Synthesis and analgesic activity of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]ind ole-1- acetic acid).

A H Katz, C A Demerson, C C Shaw, A A Asselin, L G Humber, K M Conway, G Gavin, C Guinosso, N P Jensen, D Mobilio

Ayerst Laboratories Research, Inc., Princeton, New Jersey 08543-8000.

Journal of medicinal chemistry 1988 Jun

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The synthesis of cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole -1-acetic acid, pemedolac (USAN), is described. This compound has been found to be a potent analgesic agent in primary screening. Pemedolac has been resolved and the active (+)-enantiomer assigned a 1S,4R absolute configuration on the basis of a crystallographic analysis of its (S)-(-)-borneol ester.

Citation

A H Katz, C A Demerson, C C Shaw, A A Asselin, L G Humber, K M Conway, G Gavin, C Guinosso, N P Jensen, D Mobilio. Synthesis and analgesic activity of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]ind ole-1- acetic acid). Journal of medicinal chemistry. 1988 Jun;31(6):1244-50