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 hydrogen or —C(O)R 3 ;
each R 3 is independently a saturated or unsaturated, straight or branched, optionally substituted C 1-37 hydrocarbon chain;
each R 4 is independently hydrogen or a C 1-6 aliphatic group;
-M- is
and
A is a therapeutic agent.
2. The compound according to claim 1 , wherein R 1 and R 2 are —C(O)R 3 .
3. The compound according to claim 2 , wherein each R 3 is independently a saturated or unsaturated, unbranched C 2-37 hydrocarbon chain.
4. The compound according to claim 1 , wherein at least one instance of R 4 is not hydrogen.
5. The compound according to claim 4 , wherein one instance of R 4 is C 1-4 alkyl and one instance of R 4 is hydrogen.
6. The compound according to claim 5 , wherein one instance of R 4 is methyl and one instance of R 4 is hydrogen.
7. A pharmaceutical composition comprising a compound according to claim 1 , and a pharmaceutically acceptable carrier, adjuvant, or vehicle.
8. The compound according to claim 1 , wherein the therapeutic agent is selected from testosterone, mycophenolic acid (MPA), buprenorphine, tetrahydrocannabinol (THC), cannabidiol, celecoxib, or dexamethasone.
9. The compound according to claim 8 , wherein the therapeutic agent is testosterone, tetrahydrocannabinol (THC), or cannabidiol.
10. The compound according to claim 1 , wherein at least one of R 1 and R 2 are —C(O)R 3 .