Cocaine analogs

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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546124, 546132, A61K 3146, C07D45102

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active

058344845

ABSTRACT:
Cocaine analogs are disclosed. The analogs, certain 6-alkyl substituted tropane derivatives, bind to the cocaine binding site on dopamine transporter, without interfering with the dopamine receptor. The craving for cocaine is thereby blocked. The analogs may readily be synthesized stereoselectively, and are relatively resistant to metabolic degradation.

REFERENCES:
patent: 5374636 (1994-12-01), Moldt et al.
Lomenzo et al., "Synthesis, Structure, Dopamine Transporter Affinity, and Dopamine Uptake Inhibition of Chem., vol. 40, No. 26, pp. 4406-4414, Dec. 19, 1997.
D. Simoni et al., "Methoxylation of Cocaine Reduces Binding Affinity and Produces Compounds of Differential Binding and Dopamine Uptake Inhibitory Activity: Discovery of a Weak Cocaine `Antagonist,`" J. Med. Chem., vol. 36, pp. 3975-3977 (1993).
A.P. Kozikowski et al., "A PLE-Based Resolution of Cocaine, Pseudococaine, and 6- and 7-Methoxylated Cocaine Analogues," Bioorganic &Medicinal Chemistry Letters, vol. 6, pp. 441-444 (1996).
A.P. Kozikowski et al., "Synthesis of the 6- and 7-Hydroxylated Cocaines and Pseudococaines," Tetrahedron Letters, vol. 37, pp. 5333-5336 (1996).
Z. Chen et al., "Synthesis of 6- or 7- Hydroxy and 6- or 7- Methoxy Tropanes," Tetrahedron Lett., vol. 38, pp. 1121-1124 (1997).
A. Kozikowski et al., "Dipolar Cycloaddition Route to Diverse Analogues of Cocaine: The 6- and 7- Substituted 3-Phenyltropanes," J. Org. Chem., vol. 62, pp. 503-509 (1997).
Lomenzo et al., "A Facile and Efficient Synthesis of (.+-.)-Tropan-2-one," Synthetic Communications, vol. 25, pp. 3681-3690 (1995).

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