Recent progress in the discovery of non-sarcosine based GlyT1 inhibitors

Current Topics in Medicinal Chemistry

Volumn 10, Issue 2, 2010, Pages 170-186

  Wolkenberg, Scott E ^a   Sur, Cyrille ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; 2 CHLORO N [ALPHA (2 PIPERIDINYL)BENZYL] 3 TRIFLUOROMETHYLBENZAMIDE; AZABICYCLO DERIVATIVE; CP 802079; CYCLOPEPTIDE; GLYCINE; GLYCINE DERIVATIVE; GLYCINE TRANSPORTER 1; GLYCINE TRANSPORTER 1 INHIBITOR; LY 2365109; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; ORG 24461; ORG 24598; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; PROTEIN INHIBITOR; SULFONAMIDE; UNCLASSIFIED DRUG; WS 2217; WS 2218; WS 2219; WS 2220; WS 2221; WS 2222;

BRAIN METABOLISM; COGNITION; COGNITIVE DEFECT; DRUG ACTIVITY; DRUG STRUCTURE; HUMAN; NEUROPSYCHIATRY; NEUROTRANSMISSION; NONHUMAN; REVIEW; SCHIZOPHRENIA;

ANIMALS; ANTIPSYCHOTIC AGENTS; DRUG DISCOVERY; GLYCINE PLASMA MEMBRANE TRANSPORT PROTEINS; HUMANS; SARCOSINE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77949372130     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802610790410974     Document Type: Review

References (77)

1. Aprison, M.H. The discovery of the neurotransmitter role of glycine. In: Glycine Neurotransmission; Ottersen, O.P.; Storm-Mathisen, J. Eds.; John Wiley and Sons, Chichester, UK 1990, pp. 1-23.
2. Betz, H. Ligand-gated ion channels in the brain: the amino acid receptor superfamily. Neuron, 1990, 5, 383-392.
3. Johnson, J.W.; Ascher, P. Glycine potentiates the NMDA response in cultured mouse brain neurons. Nature, 1987, 325, 529-531.
4. Bergeron, R.; Meyer, T.M.; Coyle, J.T.; Greene, R.W. Modulation of N-methyl-D-aspartate receptor function by glycine transport. Proc. Natl. Acad. Sci. USA, 1998, 95, 15730-15734.
5. Danysz W.; Parsons A.C. Glycine and N-methyl-D-aspartate receptors: physiological significance and possible therapeutic applications. Pharmacol. Rev., 1998, 50, 597-664.
6. Smith, K.E.; Borden, L.A.; Hartig, P.R.; Branchek, T.; Weinshank, R.L. Cloning and expression of a glycine transporter reveal colocalization with NMDA receptors. Neuron, 1992, 8, 927-935.
7. Liu, Q.R.; Lopez-Corcuera, B.; Mandiyan, S.; Nelson, H.; Nelson, N. Cloning and expression of a spinal cord- and brain-specific glycine transporter with novel structural features. J. Biol. Chem., 1993, 268, 22802-22808.
8. Borowsky, B.; Mezey, E.; Hoffman, B.J. Two glycine transporter variants with distinct localization in the CNS and peripheral tissues are encoded by a common gene. Neuron, 1993, 10, 851-863
9. Kim, K.M.; Kingsmore, S.F.; Han, H.; Yang-Feng, T.L.; Godinot, N.; Seldin, M.F.; Caron, M.G. Cloning of the human glycine transporter type 1: molecular and pharmacological characterization of novel isoform variants and chromosomal localization of the gene. Mol. Pharmacol., 1994, 45, 608-617.
10. Morrow, J.A.; Collie, I.T.; Dunbar, D.R.; Walker, G.B.; Shahid, M.; Hill, D.R. Molecular cloning and functional expression of the human glycine transporter GlyT2 and chromosomal localisation of the gene in the human genome. FEBS Lett., 1998, 439, 334-340.
11. Olivares, L.; Aragon, C.; Gimenez, C.; Zafra, F. Carboxyl terminus of the glycine transporter GlyT1 is necessary for correct processing of the protein. J. Biol. Chem., 1994, 269, 28004-28400.
12. Olivares, L.; Aragon, C.; Gimenez, C.; Zafra, F. The role of Nglycosylation in the targeting and activity of the GlyT1 glycine transporter. J. Biol. Chem., 1995, 270, 9437-9442.
13. Zafra, F.; Gomeza, J.; Olivares, L.; Aragon, C.; Gimenez, C; Regional distribution and developmental variation of the glycine transporters GLYT1 and GLYT2 in the rat CNS. Eur. J. Neurosci., 1995, 7, 1342-1352.
14. Martinez-Maza, R.; Poyatos, I.; Lopez-Corcuera, B.; Nunez, RE.; Gimenez, C.; Zafra, F.; Aragon, C. The role of N-glycosylation in transport to the plasma membrane and sorting of the neuronal glycine transporter GlyT2. J. Biol. Chem., 2001, 276, 2168-2173.
15. Zafra, F.; Aragon, C.; Olivares, L.; Danbolt, N.C.; Gimenez, C.; Storm-Mathisen, J. Glycine transporters are differentially expressed among CNS cells. J. Neurosci., 1995, 15, 3952-3969.
16. Mallorga, P.J.; Williams, J.B.; Jacobson, M.; Marques, R.; Chaudhary, A.; Conn, P.J.; Pettibone, D.J.; Sur, C. Pharmacology and expression analysis of glycine transporter GlyT1 with [3H]-(N-[3-(4'-fluorophenyl)-3-(4'phenylphenoxy) propyl])sarcosine. Neuropharmacology, 2003, 45, 585-593.
17. Zeng, Z.; O'Brien, J.A.; Lemaire, W.; O'Malley, S.S.; Miller, P.J.; Zhao, Z.; Wallace, M.A.; Raab, C.; Lindsley, C.W.; Sur, C.; Williams, D.L. A novel radioligand for glycine transporter 1: characterization and use in autoradiographic and in vivo brain occupancy studies. Nucl. Med. Biol., 2008, 35, 315-325.
18. Danglot, L.; Rostaing, P.; Triller, A.; Bessis, A. Morphologically identified glycinergic synapses in the hippocampus. Mol. Cell. Neurosci., 2004, 27, :394-403.
19. Cubelos, B.; Gimenez, C.; Zafra, F. Localization of the GLYT1 glycine transporter at glutamateric synapses in the rat brain. Cereb. Cortex, 2005, 15, 448-459.
20. Yee, B.K.; balic, E.; Singer, P.; Schwerdel, C.; Grampp, T.; Gabernet, L.; Knuesel, I.; Benke, D.; Feldon, J.; Mohler, H.; Boison, D. Disruption of glycine transporter 1 restricted to forebrain neurons is associated with a precognitive and antipsychotic phenotypic profile. J. Neurosci., 2006, 26, 3169-3181.
21. Supplisson, S.; Bergman, C. Control of NMDA receptor activation by a glycine transporter co-expressed in Xenopus oocytes. J. Neurosci., 1997, 17, 4580-4590.
22. Williams, J.B.; Mallorga, P.J.; Conn, P.J.; Pettibone, D.J.; Sur, C. Effects of typical and atypical antipsychotics on human glycine transporters. Schizophr. Res., 2004, 71, 103-112.
23. Atkinson, B.N.; Bell, S.C.; De Vivo, M.; Kowalski, L.R.; Lechner, S.M.; Ognyanov, V.I.; Tham, C.S.; Tsai, C.; Jia, J.; Ashton, D.; Klitenick, M.A. ALX 5407: a potent, selective inhibitor of the hGlyT1 glycine transporter. Mol. Pharmacol., 2001, 60, 1414-1420.
24. Aubrey, K.R.; Vandenberg, R.J. N[3-(4'-fluorophenyl)-3-(4'-phenylphenoxy) propyl]sarcosine (NFPS) is a selective persistent inhibitor of glycine transport. Br. J. Pharmacol., 2003, 134, 1429-1436.
25. Mezler, M.; Hornberger, W.; Mueller, R.; Schmidt, M.; Amberg, W.; Braje, W.; Ochse, M.; Schoemaker, H.; Behl, B. Inhibitors of GlyT1 affect glycine transport via discrete binding sites. Mol. Pharmacol., 2008, 74, 1705-1715.
26. Nunez, E.; Martinez-Maza, R.; Geerlings, A.; Aragon, C.; Lopez-Corcuera, B. Transmembrane domains 1 and 3 of the glycine transporter GlyT1 contain structural determinants of N[3-(4'-fluorophenyl)-3-(4'-phenylphenoxy)propyl] sarcosine specificity. Neuropharmacology, 2005, 49, 922-934.
27. Vandenberg, R.J. Mutational analysis of glutamate tarnsporters. Handb. Exp. Pharmacol., 2006, 175,113-135 2006
28. Kuryatov, A.; Laube, B.; Betz, H.; Kuhse, J. Mutational analysis of the glycine-binding site of the NMDA receptor - Structural similarity with bacterial amino acid-binding proteins. Neuron, 1994, 12, 1291-1300.
29. Berger, A.J.; Dieudonne, S.; Ascher, P. Glycine uptake governs glycine site occupancy at NMDA receptors of excitatory synapses. J. Neurophysiol., 1998, 80, 3336-3340.
30. Martina, M.; Gorfinkel, Y.; Halman, S.; Lowe, J.A.; Periyalwar, P.; Schmidt, C.J.; Bergeron, R. Glycine transporter type 1 blockade changes NMDA receptor-mediated responses and LTP in hippocampal CA1 pyramidal cells by altering extracellular glycine levels. J. Physiol., 2004, 557, 489-500.
31. Depoortere, R.; Dargazanli, G.; Estenne-Bouhtou, G.; Coste, A.; Lanneau, C.; Desvignes, C.; Poncelet, M.; Heaulme, M.; Santucci, V.; Decobert, M.; Cudennec, A.; Voltz, C.; Boulay, D.; Terranova, J.P.; Stemmelin, J.; Roger, P.; Marabout, B.; Sevrin, M.; Vigé, X.; Biton, B.; Steinberg, R.; Françon, D.; Alonso, R.; Avenet, P.; Oury-Donat, F.; Perrault, G.; Griebel, G.; George, P.; Soubrié, P.; Scatton, B. Neurochemical, electrophysiological and pharmacological profiles of the selective inhibitor of the glycine transporter-1 SSR504734, a potential new type of antipsychotic. Neurpsychopharmacol., 2005, 30, 1963-1985.
32. Boulay, D.; Pichat, P.; Dargazanli, G.; Estenne-Bouhtou, G.; Terranova, J.P.; Rogacki, N.; Stemmelin, J.; Coste, A.; Lanneau, C.; Desvignes, C.; Cohen, C.; Alonso, R.; Vigé, X.; Biton, B.; Steinberg, R.; Sevrin, M.; Oury-Donat, F.; George, P.; Bergis, O.; Griebel, G.; Avenet, P.; Scatton, B. Characterization of SSR103800, a selective inhibitor of the glycine transporter-1 in models predictive of therapeutic activity in schizophrenia. Pharmacol. Biochem. Behav., 2008, 91, 47-58.
33. Tsai, G.; Ralph-Williams, R.J.; Martina, M.; Bergeron, R.; Berger-Sweeney, J.; Dunham, K.S.; Jiang, Z.; Caine, S.B.; Coyle, J.T. Gene knockout of glycine transporter 1: characterization of the behavioral phenotype. Proc. Natl. Acad. Sci USA, 2004, 101, 8485-8490.
34. Criti, A.; Malenka, R.C Synaptic plasticity: Multiple forms, functions, and mechanisms. Neuropsychopharmacol., 2008, 33, 18-41.
35. Chen, L.; Mulhauser, M.; Yang, C.R. Glycine tranporter-1 blockade potentiates NMDA-mediated responses in rat prefrontal cortical neurons in vitro and in vivo. J. Neurophysiol., 2003, 89, 691-703.
36. Kinney, G.G.; Sur, C.; Burno, M.; Mallorga, P.J.; Williams, J.B.; Figueroa, D.J.; Wittmann, M.; Lemaire, W.; Conn, P.J. The glycine transporter type 1 inhibitor N-[3-(4'-fluorophenyl)-3-(4'-phenylphenoxy)propyl]sarcosine potentiates NMDA receptormediated responses in vivo and produces an antipsychotic profile in rodent behavior. J. Neurosci., 2003, 23, 7586-7591.
37. Manahan-Vaughan, D.; Wildforster, V.; Thomsen, C. Rescue of hippocampal LTP and learning deficits in a rat model of psychosis by inhibition of glycine transporter-1 (GlyT1). Eur. J. Neurosci., 2008, 28, 1342-1350.
38. Andreasen, N.C. Schizophrenia: the fundamental questions. Brain Res. Rev., 2000, 31, 106-112.
39. Jentsch, J.D.; Roth, R.H. The neuropsychopharmacology of phencyclidine: from NMDA receptor hypofunction to the dopamine hypothesis of schizophrenia. Neuropsychopharmacol. 1999, 20, 201-225.
40. Olney, J.W.; Newcomer, J.W.; Farber, N.B. NMDA receptor hypofunction model of schizophrenia. J. Psychiatr. Res. 1999, 33, 523-533.
41. Harsing, L.G. Jr.; Gacsalyi, I.; Szabo, G.; Schmidt, E.; Sziray, N.; Sebban, C.; Tesolin-Decros, B.; Matyus, P.; Egyed, A.; Spedding, M.; Levay, G. The glycine transporter-1 inhibitors NFPS and Org 24461: a pharmacological study. Pharmacol. Biochem. Behav., 2003, 74, 811-825.
42. Lipska, B.K.; Weinberger, D.R. Delayed effects of neonatal hippocampal damage on haloperidol-induced catalepsy and apomorphine-induced stereotypic behaviors in the rat. Brain Res. Dev. Brain Res., 1993, 75, 213-222.
43. Brown, A.; Carlyle, I.; Clark, J.; Hamilton, W.; Gibson, S.; McGarry, G.; McEachen, S.; Rae, D.; Thorn, S.; Walker, G. Discovery and SAR of org 24598-a selective glycine uptake inhibitor. Bioorg. Med. Chem. Lett., 2001, 11, 2007-2009.
44. Le Pen, G.; Kew, J.; Alberati, D.; Borroni, E.; Heitz.; M.P.; Moreau, J.L. Prepulse inhibition deficits of the startle reflex in neonatal ventral hippocampal-lesioned rats: reversal by glycine and a glycine transporter inhibitor. Biol. Psychiatry, 2003, 54, 1162-1170.
45. Hashimoto, K.; Fujita, Y.; Ishima, T.; Chaki, S.; Iyo, M. Phencyclidine-induced cognitive deficits in mice are improved by subsequent subchronic administration of the glycine transporter-1 inhibitor NFPS and D-serine. Eur. Neuropsychopharmacol., 2008, 18, 414-421.
46. Singer, P.; Feldon, J.; Yee, B.K. The glycine transporter 1 inhibitor SSR504734 enhances working memory performance in a conti nuous delayed alternation task in C57BL/6 mice. Psychopharmacology, 2009, 202, 371-384.
47. Black, M.D.; Varty, G.B.; Arad, M.; Barak, S.; De Levie, A.; Bopulay, D.; Pichat, P.; Griebel, G.; Weiner, I. Procognitive and antipsychotic efficacy of glycine transport 1 inhibitors (GlyT1) in acute and neurodevelopmental models of schizophrenia: latent inhibition studies in rat. Psychopharmacology, 2009, 202, 385-396.
48. Molander, A.; Lido, H.H.; Lof, E.; Ericson, M.; Soderpalm, B. The glycine reuptake inhibitor ORG25935 decreases ethanol intake and preference in male wistar rats. Alcohol Alcohol, 2007, 42, 11-18.
49. Gomeza, J.; Hulsmann, S.; Ohno, K.; Eulenburg, V.; Szoke, K.; Richter, D.; Betz, H. Inactivation of the glycine transporter 1 gene discloses vital role of glial glycine uptake in glycinergic inhibition. Neuron, 2003, 40, 785-796.
50. Perry, K.W.; Falcone, J.F.; Fell, M.J.; Ryder, J.W.; Yu, H.; Love, P.L.; Katner, J.; Gordon, K.D.; Wade, M.R.; Man, T.; Nomikos, G.G.; Phebus, L.A.; Cauvin, A.J.; Johnson, K.W.; Jones, C.K.; Hoffmann, B.J.; Sandusky, G.E.; Walter, M.W.; Porter, W.J.; Yang, L.; Merchant, K.M.; Shannon, H.E.; Svensson, K.A. Neurochemical and behavioral profiling of the selective GlyT1 inhibitors ALX5407 and LY2365109 indicate a preferential action in caudalvs. Cortical brain areas. Neuropharmacology, 2008, 55, 743-754.
51. Sur, C.; Kinney, G. G. The therapeutic potential of glycine transporter-1 inhibitors. Expert Opin. Investig. Drugs, 2004, 13, 515-521.
52. Slassi, A.; Egle, I. Recent progress in the use of glycine transporter-1 inhibitors for the treatment of central and peripheral nervous system disorders. Expert Opin. Ther. Pat., 2004, 14, 201-214.
53. Lowe, J. A. Novel inhibitors of the type 1 transporter for glycine (GlyT1) as antipsychotic agents. Expert Opin. Ther. Pat., 2005, 15, 1657-1662.
54. Kinney, G. G.; Sur, C. Glycine site modulators and glycine transporter-1 inhibitors as novel therapeutic targets for the treatment of schizophrenia. Curr. Neuropharmacol., 2005, 3, 35-43.
55. Hashimoto, K. Glycine transporter inhibitors as therapeutic agents for schizophrenia. Recent Pat. CNS Drug Discov., 2006, 1, 43-53.
56. Lindsley, C. W.; Shipe, W. D.; Wolkenberg, S. E.; Theberge, C. R.; Williams, D. L.; Sur, C.; Kinney, G. G. Progress towards validating the NMDA receptor hypofunction hypothesis of schizophrenia. Curr. Top. Med. Chem., 2006, 6, 771-785.
57. Lindsley, C. W.; Wolkenberg, S. E.; Kinney, G. G. Progress in the preparation and testing of glycine transporter type-1 (GlyT1) inhibitors. Curr. Top. Med. Chem., 2006, 6, 1883-1896.
58. Harsing, L. G.; Juranyi, Z.; Gacsalyi, I.; Tapolcsanyi, P.; Czompa, A.; Matyus, P. Glycine transporter type-1 and its inhibitors. Curr. Med. Chem., 2006, 13, 1017-1044.
59. Sur, C.; Kinney, G. G. Glycine transporter 1 inhibitors and modulation of NMDA receptor-mediated excitatory neurotransmission. Curr. Drug Targets, 2007, 8, 643-649.
60. Bridges, T. M.; Williams, R.; Lindsley, C. W. Design of potent GlyT1 inhibitors: in vitro and in vivo profiles. Curr. Opin. Mol. Ther., 2008, 10, 591-601.
61. Lowe, J.; Drozda, S.; Qian, W.; Peakman, M.-C.; Liu, J.; Gibbs, J.; Harms, J.; Schmidt, C.; Fisher, K.; Strick, C.; Schmidt, A.; Vanase, M.; Lebel, L. A novel, non-substrate-based series of glycine type 1 transporter inhibitors derived from high-throughput screening. Bioorg. Med. Chem. Lett., 2007, 17, 1675-1678.
62. Lowe, J. A.; Drozda, S. E.; Fisher, K.; Strick, C.; Lebel, L.; Schmidt, C.; Hiller, D.; Zandi, K. S. [3H]-(R)-NPTS, a radioligand for the type 1 glycine transporter. Bioorg. Med. Chem. Lett., 2003, 13, 1291-1292.
63. Lowe, J. A.; Hou, X.; Schmidt, C.; Tingley, F. D.; McHardy, S.; Kalman, M.; DeNinno, S.; Sanner, M.; Ward, K.; Lebel, L.; Tunucci, D.; Valentine, J. The discovery of a structurally novel class of inhibitors of the type 1 glycine transporter. Bioorg. Med. Chem. Lett., 2009, 19, 2974-2976.
64. Pinard, E.; Ceccarelli, S. M.; Stalder, H.; Alberati, D. Discovery of N-(2-aryl-cyclohexyl) substituted spiropiperidines as a novel class of GlyT1 inhibitors. Bioorg. Med. Chem. Lett., 2006, 16, 349-353.
65. Ceccarelli, S. M.; Pinard, E.; Stalder, H.; Alberati, D. Discovery of N-(2-hydroxy-2-aryl-cyclohexyl) substituted spiropiperidines as GlyT1 antagonists with improved pharmacological profile. Bioorg. Med. Chem. Lett., 2006, 16, 354-357.
66. Alberati, D.; Ceccarellia, S. M.; Jolidon, S.; Krafft, E. A.; Kurt, A.; Maier, A.; Pinard, E.; Stalder, H.; Studer, D.; Thomas, A. W.; Zimmerli, D. Design and synthesis of 4-substituted-8-(2-phenylcyclohexyl)-2,8-diaza-spiro[4. 5]decan-1-one as a novel class of GlyT1 inhibitors: achieving selectivity against the μ opioid and nociceptin/orphanin FQ peptide (NOP) receptors. Bioorg. Med. Chem. Lett., 2006, 16, 4305-4310.
67. Alberati, D.; Hainzl, D.; Jolidon, S.; Krafft, E. A.; Kurt, A.; Maier, A.; Pinard, E.; Thomas, A. W.; Zimmerli, D. Discovery of 4-substituted-8-(2- hydroxy-2-phenyl-cyclohexyl)-2,8-diazaspiro[4.5]decan-1-one as a novel class of highly selective GlyT1 inhibitors with improved metabolic stability. Bioorg. Med. Chem. Lett., 2006, 16, 4311-4315.
68. Alberati, D.; Hainzl, D.; Jolidon, S.; Kurt, A.; Pinard, E.; Thomas, A. W.; Zimmerli, D. 4-Substituted-8-(1-phenyl-cyclohexyl)-2,8-diaza-spiro[4.5] decan-1-one as a novel class of highly selective GlyT1 inhibitors with superior pharmacological and pharmacokinetic parameters. Bioorg. Med. Chem. Lett., 2006, 16, 4321-4325.
69. Pinard, E.; Alberati, D.; Borroni, E.; Fischer, H.; Hainzl, D.; Jolidon, S.; Moreau, J.-L.; Narquizian, R.; Nettekoven, M.; Norcross, R. D.; Stalder, H.; Thomas, A. W. Discovery of benzoylpiperazines as a novel class of potent and selective GlyT1 inhibitors. Bioorg. Med. Chem. Lett., 2008, 18, 5134-5139.
70. Jolidon, S.; Alberati, D.; Dowle, A.; Fischer, H.; Hainzl, D.; Narquizian, R.; Norcross, R.; Pinard, E. Design, synthesis, and structure-activity relationship of simple bis-amides as potent inhibitors of GlyT1. Bioorg. Med. Chem. Lett., 2008, 18, 5533-5536.
71. Lindsley, C. W.; Zhao, Z.; Leister, W. H.; O'Brien, J.; Lemaire, W.; Williams, D. L.; Chen, T.-B.; Chang, R. S. L.; Burno, M.; Jacobson, M. A.; Sur, C.; Kinney, G. G.; Pettibone, D. J.; Tiller, P. R.; Smith, S.; Tsou, N. N.; Duggan, M. E.; Conn, P. J.; Hartman, G. D. Design, synthesis, and in vivo efficacy of glycine transporter-1 (GlyT1) inhibitors derived from a series of [4-phenyl-1-(propylsulfonyl)piperidin-4-yl]methyl benzamides. ChemMed Chem, 2006, 1, 807-811.
72. Zhao, Z.; Leister, W. H.; O'Brien, J. A.; Lemaire, W.; Williams, D. L.; Jacobson, M. A.; Sur, C.; Kinney, G. G.; Pettibone, D. J.; Tiller, P. R.; Smith, S.; Hartman, G. D.; Lindsley, C. W.; Wolkenberg, S. E. Discovery of N-{[1-(propylsulfonyl)-4-pyridin-2-ylpiperidin-4-yl]methyl}benzamides as novel, selective and potent GlyT1 inhibitors. Bioorg. Med. Chem. Lett., 2009, 19, 1488-1491.
73. Wolkenberg, S. E.; Zhao, Z.; Wisnoski, D. D.; Leister, W. H.; O'Brien, J.; Lemaire, W.; Williams, D. L.; Jacobson, M. A.; Sur, C.; Kinney, G. G.; Pettibone, D. J.; Tiller, P. R.; Smith, S.; Gibson, C.; Ma, B. K.; Polsky-Fisher, S. L.; Lindsley, C. W.; Hartman, G. D. Discovery of GlyT1 inhibitors with improved pharmacokinetic properties. Bioorg. Med. Chem. Lett., 2009, 19, 1492-1495.
74. Zhao, Z.; O'Brien, J. A.; Lemaire, W.; Williams, D. L.; Jacobson, M. A.; Sur, C.; Pettibone, D. J.; Tiller, P. R.; Smith, S.; Hartman, G. D.; Wolkenberg, S. E.; Lindsley, C. W. Synthesis and SAR of GlyT1 inhibitors derived from a series of N-((4-(morpholine-4-carbonyl)-1-(propylsulfonyl)piperidin-4-yl) -methyl)benzamides. Bioorg. Med. Chem. Lett., 2006, 16, 5968-5972.
75. Thomson, J. L.; Blackaby, W. P.; Jennings, A. S. R.; Goodacre, S. C.; Pike, A.; Thomas, S.; Brown, T. A.; Smith, A.; Pillai, G.; Street, L. J.; Lewis, R. T. Optimisation of a series of potent, selective, and orally bioavailable GlyT1 inhibitors. Bioorg. Med. Chem. Lett., 2009, 19, 2235-2239.
76. Terui, Y.; Yi-wen, C.; Jun-ying, L.; Nozawa, O.; Ando, T.; Fukunaga, T.; Aoki, T.; Toda, Y.; Kawashima, A. WSS2220, a novel tetrapeptide with a new sulfonoamino acid, exhibits potent and selective inhibitory activity against GlyT1. Tetrahedron Lett., 2008, 49, 3067-3070.
77. Terui, Y.; Yi-wen, C.; Jun-ying, L; Ando, T.; Fukunaga, T.; Aoki, T.; Toda, Y. New cyclic tetrapeptides from Nonomuraea sp. TA-0426 that inhibit glycine transporter type 1 (GlyT1). Bioorg. Med. Chem. Lett., 2008, 18, 6321-6323.