Hapten compounds 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 comprising formula (IV):
wherein:
R 1 is selected from the group consisting of hydrogen and methyl; and
L comprises a linker of 7 to 10 contiguous atoms attached to the benzene ring at the meta position, the atoms being selected from the group consisting of a carbon atom of a hydrocarbyl group, a carbon atom of a substituted hydrocarbyl group, and a heteroatom.
2. A compound comprising formula (IX):
wherein:
R 1 is selected from the group consisting of hydrogen and methyl;
n is an integer greater than or equal to 3;
L comprises a linker of 7 to 10 contiguous atoms attached to the benzene ring at the meta position, the atoms being selected from the group consisting of a carbon atom of a hydrocarbyl group, a carbon atom of a substituted hydrocarbyl group, and a heteroatom;
X is a carrier molecule that elicits an immunogenic response; and
R 4 is selected from the group consisting of a direct bond, hydrocarbyl, and substituted hydrocarbyl.
3. The compound of claim 2 , wherein R 4 is [N-maleimidomethyl]cyclohexane-1-carboxylate.
4. A compound comprising formula (V):
wherein:
R 1 is selected from the group consisting of hydrogen and methyl;
R 2 is a heteroatom; and
L comprises a linker of 6 to 9 contiguous atoms attached to the benzene ring at the meta position, the atoms being selected from the group consisting of a carbon atom of a hydrocarbyl group, a carbon atom of a substituted hydrocarbyl group, and a heteroatom.
5. The compound of claim 4 , wherein R 2 is oxygen.
6. The compound of claim 5 , wherein L is (CH 2 ) m , wherein m is an integer between 6 and 9.
7. A compound comprising formula (X):
wherein:
R 1 is selected from the group consisting of hydrogen and methyl;
R 2 is a heteroatom;
L comprises a linker of 6 to 9 contiguous atoms attached to the benzene ring at the meta position, the atoms being selected from the group consisting of a carbon atom of a hydrocarbyl group, a carbon atom of a substituted hydrocarbyl group, and a heteroatom;
n is an integer greater than or equal to 3;
X is a carrier molecule that elicits an immunogenic response; and
R 4 is selected from the group consisting of a direct bond, hydrocarbyl, and substituted hydrocarbyl.
8. The compound of claim 7 , wherein R 4 is [N-maleimidomethyl]cyclohexane-1-carboxylate.
9. The compound of claim 1 , wherein L is selected from the group consisting of (CH 2 ) m , wherein m is an integer between 7 and 10, and O(CH 2 ) m , wherein m is an integer between 6 and 9.
10. The compound of claim 1 , wherein L is O(CH 2 ) 5 CONH(CH 2 ) 2 .
11. The compound of claim 1 , wherein L is O(CH 2 ) 9 .
12. The compound of claim 2 , wherein L is selected from the group consisting of (CH 2 ) m , wherein m is an integer between 7 and 10, and O(CH 2 ) m , wherein m is an integer between 6 and 9.
13. The compound of claim 2 , wherein L is O(CH 2 ) 5 CONH(CH 2 ) 2 .
14. The compound of claim 2 , wherein L is O(CH 2 ) 9 .
15. The compound of claim 5 , wherein L is (CH 2 ) 5 CONH(CH 2 ) 2 .
16. The compound of claim 5 , wherein L is (CH 2 ) 9 .
17. The compound of claim 7 , wherein R 2 is oxygen.
18. The compound of claim 17 , wherein L is (CH 2 ) m , wherein m is an integer between 6 and 9.
19. The compound of claim 17 , wherein L is (CH 2 ) 5 CONH(CH 2 ) 2 .
20. The compound of claim 17 , wherein L is (CH 2 ) 9 .