US 7,576,100 B2
Muscarinic agonists
Niels Skjaerbaek, Vedbaek (Denmark); Kristian Norup Koch, Munich (Germany); Bo Lennart Mikael Friberg, Vellinge (Sweden); and Bo-Ragnar Tolf, Malmö (Sweden)
Assigned to Acadia Pharmaceuticals, Inc., San Diego, Calif. (US)
Filed on May 03, 2006, as Appl. No. 11/417,867.
Application 11/417867 is a continuation of application No. 10/329455, filed on Dec. 23, 2002.
Claims priority of provisional application 60/344722, filed on Dec. 28, 2001.
Prior Publication US 2006/0199810 A1, Sep. 07, 2006
Int. Cl. A61P 25/00 (2006.01); A61K 31/47 (2006.01); C07D 215/00 (2006.01)
U.S. Cl. 514—312  [514/314; 546/157; 546/158; 546/165; 546/176] 20 Claims
 
1. A compound of formula I, as well as salts and isomers thereof

OG Complex Work Unit Drawing
wherein
R1 is a monoradical selected from the group consisting of optionally substituted C1-6-alkyl, optionally substituted C1-6-alkylidene, optionally substituted C2-6-alkenyl, optionally substituted C2-6-alkynyl, optionally substituted O—C1-6-alkyl, optionally substituted O—C2-6-alkenyl, optionally substituted O—C2-6-alkynyl; optionally substituted S—C1-6-alkyl, optionally substituted S—C2-6-alkenyl, optionally substituted S—C2-6-alkynyl;
m is 0, 1 or 2;
C3-C4 is CH2—CH or CH═C, or C4 is CH and C3 is absent;
R2 and R3 are independently selected from the group consisting of hydrogen, optionally substituted C1-6 alkyl, optionally substituted O—C1-6 alkyl, halogen, hydroxy or selected such that R2 and R3 together form a ring system, wherein the ring system is formed by selecting R2, R3, m, and C3-C4 such that

OG Complex Work Unit Drawing
is selected from the group consisting of

OG Complex Work Unit Drawing
wherein R8 is present 0, 1, or 2 times and is independently selected from the group consisting of optionally substituted C1-6 alkyl, optionally substituted O—C1-6 alkyl, halogen, and hydroxy;
each R4 and R5 is independently selected from the group consisting of hydrogen, halogen, hydroxy, optionally substituted C1-6-alkyl, optionally substituted O—C1-6 alkyl, optionally substituted aryl-C1-6 alkyl, and optionally substituted arylheteroalkyl;
L1 and L2 are separately biradicals having the formula —C(R6)═C(R7);
Y is selected from the group consisting of O, S, and H2;
X is a biradical selected from the group consisting of —C(R6)(R7)—C(R6)(R7)— and —C(R6)═C(R7)—, wherein R6 and R7 are independently selected from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, NRNRN, N(RN)—C(O)—N(RN), optionally substituted C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, optionally substituted O—C1-6-alkyl, optionally substituted O-aryl, optionally substituted O—C2-6-alkenyl, optionally substituted O—C2-6-alkynyl
wherein RN is selected from the group consisting of hydrogen, and optionally substituted C1-6-alkyl.