Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-11-28
2002-08-27
Davis, Zinna Northington (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S257000, C546S258000
Reexamination Certificate
active
06441002
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to polymorphic, amorphous and hydrated forms of the title compound which has the chemical structure shown below:
The compound is a potent and selective cyclooxygenase-2 (COX-2) inhibitor, useful primarily in the treatment of inflammation, pain and fever as well as other COX-2 mediated diseases, such as described in PCT Publication Nos. WO096/10012 and W096/16934. Compound A is described in U.S. Pat. No. 5,861,419 granted on Jan. 19, 1999 (Example 23) incorporated by reference in its entirety.
Bipyridyl compounds generally are highly crystalline, poorly water soluble and hydrophobic, resulting in difficulties in the preparation of pharmaceutical formulations and problems associated with bioavailability. Accordingly, efforts were made to discover other forms of Compound A and to investigate the properties thereof. There were discovered three additional polymorphic forms, an amorphous form and two hydrates.
SUMMARY OF THE INVENTION
Polymorphic forms of Compound A, for purposes of this invention, are identified as Form I (onset of melting, m.p. 134-136° C., peak m.p. 138° C.), Form II (onset of melting, m.p~131° C., peak m.p. 133° C.), Form III (onset of melting, m.p.~133° C., peak m.p. 135° C) and Form IV (onset of melting, m.p.~134° C., peak m.p. 136° C.). Forms I through IV are anhydrous. An amorphous form and two hydrates have also been identified.
REFERENCES:
patent: 5321033 (1994-06-01), Down et al.
patent: 5861419 (1999-01-01), Dube et al.
patent: 6040319 (2000-03-01), Corley et al.
patent: 6040450 (2000-03-01), Davies et al.
patent: 6127545 (2000-10-01), Pye et al.
patent: 6130334 (2000-10-01), Pye et al.
patent: 6204387 (2001-03-01), Davies et al.
patent: 6252116 (2001-06-01), Corley et al.
patent: WO 98/03484 (1998-01-01), None
patent: WO 99/55830 (1999-11-01), None
patent: WO 01/92230 (2001-12-01), None
Biles, J. A., Journal of Pharmaceutical Sciences, vol. 51, No. 7, pp. 601-617, 1962.
R.W. Friesen, et al., Bioorganic & Medicinal Chemistry Letters, (1998), vol. 8, No. 19, pp. 2777-2782.
Jean-Francois Marcoux, et al., J. Org. Chem., (2001), vol. 66, No. 12, pp. 4194-4199.
Ian W. Davies, et al., J. Org. Chem., (2000), vol. 65, No. 25, pp. 8415-8420.
Jean-Francois Marcoux, et al., Organic Letters, (2000), vol. 2, No. 15, pp. 2339-2341.
Ian W. Davies, et al., J. Org. Chem., (2000), vol. 65, No. 15, pp. 4571-4574.
Clas Sophie Dorothee
Crocker Louis S.
Dalton Chad
Davies Ian
McCauley James A.
Davis Zinna Northington
Merck & Co. , Inc.
Rose David L.
Yuro Raynard
LandOfFree
Polymorphic, amorphous and hydrated forms of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Polymorphic, amorphous and hydrated forms of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polymorphic, amorphous and hydrated forms of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2918633