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US 4,728,663 AGranted
N-[(1H-imidazol-1-yl)alkyl]benz[cd]-indol-2-amines and use in inhibiting thromboxane synthetase enzyme
AssigneeAmerican Cyanamid Company
InventorsAndrew S. Tomcufcik, Walter E. Meyer, Peter S. Chan, David L. Crandall
Life of this patent
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Abstract
N-[(1H-imidazol-1-yl)alkyl]benz[cd]-indol-2 amines useful as inhibitors of thromboxane synthetase enzyme, hypotensive agents and cardioprotective agents are described.
Claims23
A compound of the formula:
- ##STR5## wherein R.sub.1 is hydrogen, bromo, chloro or dimethylaminosulfonamide;
- R.sub.2 is hydrogen or alkyl(C.sub.1 -C.sub.3);
- R.sub.3 is hydrogen, alkyl(C.sub.1 -C.sub.3) or phenyl;
- R.sub.4 is hydrogen or when taken together with R.sub.2 is --CH.dbd.CH--CH.dbd.CH--;
- R.sub.5 is hydrogen or chloro;
- and Q is --(CH.sub.2).sub.n.sup.--, where n is an integer 2-12, ##STR6## and the pharmacologically acceptable salts thereof.
3 more elements
The compound according to claim 1, 6-bromo-N-[3-(1H-imidazol-1-yl)butyl]benz[cd]indol-2-amine.
The compound according to claim 1, 6-bromo-N-[5-(1H-imidazol-1-yl)pentyl]benz[cd]indol-2-amine.
The compound according to claim 1, 6,8-dichloro-N-[5-(1H-imidazol-1-yl)pentyl]benz[cd]indol-2-amine.
A process for producing a compound of the formula:
- ##STR7## wherein R.sub.1 is hydrogen, bromo, chloro or dimethylaminosulfonamide;
- R.sub.2 is of hydrogen, or alkyl(C.sub.1 -C.sub.3), R.sub.3 is hydrogen, alkyl(C.sub.1 -C.sub.3), or phenyl;
- R.sub.4 is hydrogen or when taken together with R.sub.2 is --CH.dbd.CH--CH.dbd.CH;
- R.sub.5 is hydrogen or chloro;
- and Q is --(CH.sub.2).sub.n.sup.--, where n is an integer 2-12, ##STR8## and the pharmacologically acceptable salts which comprises reacting a substituted 2-methylthiobenz[cd]indole salt of the structure ##STR9## where X is halogen, methylsulfate, sulfate, or the like with a substituted (1H-imidazol-1-yl)alkanamine of the formula ##STR10## in a solvent such as ethanol at reflux temperature for 6-24 hours.
2 more elements
Dependencies are inferred from the claim text.