1018978-85-2Relevant articles and documents
Selective Heteroaryl N-Oxidation of Amine-Containing Molecules
Dyer, Robert M. B.,Hahn, Philip L.,Hilinski, Michael K.
, p. 2011 - 2014 (2018)
The first examples of nonenzymatic N-oxidation of heteroarenes in the presence of amines are reported. Pyridine, quinoline, and isoquinoline N-oxides are selectively formed in the presence of more reactive aliphatic and alicyclic amines by use of an in situ protonation strategy and an iminium salt organocatalyst. Application to late-stage functionalization that mimics phase 1 metabolism of small-molecule drugs is also demonstrated.
Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists
Schmidt, Robert G.,Bayburt, Erol K.,Latshaw, Steven P.,Koenig, John R.,Daanen, Jerome F.,McDonald, Heath A.,Bianchi, Bruce R.,Zhong, Chengmin,Joshi, Shailen,Honore, Prisca,Marsh, Kennan C.,Lee, Chih-Hung,Faltynek, Connie R.,Gomtsyan, Arthur
, p. 1338 - 1341 (2011/04/23)
Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition.
2-Benzimidazolyl-9-(chroman-4-yl)-purinone derivatives as JAK3 inhibitors
Cole, Andrew G.,Bohnstedt, Adolph C.,Paradkar, Vidyadhar,Kingsbury, Celia,Quintero, Jorge G.,Park, Haengsoon,Lu, Yingchun,You, Ming,Neagu, Irina,Diller, David J.,Letourneau, Jeffrey J.,Shao, Yuefei,James, Ray A.,Riviello, Christopher M.,Ho, Koc-Kan,Lin, Tsung H.,Wang, Bojing,Appell, Kenneth C.,Sills, Matthew,Quadros, Elizabeth,Kimble, Earl F.,Ohlmeyer, Michael H.J.,Webb, Maria L.
scheme or table, p. 6788 - 6792 (2010/06/12)
A novel class of Janus tyrosine kinase 3 (JAK3) inhibitors based on a 2-benzimidazoylpurinone core structure is described. Through substitution of the benzimidazoyl moiety and optimization of the N-9 substituent of the purinone, compound 24 was identified incorporating a chroman-based functional group. Compound 24 shows excellent kinase activity, good oral bioavailability and demonstrates efficacy in an acute mechanistic mouse model through inhibition of interleukin-2 (IL-2) induced interferon-γ (INF-γ) production.
8-SUBSTITUTED 2-(BENZIMIDAZOLYL)PURINE DERIVATIVES FOR IMMUNOSUPPRESSION
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Page/Page column 9, (2008/06/13)
The present invention provides novel purines useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formula I:
7-Substituted Purine Derivatives for Immunosuppression
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Page/Page column 31, (2008/12/05)
The present invention provides novel purinone and related derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formula III:
Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof
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Page/Page column 14, (2008/06/13)
Compounds that are antagonists of the VR1 receptor, having formula (I) [image] or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A1, A2, A3, A4, R7, R8, R9, X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.
