Back to results
US 11,999,694 B2Granted
Delivery of therapeutic alkaloid compounds
AssigneeSensorium Therapeutics, Inc.
InventorsJacob M. Hooker, Michael S. Placzek
Life of this patent
Estimating the term…
Abstract
Disclosed are prodrug compounds that can be converted to mesembrine under biologically relevant conditions, such as hydrolysis in vivo; and related methods of preparing and using these compounds. Stable preparations of isolated mesembrine stereoisomers are also provided.
Claims21
A compound of formula (I):
- or a pharmaceutically acceptable salt thereof, wherein
- R1is or C1-C7alkyl or H;
- and
- ring A
- wherein * denotes the attachment points of ring A to the compound of formula (I), and wherein
- R3 is —OSi(C1-C6 alkyl)3, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)C3-C10 cycloalkyl, —OC(O)phenyl, —OC(O)-5- to 7-membered heteroaryl, wherein each hydrogen atom in C1-C6 alkyl, C2-C6 alkenyl, C3-C10 cycloalkyl, phenyl, and 5- to 7-membered heteroaryl is optionally substituted by halogen, C1-C6 alkyl, C1-C3 alkoxy, nitro, —N(C1-C3 alkyl)2, C1-C3 haloalkyl, cyano, phenyl, phenoxy or —O(CH2)pOCH3;
- and
- p is 2, 3, or 4.
5 more elements
A compound of formula (IIIb-1)
- or a pharmaceutically acceptable salt thereof, wherein:
- R1 is methyl;
- and
- R3 is —OC(O)C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted;
- or
- R3 is —OC(O)phenyl, wherein the phenyl is optionally monosubstituted with an unsubstituted C1-C6 alkyl.
3 more elements
A compound of the formula:
- or a pharmaceutically acceptable salt thereof, wherein R3 is —OC(O)alkyl optionally substituted by alkoxy, —OH, halogen, or −O(CH2)pCH3;
- and p is 2, 3, or 4.
Dependencies are inferred from the claim text.