Pazinaclone (DN-2327) is a

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but ...

and

anxiolytic An anxiolytic (; also antipanic or antianxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxie ...

drug in the cyclopyrrolone family of drugs. Some other cyclopyrrolone drugs include zopiclone and eszopiclone. Pazinaclone has a very similar pharmacological profile to the

benzodiazepine Benzodiazepines (BZD, BDZ, BZs), sometimes called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, ...

s including sedative and anxiolytic properties, but with less amnestic effects, and at low doses it is a relatively selective anxiolytic, with sedative effects only appearing at higher doses. Pazinaclone produces its sedative and anxiolytic effects by acting as a

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonist ...

at GABA_A benzodiazepine receptors, although pazinaclone is more subtype-selective than most benzodiazepines.

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 .5ecane results in formation of the corresponding amide, pazinaclone.

References

{{GABAAR PAMs Cyclopyrrolones Sedatives Isoindolines Lactams Acetamides Naphthyridines GABAA receptor positive allosteric modulators

Synthesis

See also

References