AW-15'1129

AW-15'1129

Clinical data
Other names	BRN 0620708
Identifiers
IUPAC name 5-(4-Chlorophenyl)-2,3,5,6-tetrahydroimidazo[1,2-c]quinazoline
CAS Number	23597-98-0
PubChem CID	211824
ChemSpider	183656
ChEMBL	ChEMBL1995532
CompTox Dashboard (EPA)	DTXSID00946398
Chemical and physical data
Formula	C16H14ClN3
Molar mass	283.76 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CN2C(NC3=CC=CC=C3C2=N1)C4=CC=C(C=C4)Cl
InChI 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.

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

Patents: ^{[1] [2]} Reference: ^{[3] [4] [5]}

Synthesis

Precursor is made from 2-aminobenzonitrile [1885-29-6] via cyclic aminal formation with the ethylenediamine. ^[6]

Ex 1: o-(1,4,5,6-tetrahydropyrimidin-2-yl)aniline [68100-63-0] hydrochloride salt [NA] (1) and benzaldehyde (2) are refluxed together in alcoholic acid to give 6-phenyl-2,3,6,7-tetrahydro-4H-pyrimido[1,2-c]quinazoline hydrochloride (3). Reduction with potassium borohydride gives 5-phenyl-2,3,5,6-tetrahydro-imidazo[1,2-c]quinazoline (4).

See also

• Mazindol
• Dazadrol
• Trazium

References

1. Othmar Dr Schindler, GB1042299 (1966 to Wander AG).
2. Schindler Othmar, US3309369 (1967 to Wander AG).
3. 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.
4. B. Roth, J. Faber and S. Nevs̈imalova, Activ. Nerv. Super., 14, 35 (1972).
5. 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.
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.