HAPTEN COMPOUNDS AND COMPOSITIONS AND USES THEREOF

• US 20100143391A1
• Filed: 04/18/2008
• Published: 06/10/2010
• 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: Carroll, F. Ivy, Gunnell, Melinda, Owens, S. Michael
• Granted Patent: US 8,853,146 B2
• Time in Patent Office: Days
• US Class Current: 424/184.100
• 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 (I):

5. The compound of claim 1, wherein L is selected from the group consisting of:

7. The compound of claim 1, wherein the compound comprises formula (VI):

2-4. -4. (canceled)

6. (canceled)

8-9. -9. (canceled)

10. A compound comprising formula (II):

14. The compound of claim 10, wherein L is selected from the group consisting of:

16. The compound of claim 10, wherein the compound comprises formula (VII):

18. The compound of claim 16, wherein R₃ is selected from the group consisting of (CH₂)₄ and (CH₂)₄NHCO(CH₂)₅.

20. The compound of claim 10, wherein the compound comprises formula (III):

21. The compound of claim 20, wherein R₂ is oxygen.

22. The compound of claim 21, wherein L is

23. The compound of claim 20, wherein the compound comprises formula (VIII):

25. The compound of claim 23, wherein R₃ is selected from the group consisting of (CH₂)₄ and (CH₂)₄NHCO(CH₂)₅.

11-13. -13. (canceled)

15. (canceled)

17. (canceled)

19. (canceled)

24. (canceled)

26. (canceled)

27. A compound comprising formula (IV):

31. The compound of claim 27, wherein L is selected from the consisting of

33. The compound of claim 27, wherein the compound comprises formula (IX):

35. The compound of claim 33, wherein R₄ is [N-maleimidomethyl]cyclohexane-1-carboxylate.

37. The compound of claim 27, wherein the compound comprises formula (V):

38. The compound of claim 37, wherein R₂ is oxygen.

39. The compound of claim 38, wherein L is

40. The compound of claim 37, wherein the compound comprises formula (X):

42. The compound of claim 40, wherein R₄ is [N-maleimidomethyl]cyclohexane-1-carboxylate.

28-30. -30. (canceled)

32. (canceled)

34. (canceled)

36. (canceled)

41. (canceled)

43. (canceled)

44. A composition comprising a compound selected from the group consisting of a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), a compound of formula (VIII), a compound of formula (IX), and a compound of formula (X).

45-52. -52. (canceled)

53. A method for generating specific antibodies for a compound selected from the group consisting of a compound of formula (I), a compound of formula (II), a compound of formula (III), a compound of formula (IV), a compound of formula (V), a compound of formula (VI), a compound of formula (VII), a compound of formula (VIII), a compound of formula (IX), and a compound of formula (X);

the method comprising administering the compound to a subject.

54-56. -56. (canceled)