Synthetic route to dronabinol

Details Synthetic route to dronabinol Synthetic route to dronabinol

2008-01-29

2008-01-29

Solola, Taofiq (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

10954345

ABSTRACT:
Dronabinol, the tetrahydrocannabinol compound which comprises the active constituent of marijuana and is pharmaceutically useful as an antiemetic, is prepared by a process involving reaction of cis-menth-1-enc-3,8-diol with olivetol to form 1,3-dihydroxy-2-[(1R,6R)-6-(2-hydroxyprop-2-yl)-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene; and cyclizing the 1,3-dihydroxy-2-[(1R,6R)-6-(2-hydroxyprop-2-yl)-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene so formed to obtain dronabinol. A novel synthesis of cis-menth-1-ene-3,8-diol is also provided.

REFERENCES:
patent: 3656906 (1972-04-01), Bullock
patent: 3734930 (1973-05-01), Razdan et al.
patent: 4116979 (1978-09-01), Razdan et al.
patent: 4381399 (1983-04-01), Olsen et al.
patent: 5227537 (1993-07-01), Stoss et al.
patent: WO 02/070506 (2002-09-01), None
patent: WO 02/096899 (2002-12-01), None
Vaultier et. al., 1987; vol. 28, No. 36; pp. 4169-4172 “Tetrahedron Letters” , Great Britain.
Anglea et. al., 1987; vol. 43, No. 23; pp. 5537-5543 “Tetrahedron”, Great Britain.
Handrick et. al., 1979; No. 8; pp. 681-684 “Tetrahedron Letters”, Great Britain.
Banks et. al., 1981; vol. 1; pp. 1096-1102 “J. Chem. Soc., Perkin Trans”, Scotland.
Parsons et .al; 1980; pp. 197-198 “J. Chem. Soc., Chem. Commun.”, Southampton.
Walter R. Benn, 1968; vol. 33, No. 8; pp. 3113-3118 “Steroidal C-17 Allene Acetates”, Chicago, Illinois.
Snider, B. B. and Amin, S. G., 1978; vol. 8; pp. 117-125 “Synthetic Communication”, New Jersey.
Garrett et. al., 1978; vol. 67, No. 1; pp. 27-32 “Journal of Pharmaceutical Sciences”, The Netherlands.
Synlett, 1991; pp. 553-554 by Stoss et al, “A Useful Approach Towards Δ9-Tetrahydrocannabinol”, Germany.
“Helvetica Chimica Acta”, 1988; vol. 71; pp. 209-217 Zurich by Burkard et al.
Schlossarczyk et. al, 1973; vol. 56, No. 3; pp. 875-944 “Helvetica Chimica Acta”, Zurich.
Evans et. al, 1999; vol. 121; pp. 7582-7594 “Journal of the American Chemical Society”, Massachusetts.
“Izveshya Akademii Nauk SSSR, Seriya Khimicheskaya”, 1979; No. 5; pp. 1049-1052. by Arbuzov et al.

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