AW-15'1129
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| Other names | BRN 0620708 |
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| Formula | C16H14ClN3 |
| Molar mass | 283.76 g·mol−1 |
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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
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.
See also
References
- ↑ 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.
- ↑ Roth B, Faber J, Nevsímalová S (1972). "A clinical and polygraphic study of the effect of a new imidazo-quinazoline derivative in narcolepsy-cataplexy. The relationship between the antidepressant and anticataplectic effects of the drug". Activitas Nervosa Superior. 14 (1): 35–9. PMID 4336749.
- ↑ Kaiser C, Zirkle CL (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 978-0-12-040508-4.
- ↑ GB 1042299, "Quinazoline derivatives", published 14 September 1966, assigned to Wander AG
- ↑ US 3309369, Schindler O, "Imidazo- and pyrimido-quinazolines", issued 14 March 1967, assigned to Wander AG
- ↑ 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.