Hapten compounds and compositions and uses thereof

• US 8,853,146 B2
• Filed: 04/18/2008
• Issued: 10/07/2014
• Est. Priority Date: 04/20/2007
• Status: Active Grant

• Current Assignee: Bioventures, LLC
• Original Assignee: The Board of Trustees of the University of Arkansas (University of Arkansas System)
• Inventors: Owens, S. Michael, Gunnell, Melinda, Carroll, F. Ivy
• Primary Examiner(s): Zucker, Paul A
• Application Number:
  US12/596,765
• Publication Number:
  US 20100143391A1
• Time in Patent Office: 2,363 Days
• US Class Current: 514/1.1
• CPC Class Codes: A61K 39/385 Haptens or antigens, bound to carriers
• CPC Class Codes: C07C 217/60 linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• CPC Class Codes: C07C 229/34 the carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 323/12 the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 323/29 the carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07K 16/44 against material not provided for elsewhere , e.g. haptens, metals, DNA, RNA, amino acids
• CPC Class Codes: C07K 2317/56 variable (Fv) region, i.e. VH and/or VL
• CPC Class Codes: C07K 2319/40 containing a tag for immunodetection, or an epitope for immunisation

Abstract

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.

Claims

1. A compound comprising formula (IV):

9. The compound of claim 1, wherein L is selected from the group consisting of (CH₂)_m, wherein m is an integer between 7 and 10, and O(CH₂)_m, wherein m is an integer between 6 and 9.

10. The compound of claim 1, wherein L is O(CH₂)₅CONH(CH₂)₂.

11. The compound of claim 1, wherein L is O(CH₂)₉.

2. A compound comprising formula (IX):

3. The compound of claim 2, wherein R₄ is [N-maleimidomethyl]cyclohexane-1-carboxylate.

12. The compound of claim 2, wherein L is selected from the group consisting of (CH₂)_m, wherein m is an integer between 7 and 10, and O(CH₂)_m, wherein m is an integer between 6 and 9.

13. The compound of claim 2, wherein L is O(CH₂)₅CONH(CH₂)₂.

14. The compound of claim 2, wherein L is O(CH₂)₉.

4. A compound comprising formula (V):

5. The compound of claim 4, wherein R₂ is oxygen.

6. The compound of claim 5, wherein L is (CH₂)_m, wherein m is an integer between 6 and 9.

15. The compound of claim 5, wherein L is (CH₂)₅CONH(CH₂)₂.

16. The compound of claim 5, wherein L is (CH₂)₉.

7. A compound comprising formula (X):

8. The compound of claim 7, wherein R₄ is [N-maleimidomethyl]cyclohexane-1-carboxylate.

17. The compound of claim 7, wherein R₂ is oxygen.

18. The compound of claim 17, wherein L is (CH₂)_m, wherein m is an integer between 6 and 9.

19. The compound of claim 17, wherein L is (CH₂)₅CONH(CH₂)₂.

20. The compound of claim 17, wherein L is (CH₂)₉.