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US 5,635,528 AGranted
Intermediates to tetrahydro-beta-carbolines
AssigneeEli Lilly and Company
InventorsJames E. Audia, James J. Droste, Deborah A. Evrard, Pawel Fludzinski, Gwyn L. Murdoch, David L. Nelson
Life of this patent
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Abstract
3-Ethanamine and 3-ethanamine related compounds are provided that are useful intermediates and have beneficial central nervous system activity.
Claims9
A compound of the Formula (VI) ##STR125## wherein:
- R.sub.3 is hydrogen or C.sub.1 -C.sub.3 alkyl;
- A is selected from the group consisting of ##STR126## wherein R.sub.6 and R.sub.7 are, independently, hydrogen, C.sub.1 -C.sub.6 alkyl,
- C.sub.2 -C.sub.6 alkenyl, halo, halo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.2 -C.sub.6)alkenyl, COR.sub.5,
- C.sub.1 -C.sub.10 alkanoyl, CO.sub.2 R.sub.5, (C.sub.1 -C.sub.6 alkyl).sub.m amino, NO.sub.2, --SR.sub.5, or OR.sub.5 ;
- R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.5, is C.sub.1 -C.sub.4 alkyl;
- R.sub.8 is selected from the group consisting of an R.sub.6 group, substituted C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl-(C.sub.3 -C.sub.8 )alkyl, C.sub.5 -C.sub.8 cycloalkenyl, substituted C.sub.5 -C.sub.8 cycloalkenyl, C.sub.5 -C.sub.8 cycloalkenyl-(C.sub.1 -C.sub.3)alkyl, and C.sub.7 -C.sub.16 arylalkyl;
- R.sub.9 and R.sub.10 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, substituted C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl-(C.sub.1 -C.sub.3)alkyl, C.sub.5 -C.sub.8 cycloalkenyl-(C.sub.1 -C.sub.3)alkyl, C.sub.7 -C.sub.16 arylalkyl;
- R.sub.12 is hydrogen or C.sub.1 -C.sub.3 alkyl;
- m is 1 or 2;
- provided that,
- a) when A is ##STR127## and R.sub.6 and R.sub.7 are hydrogen, halo or OR.sub.5, then R.sub.8 cannot be hydrogen;
- b) when A is formula IV', R.sub.6 is OR.sub.5, and R.sub.9, R.sub.10 and R.sub.12 are each hydrogen, then only one of R.sub.7 and R.sub.8 can be halo;
- c) when R.sub.9, R.sub.10 and R.sub.12 are each hydrogen, and
- (i) two of R.sub.6, R.sub.7 and R.sub.8 are selected from halo, C.sub.1 -C.sub.6 alkyl, OR.sub.5, and --SR.sub.5, then the third R.sub.6, R.sub.7 or R.sub.8 substituent cannot be hydrogen;
- or
- (ii) one of R.sub.6, R.sub.7 and R.sub.8 is halo, then it must be located at the 7- position of the VI compound;
- and
- d) when R.sub.9 and R.sub.10 are each hydrogen, R.sub.12 is hydrogen or C.sub.1 -C.sub.3 alkyl, and two of R.sub.6, R.sub.7 and R.sub.8 are hydrogen, then the third R.sub.6, R.sub.7 or R.sub.8 cannot be C.sub.1 -C.sub.6 alkyl, halo, halo(C.sub.1 -C.sub.6)alkyl, NO.sub.2, --SR.sub.5, or --OR.sub.5 ;
- or a pharmaceutically acceptable salt or solvate thereof.
17 more elements
Dependencies are inferred from the claim text.