3-Hydroxy carbazole derivatives
AssigneeSterling Drug Inc.
InventorAram Mooradian
Life of this patent
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Abstract
3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.
Claims8
A 3-(OZ)-9-R.sub.4 -1,2,3,4-tetrahydrocarbazole having the formula ##STR24## where Z is hydrogen or ##STR25## R.sub.4 is hydrogen, lower-alkyl, Ar-lower-alkyl, carboxy-lower-alkyl or lower-alkoxy-carbonyl-lower-alkyl, or R.sub.4 is Y-NR'R", where R' and R" are lower-alkyl and Y is lower-alkylene;
- Q'.sub.1 is selected from hydrogen, lower-alkoxy and halo;
- Q'.sub.2 is selected from hydrogen, non-tertiary-lower-alkyl, lower-alkoxy and halo;
- Q'.sub.3 and Q'.sub.4 each are hydrogen;
- and
- Ar is phenyl or phenyl mono-substituted by lower-alkyl or halo;
- where lower-alkyl and lower-alkoxy, every occurrence, have from one to six carbon atoms and lower-alkylene has from two to four carbon atoms;
- provided that when Z is hydrogen then R.sub.4 cannot be lower-alkoxycarbonyl-lower-alkyl, and when R.sub.4 is hydrogen or lower-alkyl at least one of Q'.sub.1 and Q'.sub.2 is other than hydrogen or lower-alkyl.
A 3-(OZ.sub.1)-9-R'.sub.4 -1,2,3,4-tetrahydrocarbazole having the formula ##STR27## where Z.sub.1 is Ar-SO.sub.2 -;
- R'.sub.4 is hydrogen, lower-alkyl, Ar-lower-alkyl or carboxy-lower-alkyl, or R'.sub.4 is Y-NR'R", where R' and R" are lower-alkyl and Y is lower-alkylene;
- Q'.sub.1 is selected from hydrogen, lower alkoxy and halo;
- Q'.sub.2 is selected from hydrogen, non-tertiary lower-alkyl, lower-alkoxy and halo;
- Q'.sub.3 and Q'.sub.4 each are hydrogen;
- and Ar is phenyl or phenyl mono-substituted by lower-alkyl or halo;
- where lower-alkyl and lower-alkoxy, every occurrence, have from one to six carbon atoms and lower-alkylene has from two to four carbon atoms.
Dependencies are inferred from the claim text.