Neuroactive substituted cyclopent[a]anthracenes as modulators for GABA type-A receptors
The present disclosure is generally directed to neuroactive substituted cyclopent[a]anthracenes as referenced herein, and pharmaceutically acceptable salts thereof, for use as, for example, an anesthetic, and/or in the treatment of disorders relating to GABA function and activity. The present disclosure is further directed to pharmaceutical compositions comprising such compounds.
1. A compound of Formula (II-a):
wherein R 2 is H, ═O, ═CHCN, ═CHCO 2 R w , where R w is optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 4 alkenyl, or optionally substituted C 2 -C 4 alkynyl, α-CN, α-OH, α-OR v , where R v is optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 4 alkenyl, or optionally substituted C 2 -C 4 alkynyl, α-NO 2 , spiroepoxy, or C(O)R u , where R u is optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 4 alkenyl, or optionally substituted C 2 -C 4 alkynyl;
R 3 is H, ═O, ═CHCN, ═CHCO 2 R t , where R t is optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 4 alkenyl, or optionally substituted C 2 -C 4 alkynyl, —CN, α-OH, α-OR s , where R s is optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 4 alkenyl, or optionally substituted C 2 -C 4 alkynyl, α-NO 2 , spiroepoxy, or C(O)R r , where R r is optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 4 alkenyl, or optionally substituted C 2 -C 4 alkynyl; and,
- - - denotes an optional C—C bond, resulting in a C═C bond between C 2 -C 3 .
2. The compound of claim 1 having the structure:
or a pharmaceutically acceptable salt thereof.
3. The compound of claim 1 having the structure:
or a pharmaceutically acceptable salt thereof.
4. The compound of claim 1 having the structure:
or a pharmaceutically acceptable salt thereof.
5. The compound of claim 1 having the structure:
or a pharmaceutically acceptable salt thereof.
6. A method of inducing anesthesia in a subject in need thereof, said method comprising administering to the subject a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.