Methamphetamine-like hapten compounds, linkers, carriers and compositions and uses thereof

• US 8,299,222 B2
• Filed: 11/03/2009
• Issued: 10/30/2012
• Est. Priority Date: 04/20/2000
• Status: Expired due to Fees

• Current Assignee: Bioventures, LLC
• Original Assignee: The Board of Trustees of the University of Arkansas (University of Arkansas System)
• Inventors: Owens, Samuel M., Carroll, Frank Ivy, Abraham, Philip
• Primary Examiner(s): Haq, Shafiqul
• Application Number:
  US12/611,708
• Publication Number:
  US 20100055126A1
• Time in Patent Office: 1,092 Days
• Field of Search: None
• US Class Current: 530/403
• CPC Class Codes: A61K 2039/505 comprising antibodies
• CPC Class Codes: A61K 31/13 Amines A61K31/04 takes precedence
• CPC Class Codes: A61K 31/137 Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
• CPC Class Codes: C07B 2200/07 Optical isomers
• 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 233/18 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07K 16/44 against material not provided for elsewhere , e.g. haptens, metals, DNA, RNA, amino acids
• CPC Class Codes: C07K 2317/55 Fab or Fab'
• CPC Class Codes: G01N 33/946 CNS-stimulants, e.g. cocaine, amphetamines
• CPC Class Codes: Y10S 436/823 Immunogenic carrier or carrier per se
• CPC Class Codes: Y10S 436/901 Drugs of abuse, e.g. narcotics, amphetamine
• CPC Class Codes: Y10T 436/173845 Amine and quaternary ammonium

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 of the formula:

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 R₃ is selected from the group consisting of (CH₂)₄ and (CH₂)₄NHCO(CH₂)₅.

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

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