Imiquimod production process

Details Imiquimod production process Imiquimod production process

2007-02-14

2010-02-09

Solola, Taofiq A (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07659398

ABSTRACT:
The present invention provides a process for preparing highly pure 4-amino-1-isobutyl-1H-imidazo[4,5-c]quinoline (imiquimod). The process preferably includes heating 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline of formula (II) with ammonia in a polar aprotic solvent at relatively moderate pressure to produce imiquimod, and optionally purifying the imiquimod. The process of the present invention can produce highly pure imiquimod in high yield.

REFERENCES:
patent: 4689338 (1987-08-01), Gerster
patent: 4929624 (1990-05-01), Gerster et al.
patent: 4988815 (1991-01-01), André et al.
patent: 5175296 (1992-12-01), Gerster
patent: 5367076 (1994-11-01), Gerster
patent: 7323568 (2008-01-01), Naddaka et al.
patent: 2005/0085500 (2005-04-01), Gutman et al.
patent: 2006/0004202 (2006-01-01), Razzetti et al.
patent: 2007/0010675 (2007-01-01), Allegrini et al.
patent: 2007/0135640 (2007-06-01), Naddaka et al.
patent: 2008/0177074 (2008-07-01), Naddaka et al.
patent: 1609792 (2005-12-01), None
patent: WO 2005/033049 (2005-04-01), None
patent: WO 2005/033049 (2005-04-01), None
patent: WO 2006/070379 (2006-07-01), None
patent: WO 2006/100226 (2006-09-01), None
patent: WO 2008/090550 (2008-07-01), None
patent: WO 2008/090550 (2008-07-01), None
patent: WO 2008/099377 (2008-08-01), None
patent: WO 2008/099377 (2008-08-01), None
Office Action dated Jun. 7, 2007 in U.S. Appl. No. 11/298,711.
Bredereck et al., “Umsetzungen von Halogenverbindungen mit Formamid (Formamid-Reaktionen, III. Mitteilung. II. Mitteil.: G. Theilig, Chem. Ber. 86, 96 [1953]),”Chemische Berichte, 87(4), 537-546 (1954).
P. Jacobson, “Ueber die Einwirkung von Dinitrochlorbenzol auf Kaliumbenzoat und auf Acetamid,”Berichte der Deutschen Hemischen Gesellschaft, 32, 3539-3540 (1899).
Pachter et al., “Methylation of Some Amides in Acetone,”J. Am. Chem. Soc., 74, 1321-1322 (1952).
Rondestvedt Jr. “Aminations With Ammonia and Formamide. Synthesis of Terephtalamic Acid and of p-Nitroaniline,”J. Org. Chem., 42(19), 3118-3123 (1977).
Sarges et al., “4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants”, J. Med Chem, vol. 33, No. 8, pp. 2240-2254 (Aug. 1990).

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