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Hapten-carrier conjugates for use in drug-abuse therapy and methods for preparation of same

  • US 5,876,727 A
  • Filed: 09/30/1996
  • Issued: 03/02/1999
  • Est. Priority Date: 03/31/1995
  • Status: Expired due to Term
First Claim
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1. A nicotine hapten-carrier conjugate comprising the structure shown in FIG. 17b, wherein A, B, C, D, E and F are side chains of nicotine, which are independently selected from the group consisting of chemical moieties, said chemical moieties are identified by CJ reference number:

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    space="preserve" listing-type="tabular">______________________________________CJ 0 QCJ 1 (CH.sub.2).sub.n QCJ 1.1 CO.sub.2 QCJ 1.2 COQCJ 1.3 OCH.sub.3CJ 2 OCO(CH.sub.2).sub.n QCJ 2.1 OCOCH═

    QCJ 2.2 OCOCH(O)CH.sub.2CJ 2.3 OCO(CH.sub.2).sub.n CH(O)CH.sub.2CJ 3 CO(CH.sub.2)nCOQCJ 3.1 CO(CH.sub.2).sub.n CNQCJ 4 OCO(CH.sub.2).sub.n COQCJ 4.1 OCO(CH.sub.2).sub.n CNQCJ 5 CH.sub.2 OCO(CH.sub.2).sub.n COQCJ 5.1 CH.sub.2 OCO(CH.sub.2).sub.n CNQCJ 6 CONH(CH.sub.2).sub.n QCJ 7 Y(CH.sub.2).sub.n QCJ 7.1 CH.sub.2 Y(CH.sub.2).sub.n QCJ 8 OCOCH(OH)CH.sub.2 QCJ 8.1 OCO(CH.sub.2).sub.n CH(OH)CH.sub.2 QCJ 9 OCOC.sub.6 H.sub.5CJ 10 See FIG. 2bCJ 11 YCO(CH.sub.2).sub.n COQ;

    ______________________________________wherein Y is sulfur (S), oxygen (O), or an amine (NH), wherein n is an integer from 3 to 20, and wherein Q is selected from the group consisting of;

    H, OH, OCH3, CH2, CH3, COOH, halogens, activated esters, acyl halides, acyl azides, alkyl halides, N-maleimides, imino esters, isocyarlate, isothiocyanate, and a T cell epitope-containing carriers;

    with the proviso that Q in at least one of A, B, C, D, E, or F comprises a carrier containing at least one T cell epitope said carrier selected from the group consisting of cholera toxin B (CTB), diphtheria toxin, tetanus toxoid, pertussis toxin, ricin B subunit, retrovirus nucleoprotein (retro NP), rabies ribonucleoprotein (Rabies RNP), Tobacco Mosaic Virus, and vesicular stomatitis vius nudeocapsid protein (VSV-N).

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