Pazinaclone
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Pazinaclone (DN-2327) is a
cyclopyrrolone family of drugs. Some other cyclopyrrolone drugs include zopiclone and eszopiclone
.
Pazinaclone has a very similar pharmacological profile to the
amnestic effects,[1] and at low doses it is a relatively selective anxiolytic, with sedative effects only appearing at higher doses.[2]
Pazinaclone produces its sedative and anxiolytic effects by acting as a partial agonist at GABAA benzodiazepine receptors, although pazinaclone is more subtype-selective than most benzodiazepines.[3]
Synthesis
Reaction of 2-amino-7-chloro-1,8-
naphthyridine with phthalic anhydride
leads to the corresponding phthalimide. Selective reduction of one of the imide carbonyl groups in essence converts that to an aldehyde. Condensation with tert-butyl(triphenylphosphoranylidene)acetate gives the Wittig product.
The carboxylic acid is then treated with diethyl cyanophosphonate to convert that to an activated acid cyanide; reaction with 1,4-dioxa-8-azaspiro[4.5]decane results in formation of the corresponding amide, pazinaclone.