87151-63-1Relevant articles and documents
A practical synthesis of the kappa opioid receptor selective agonist (+)-5R,7S,8S-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxospiro[4,5]dec-8-yl] benzeneacetamide (U69,593)
McElroy, Timothy,Thomas, James B.,Brine, George A.,Navarro, Hernan A.,Deschamps, Jeffrey,Carroll, F. Ivy
, p. 943 - 947 (2008/12/23)
A novel approach to the synthesis of the kappa opioid receptor agonist U69,593 has been developed. This approach improves upon current literature methods by substituting stable and isolable cyclic sulfates for the unstable epoxides. The new approach provides access to gram quantities of the target compound and displays excellent control of the relative stereochemistry. The absolute stereochemistry as well as biological activity of the U69,593 produced by this new method was verified using X-ray crystal structure analysis and binding assays for the kappa opioid receptor. Georg Thieme Verlag Stuttgart.
Analgesic 1-oxa-, aza- and thia-spirocyclic compounds
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, (2008/06/13)
Mono-Oxa-, thiaspirocyclic-benzene-acetamide and -benzamide compounds of the formula STR1 wherein p, n, m, A, E, R, R1, R2, X, Y and Z are as defined in the specification, e.g., (±)-(5α,7α,9β)-3,4-dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]benzeneacetamide, and the pharmacologically acceptable salts thereof, are useful as analgesic compounds having low physical dependence liability, compared to morphine and methodone, and low dysphoria side effects. Some of these compounds have potent analgesic activity when administered orally, and some have low CNS sedative side effects. Pharmaceutical compositions and methods for using these compounds as analgesics are disclosed. Processes for preparing this class of compounds are also disclosed.