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A practical synthesis of renin inhibitor MK-1597 (ACT-178882) via catalytic enantioselective hydrogenation and epimerization of piperidine intermediate.
Molinaro C, Shultz S, Roy A, Lau S, Trinh T, Angelaud R, O'Shea PD, Abele S, Cameron M, Corley E, Funel JA, Steinhuebel D, Weisel M, Krska S. Molinaro C, et al. Among authors: steinhuebel d. J Org Chem. 2011 Feb 18;76(4):1062-71. doi: 10.1021/jo102070e. Epub 2011 Jan 20. J Org Chem. 2011. PMID: 21250716
Asymmetric hydrogenation of protected allylic amines.
Steinhuebel DP, Krska SW, Alorati A, Baxter JM, Belyk K, Bishop B, Palucki M, Sun Y, Davies IW. Steinhuebel DP, et al. Org Lett. 2010 Sep 17;12(18):4201-3. doi: 10.1021/ol101804e. Org Lett. 2010. PMID: 20735080
1,3,8-Triazaspiro[4.5]decane-2,4-diones as efficacious pan-inhibitors of hypoxia-inducible factor prolyl hydroxylase 1-3 (HIF PHD1-3) for the treatment of anemia.
Vachal P, Miao S, Pierce JM, Guiadeen D, Colandrea VJ, Wyvratt MJ, Salowe SP, Sonatore LM, Milligan JA, Hajdu R, Gollapudi A, Keohane CA, Lingham RB, Mandala SM, DeMartino JA, Tong X, Wolff M, Steinhuebel D, Kieczykowski GR, Fleitz FJ, Chapman K, Athanasopoulos J, Adam G, Akyuz CD, Jena DK, Lusen JW, Meng J, Stein BD, Xia L, Sherer EC, Hale JJ. Vachal P, et al. Among authors: steinhuebel d. J Med Chem. 2012 Apr 12;55(7):2945-59. doi: 10.1021/jm201542d. Epub 2012 Feb 27. J Med Chem. 2012. PMID: 22364528
Direct asymmetric reductive amination.
Steinhuebel D, Sun Y, Matsumura K, Sayo N, Saito T. Steinhuebel D, et al. J Am Chem Soc. 2009 Aug 19;131(32):11316-7. doi: 10.1021/ja905143m. J Am Chem Soc. 2009. PMID: 19637921
Discovery of MK-4688: an Efficient Inhibitor of the HDM2-p53 Protein-Protein Interaction.
Reutershan MH, Machacek MR, Altman MD, Bogen S, Cai M, Cammarano C, Chen D, Christopher M, Cryan J, Daublain P, Fradera X, Geda P, Goldenblatt P, Hill AD, Kemper RA, Kutilek V, Li C, Martinez M, McCoy M, Nair L, Pan W, Thompson CF, Scapin G, Shizuka M, Spatz ML, Steinhuebel D, Sun B, Voss ME, Wang X, Yang L, Yeh TC, Dussault I, Marshall CG, Trotter BW. Reutershan MH, et al. Among authors: steinhuebel d. J Med Chem. 2021 Nov 11;64(21):16213-16241. doi: 10.1021/acs.jmedchem.1c01524. Epub 2021 Oct 29. J Med Chem. 2021. PMID: 34714078
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