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US 12,441,683 B2Granted
7-methyl indole analogs and dosage forms containing the same
AssigneeKuleon LLC
InventorDavid Gilles
Life of this patent
Estimating the term…
Abstract
Hallucinogenic and non-hallucinogenic serotonin receptor agonists are disclosed herein in addition to methods of making and using the same.
Claims20
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:
- 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.
16 more elements
A composition comprising a homogenous mixture of:
- a pharmaceutically acceptable carrier;
- and
- at least one compound selected from
- or a salt, solvate, hydrate, or prodrug thereof.
1 more element
A crystalline compound selected from
- and salts thereof.
Dependencies are inferred from the claim text.