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Improving the pharmacokinetic and CYP inhibition profiles of azaxanthene-based glucocorticoid receptor modulators-identification of (S)-5-(2-(9-fluoro-2-(4-(2-hydroxypropan-2-yl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)-2-methylpropanamido)-N-(tetrahydro-2H-pyran-4-yl)-1,3,4-thiadiazole-2-carboxamide (BMS-341).
Yang MG, Dhar TG, Xiao Z, Xiao HY, Duan JJ, Jiang B, Galella MA, Cunningham M, Wang J, Habte S, Shuster D, McIntyre KW, Carman J, Holloway DA, Somerville JE, Nadler SG, Salter-Cid L, Barrish JC, Weinstein DS. Yang MG, et al. Among authors: wang j. J Med Chem. 2015 May 28;58(10):4278-90. doi: 10.1021/acs.jmedchem.5b00257. Epub 2015 May 7. J Med Chem. 2015. PMID: 25905990
Discovery of acylurea isosteres of 2-acylaminothiadiazole in the azaxanthene series of glucocorticoid receptor agonists.
Gong H, Yang M, Xiao Z, Doweyko AM, Cunningham M, Wang J, Habte S, Holloway D, Burke C, Shuster D, Gao L, Carman J, Somerville JE, Nadler SG, Salter-Cid L, Barrish JC, Weinstein DS. Gong H, et al. Among authors: wang j. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3268-73. doi: 10.1016/j.bmcl.2014.06.010. Epub 2014 Jun 13. Bioorg Med Chem Lett. 2014. PMID: 24980053
Rationally Designed, Conformationally Constrained Inverse Agonists of RORγt-Identification of a Potent, Selective Series with Biologic-Like in Vivo Efficacy.
Marcoux D, Duan JJ, Shi Q, Cherney RJ, Srivastava AS, Cornelius L, Batt DG, Liu Q, Beaudoin-Bertrand M, Weigelt CA, Khandelwal P, Vishwakrishnan S, Selvakumar K, Karmakar A, Gupta AK, Basha M, Ramlingam S, Manjunath N, Vanteru S, Karmakar S, Maddala N, Vetrichelvan M, Gupta A, Rampulla RA, Mathur A, Yip S, Li P, Wu DR, Khan J, Ruzanov M, Sack JS, Wang J, Yarde M, Cvijic ME, Li S, Shuster DJ, Borowski V, Xie JH, McIntyre KW, Obermeier MT, Fura A, Stefanski K, Cornelius G, Hynes J Jr, Tino JA, Macor JE, Salter-Cid L, Denton R, Zhao Q, Carter PH, Dhar TGM. Marcoux D, et al. Among authors: wang j. J Med Chem. 2019 Nov 14;62(21):9931-9946. doi: 10.1021/acs.jmedchem.9b01369. Epub 2019 Oct 31. J Med Chem. 2019. PMID: 31638797
Tricyclic sulfones as potent, selective and efficacious RORγt inverse agonists - Exploring C6 and C8 SAR using late-stage functionalization.
Shi Q, Xiao Z, Yang MG, Marcoux D, Cherney RJ, Yip S, Li P, Wu DR, Weigelt CA, Sack J, Khan J, Ruzanov M, Wang J, Yarde M, Ellen Cvijic M, Li S, Shuster DJ, Xie J, Sherry T, Obermeier M, Fura A, Stefanski K, Cornelius G, Chacko S, Shu YZ, Khandelwal P, Hynes J Jr, Tino JA, Salter-Cid L, Denton R, Zhao Q, Dhar TGM. Shi Q, et al. Among authors: wang j. Bioorg Med Chem Lett. 2020 Dec 1;30(23):127521. doi: 10.1016/j.bmcl.2020.127521. Epub 2020 Aug 31. Bioorg Med Chem Lett. 2020. PMID: 32882417
Tricyclic-Carbocyclic RORγt Inverse Agonists-Discovery of BMS-986313.
Yang MG, Beaudoin-Bertrand M, Xiao Z, Marcoux D, Weigelt CA, Yip S, Wu DR, Ruzanov M, Sack JS, Wang J, Yarde M, Li S, Shuster DJ, Xie JH, Sherry T, Obermeier MT, Fura A, Stefanski K, Cornelius G, Khandelwal P, Karmakar A, Basha M, Babu V, Gupta AK, Mathur A, Salter-Cid L, Denton R, Zhao Q, Dhar TGM. Yang MG, et al. Among authors: wang j. J Med Chem. 2021 Mar 11;64(5):2714-2724. doi: 10.1021/acs.jmedchem.0c01992. Epub 2021 Feb 16. J Med Chem. 2021. PMID: 33591748
Azaxanthene based selective glucocorticoid receptor modulators: design, synthesis, and pharmacological evaluation of (S)-4-(5-(1-((1,3,4-thiadiazol-2-yl)amino)-2-methyl-1-oxopropan-2-yl)-5H-chromeno[2,3-b]pyridin-2-yl)-2-fluoro-N,N-dimethylbenzamide (BMS-776532) and its methylene homologue (BMS-791826).
Weinstein DS, Gong H, Doweyko AM, Cunningham M, Habte S, Wang JH, Holloway DA, Burke C, Gao L, Guarino V, Carman J, Somerville JE, Shuster D, Salter-Cid L, Dodd JH, Nadler SG, Barrish JC. Weinstein DS, et al. Among authors: wang jh. J Med Chem. 2011 Oct 27;54(20):7318-33. doi: 10.1021/jm200879j. Epub 2011 Oct 3. J Med Chem. 2011. PMID: 21899328
Discovery of BMS-986251: A Clinically Viable, Potent, and Selective RORγt Inverse Agonist.
Cherney RJ, Cornelius LAM, Srivastava A, Weigelt CA, Marcoux D, Duan JJ, Shi Q, Batt DG, Liu Q, Yip S, Wu DR, Ruzanov M, Sack J, Khan J, Wang J, Yarde M, Cvijic ME, Mathur A, Li S, Shuster D, Khandelwal P, Borowski V, Xie J, Obermeier M, Fura A, Stefanski K, Cornelius G, Tino JA, Macor JE, Salter-Cid L, Denton R, Zhao Q, Carter PH, Dhar TGM. Cherney RJ, et al. Among authors: wang j. ACS Med Chem Lett. 2020 Mar 31;11(6):1221-1227. doi: 10.1021/acsmedchemlett.0c00063. eCollection 2020 Jun 11. ACS Med Chem Lett. 2020. PMID: 32551004 Free PMC article.
Annulation reaction enables the identification of an exocyclic amide tricyclic chemotype as retinoic acid Receptor-Related orphan receptor gamma (RORγ/RORc) inverse agonists.
Marcoux D, Bertrand MB, Weigelt CA, Yip S, Galella M, Park H, Wu DR, Wang J, Yarde M, Cvijic ME, Li S, Hynes J Jr, Tino JA, Zhao Q, Dhar TGM. Marcoux D, et al. Among authors: wang j. Bioorg Med Chem Lett. 2020 Oct 1;30(19):127466. doi: 10.1016/j.bmcl.2020.127466. Epub 2020 Aug 5. Bioorg Med Chem Lett. 2020. PMID: 32763309
Novel Tricyclic Pyroglutamide Derivatives as Potent RORγt Inverse Agonists Identified using a Virtual Screening Approach.
Liu Q, Batt DG, Weigelt CA, Yip S, Wu DR, Ruzanov M, Sack JS, Wang J, Yarde M, Li S, Shuster DJ, Xie JH, Sherry T, Obermeier MT, Fura A, Stefanski K, Cornelius G, Khandelwal P, Tino JA, Macor JE, Salter-Cid L, Denton R, Zhao Q, Dhar TGM. Liu Q, et al. Among authors: wang j. ACS Med Chem Lett. 2020 Nov 6;11(12):2510-2518. doi: 10.1021/acsmedchemlett.0c00496. eCollection 2020 Dec 10. ACS Med Chem Lett. 2020. PMID: 33335675 Free PMC article.
Azatricyclic Inverse Agonists of RORγt That Demonstrate Efficacy in Models of Rheumatoid Arthritis and Psoriasis.
Liu Q, Xiao HY, Batt DG, Xiao Z, Zhu Y, Yang MG, Li N, Yip S, Li P, Sun D, Wu DR, Ruzanov M, Sack JS, Weigelt CA, Wang J, Li S, Shuster DJ, Xie JH, Song Y, Sherry T, Obermeier MT, Fura A, Stefanski K, Cornelius G, Chacko S, Khandelwal P, Dudhgaonkar S, Rudra A, Nagar J, Murali V, Govindarajan A, Denton R, Zhao Q, Meanwell NA, Borzilleri R, Dhar TGM. Liu Q, et al. Among authors: wang j. ACS Med Chem Lett. 2021 Apr 30;12(5):827-835. doi: 10.1021/acsmedchemlett.1c00112. eCollection 2021 May 13. ACS Med Chem Lett. 2021. PMID: 34055233 Free PMC article.
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