Lymphatic system-directing lipid prodrugs
The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a provided lipid prodrug or a pharmaceutical composition thereof.
1. A compound of Formula X-b:
wherein R 1 and R 2 are each independently a fatty acid having a C 4 -C 18 chain;
one instance of R 4 is hydrogen and one instance of R 4 is methyl;
-M- is
and
A is cannabidiol.
2. A pharmaceutical composition comprising the compound according to claim 1 , and a pharmaceutically acceptable carrier, adjuvant, or vehicle.
3. The pharmaceutical composition according to claim 2 , wherein the pharmaceutical composition is formulated for oral administration.
4. An oral dosage form comprising the compound according to claim 1 .
5. The oral dosage form of claim 4 , further comprising a lipid-based vehicle.
6. The oral dosage form of claim 4 , wherein the oral dosage form comprises a self-emulsifying drug delivery system (SEDDS).
7. The oral dosage form of claim 4 , wherein the oral dosage form is a capsule.
8. The compound according to claim 1 , wherein R 1 and R 2 are each independently a fatty acid having a C 6 -C 16 chain.
9. The compound according to claim 8 , wherein each fatty acid is a saturated fatty acid.
10. The compound according to claim 9 , wherein each saturated fatty acid is a straight-chain fatty acid.
11. The compound according to claim 1 , wherein the compound is: