Process and intermediates for preparing naphthyridonecarboxylic

Details Process and intermediates for preparing naphthyridonecarboxylic Process and intermediates for preparing naphthyridonecarboxylic

1996-10-07

1999-07-27

Huang, Evelyn Mei

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548452, C07D47104, C07D20902

Patent

active

059292407

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

This invention relates to novel processes and intermediates for the preparation of pharmaceutically acceptable acid salts, of the formula ##STR1## wherein R.sup.1 H is a pharmaceutically acceptable acid, selected from the group consisting of R.sup.4 SO.sub.3 H, R.sup.4 PO.sub.3 H and YH wherein phenyl or naphthyl wherein the substituent is (C.sub.1 -C.sub.6)alkyl; and PO.sub.4, of the naphthyridone antibiotic 6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid.
The antibacterial activity of the aforementioned naphthyridone antibiotic is described in U.S. Pat. Nos. 5,164,402 and 5,229,396 issued Nov. 17, 1992 and Jul. 20, 1993, respectively, the disclosures of which are hereby incorporated herein by reference in their entirety. The foregoing patents are assigned in common with the present application.


SUMMARY OF THE INVENTION

In a first embodiment the present invention relates to a process for preparing a compound of the formula ##STR2## wherein R.sup.1 H is a pharmaceutically acceptable acid selected from the group consisting of R.sup.4 SO.sub.3 H, R.sup.4 PO.sub.3 H and YH wherein phenyl or naphthyl wherein the substituent is (C.sub.1 -C.sub.6)alkyl; and PO.sub.4, which comprises treating a compound of the formula ##STR3## wherein R.sup.2 is (C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.6)alkyl or hydrogen and R.sup.3 is NO.sub.2 or NH.sub.2 ; defined above; or compound of the formula R.sup.1 H wherein R.sup.1 H is as defined above.
The invention also relates to a process for preparing a compound of the formula II wherein R.sup.3 is NH.sub.2 and R.sup.2 is as defined above by treating a compound of the formula II wherein R.sup.3 is NO.sub.2 with a reducing agent in the presence of a compound of the formula R.sup.1 H wherein R.sup.1 H is as defined above.
In another embodiment, the present invention relates to a process for preparing a compound of the formula II wherein R.sup.3 is NO.sub.2 comprising reacting the compound of the formula ##STR4## with a compound of the formula ##STR5## wherein R.sup.2 is as defined above and J is a suitable leaving group.
In accordance with another embodiment of the invention, the compound of the formula IV is prepared by treating a compound of the formula ##STR6## wherein R is selected from hydrogen (C.sub.1 -C.sub.6) alkyl or (C.sub.6 -C.sub.10)aryl wherein said aryl group may be substituted, optionally, with one or more substituents independently selected from halo, nitro, (C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) alkoxy, amino and trifluoromethyl, with an N-dealkylating agent. Preferably R is phenyl or hydrogen. The compound of formula V may be prepared by treating the compound of formula ##STR7## wherein R is as defined above, with a reducing agent. The compound of formula VI is prepared by treating a compound of the formula ##STR8## wherein R is as defined above, with a compound of the formula X--CH.sub.2 --NO.sub.2, wherein X is a suitable leaving group, in the presence of a base. A preferred base is 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine.
Yet another embodiment of the invention relates to a process for the preparation of a compound of formula I which comprises the steps of X--CH.sub.2 --NO.sub.2, wherein X is a leaving group, in the presence of a base to form a compound of the formula VI which is then treated with a reducing agent to form the compound of the formula V; the compound of formula IV; ##STR9## wherein R.sup.2 is as defined above and J is a suitable leaving group, to form a compound of the formula II wherein R.sup.3 is NO.sub.2 ; and reducing agent comprising hydrogen in the presence of a catalyst or a metal and an acid of the formula R.sup.1 H, as defined above, to form as defined above, or R.sup.1 H is a compound of the formula YH or R.sup.4 SO.sub.3 H, wherein Y and R.sup.4 are as defined above, the compound of the formula I; or treating said compound with a compound of the formula R.sup.1 H, which may be the same as or different from the R.sup.1 H of the reducing step, or a compound of the formula R.sup.

REFERENCES:
patent: 5164402 (1992-11-01), Brighty
patent: 5256791 (1993-10-01), Braish

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