Recent progress on nuclear receptor RORγ modulators

Bioorganic and Medicinal Chemistry Letters

Volumn 26, Issue 18, 2016, Pages 4387-4393

  Cyr, Patrick ^a   Bronner, Sarah M ^a   Crawford, James J ^a  

^a GENENTECH INC   (United States)

Author keywords

IL 17; RORc; ROR

Indexed keywords

INTERLEUKIN 17; RETINOID RELATED ORPHAN RECEPTOR GAMMA;

AGONISTS; ANIMAL; CELL DIFFERENTIATION; CELL NUCLEUS; HELPER CELL; METABOLISM; MOUSE; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL DIFFERENTIATION; CELL NUCLEUS; INTERLEUKIN-17; MICE; NUCLEAR RECEPTOR SUBFAMILY 1, GROUP F, MEMBER 3; STRUCTURE-ACTIVITY RELATIONSHIP; T-LYMPHOCYTES, HELPER-INDUCER;

EID: 84983087609     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2016.08.012     Document Type: Review

References (88)

1. 1 Mangelsdorf, D.J., Thummel, C., Beato, M., Herrlich, P., Schütz, G., Umesono, K., Blumberg, B., Kastner, P., Mark, M., Chambon, P., Evans, R.M., Cell, 83, 2005, 835.
2. 2 Burris, T.P., Solt, L.A., Wang, Y., Crumbley, C., Banerjee, S., Griffett, K., Lundasen, T., Hughes, T., Kojetin, D.J., Pharmacol. Rev., 65, 2013, 710.
3. 3 Kliewer, S.A., Lehmann, J.M., Willson, T.M., Science, 284, 1999, 757.
4. 4 Robinson-Rechavi, M., Garcia, H.E., Laudet, V., J. Cell Sci., 116, 2003, 585.
5. 5 Overington, J.P., Al-Lazikani, B., Hopkins, A.L., Nat. Rev. Drug Disc., 5, 2006, 993.
6. 6 Ottow, E., Weinmann, H., Nuclear Receptors as Drug Targets: A Historical Perspective of Modern Drug Discovery. Ottow, E., Weinmann, H., (eds.) Nuclear Drug Receptors as Targets, 1st ed., 2008, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 1–17.
7. 7 Becker-André, M., André, E., DeLamarter, J.F., Biochem. Biophys. Res. Commun., 194, 1993, 1371.
8. 8 Hirose, T., Smith, R.J., Jetten, A.M., Biochem. Biophys. Res. Commun., 205, 1994, 1976.
9. 9 McEwan, I.J., Nuclear Receptors: One Big Family. Walker, J.M., (eds.) Methods in Molecular Biology: The Nuclear Receptor Superfamily, Vol. 505, 2009, Springer, Berlin, 3–18.
10. 10 Zhang, Y., Luo, X.-Y., Wu, D.-H., Xu, Y., Acta Pharmacol. Sin., 36, 2015, 71.
11. 11 Fauber, B.P., Magnuson, S., J. Med. Chem., 57, 2014, 5871.
12. 12 Jin, L., Martynowski, D., Zheng, S., Wada, T., Xie, W., Li, Y., Mol. Endocrinol., 24, 2010, 923.
13. 13 The 25-hydroxycholesterol is represented with the same stereochemistry than reported in Ref. 12.
14. 14 Kojetin, D.J., Burris, T.P., Nat. Rev. Drug Disc., 13, 2014, 197.
15. 15 Ivanov, I.I., McKenzie, B.S., Zhou, L., Tadokoro, C.E., Lepelley, A., Lafaille, J.J., Cua, D.J., Littman, D.R., Cell, 126, 2006, 1121.
16. 16 Yang, X.O., Pappu, B.P., Nurieva, R., Akimzhanov, A., Kang, H.S., Chung, Y., Ma, L., Shah, B., Panopoulos, A.D., Schluns, K.S., Watowich, S.S., Tian, Q., Jetten, A.M., Dong, C., Immunity, 28, 2008, 29.
17. 17 Meissburger, B., Ukropec, J., Roeder, E., Beaton, N., Geiger, M., Teupser, D., Civan, B., Langhans, W., Nawroth, P.P., Gasperikova, D., Rudofsky, G., Wolfrum, C., EMBO Mol. Med., 3, 2011, 637.
18. 18 Bettelli, E., Oukka, M., Kuchroo, V.K., Nat. Immunol., 8, 2007, 345.
19. 19 Dong, C., Cell Res., 24, 2014, 901.
20. 20 Isono, F., Fujita-Sato, S., Ito, S., Drug Discovery Today, 19, 2014, 1205.
21. 21 Miossec, P., Kolls, J.K., Nat. Rev. Drug Disc., 11, 2012, 763.
22. 22 Novartis press release: Novartis announces FDA approval for first IL-17A antagonist Cosentyx(TM) (secukinumab) for moderate-to-severe plaque psoriasis patients, https://www.novartis.com/news/media-releases/novartis-announces-fda-approval-first-il-17a-antagonist-cosentyxtm-secukinumab (accessed 23 February 2016).
23. 23 FDA approves new psoriasis drug Taltz, http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm491872.htm (accessed 28 March 2016).
24. 24 Nishiyama, Y., Nakamura, M., Misawa, T., Nakagomi, M., Makishima, M., Ishikawa, M., Hashimoto, Y., Bioorg. Med. Chem., 22, 2014, 2799.
25. 25 Toyama, H., Nakamura, M., Hashimoto, Y., Fujii, S., Bioorg. Med. Chem., 23, 2015, 2982.
26. 26 Gege, C., Schlüter, T., Hoffmann, T., Bioorg. Med. Chem. Lett., 24, 2014, 5265.
27. 27 Muegge, I., Collin, D., Cook, B., Hill-Drzewi, M., Horan, J., Kugler, S., Labadia, M., Li, X., Smith, L., Zhang, Y., Bioorg. Med. Chem. Lett., 25, 2015, 1892.
28. 28 Gege, C., Expert Opin. Ther. Pat., 25, 2015, 1215.
29. 29 Song, Y., Xue, X., Wu, X., Wang, R., Xing, Y., Yan, W., Zhou, Y., Qian, C.-N., Zhang, Y., Xu, Y., Eur. J. Med. Chem., 116, 2016, 13.
30. 30 Wang, Y., Kumar, N., Nuhant, P., Cameron, M.D., Istrate, M.A., Roush, W.R., Griffin, P.R., Burris, T.P., ACS Chem. Biol., 5, 2010, 1029.
31. 31 Kumar, N., Solt, L.A., Conkright, J.J., Wang, Y., Istrate, M.A., Busby, S.A., Garcia-Ordonez, R., Burris, T.P., Griffin, P.R., Mol. Pharmacol., 77, 2010, 228.
32. 32 Wang, Y., Billon, C., Walker, J.K., Burris, T.P., ACS Chem. Neurosci., 7, 2016, 143.
33. 33 Zhang, W., Zhang, J., Fang, L., Zhou, L., Wang, S., Xiang, Z., Li, Y., Wisely, B., Zhang, G., An, G., Wang, Y., Leung, S., Zhong, Z., Mol. Pharmacol., 82, 2012, 583.
34. 34 Yang, T., Liu, Q., Cheng, Y., Cai, W., Ma, Y., Yang, L., Wu, Q., Orband-Miller, L.A., Zhou, L., Xiang, Z., Huxdorf, M., Zhang, W., Zhang, J., Xiang, J.-N., Leung, S., Qiu, Y., Zhong, Z., Elliott, J.D., Lin, X., Wang, Y., ACS Med. Chem. Lett., 5, 2014, 65.
35. 35 René, O., Fauber, B.P., de Leon Boenig, G., Burton, B., Eidenschenk, C., Everett, C., Gobbi, A., Hymowitz, S.G., Johnson, A.R., Kiefer, J.R., Liimatta, M., Lockey, P., Norman, M., Ouyang, W., Wallweber, H.A., Wong, H., ACS Med. Chem. Lett., 6, 2015, 276.
36. 36 Fujita-Sato, S., Ito, S., Isobe, T., Ohyama, T., Wakabayashi, K., Morishita, K., Ando, O., Isono, F., J. Biol. Chem., 286, 2011, 31409.
37. 37 Leeson, P.D., Springthorpe, B., Nat. Rev. Drug Disc., 6, 2007, 881.
38. 38 Olsson, R.I., Xue, Y., von Berg, S., Aagaard, A., McPheat, J., Hansson, E.L., Bernström, J., Hansson, P., Jirholt, J., Grindebacke, H., Leffler, A., Chen, R., Xiong, Y., Ge, H., Hansson, T.G., Narjes, F., ChemMedChem, 11, 2016, 207.
39. 39 Chang, M.R., Dharmarajan, V., Doebelin, C., Garcia-Ordonez, R.D., Novick, S.J., Kuruvilla, D.S., Kamenecka, T.M., Griffin, P.R., ACS Chem. Biol., 11, 2016, 1012.
40. 40 Fierce Biotech article: Eyeing buyout, Celgene paying $105M to partner on Lycera's anti-cancer T cell tech, http://www.fiercebiotech.com/partnering/eyeing-buyout-celgene-paying-105m-to-partner-on-lycera-s-anti-cancer-t-cell-tech (accessed 27 July 2016).
41. 41 Aicher, T. D.; Taylor, C. B.; Van Huis, C. A. WO 2015/171610, 2015.
42. 42 Aicher, T. D.; Skalitzky, D. J.; Taylor, C. B.; Van Huis, C. A. WO 2015/171558, 2015.
43. 43 Glick, G. D.; Toogood, P. L.; Hu, X.; Aicher, T. D.; Celeste, L. L.; Liu, X.; Taylor, C. B.; Van Huis, C. A. WO 2015/131035, 2015.
44. 44 Smith, S.H., Peredo, C.E., Takeda, Y., Bui, T., Neil, J., Rickard, D., Millerman, E., Therrien, J., Nicodeme, E., Brusq, J., Birault, V., Viviani, F., Hofland, H., Jetten, A.M., Cote-Sierra, J., PLoS One, 11, 2016, e0147979, 10.1371/journal.pone.0147979.
45. 45 Study of Safety and Efficacy of Topical GSK2981278 in Plaque Psoriasis, https://clinicaltrials.gov/ct2/show/NCT02548052?term=GSK2981278&rank=1 (accessed 18 March 2016).
46. 46 Drug Profile GSK 2981278, http://adisinsight.springer.com/drugs/800043256 (accessed 18 March 2016).
47. 47 Birault, V.; Cambell, A. J.; Harrison, S. A.; Le, J. WO 2015/061515, 2015.
48. 48 Wang, Y.; Cai, W.; Liu, Q.; Xiang, J. WO 2012/027965, 2012.
49. 49 Wang, Y.; Cai, W.; Liu, Q.; Meng, Q.; Cheng, Y.; Yang, T.; Zhang, G.; Xiang, J.; Wu, C. WO 2013/029338, 2013.
50. 50 Birault, V.; Campbell, A. J.; Harrison, S.; Le, J. WO 2013/045431, 2013.
51. 51 Baloglu, E.; Ghosh, S.; Lobera, M.; Schmidt, D.; Wang, Y. WO 2013/085890, 2013.
52. 52 Birault, V.; Campbell, A. J.; Harrison, S.; Le, J.; Shukla, L. WO 2013/160418, 2013.
53. 53 Birault, V.; Campbell, A. J.; Harrison, S.; Le, J.; Shukla, L. WO 2013/160419, 2013.
54. 54 Han, F.; Lei, H.; Lin, X.; Meng, Q.; Wang, Y. WO 2014/086894, 2014.
55. 55 Deng, J.; Lei, H.; Ma, X.; Lin, X. WO 2015/180612, 2015.
56. 56 Deng, J.; Lei, H.; Ma, X.; Ren, F.; Cai, W.; Lin, X. WO 2015/180613, 2015.
57. 57 Lei, H.; Ma, X.; Ren, F.; Lin, X.; Marquis, R. W., Jr. WO 2015/180614, 2015.
58. 58 Wang, Y., Yang, T., Liu, Q., Ma, Y., Yang, L., Zhou, L., Xiang, Z., Cheng, Z., Lu, S., Orband-Miller, L.A., Zhang, W., Wu, Q., Zhang, K., Li, Y., Xiang, J.-N., Elliott, J.D., Leung, S., Ren, F., Lin, X., Bioorg. Med. Chem., 23, 2015, 5293.
59. 59 Skepner, J., Ramesh, R., Trocha, M., Schmidt, D., Baloglu, E., Lobera, M., Carlson, T., Hill, J., Orband-Miller, L.A., Barnes, A., Boudjelal, M., Sundrud, M., Ghosh, S., Yang, J., J. Immunol., 192, 2014, 2564.
60. 60 Skepner, J., Trocha, M., Ramesh, R., Qu, X.A., Schmidt, D., Baloglu, E., Lobera, M., Davis, S., Noal, M.A., Carlson, T.J., Hill, J., Ghosh, S., Sundrud, M.S., Yang, J., Immunology, 145, 2015, 347.
61. 61 Wang, Y., Cai, W., Cheng, Y., Yang, T., Liu, Q., Zhang, G., Meng, Q., Han, F., Huang, Y., Zhou, L., Xiang, Z., Zhao, Y., Xu, Y., Cheng, Z., Lu, S., Wu, Q., Xiang, J.-N., Elliott, J.D., Leung, S., Ren, F., Lin, X., ACS Med. Chem. Lett., 6, 2015, 787.
62. 62 Xiao, S., Yosef, N., Yang, J., Wang, Y., Zhou, L., Zhu, C., Wu, C., Baloglu, E., Schmidt, D., Ramesh, R., Lobera, M., Sundrud, M.S., Tsai, P.-Y., Xiang, Z., Wang, J., Xu, Y., Lin, X., Kretschmer, K., Rahl, P.B., Young, R.A., Zhong, Z., Hafler, D.A., Regev, A., Ghosh, S., Marson, A., Kuchroo, V.K., Immunity, 40, 2014, 477.
63. 63 Withers, D.R., Hepworth, M.R., Wang, X., Mackley, E.C., Halford, E.E., Dutton, E.E., Marriott, C.L., Brucklacher-Waldert, V., Veldhoen, M., Kelsen, J., Baldassano, R.N., Sonnenberg, G.F., Nat. Med., 22, 2016, 319.
64. 64 Vitae Pharmaceuticals press release: Vitae Pharmaceuticals Achieves Proof-of-Concept with First-in-Class RORγt Inhibitor in Mild to Severe Psoriasis, http://ir.vitaepharma.com/phoenix.zhtml?c=219654&p=irol-newsArticle&ID=2149044 (accessed 29 March 2016).
65. 65 An ascending multiple dose study with VTP-43742 in healthy volunteers and psoriatic patients, https://clinicaltrials.gov/ct2/show/NCT02555709?term=VTP-43742&rank=1 (accessed 29 March 2016).
66. 66 Gege, C., Expert Opin. Ther. Pat., 26, 2016, 737.
67. 67 Claremon, D. A.; Dillard, L. W.; Dong, C.; Fan, Y.; Jia, L.; Liu, Z.; Lotesta, S. D.; Marcus, A.; Singh, S. B.; Tice, C. M.; Yuan, J.; Zhao, W.; Zheng, Y.; Zhuang, L. WO 2015/116904, 2015.
68. 68 Claremon, D. A.; Dillard, L. W.; Dong, C.; Fan, Y.; Jia, L.; Lotesta, S. D.; Marcus, A.; Singh, S. B.; Tice, C. M.; Yuan, J.; Zhao, W.; Zheng, Y.; Zhuang, L. WO 2016/061160, 2016.
69. 69 Claremon, D. A.; Dillard, L. W.; Dong, C.; Fan, Y.; Lotesta, S. D.; Marcus, A.; Singh, S. B.; Tice, C. M.; Yuan, J.; Zhao, W.; Zhuang, L. US 2016/0122345, 2016.
70. 70 Maeba, T.; Maeda, K.; Kotoku, M.; Hirata, K.; Seki, N.; Yamanaka, H.; Sakai, T.; Hirashima, S.; Obika, S.; Shiozaki, M.; Yokota, M. WO 2012/147916, 2012.
71. 71 Kotoku, M.; Maeba, T.; Seki, N.; Hirashima, S.; Fujioka, S.; Obika, S.; Yamanaka, H.; Yokota, M.; Sakai, T.; Hirata, K.; Maeda, K.; Shiozaki, M.; Shinagawa, Y.; Ikenogami, T.; Doi, S.; Oka, T.; Matsuo, T.; Suwa, Y.; Ito, K.; Noji, S.; Hara, Y. WO 2014/065413, 2014.
72. 72 Search results on clinicaltrials.gov for: Japan Tobacco, https://clinicaltrials.gov/ct2/results?term=japan+tobacco&Search=Search (accessed 14th March 2016).
73. 73 Japan Tobacco clinical development, https://www.jt.com/investors/results/S_information/pharmaceuticals/pdf/20160502_11.pdf (accessed 27 July 2016).
74. 74 Hirata, K., Kotoku, M., Seki, N., Maeba, T., Maeda, K., Hirashima, S., Sakai, T., Obika, S., Hori, A., Hase, Y., Yamaguchi, T., Katsuda, Y., Hata, T., Miyagawa, N., Arita, K., Nomura, Y., Asahina, K., Aratsu, Y., Kamada, M., Adachi, T., Noguchi, M., Doi, S., Crowe, P., Bradley, E., Steensma, R., Tao, H., Fenn, M., Babine, R., Li, X., Thacher, S., Hashimoto, H., Shiozaki, M., ACS Med. Chem. Lett., 7, 2016, 23.
75. 75 Arrien Pharmaceuticals news and scientific events, http://www.arrienpharma.com/news.php (accessed 26 May 2016).
76. 76 Vankayalapati, H.; Yerramreddy, V. WO 2015/038350, 2015.
77. 77 Fauber, B.P., Gobbi, A., Robarge, K., Zhou, A., Barnard, A., Cao, J., Deng, Y., Eidenschenk, C., Everett, C., Ganguli, A., Hawkins, J., Johnson, A.R., La, H., Norman, M., Salmon, G., Summerhill, S., Ouyang, W., Tang, W., Wong, H., Bioorg. Med. Chem. Lett., 25, 2015, 2907.
78. 78 Fauber, B.P., Gobbi, A., Savy, P., Burton, B., Deng, Y., Everett, C., La, H., Johnson, A.R., Lockey, P., Norman, M., Wong, H., Bioorg. Med. Chem. Lett., 25, 2015, 4109.
79. 79 Fauber, B.P., René, O., Deng, Y., DeVoss, J., Eidenschenk, C., Everett, C., Ganguli, A., Gobbi, A., Hawkins, J., Johnson, A.R., La, H., Lesch, J., Lockey, P., Norman, M., Ouyang, W., Summerhill, S., Wong, H., J. Med. Chem., 58, 2015, 5308.
80. 80 Scheepstra, M., Leysen, S., van Almen, G.C., Miller, J.R., Piesvaux, J., Kutilek, V., van Eenennaam, H., Zhang, H., Barr, K., Nagpal, S., Soisson, S.M., Kornienko, M., Wiley, K., Elsen, N., Sharma, S., Correll, C.C., Trotter, B.W., van der Stelt, M., Oubrie, A., Ottmann, C., Parthasarathy, G., Brunsveld, L., Nat. Commun., 6, 2015, 8833.
81. 81 Chao, J., Enyedy, I., Van Vloten, K., Marcotte, D., Guertin, K., Hutchings, R., Powell, N., Jones, H., Bohnert, T., Peng, C.-C., Silvian, L., Hong, V.S., Little, K., Banerjee, D., Peng, L., Taveras, A., Viney, J.L., Fontenot, J., Bioorg. Med. Chem. Lett., 25, 2015, 2991.
82. 82 Wang, T., Banerjee, D., Bohnert, T., Chao, J., Enyedy, I., Fontenot, J., Guertin, K., Jones, H., Lin, E.Y., Marcotte, D., Talreja, T., Van Vloten, K., Bioorg. Med. Chem. Lett., 25, 2015, 2985.
83. 83 Banerjee, D., Zhao, L., Wu, L., Palanichamy, A., Ergun, A., Peng, L., Quigley, C., Hamann, S., Dunstan, R., Cullen, P., Allaire, N., Guertin, K., Wang, T., Chao, J., Loh, C., Fontenot, J.D., Immunology, 147, 2015, 399.
84. 84 Enyedy, I.J., Powell, N.A., Caravella, J., van Vloten, K., Chao, J., Banerjee, D., Marcotte, D., Silvian, L., McKenzie, A., Hong, V.S., Fontenot, J.D., Bioorg. Med. Chem. Lett., 26, 2016, 2459.
85. 85 Takeda pipeline, http://www.takeda.com/research/files/pipeline_20160510_en.pdf (accessed 27 July 2016).
86. 86 Hu, X.; Liu, X.; Moisan, J.; Paulos, C.; Wang, Y.; Spooner, C.; Lesch, C.; Morgan, R.; Mertz, D.; Bousley, D.; Taylor, C.; Van Huis, C.; Skalitzky, D.; Aicher, T.; Toogood, P.; Carter, L. Presented at the AACR annual meeting, New Orleans, LA, April 2016; abstract 565.
87. 87 Ueda, E., Kurebayashi, S., Sakaue, M., Backlund, M., Koller, B., Jetten, A.M., Cancer Res., 62, 2002, 901.
88. 88 Wang, J., Zou, J.X., Xue, X., Cai, D., Zhang, Y., Duan, Z., Xiang, Q., Yang, J.C., Louie, M.C., Borowsky, A.D., Gao, A.C., Evans, C.P., Lam, K.S., Xu, J., Kung, H.-J., Evans, R.M., Xu, Y., Chen, H.-W., Nat. Med., 22, 2016, 488.