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US 2022/0183998 A1Published application
Use of 8,9- dihydrocannabidiol compounds
AssigneeThe Regents of the University of California
InventorsMark MASCAL, Nikolay SHEVCHENKO
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Abstract
The present invention provides a method of treating or mitigating seizures comprising compounds as described herein.
Claims24
A method of treating or mitigating a seizure, comprising administering to a subject in need thereof, a therapeutically effective amount of a compound of Formula I:
- or a pharmaceutically acceptable salt thereof, without inducing hypnotic effects in the subject, thereby treating the seizure,
- wherein:
- n is 1 or 2;
- R1a and R1d are each independently —CO2R1c, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl, wherein at least one of R1a or R1d is methyl or isopropyl;
- R1b and R1c are each independently hydrogen or oxygen;
- alternatively, when R1b is oxygen, R1b is combined with R1a and the atoms to which they are attached to form an epoxide ring;
- alternatively, R1b is combined with R1d and the atoms to which they are attached to form a C4-8 cycloalkyl, wherein the cycloalkyl is substituted with 1-3 R1c groups;
- R1c is H, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- R2a is —OR2f, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- R2b and R2c are each independently hydrogen, halogen, —OR2f, or —NR2fR2g;
- R2d and R2c are each independently —OH, —OC(O)R2f, —OR2f, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- alternatively, R2d and R1a are combined with the atoms to which they are attached to form a C6-12 heterocycloalkyl;
- alternatively, R2d and R1b are combined with the atoms to which they are attached to form a C5-12 heterocycloalkyl;
- R2f and R2g are each independently hydrogen, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- dashed lines a, b, and c are each independently absent or a bond, wherein when n is 2, dashed line a is absent, wherein when R1b is oxygen and not combined with R1a to form an epoxide ring, dashed line b is the bond, and wherein when R1c is oxygen, dashed line c is the bond;
- and
- dashed circle d is absent or is 1, 2, or 3 bonds.
14 more elements
A compound of Formula IA-1:
- wherein
- n is 1 or 2;
- R1a is —CO2R1c, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- R1b is hydrogen or oxygen;
- alternatively, when R1b is oxygen, R1b is combined with R1a and the atoms to which they are attached to form an epoxide ring;
- R1d is C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- R2a is —OR2d, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- R2d and R2c are each independently —OH, —OC(O)R2f, —OR2f, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- R2f is hydrogen, C1-20 alkyl, C2-20 alkenyl or C2-20 alkynyl;
- and
- dashed circle d is absent or is 1, 2, or 3 bonds
- wherein when R1a is methyl, R1d is isopropyl, R2d and R2c are both —OH, and R2a is C1-20 alkyl, then the compound is not
- and
- wherein when R1a is methyl, R1d is propyl, R2b is pentyl, and R2a and R2c are both —OH, then the compound is not
11 more elements
Dependencies are inferred from the claim text.