Synthesis of thienopyridinone compounds and related intermediates
View Patent ↗The invention relates to 5-HT receptor agonists and partial agonists. Novel thienopyridinone compounds represented by Formula I, and synthesis and uses thereof for treating diseases mediated directly or indirectly by 5-HT receptors, are disclosed. Such conditions include Alzheimer's disease, cognition disorders, irritable bowel syndrome, nausea, emesis, vomiting, prokinesia, gastroesophageal reflux disease, nonulcer dyspepsia, depression, anxiety, urinary incontinence, migraine, arrhythmia, atrial fibrillation, ischemic stroke, gastritis, gastric emptying disorders, feeding disorders, gastrointestinal disorders, constipation, erectile dysfunction, and respiratory depression. Methods of preparation and novel intermediates and pharmaceutical salts thereof are also included.
1. A method for making a compound of the formula
wherein
R 1 is (C 1 -C 8 ) branched or unbranched alkyl;
R 2 and R 3 , taken together, form a substituted or unsubstituted piperidine ring; and
n is 1, 2, 3, 4, 5 or 6;
the method comprising the steps of heating in an organic solvent a mixture comprising a substituted or unsubstituted piperidinyl alkylamine and an intermediate having the formula
wherein R 1 and R 2 are H; and R 3 and R 4 are independently selected from the group consisting of methyl, ethyl and isopropyl.
2. The method of claim 1 , wherein the intermediate is methyl 6,7-dihydro-4-hydroxy-7-isopropyl-6-oxothieno-[2,3-b]pyridine-5-carboxylate.