Process for preparing 3-fluoroquinolines

Details Process for preparing 3-fluoroquinolines Process for preparing 3-fluoroquinolines

2004-11-10

2008-07-08

Seaman, D. Margaret (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S180000

Reexamination Certificate

active

07396934

ABSTRACT:
The invention relates to a novel preparation of 3-fluoroquinolines of formula (I)in which R1, R2, R3and R4represent:a) a fluorine;b) an alkyl optionally substituted with one to three fluorines, with OR5in which R5is an alkyl, a hydrogen or a hydroxyl-protecting group, or with NR′R″ in which R′ and R″ represent an alkyl, a hydrogen or an amino-protecting group;c) OR6in which R6represents a hydrogen, a phenol-protecting group or an alkyl, optionally substituted with a fluorine, with OR5or with NR′R″ as defined above;d) NR′1R″1in which R′1and R″1have the values of R′ et R″ or represent an alkyl substituted with a fluorine, with OR5or NR′R″ as defined above;e) CO2Ra, in which Rarepresents hydrogen, alkyl or a carboxyl-protecting group, and also novel intermediate compounds.The quinolines of formula (I) are intermediates useful in the preparation of compounds having antibacterial activity, described in particular in applications WO 02/40474 or WO 02/72572.

REFERENCES:
patent: WO 2005/049575 (2005-06-01), None
Roe, J Am Chem Soc, vol. 71, pp. 1785-1786, 1949.
Elderfield, J Am CHem Soc, vol. 68, pp. 1589-1591, 1946.
Arthur Roe et al., The Preparation of Heterocyclic Fluorine Compounds by the Schiemann Reaction, J. Am. Chem. Soc. (1949, pp. 1785-1786, vol. 71).
International Search Report issued May 13, 2005 in PCT/FR2004/002910 (1 page), with English translation (1 page).
Preliminary International Search Report issued Oct. 7, 2005 in PCT/FR2004/002910 (5 pages), with English translation (4 pages).

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