Synthesis and solid-phase purification of anthranilic sulfonamides as CCK-2 ligands.
A novel strategy for the synthesis of cholecystokinin-2 receptor ligands was developed. The route employs a solution-phase synthesis of a series of anthranilic sulfonamides followed by a resin capture purification strategy to produce multi-milligram quantities of compounds for bioassay. The synthesis was used to produce >100 compounds containing various functional groups, highlighting the general applicability of this strategy and to address specific metabolism issues in our CCK-2 program.
Woods
Craig R
CR
Johnson & Johnson Pharmaceutical Research and Development, 3210 Merryfield Row, San Diego, CA 92121, USA. cwoods4@prdus.jnj.com
Hack
Michael D
MD
Allison
Brett D
BD
Phuong
Victor K
VK
Rosen
Mark D
MD
Morton
Magda F
MF
Prendergast
Clodagh E
CE
Barrett
Terrance D
TD
Shankley
Nigel P
NP
Rabinowitz
Michael H
MH
D000818:Animals; D002766:Cholecystokinin / Q000378:metabolism*; D020650:Combinatorial Chemistry Techniques; D015195:Drug Design; D006801:Humans; D008024:Ligands; D008862:Microsomes, Liver / Q000187:drug effects; D015394:Molecular Structure; D051381:Rats; D043887:Receptor, Cholecystokinin B / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D008024:Ligands; D043887:Receptor, Cholecystokinin B; D013449:Sulfonamides; D062367:ortho-Aminobenzoates; D002766:Cholecystokinin