Methamphetamine derivatives and conjugates for immunoassay

• US 7,294,649 B2
• Filed: 12/17/2004
• Issued: 11/13/2007
• Est. Priority Date: 12/17/2004
• Status: Active Grant

• Current Assignee: Roche Diagnostics Operations Incorporated (Roche Holding AG)
• Original Assignee: Roche Diagnostics Operations Incorporated (Roche Holding AG)
• Inventors: Hui, Raymond A., Vitone, Stephen S.
• Primary Examiner(s): McKane; Joseph K.
• Assistant Examiner(s): Coppins; Janet L
• Application Number:
  US11/016,619
• Publication Number:
  US 20060134711A1
• Time in Patent Office: 1,061 Days
• Field of Search: 548/545, 564/163, 564/336, 514/425, 514/649
• US Class Current: 514/425
• 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: C07C 271/16 to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 331/28 having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 207/404 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
• CPC Class Codes: C07K 16/44 against material not provided for elsewhere , e.g. haptens, metals, DNA, RNA, amino acids
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
• CPC Class Codes: Y10S 436/815 Test for named compound or class of compounds
• CPC Class Codes: Y10S 436/901 Drugs of abuse, e.g. narcotics, amphetamine
• CPC Class Codes: Y10T 436/13 Tracers or tags
• CPC Class Codes: Y10T 436/173845 Amine and quaternary ammonium

Abstract

Compounds of methamphetamine derivatives having a meta-substituted alkyl linker on the benzene ring and a protective group on the nitrogen of the methamphetamine hapten. Such compounds have the structure

wherein R₁ is an alkyl linker comprising 2-15 carbon atoms and 0-6 heteroatoms, R₂ is a leaving group, and R₃ is a protecting group.

Claims

1. A compound having the formula

2. The compound of claim 1 wherein R₃ is trifluoroacetyl.

3. A compound having the formula

4. The compound of claim 3

5. The compound 4-{[4-(3-{(S)-2[methyl-(2,2,2trifluoro-acetyl)-amino]-propyl}-phenoxy)-butyrylamino]-methyl}-benzoicacid 2,5-dioxo-pyrrolidin-1-yl ester having the formula

6. The compound having the formula