Novel synergistic opioid-cannabinoid codrug for pain management
AssigneeUniversity of Kentucky
InventorsJoseph R. Holtman, Peter A. Crooks, Harpreet K. Dhooper
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Abstract
Compounds including an opioid, and a cannabinoid covalently bound by a linker; pharmaceutical formulations including codrugs; methods of manufacture as well as methods of treatment are disclosed.
Claims34
A compound of the following formula:
- wherein n is an integer from 1 to 5;
- and the linker is selected from the group consisting of the following formulas:
- wherein Y is O or S;
- wherein Y is O or S;
- wherein Y is O or S;
- wherein X is a bond or a C1-20 alkylene;
- wherein X is a bond or a C1-20 alkylene;
- wherein X is a bond or a C1-20 alkylene;
- and
- wherein X is a bond or a C1-20 alkylene and wherein R1 is a cannabinoid and R2, or R2, R3 are an opioid molecule.
A pharmaceutical composition comprising:
- an analgesically effective amount of a compound selected from the group consisting of:
- Compound 1:
- wherein R is H or CH3;
- and X is a bond, or alkylene;
- Compound 2:
- wherein X is a bond or alkylene;
- Compound 3:
- wherein Y is O or S;
- and R is CH3;
- and
- Compound 4:
- Y is O or S;
- and at least one pharmaceutically acceptable excipient.
The pharmaceutical composition wherein the release of the codrug is substantially controlled for about 12-24 hours.
A method of synthesis of a codrug comprising a linker, an opioid and a cannabinoid, said method comprising:
- a) covalently bonding a first attachment point of the linker to the opioid;
- b) covalently bonding a second attachment point of the linker to a cannabinoid;
- and
- c) recovering the codrug.
The method of claim 26 wherein the codrug substantially remains intact until it reaches the site of action of at least the opioid or the cannabinoid.
A method of treatment comprising:
- joining an opioid together with a cannabinoid using a linker to form a cleavable codrug;
- and
- administering an analgesically effective amount of the codrug to a human patient.
Dependencies are inferred from the claim text.