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US 5,627,199 AGranted
6-heterocyclic-4-amino-1,2,2A,3,4,5-hexahydrobenz [CD] indoles
AssigneeEli Lilly and Company
InventorsRichard N. Booher, David E. Lawhorn, Michael J. Martinelli, Charles J. Paget, Jr., John M. Schaus
Life of this patent
Estimating the term…
Abstract
6-Heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.
Claims11
A compound of the formula ##STR15## wherein:
- R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, cyclopropylmethyl, phenyl (C.sub.1 -C.sub.4 alkyl), naphthyl (C.sub.1 -C.sub.4 alkyl), phenyl (C.sub.1 -C.sub.4 alkyl) substituted with one or two substituents selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 thioalkyl, nitro, C.sub.1 -C.sub.3 alkyl or trifluoromethyl, naphthyl (C.sub.1 -C.sub.4 alkyl) substituted with one or two substituents selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 thioalkyl, nitro, C.sub.1 -C.sub.3 alkyl or trifluoromethyl, --(CH.sub.2).sub.n S(C.sub.1 -C.sub.4 alkyl), --C(O)R.sup.4, or --(CH.sub.2).sub.n C(O)NR.sup.5 R.sup.6 ;
- R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, cyclopropylmethyl or C.sub.3 -C.sub.4 alkenyl;
- R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or an amino blocking group;
- n is 1-4;
- R.sup.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or phenyl;
- R.sup.5 and R.sup.6 are independently hydrogen, C.sub.1 -C.sub.4 alkyl, or C.sub.5 -C.sub.8 cycloalkyl with the proviso that when one of R.sup.5 or R.sup.6 is a cycloalkyl the other is hydrogen;
- HET is a heterocyclic ring selected from the group consisting of ##STR16## where R is hydrogen, C.sub.1 -C.sub.3 alkyl, halogen, hydroxy, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 thioalkyl, NH.sub.2, CN or phenyl;
- or pharmaceutically acceptable salts thereof.
5 more elements
Dependencies are inferred from the claim text.