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US 5,470,853 AGranted
6-substituted-hexahydrobenz [CD] indoles
AssigneeEli Lilly and Company
InventorsMichael E. Flaugh, Michael J. Martinelli
Life of this patent
Estimating the term…
Abstract
The present invention provides 4-amino-6-substituted-hexahydrobenz[cd]indoles which are useful in treating disease states which can be benefited by an alteration of 5-HT.sub.1.sbsb.A receptors.
Claims7
A substantially pure stereoisomer of a compound of the formula ##STR11## wherein A is ##STR12## CN, NO.sub.2, NR.sup.5 R.sup.6, NHC(O)R.sup.6, NHSO.sub.2 R.sup.6, 5(C.sub.1 -C.sub.4 alkyl) or CF.sub.3 ;
- R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, cyclopropylmethyl, phenyl-substituted C.sub.1 -C.sub.4 alkyl, --COR.sup.4, --(CH.sub.2).sub.n S (C.sub.1 -C.sub.4 alkyl), or --(CH.sub.2).sub.n CONR.sup.9 R.sup.10 ;
- R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or cyclopropylmethyl;
- Q is OR.sup.3, SR.sup.3, NR.sup.5 R.sup.6 or hydrogen;
- R.sup.3 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkyl substituted with one or two moieties independently selected from C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 alkylthio or nitro, aryl, aryl substituted with one or two moieties independently selected from C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 alkylthio, nitrO, C.sub.1 -C.sub.3 alkyl or trifluoromethy, aryl (C.sub.1 -C.sub.4 alkyl), aryl (C.sub.1 -C.sub.4 alkyl) substituted with one or two moleties independently selected from C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 alkylthio, nitro, C.sub.1 -C.sub.3 alkyl or trifluoromethyl, or C.sub.3 -C.sub.7 cycloalkyl;
- 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, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkyl substituted with a phenyl group, phenyl, or together form a C.sub.3 -C.sub.5 heterocyclic ring;
- R.sup.9 and R.sup.10 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.9 or R.sup.10 is a cycloalkyl the other is hydrogen;
- B is hydrogen, C.sub.1 -C.sub.4 alkyl, or an amino-blocking group;
- X is oxygen or sulfur;
- wherein the configuration at position 2a is S and the configuration at position 4 is R;
- or a pharmaceutically acceptable salt thereof.
9 more elements
A substantially pure stereoisomer of a compound of the formula ##STR13## wherein:
- A is ##STR14## NR.sup.5 R.sup.6, NHC(O)R.sup.6, NHSO.sub.2 R.sup.6, or CF.sub.3 ;
- R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, cyclopropylmethyl, phenyl-substituted C.sub.1 -C.sub.4 alkyl, --COR.sup.4, --(CH.sub.2).sub.n S(C.sub.1 -C.sub.4 alkyl) , or --(CH.sub.2).sub.n CONR.sup.9 R.sup.10 ;
- R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or cyclopropylmethyl;
- Q is OR.sup.3, SR.sup.3, NR.sup.5 R.sup.6 or hydrogen;
- R.sup.3 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkyl substituted with one or two moieties independently selected from C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 alkylthio or nitro, aryl, aryl substituted with one or two moieties independently selected from C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 alkylthio, nitro, C.sub.1 -C.sub.3 alkyl or trifiuoromethyl, aryl (C.sub.1 -C.sub.4 alkyl), aryl (C.sub.1 -C.sub.4 alkyl) substituted with one or two moieties independently selected from C.sub.1 -C.sub.3 alkoxy, halo, hydroxy, C.sub.1 -C.sub.3 alkylthio, nitro, C.sub.1 -C.sub.3 alkyl or trifluoromethyl, or C.sub.3 -C.sub.7 cycloalkyl;
- 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, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkyl substituted with a phenyl group, phenyl, or together form a C.sub.3 -C.sub.5 heterocyclic ring, with the proviso that R.sup.5 and R.sup.6 are not both hydrogen;
- R.sup.9 and R.sup.10 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.9 or R.sup.10 is a cycloalkyl the other is hydrogen;
- B is hydrogen, C.sub.1 -C.sub.4 alkyl, or an amino-blocking group;
- x is oxygen or sulfur;
- or a pharmaceutically acceptable salt thereof.
9 more elements
Dependencies are inferred from the claim text.