US 12,486,228 B2
N-substituted indoles and use as allosteric modulators of cannabinoid receptors
Ganeshsingh A. Thakur, Cambridge, MA (US); and Sumanta Garai, Jamaica Plain, MA (US)
Assigned to Northeastern University, Boston, MA (US)
Appl. No. 17/054,056
Filed by Northeastern University, Boston, MA (US)
PCT Filed Jun. 26, 2019, PCT No. PCT/US2019/039354
§ 371(c)(1), (2) Date Nov. 9, 2020,
PCT Pub. No. WO2020/006152, PCT Pub. Date Jan. 2, 2020.
Claims priority of provisional application 62/690,317, filed on Jun. 26, 2018.
Prior Publication US 2021/0355084 A1, Nov. 18, 2021
Int. Cl. C07D 209/12 (2006.01); A61P 27/06 (2006.01); C07D 209/18 (2006.01); C07D 401/04 (2006.01); C07D 403/06 (2006.01); C07D 409/04 (2006.01); C07D 417/04 (2006.01)
CPC C07D 209/12 (2013.01) [A61P 27/06 (2018.01); C07D 209/18 (2013.01); C07D 401/04 (2013.01); C07D 403/06 (2013.01); C07D 409/04 (2013.01); C07D 417/04 (2013.01)] 19 Claims
 
1. A compound having a structure according to Formula I

OG Complex Work Unit Chemistry
wherein
X and Y are CH;
Z is (CH2)k, and k is 0 to 4;
A is an unsaturated carbocyclic ring and n is 2;
B is phenyl or a 5 to 6 membered heteroaryl ring;
R1 is H, OH, ═CH2, or C1 to C5 alkyl, linear or branched, optionally substituted with CO2H, CONH2, or —C═C—;
R2 is H, halogen, or alkyl;
R4 is H, halogen, alkoxy, OH, alkyl, haloalkyl, optionally substituted, alkyne, NO2, CN, CO2R, NR2, a deuterated alkyl group, a five- or six-membered heterocyclic ring, a (hetero)aromatic ring, or SO2NHR, wherein R is independently H or alkyl, optionally substituted;
R3 is H;
R5 is H;
R6 is CO2H; (CHR7)pCO2R7; CN; CONH2; alkoxy; CONR7R8; aryl; heterocyclic ring; CH═CHCO2R7; or (CHR7)yCOR7; wherein R7 and R8, including each of R7, is independently H or alkyl, optionally substituted, p is 2 to 4 and y is 0 to 4;
* represents a chiral center; and
m is 0 to 5, with the proviso that, when m=0, R1 and R6 are bonded to the atom marked with *.