- A novel series of potent and selective EP4 receptor ligands: Facile modulation of agonism and antagonism
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A novel series of EP4 ligands, based on a benzyl indoline scaffold, has been discovered. It was found that agonism and antagonism in this series can be easily modulated by minor modifications on the benzyl group. The pharmacokinetic, metabolic
- Boyd, Michael J.,Berthelette, Carl,Chiasson, Jean-Franois,Clark, Patsy,Colucci, John,Denis, Danielle,Han, Yongxin,Lévesque, Jean-Francois,Mathieu, Marie-Claude,Stocco, Rino,Therien, Alex,Rowland, Steve,Wrona, Mark,Xu, Daigen
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scheme or table
p. 484 - 487
(2011/02/27)
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- INDOLE AND INDOLINE CYCLOPROPYL AMIDE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS
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The invention is directed to indole and indoline cyclopropyl amide derivatives as EP4 receptor antagonists useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoid arthritis and cancer. Ph
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Page/Page column 22-23
(2008/12/08)
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- INDOLINE AMIDE DERIVATIVES AS EP4 RECEPTOR LIGANDS
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The invention is directed to indoline amide derivatives as EP4 receptor ligands, antagonists or agonists, useful for the treatment of EP4 mediated diseases or conditions, such as acute and chronic pain, osteoarthritis, rheumatoid arthritis, cancer and gla
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Page/Page column 21
(2008/06/13)
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- Asymmetric Deprotonations: Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/ (-)-Sparteine
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The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.
- Bertini Gross, Kathleen M.,Jun, Young M.,Beak, Peter
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p. 7679 - 7689
(2007/10/03)
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- DIRECTED LITHIATION OF 1-(tert-BUTOXYCARBONYL)INDOLINES. A CONVENIENT ROUTE TO 7-SUBSTITUTED INDOLINES
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1-(tert-Butoxycarbonyl)indolines were regioselectively lithiated at 7-position with s-BuLi-TMEDA in ether or THF at -78 deg C.The lithiated species were reacted with a range of electrophiles to give 7-substituted indoline derivatives.
- Iwao, Masatomo,Kuraishi, Tsukasa
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p. 1031 - 1038
(2007/10/02)
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