Cartazolate
Systematic (IUPAC) name | |
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ethyl 4-(butylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
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Clinical data | |
Legal status |
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Routes of administration |
Oral |
Identifiers | |
CAS Number | 34966-41-1 |
ATC code | none |
PubChem | CID: 37015 |
ChemSpider | 33966 |
UNII | 8K93Z46WPY |
ChEMBL | CHEMBL8184 |
Chemical data | |
Formula | C15H22N4O2 |
Molecular mass | 290.36 g/mol |
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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
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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- ↑ US Patent 3966746 Amino derivatives of pyrazolopyridine carboxamides
- ↑ http://www.orgsyn.org/demo.aspx?prep=cv6p0010
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- Amines
- Pyrazolopyridines
- Ethyl esters
- GABAA receptor positive allosteric modulators
- Adenosine receptor antagonists
- Phosphodiesterase inhibitors