Synthesis of 1-Tetrazolylalkan-2-amines and -carbamates

REFERENCES

• Kaptur , M. ; Schulze Elfringhoff , A. ; Lehr , M. Structure–activity relationship studies on 1-(5-carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A2 α: Variation of the activated ketone moiety . Bioorg. Med. Chem. Lett. 2011 , 21 , 1773 – 1776 .
   PubMed Web of Science ®Google Scholar
• Kaptur , M. Indole-5-carboxylic acid derivatives as inhibitors of cytosolic phospholipase A2 α. PhD dissertation, University of Münster, 2010 .
   Google Scholar
• Mueller , R. ; Street , L. J. ; Rachwal , S. ; Alisala , K. Preparation of substituted triazinone derivatives and analogs as glutamatergic response enhancers. WO Patent 2009038752, 2009 .
   Google Scholar
• Mueller , R. ; Lee , S. ; O'Hare , S. ; Rogers , G. ; Rachwal , S. ; Street , L. Benzotriazinone derivatives as AMPA receptor enhancers and their preparation, pharmaceutical compositions, and use in treatment of diseases. WO Patent 2008085505, 2008 .
   Google Scholar
• Goldstein , D. M. ; Soth , M. ; Gabriel , T. ; Dewdney , N. ; Kuglstatter , A. ; Arzeno , H. ; Chen , J. ; Bingenheimer , W. ; Dalrymple , S. A. ; Dunn , J. ; Farrell , R. ; Frauchiger , S. ; La Fargue , J. ; Ghate , M. ; Graves , B. ; Hill , R. J. ; Li , F. ; Litman , R. ; Loe , B. ; McIntosh , J. ; McWeeney , D. ; Papp , E. ; Park , J. ; Reese , H. F. ; Roberts , R. T. ; Rotstein , D. ; San Pablo , B. ; Sarma , K. ; Stahl , M. ; Sung , M. L. ; Suttman , R. T. ; Sjogren , E. B. ; Tan , Y. ; Trejo , A. ; Welch , M. ; Weller , P. ; Wong , B. R. ; Zecic , H. Discovery of 6-(2,4-difluorophenoxy)-2-[3-hydroxy-1-(2-hydroxyethyl)propylamino]-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (pamapimod) and 6-(2,4-difluorophenoxy)-8-methyl-2-(tetrahydro-2H-pyran-4-ylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (R1487) as orally bioavailable and highly selective inhibitors of p38α mitogen-activated protein kinase. J. Med. Chem. 2011, 54, 2255–2265.
   PubMed Web of Science ®Google Scholar
• Maier , T. Process for the fermentative non-proteinogenic production of L-amino acids. EP Patent 1191106, 2002 .
   Google Scholar
• Maier , T. H. Semisynthetic production of unnatural L-α-amino acids by metabolic engineering of the cysteine-biosynthetic pathway . Nat. Biotechnol. 2003 , 21 , 422 – 427 .
   PubMed Web of Science ®Google Scholar
• Elhalem , E. ; Bailey , B. N. ; Docampo , R. ; Ujváry , I. ; Szajnman , S. H. ; Rodriguez , J. B. Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi . J. Med. Chem. 2002 , 45 , 3984 – 3999 .
   PubMed Web of Science ®Google Scholar
• Giles , P. R. ; Roger-Evans , M. ; Soukup , M. ; Knight , J. An improved process for the N-alkylation of indoles using chiral N-protected 2-methylaziridines . Org. Process Res. Dev. 2003 , 7 , 22 – 24 .
   Web of Science ®Google Scholar
• Zhong , W. ; Hitchcock , S. ; Patel , V. F. ; Croghan , M. ; Dineen , T. ; Harried , S. ; Horne , D. ; Judd , T. ; Kaller , M. ; Kreiman , C. ; Lopez , P. ; Monenschein , H. ; Nguyen , T. ; Weiss , M. ; Xue , Q. ; Yang , B. Substituted hydroxyethyl amine compounds as beta-secretase modulators and their preparation and use in the treatment of Alzheimer's disease and related conditions. WO Patent 2008147547, 2008 .
   Google Scholar
• Dack , K. N. ; Owen , D. R. ; Watson , C. A. L. Preparation of cyclopentyl glutaramide derivatives as neutral endopeptidase inhibitors. WO Patent 2004056787, 2004 .
   Google Scholar
• Farthing , C. N. ; Baldwin , J. E. ; Russell , A. T. ; Schofield , C. J. ; Spivey , A. C. Syntheses of (S)-β-pyrazolylalanine and (S)-quisqualic acid from serine-derived aziridine . Tetrahedron Lett. 1996 , 37 , 5225 – 5226 .
   Web of Science ®Google Scholar