scholar
• Booth R. Compounds and methods for modulating serotonin receptors in the periphery. WO 2016/187377. 2016.
   Google Scholar
• Booth RG. Compounds and methods for modulating serotonin receptors in the periphery. US 2018/0125798. 2018.
   Google Scholar
• Zhang Y, Jin C, Zhou R. Substituted piperazine compounds and methods of use thereof. US 2016/0244429. 2016.
   Google Scholar
• Zajdel P, Marciniec K, Kamiński K, et al., (Quinoline or isoquinoline)sulfonamides of cyclic amines as antipsychotic drugs. WO 2016/003296. 2016.
   Google Scholar
• Zajdel P, Kos T, Marciniec K, et al. Novel multi-target azinesulfonamides of cyclic amine derivatives as potential antipsychotics with pro-social and pro-cognitive effects. Eur J Med Chem. 2018;145:790–804.
   PubMed Web of Science ®Google Scholar
• Sniecikowska J, Bucki A, Varney MA. compounds for treating disorders sensitive to serotoninergic regulation controlled by the 5-HT1A receptors. WO 2017/220799. 2017.
   Google Scholar
• Bollinger S, Hübner H, Heinemann FW, et al. Novel pyridylmethylamines as highly selective 5-HT1A superagonists. J Med Chem. 2010;53:7167–7179.
   PubMed Web of Science ®Google Scholar
• Vacher B, Colpaert F, Maurel JL. Novel derivatives of Aryl-{4-halogeno-4-[aminomethyl]-piperinin-1-yl}-methanone their method of preparation and their use as medicinal products. WO 2010/139758. 2010.
   Google Scholar
• Guertin P. Methods and uses for inducing or facilitaing micturition in a patient in need thereof. WO 2015/127558. 2015.
   Google Scholar
• Guertin P. Methods and uses for inducing or facilitaing defecation in a patient in need thereof. WO 2015/127556. 2015.
   Google Scholar
• Muñoz A, Li Q, Gardoni F, et al. Combined 5-HT1A and 5-HT1B receptor agonists for the treatment of L-DOPA-induced dyskinesia. Brain. 2008;131:3380–3394.
   PubMed Web of Science ®Google Scholar
• Muñoz A, Carlsson T, Tronci E, et al. Serotonin neuron-dependent and -independent reduction of dyskinesia by 5-HT1A and 5-HT1B receptor agonists in the rat Parkinson model. Exp Neurol. 2009;219:298–307.
   PubMed Web of Science ®Google Scholar
• Hansen JB, Thomsen MS, Mikkelsen JD, et al., Orally available pharmaceutical formulation suitable for improved management of movement disorders. WO 2013/156035. 2013.
   Google Scholar
• Hansen JB, Thomsen MS, Mikkelsen JD. Combinations of serotonin receptor agonists for treatment of movement disorders. US 2014/0221385. 2014.
   Google Scholar
• Hansen JB, Thomsen MS. The use of serotonin receptor agonists for treatment of movement disorders. WO 2013/004249. 2013.
   Google Scholar
• Hansen JB, Thomsen MS. Use of buspirone metabolites. WO 2015/197079. 2015.
   Google Scholar
• Leśniak D, Jastrzębski S, Podlewska S, et al. Quo vadis G protein-coupled receptor ligands? A tool for analysis of the emergence of new groups of compounds over time. Bioorg Med Chem Lett. 2017;27:626–631.
   PubMed Web of Science ®Google Scholar
• Wong CH, Siah KW, Lo AW. Estimation of clinical trial success rates and related parameters. Biostatistics. 2018;1–14. Available from: https://academic.oup.com/biostatistics/advance-article/doi/10.1093/biostatistics/kxx069/4817524
   PubMedGoogle Scholar
• Andrade C. Ketamine for depression, 1: clinical summary of issues related to efficacy, adverse effects, and mechanism of action. J Clin Psychiat. 2017;78:e415–e419.
   PubMed Web of Science ®Google Scholar
• Zanos P, Gould TD. Mechanisms of ketamine action as an antidepressant, Mol Psychiatr. 2018;23:801–811.
   PubMed Web of Science ®Google Scholar
• Thibaut F. Anxiety disorders: a review of current literature. Dialogues Clin Neurosci. 2017;19:87–88.
   PubMed Web of Science ®Google Scholar
• Remes O, Brayne C, van der Linde R, et al. A systematic review of reviews on the prevalence of anxiety disorders in adult populations. Brain Behav. 2016;6:e00497.
   PubMed Web of Science ®Google Scholar
• Williams T, Hattingh CJ, Kariuki CM, et al. Pharmacotherapy for social anxiety disorder (SAnD), cochrane database sys. Rev. 2017. DOI:10.1002/14651858.CD001206.pub3.
   Google Scholar