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US 2026/0242371 A1Published application
Lipid prodrugs of bromolysergide and uses thereof
AssigneeSeaport Therapeutics, Inc.
InventorsJamie Simpson, Tim Quach, Daniel Kenneth Bonner, Michael C. Chen, Michaela Anne Gold
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Abstract
Disclosed herein are lipid prodrugs of bromolysergide (2-bromo-LSD) (2-bromo-lysergic acid diethylamide) that achieve improved pharmacokinetic properties and allow easier chronic dosing of patients. The disclosed lipid prodrugs are suitable for the treatment of cluster headache and mood disorders in human subjects.
Claims34
A compound of Formula I:
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 and R2 are each independently hydrogen or —C(O)R3;
- each R3 is independently a saturated or unsaturated, straight or branched, optionally substituted C2-37 hydrocarbon chain;
- X is —O—;
- R4 and R5 are each independently hydrogen or C1-4 aliphatic optionally substituted with 1, 2, 3, 4, 5, or 6 deuterium or halogen atoms, or R4 and R5 taken together with the carbon to which they are attached form a C3-C8 cycloalkyl;
- M is absent or a self-immolative group;
- n is 0-18;
- and
- m and q are each independently 0-6.
6 more elements
A compound of Formula II:
- wherein R1 and R2 are each independently —C(O)R3;
- and
- each R3 is independently a saturated or unsaturated, straight or branched, optionally substituted C3-17 hydrocarbon chain.
A compound of Formula III:
- wherein R1 and R2 are each independently —C(O)R3;
- and
- each R3 is independently a saturated or unsaturated, straight or branched, optionally substituted C3-17 hydrocarbon chain.
The compound of any one of claims 15-18, wherein the compound is:
A compound of Formula IV:
- wherein R1 and R2 are each independently —C(O)R3;
- and
- each R3 is independently a saturated or unsaturated, straight or branched, optionally substituted C3-17 hydrocarbon chain.
A compound of Formula V:
- wherein R1 and R2 are each independently —C(O)R3;
- and
- each R3 is independently a saturated or unsaturated, straight or branched, optionally substituted C3-17 hydrocarbon chain.
Dependencies are inferred from the claim text.