Tricyclic steroid analogs
AssigneeWashington University
InventorsDouglas F. Covey, Yuefei Hu, Charles F. Zorumski
Life of this patent
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Abstract
Novel tricyclic steriod analogs are disclosed which are 1H-benz[e]indene dodecahydro compounds that are useful for enhancing GABA-induced chloride currents at the GABA receptor/chloride ionophore complex and can be represented by the following structural formulas: ##STR1## wherein R.sub.1 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl; R.sub.2 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl, in which R.sub.1 and R.sub.2 can be the same or different; R.sub.3 =H or CH.sub.3 ; R.sub.4 =H or CH.sub.3, in which R.sub.3 and R.sub.4 can be the same or different; R.sub.5 =H; R.sub.6 =H; R.sub.5,R.sub.6 =.dbd.O(carbonyl); R.sub.7 =H; R.sub.8 =a hydrogen bond accepting group. R.sub.7,R.sub.8 =.dbd.O(carbonyl); and R'=an ester group.
Claims10
A 1H-benz[e]indene dodecahydro compound of the following structural formula:
- ##STR37## wherein R.sub.1 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl;
- R.sub.2 =H or C.sub.1 -C.sub.4 alkyl or fluoroalkyl, in which R.sub.1 and R.sub.2 can be the same or different;
- R.sub.3 =H or CH.sub.3 ;
- R.sub.4 =H or CH.sub.3, in which R.sub.3 and R.sub.4 can be the same or different;
- R.sub.5 =H;
- R.sub.6 =H;
- R.sub.5,R.sub.6 =.dbd.O(carbonyl);
- R.sub.7 =H;
- R.sub.8 =a hydrogen bond accepting group.
- R.sub.7,R.sub.8 =.dbd.O(carbonyl);
- and
- R'=H or an ester group,
- wherein said ester group (R') is a group derived from reaction between a hydroxyl group with a C.sub.1 -C.sub.18 organic acid, acid halide or anhydride, and said hydrogen bond accepting group (R.sub.8) is (1) a keton, --CO--R", wherein R" is a C.sub.1 -C.sub.4 alkyl or fluoroalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group, (2) an .alpha.-hydroxy ketone, --CO-- CH.sub.2 OH, or ester thereof, --CO--CO.sub.2 OXOR''', wherein X.dbd.C, P.dbd.O(OR'''), or S.dbd.O, and R''' is a C.sub.1 -C.sub.20 alkyl group, (3) an alkyl ester of a carboxylic acid, --COOR'' or --CH.sub.2 COOR''', wherein R'''is a C.sub.1 -C.sub.20 alkyl group, (4) an amine NHR" or N(R").sub.2, wherein R" is a C.sub.1 -C.sub.4 alkyl or fluoroalkyl group or a C.sub.3 -C.sub.6 cycloalklyl group, (5) a nitrile, CN, or a .gamma.-lactone ##STR38##
A compound having the structure ##STR42##
A compound having the structure ##STR43## wherein R is H or CH.sub.3.
A compound having the structure ##STR44##
A compound having the structure ##STR45## wherein R is H or CH.sub.3.
Dependencies are inferred from the claim text.