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AW-15'1129

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AW-15'1129
Clinical data
Other namesBRN 0620708
Identifiers
  • 5-(4-Chlorophenyl)-2,3,5,6-tetrahydroimidazo[1,2-c]quinazoline
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H14ClN3
Molar mass283.76 g·mol−1
3D model (JSmol)
  • C1CN2C(NC3=CC=CC=C3C2=N1)C4=CC=C(C=C4)Cl
  • InChI=1S/C16H14ClN3/c17-12-7-5-11(6-8-12)15-19-14-4-2-1-3-13(14)16-18-9-10-20(15)16/h1-8,15,19H,9-10H2
  • Key:HSZXGIDMRWNJCF-UHFFFAOYSA-N

AW-15'1129 is a drug with an imidazo-quinazoline based structure. The pharmacology is described as antidepressant based on strong adrenergic and anti-REM effects. It was invented by Othmar Dr Schindler of Wander AG in the 1960's. Although the drug is not known to have ever been commercialized, it is a representative example of a psychochemical based on a rational synthetic design.[1][2][3]

In the patent the dosage of API is formulated to a strength of 4mg per tablet.[4][5]

Synthesis

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2-aminobenzonitrile is reacted with ethylenediamine to give the cyclic aminal.[6]

This is then refluxed with benzaldehyde in alcoholic acid to give 6-phenyl-2,3,6,7-tetrahydro-4H-pyrimido[1,2-c]quinazoline. Reduction with potassium borohydride gives 5-phenyl-2,3,5,6-tetrahydro-imidazo[1,2-c]quinazoline.

See also

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References

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  1. ^ Stille, G., Lauener, H., Eichenberger, E., Matussek, N., Pöldinger, W. (May 1968). "Observations concerning adrenergic functions and antidepressant activity: Pharmacological, biochemical and clinical results with a new imidazo-quinazoline derivative 1". Pharmacopsychiatry. 1 (2): 123–135. doi:10.1055/s-0028-1094213.
  2. ^ B. Roth, J. Faber and S. Nevs̈imalova, Activ. Nerv. Super., 14, 35 (1972).
  3. ^ Kaiser, C., Zirkle, C. L. (1973). "Annual Reports in Medicinal Chemistry". Chapter 2. Antidepressives and Stimulants. Annual Reports in Medicinal Chemistry. Vol. 8. Elsevier. pp. 11–19. doi:10.1016/S0065-7743(08)61230-0. ISBN 9780120405084.
  4. ^ Othmar Dr Schindler, GB1042299 (1966 to Wander AG).
  5. ^ Schindler Othmar, US3309369 (1967 to Wander AG).
  6. ^ Kwok, R. (August 1978). "Preparation of some tricyclic fused ring iminopyrido[3,2- e ]pyrimidines". Journal of Heterocyclic Chemistry. 15 (5): 877–880. doi:10.1002/jhet.5570150531.
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