Pazinaclone (DN-2327) is a

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or Psychomotor agitation, excitement. They are central nervous system (CNS) Depressant, depressants and interact with brain activity, causing its decelera ...

and

anxiolytic An anxiolytic (; also antipanic or anti-anxiety 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 Cyclopyrrolones are a family of hypnotic and anxiolytic nonbenzodiazepine drugs with similar pharmacological profiles to the benzodiazepine derivatives. Although cyclopyrrolones are chemically unrelated to benzodiazepines, they function via the G ...

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), colloquially known as "benzos", are a class of central nervous system (CNS) depressant, depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed t ...

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 (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

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

Synthesis

Reaction of 2-amino-7-chloro-1,8-

naphthyridine Diazanaphthalenes are a class of aromaticity, aromatic heterocyclic compound, heterocyclic chemical compounds that have the formula C8H6N2. They consist of a naphthalene double ring in which two of the carbon atoms have been replaced with nitrogen a ...

with

phthalic anhydride Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commer ...

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