Cartazolate

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Cartazolate
Cartazolate.png
Systematic (IUPAC) name
ethyl 4-(butylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
Clinical data
Legal status
  • Uncontrolled
Routes of
administration
Oral
Identifiers
CAS Number 34966-41-1
ATC code none
PubChem CID: 37015
ChemSpider 33966
UNII 8K93Z46WPY YesY
ChEMBL CHEMBL8184
Chemical data
Formula C15H22N4O2
Molecular mass 290.36 g/mol
  • O=C(C1=CN=C(N(CC)N=C2)C2=C1NCCCC)OCC

Cartazolate (SQ-65,396) is a drug of the pyrazolopyridine class. It acts as a GABAA receptor positive allosteric modulator at the barbiturate binding site of the complex and has anxiolytic effects in animals.[1][2][3][4] It is also known to act as an adenosine antagonist at the A1 and A2 subtypes and as a phosphodiesterase inhibitor.[5][6] Cartazolate was tested in human clinical trials and was found to be efficacious for anxiety but was never marketed.[7] It was developed by a team at E.R. Squibb and Sons in the 1970s.[8]

Synthesis

Cartazolate and Etazolate synthesis: HOEHN H, DENZEL T; DE 2123318  (1970 to E. R. Squibb & Sons Inc.).

Condensation of aminopyrazole (1) with Diethyl ethoxymethylenemalonate (2) gives the product of the addition-elimination (3). The product tautomerizes spontaneously to the hydroxypyridine (4). The hydroxyl group is then converted to the chloro derivative by means of phosphorus oxychloride (5) Displacement of halogen by n-butylamine gives the antidepressant compound cartazolate. Displacement of halogen by the basic nitrogen of acetone hydrazone[9] affords the antidepressant etazolate.

See also

References

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  8. US Patent 3966746 Amino derivatives of pyrazolopyridine carboxamides
  9. http://www.orgsyn.org/demo.aspx?prep=cv6p0010