Substituted pyran derivatives
Certain 3,6-disubstituted and 2,4,5-trisubstituted pyran derivatives that exhibit potent activity on monoamine transport systems are provided. The 3,6 and 2,4,5 pyrans are useful in probing the effects of their binding to monoamine transporter systems and the corresponding relationships to various afflictions affecting the CNS, or as a treatment for various CNS-related disorders in which the monoamine transport and related systems are implicated.
1. A compound having formula I:
or a pharmaceutically acceptable salt thereof;
wherein;
p is 0 to 5;
R is
W is OH;
R 1 is C 1-4 alkyl, C 2-6 alkenyl, C 2-6 optionally halogenated alkynyl, C 2-6 hydroxyalkynyl, halo, —CN, —COOR 2 , C 5-10 cycloalkyl, C 2-18 alkenyl, —OH, —NO 2 , —NHR 2 , or —OR 2 ; and
R 2 is C 1-8 alkyl, C 5-6 cycloalkyl, or C 2-8 alkenyl;
the dashed line is an optional bond;
X and Z are each independently S, N, O, or NR 4 ;
Y is C═O, C═S, N, or NR 4 ; and
R 4 is H or C 1-8 alkyl.
2. A compound having a formula selected from the group consisting of:
pharmaceutically acceptable salts thereof.
3. The compound of claim 1 having a formula selected from the group consisting of:
and pharmaceutically acceptable salts thereof.
4. A compound selected from the group consisting of:
and pharmaceutically acceptable salts thereof.