US 12,091,408 B2
Store overload-induced calcium release inhibitors and methods for producing and using the same
Tom Back, Calgary (CA); Wayne Chen, Calgary (CA); Chris Smith, Calgary (CA); and Dawei Jiang, Watertown, MA (US)
Assigned to UTI Limited Partnership, Calgary (CA)
Appl. No. 14/915,368
Filed by Tom Back, Calgary (CA); Wayne Chen, Calgary (CA); Chris Smith, Calgary (CA); Dawei Jiang, Watertown, MA (US); and UTI Limited Partnership, Calgary (CA)
PCT Filed Sep. 27, 2014, PCT No. PCT/US2014/057918
§ 371(c)(1), (2) Date Feb. 29, 2016,
PCT Pub. No. WO2015/031914, PCT Pub. Date Mar. 5, 2015.
Claims priority of provisional application 61/872,533, filed on Aug. 30, 2013.
Prior Publication US 2016/0214973 A1, Jul. 28, 2016
Int. Cl. C07D 419/12 (2006.01); C07C 217/28 (2006.01); C07C 217/32 (2006.01); C07C 217/34 (2006.01); C07C 217/38 (2006.01); C07C 217/54 (2006.01); C07C 217/92 (2006.01); C07C 233/20 (2006.01); C07D 209/08 (2006.01); C07D 209/88 (2006.01); C07D 215/227 (2006.01); C07D 231/56 (2006.01); C07D 235/06 (2006.01); C07D 235/08 (2006.01); C07D 265/36 (2006.01); C07D 279/16 (2006.01); C07D 279/20 (2006.01); C07D 279/34 (2006.01); C07D 281/10 (2006.01); C07D 401/12 (2006.01); C07D 405/12 (2006.01); C07D 413/12 (2006.01); C07D 417/06 (2006.01)
CPC C07D 419/12 (2013.01) [C07C 217/28 (2013.01); C07C 217/32 (2013.01); C07C 217/34 (2013.01); C07C 217/38 (2013.01); C07C 217/54 (2013.01); C07C 217/92 (2013.01); C07C 233/20 (2013.01); C07D 209/08 (2013.01); C07D 209/88 (2013.01); C07D 215/227 (2013.01); C07D 231/56 (2013.01); C07D 235/06 (2013.01); C07D 235/08 (2013.01); C07D 265/36 (2013.01); C07D 279/16 (2013.01); C07D 279/20 (2013.01); C07D 279/34 (2013.01); C07D 281/10 (2013.01); C07D 401/12 (2013.01); C07D 405/12 (2013.01); C07D 413/12 (2013.01); C07D 417/06 (2013.01); C07C 2603/18 (2017.05); C07C 2603/74 (2017.05)] 9 Claims
 
1. A compound of the formula:
R1—X1-L-X2—R2
wherein
R1 is selected from the group consisting of: carbazol-2-yl; carbazol-3-yl; and carbazol-4-yl, each of which is optionally substituted;
X1 is O;
X2 is O;
R2 is selected from the group consisting of substituted phenyl; substituted benzyl;
optionally substituted benzo[d]oxazolyl, and optionally substituted benzofuranyl; and
L is a linker selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein m is 1 or 2; and n is 1 to 4;
provided
when R1 is optionally substituted carbazol-4-yl, then R2 is optionally substituted benzyl;
when R1 is unsubstituted carbazol-3-yl, then linker L has at least 7 backbone atoms in the chain; and
when R1 is unsubstituted carbazol-2-yl, then linker L has at least 7 backbone atoms in the chain, and
R2 is benzo[d]oxazolyl, benzofuranyl, or phenyl substituted with at least one substituent selected from halide and haloalkyl.