Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2003-01-14
2004-01-06
Rotman, Alan L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06673935
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to the Form V polymorph of Compound A having the chemical structure shown below:
as well as a process for synthesizing the Form V polymorph.
Compound A exists in five polymorphic forms (Forms I-V), an amorphous form and two hydrated forms. 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. WO96/10012 and WO96/16934. Compound A is described in U.S. Pat. No. 5,861,419 granted on Jan. 19, 1999 (Example 23), which is hereby incorporated by reference in its entirety. A process for making Compound A is described in U.S. Pat. No. 6,040,319 granted on Mar. 21, 2000, which is hereby incorporated by reference in its entirety. The present invention unexpectedly provides for a novel, robust process for making a Form V polymorph of compound A from any one of Forms I, II, III or IV or any mixture of polymorphs of compound A.
SUMMARY OF THE INVENTION
This invention encompasses the Form V polymorph of structural formula A:
which is useful in the treatment of cyclooxygenase-2 mediated diseases.
The invention encompasses certain pharmaceutical compositions for the treatment of cyclooxygenase-2 mediated diseases comprising the Form V polymorph of Compound A. The invention also encompasses a process for synthesizing the Form V polymorph of Compound A comprising: combining polymorph I, II, III or IV of Compound A with isopropyl acetate; heating to an elevated temperature less than about 75° C.; and cooling to a low temperature to produce the Form V polymorph.
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Crocker Louis S.
Davies Ian W.
Kotliar Andrew
Osifchin Richard G.
Merck & Co. , Inc.
Robinson Binta
Rose David L.
Rotman Alan L.
Yuro Raynard
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