US 7,517,871 B2
Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders
Fredrik Ek, Lund (Sweden); Roger Olsson, Bunkeflo Strand (Sweden); and Jörgen Ohlsson, Lund (Sweden)
Assigned to Acadia Pharmaceuticals, Inc., San Diego, Calif. (US)
Filed on May 03, 2006, as Appl. No. 11/417,859.
Application 11/417859 is a continuation of application No. 11/019555, filed on Dec. 21, 2004.
Claims priority of provisional application 60/531927, filed on Dec. 22, 2003.
Claims priority of provisional application 60/548090, filed on Feb. 24, 2004.
Claims priority of provisional application 60/548604, filed on Feb. 27, 2004.
Prior Publication US 2006/0199798 A1, Sep. 07, 2006
Int. Cl. A61P 25/00 (2006.01); A61K 31/553 (2006.01); C07D 267/20 (2006.01)
U.S. Cl. 514—211.13  [540/551] 21 Claims
 
1. A compound having the structure set forth in Formula I:

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof, wherein:
A has the structure

OG Complex Work Unit Drawing
wherein each bond represented by a dashed and solid line in A represents a carbon-carbon single bond;
a, b, c, and d are each carbon;
e, f g, and h are each carbon;
X is nitrogen;
X′ is C;
L is absent;
each n is 1;
Y is nitrogen;
W is nitrogen;
R1 is hydrogen;
R2, R3, and R4 are each hydrogen;
R5 is selected from the group consisting of halogen, optionally substituted C1-6 alkyl, optionally substituted C1-6 alkyloxy, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6-alkoxyalkyl, optionally substituted C1-6 alkylthio, perhaloalkyl, CN, COR10, CONHR10, NHCONHR10, SO2NHR10, SO2R10, OSO2R10, NO2, NHCOR10;
R6, R7, and R9 are each hydrogen;
R8 is selected from the group consisting of halogen, optionally substituted C1-6 alkyl, optionally substituted C1-6 alkyloxy, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted C1-6-alkoxyalkyl, optionally substituted C1-6 alkylthio, perhaloalkyl, CN, COR10, CONHR10, NHCONHR10, SO2NHR10, SO2R10, OSO2R10, NO2, NHCOR10;
Z is oxygen;
R10 is selected from the group consisting of hydrogen, optionally substituted C1-6 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted C2-6 alkenyl, optionally substituted C2-6 alkynyl, optionally substituted aryl, optionally substituted arylalkyl, and perhaloalkyl; and
each bond represented by a dashed and solid line in Formula I represents a carbon-carbon double bond.