Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1984-11-27
1988-10-04
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
424 11, 424 9, A61K 4300, A61K 4902, C07D48908
Patent
active
047757590
ABSTRACT:
Fluorinated derivatives 3,14-dihydroxy-4,5.alpha.-epoxy-6.beta.-fluoro-17-methylmorphinan ("fluorooxymorphone"; FOXY, compound 10) and 17-cyclopropylmethyl-3,14-dihydroxy-4,5.alpha.-epoxy-6.beta.-fluoromorphin an (CYCLOFOXY, compound 18) are prepared based upon the structures of the potent opioid agonist oxymorphone 4 and the antagonist naltrexone 11, respectively. Fluorine was introduced in the final stages of synthesis by a facile nucleophilic displacement with fluoride ion of the 6.alpha.-triflate functions in 8 and 16. The synthetic procedures were suitable for the production of the corresponding positron emitting .sup.18 F-labeled analogs .sup.18 F-FOXY and .sup.18 F-CYCLOFOXY, which are useful for in vivo studies of the opioid receptor system using positron emission transaxial tomography. In addition, the tritiation of FOXY (10) to high specific activity is noted.
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Burke, Jr. Terrence R.
Channing Michael A.
Eckelman William C.
Larson Steven M.
Pert Candace B.
Daus Donald G.
Rivers Diana G.
The United States of America as represented by the Department of
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