1227259-18-8Relevant articles and documents
An efficient large-scale synthesis of a naphthylacetic acid CRTH2 receptor antagonist
Shu, Lianhe,Wang, Ping,Gu, Chen,Liu, Wen,Alabanza, Lady Mae,Zhang, Yingchao
, p. 651 - 657 (2013)
An efficient and practical synthesis of a naphthylacetic acid CRTH2 receptor antagonist is reported. Michael addition of ethyl t-butyl malonate to an allenoate afforded a triester, which was selectively hydrolyzed and decarboxylated to give a benzylidenepentanedioic acid monoester. Treatment of this compound with potassium acetate and acetic anhydride produced the naphthylacetate core. The triflate of the key building block was coupled with a zinc reagent of the side chain under improved Negishi coupling conditions to afford the target product. The process was successfully scaled up to produce over 2 kg of the API.
NAPHTHYLACETIC ACIDS
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Page/Page column 33, (2010/06/13)
The invention is concerned with the compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein W, X, Y, and R1-R7 are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds of formula I are antagonists or partial agonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.