Dextrorphan prodrugs and processes for making and using them
The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and/or vitamin compounds chemically conjugated to dextrorphan, (+)-17-methylmorphinan-3-ol), to form novel prodrugs and compositions of dextrorphan.
1. A compound having the following general formula:
where L 2 is absent, or is
Y 2 is absent, or [A-X—Z] n
where A and Z are independently absent or selected from —O—, —S— or —(CR 1 R 2 ) k —
and where X is —(CR 1 R 2 ) k —,
J is [M-W] p
where M is —(CR 3 R 4 ) q —; and W is absent, or —O— or —S—
R 1 , R 2 , R 3 , R 4 are each independently selected from H, alkyl, aryl, alkylaryl, alkoxy, haloalkyl, or haloaryl
n and k are independently selected from 1-4
p and q are independently selected from 1-4
G m 2 is selected independently for each repeating subunit from, oxoacid, polyethylene glycol having from 2 to 5 ethylene oxide units, or a vitamin compound, and m is 1-4;
or a pharmaceutically acceptable salt thereof.
2. The compound of claim 1 , wherein where L 2 and Y 2 are absent, M is —(CR 3 R 4 ) q , G 2 is at least one oxoacid, and m is 1-3.
3. The compound of claim 1 , wherein the at least one oxoacid is acetic acid.
4. The compound of claim 1 wherein the compound is N-(acetyl-OCH 2 )-dextrorphanium having the following structural formula:
or a pharmaceutically acceptable salt thereof.