US 12,187,678 B2
Methods of treating psychological disorders through the administration of serotonin 5-HT2C receptor modulators
David Gilles, Seattle, WA (US)
Assigned to Kuleon, LLC, Seattle, WA (US)
Filed by Kuleon, LLC, Seattle, WA (US)
Filed on Jul. 28, 2023, as Appl. No. 18/360,976.
Application 18/360,976 is a continuation of application No. 18/306,652, filed on Apr. 25, 2023, granted, now 11,780,807.
Application 18/306,652 is a continuation of application No. PCT/US2022/040048, filed on Aug. 11, 2022.
Claims priority of provisional application 63/325,515, filed on Mar. 30, 2022.
Claims priority of provisional application 63/319,200, filed on Mar. 11, 2022.
Claims priority of provisional application 63/314,379, filed on Feb. 26, 2022.
Claims priority of provisional application 63/314,377, filed on Feb. 26, 2022.
Claims priority of provisional application 63/314,378, filed on Feb. 26, 2022.
Claims priority of provisional application 63/301,196, filed on Jan. 20, 2022.
Claims priority of provisional application 63/292,567, filed on Dec. 22, 2021.
Claims priority of provisional application 63/285,656, filed on Dec. 3, 2021.
Claims priority of provisional application 63/285,688, filed on Dec. 3, 2021.
Claims priority of provisional application 63/285,679, filed on Dec. 3, 2021.
Claims priority of provisional application 63/239,965, filed on Sep. 2, 2021.
Claims priority of provisional application 63/239,964, filed on Sep. 2, 2021.
Claims priority of provisional application 63/239,963, filed on Sep. 2, 2021.
Claims priority of provisional application 63/238,132, filed on Aug. 28, 2021.
Claims priority of provisional application 63/238,134, filed on Aug. 28, 2021.
Claims priority of provisional application 63/238,133, filed on Aug. 28, 2021.
Claims priority of provisional application 63/238,135, filed on Aug. 28, 2021.
Claims priority of provisional application 63/232,548, filed on Aug. 12, 2021.
Claims priority of provisional application 63/232,614, filed on Aug. 12, 2021.
Claims priority of provisional application 63/232,539, filed on Aug. 12, 2021.
Prior Publication US 2024/0124397 A1, Apr. 18, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 209/04 (2006.01)
CPC C07D 209/04 (2013.01) 34 Claims
 
1. A method of treating a psychological disorder, comprising administering to a subject in need thereof at least one compound of Formula I:

OG Complex Work Unit Chemistry
wherein
X and Y are each independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, and optionally substituted C2-C8 alkenyl, or Y is taken together with X and the nitrogen atom therebetween to form a 3- to 7-membered heterocyclic ring optionally including 1 to 2 additional ring heteromoieties selected from O, S, S (O), SO2, and NR9;
W1 is selected from O, Se, Se (O), SeO2, S, S (O), and SO2;
W2 is selected from —CD2—,—CHD—,—(CD2)2—,—CH2—and —(CH2)2—;
Z4 is selected from N and CR4;
Z5 is selected from N and CR5;
Z6 is selected from N and CR6;
Z7 is selected from N and CR7,
R2, R3, R3′, R6 and R7 are each independently selected from hydrogen, deuterium, —N(R9)2, —SR9, halo, optionally substituted C1-C8 alkyl, —C1-C8 alkoxy, and optionally substituted C2-C8 alkenyl, or Y is absent and R3 taken together with carbon to which it is attached and the nitrogen atom to which X is attached form a 3- to 7-membered heterocyclic ring optionally including 1 to 2 additional ring heteromoieties selected from O, S, S (O), SO2, and NR9;
R4 and R5 are each independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, halo, hydroxyl, —N(R9)2,—SR9,—C1-C8 alkoxy, —OC(O)R8,—OC(O)OR8,—OP(O)O2(R9)2, and —OSO2R8;
R8 is selected from optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl;
R9 is independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl; and
salts, solvates, hydrates, and prodrugs thereof.