Polymorphs of the prodrug 6-N-(L-ALA-L-ALA)-trovafloxacin

Details Polymorphs of the prodrug 6-N-(L-ALA-L-ALA)-trovafloxacin Polymorphs of the prodrug 6-N-(L-ALA-L-ALA)-trovafloxacin

1998-01-30

2000-06-27

Huang, Evelyn Mei

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546123, A61K 314375, A61P 3104, C07D47104

Patent

active

060807563

DESCRIPTION:

BRIEF SUMMARY
This application is the National phase of PCT/IB96/00653, filed on Jul. 5, 1996.


BACKGROUND OF THE INVENTION

This invention relates to a prodrug of trovafloxacin having the formula ##STR2## selected from the group consisting of polymorph PII and the monohydrate PII.M and pseudomorph PII.PS thereof and processes for their preparation. The invention further relates to methods of using, and pharmaceutical compositions comprising, the compounds of the invention for treatment of bacterial infections in mammals.
The antibacterial activity of trovafloxacin is described in U.S. Pat. Nos. 5,164,402 (the '402 patent) and 5,229,396 (the '396 patent) 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. A polymorph PI of the compound of formula I and methods for its preparation are also described in the above-indicated patents.


SUMMARY OF THE INVENTION

In a first embodiment the present invention relates to a prodrug of trovafloxacin having the formula ##STR3## wherein said prodrug is selected from the group comprising a) a polymorph PII exhibiting the following X-ray powder diffraction pattern


______________________________________ Peak no. 1 2 3 4 5 6 7 8 9 ______________________________________ 2.sub.-- .theta..sub.-- 3.4 6.8 13.5 16.8 19.6 20.3 23.1 25.7 27.8 (.degree.) Cu d space 26.0 13.1 6.6 5.3 4.5 4.4 3.8 3.5 3.2 ______________________________________ pattern


______________________________________ Peak no. 1 2 3 4 5 6 7 8 ______________________________________ 2.sub.-- .theta..sub.-- (.degree.) Cu 3.6 7.3 13.7 14.5 17.1 21.0 23.6 26.7 d space 24.2 12.2 6.5 6.1 5.2 4.2 3.8 3.3 ______________________________________ pattern
According to a second embodiment of the invention there is provided a process for preparing prodrug PII, as described above, which comprises treating the prodrug, PI, of the formula I, exhibiting the X-ray powder diffraction pattern, below, with dry ethanol.
According to another aspect, of the above embodiment, the invention provides a process for preparing a monohydrate, PII.M, as described above, of the polymorph, PII, which comprises
Yet another aspect, of the above embodiment of the invention provides a process for preparing a pseudomorph, PII.PS, as described above, of the monohydrate PII.M. which comprises vacuum drying the monohydrate PII.M.
The invention also provides pharmaceutical compositions comprising an antibacterially effective amount of a compound of formula I, as described above, together with a pharmaceutically acceptable diluent or carrier.
In another embodiment the invention provides a method for treating bacterial infection in a mammal which comprises administering to said mammal a bacterial infection treating effective amount a compound of formula I, as described above.
A third embodiment of the invention provides a prodrug of trovafloxacin consisting of the polymorph PII, characterized by the X-ray diffraction pattern, described above, which is prepared by treating the polymorph PI, characterized by the X-ray diffraction pattern described above, with dry ethanol.
According to another aspect of the above embodiment there is provided a prodrug of trovafloxacin consisting of the monohydrate PII.M of polymorph PII, characterized by the X-ray diffraction pattern described above, which is prepared by pattern described above, with an organic solvent containing water;
Yet another aspect of the above embodiment provides a prodrug of trovafloxacin consisting of its pseudomorph PII.PS characterized by the X-ray diffraction pattern described above, which is prepared by vacuum drying the monohydrate PII.M.


DETAILED DESCRIPTION OF THE INVENTION

This invention relates to a prodrug, of trovafloxacin, having the formula ##STR4## selected from the group consisting a polymorph PII and the monohydrate PII.M and pseudomorph PII.PS thereof and pharmaceutical compositions c

REFERENCES:
patent: 5164402 (1992-11-01), Brighty
patent: 5229396 (1993-07-01), Brighty

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