US 12,441,683 B2
7-methyl indole analogs and dosage forms containing the same
David Gilles, Tacoma, WA (US)
Assigned to Kuleon, LLC, Seattle, WA (US)
Filed by Kuleon LLC, Seattle, WA (US)
Filed on May 22, 2025, as Appl. No. 19/215,938.
Application 19/215,938 is a continuation of application No. 18/968,441, filed on Dec. 4, 2024, granted, now 12,344,582.
Application 18/968,441 is a continuation of application No. 18/360,976, filed on Jul. 28, 2023, granted, now 12,187,678, issued on Jan. 5, 2025.
Application 18/360,976 is a continuation of application No. 18/306,652, filed on Apr. 25, 2023, granted, now 11,780,807, issued on Oct. 10, 2023.
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 63/314,378, filed on Feb. 26, 2022.
Claims priority of provisional application 63/314,377, 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 63/285,688, filed on Dec. 3, 2021.
Claims priority of provisional application 63/285,656, filed on Dec. 3, 2021.
Claims priority of provisional application 63/285,679, filed on Dec. 3, 2021.
Claims priority of provisional application 63/239,964, filed on Sep. 2, 2021.
Claims priority of provisional application 63/239,965, filed on Sep. 2, 2021.
Claims priority of provisional application 63/239,963, filed on Sep. 2, 2021.
Claims priority of provisional application 63/238,135, filed on Aug. 28, 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 63/232,548, 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 2025/0282722 A1, Sep. 11, 2025
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 209/04 (2006.01)
CPC C07D 209/04 (2013.01) 20 Claims
 
1. A composition comprising:
a pharmaceutically acceptable carrier; and
0.01 mg to 1,000 mg of at least one compound selected from compounds 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 NR9, O, Se, Se(O), SeO2, S, S(O), and SO2;
W2 is selected from —CD2-, —CHD-, —(CD2)2-, —CH2— and —(CH2)2—;
Z4 is CR4;
Z5 is selected from N and CR5;
Z6 is selected from N and CR6;
Z7 is CR7;
R2, R3, R3′, and R6 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 is selected from hydroxyl, C1-C8 alkoxy, —OC(O)R8, —OC(O)OR8, —OP(O)O2 (R9)2, and —OSO2R8;
R5 is 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;
R7 is C1-C8 alkyl;
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.