Methamphetamine-like hapten compounds, linkers, carriers and compositions and uses thereof
View Patent ↗The invention generally relates to hapten compounds comprising either (+) methamphetamine or (+) amphetamine conjugated to a linker. Generally speaking, hapten compounds of the invention may be used to elicit an immune response to one or more of (+) methamphetamine, (+) amphetamine, or (+) MDMA.
1. A compound of the formula:
wherein:
R 1 is selected from the group consisting of hydrogen and methyl;
n is an integer greater than or equal to 2;
X is a carrier molecule that elicits an immunogenic response;
R 3 is selected from the group consisting of a direct bond, hydrocarbyl, and substituted hydrocarbyl; and
L is selected from the group consisting of O(CH 2 ) 5 and O(CH 2 ) 9 , wherein indicates point of attachement to the benzene ring.
2. The compound of claim 1 , wherein the X is a protein selected from the group consisting of KLH, ovalbumin, BSA, cationized BSA, thyroglobulin, a bacterial toxin and a bacterial toxoid.
3. The compound of claim 2 , wherein R 3 is selected from the group consisting of (CH 2 ) 4 and (CH 2 ) 4 NHCO(CH 2 ) 5 .
4. The compound of claim 1 , wherein L is O(CH 2 ) 9 .
5. The compound of claim 1 , wherein L is O(CH 2 ) 5 .
6. A composition comprising a compound of claim 1 .
7. The composition of claim 6 , further comprising an adjuvant.
8. The composition of claim 7 , wherein the adjuvant is pharmaceutically acceptable for use in a human subject.
9. The composition of claim 7 , wherein the adjuvant is selected from the group consisting of alum, TiterMax Gold, Ribi, ASO4, Freund's complete adjuvant, and Freund's incomplete adjuvant.
10. The composition of claim 7 , further comprising a pharmaceutically acceptable excipient.
11. A method for eliciting an immune response in a subject, the method comprising administering the composition of claim 7 to the subject.
12. The method of claim 11 , wherein the subject is selected from the group consisting of a rodent, a non-human primate, and a human.