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US 5,965,735 AGranted
Process for preparing flunixin and intermediates thereof
AssigneeSchering Corporation
InventorsHenry J. Doran, Donal J. Coveney
Life of this patent
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Abstract
Process for preparing a key intermediate, 2-methyl-3-trifluoromethylaniline (MTA) of Flunixin, as well as novel intermediates thereof are described.
Claims3
A process for preparing flunixin and pharmaceutically acceptable salts thereof, comprising:
- a) methylating a compound of formula (III):
- ##STR19## wherein Z is hydrogen to give compound (V) ##STR20## wherein Z is defined as before;
- b)In a first alternative, for compounds of formula (V) wherein Z is H, separating compound (V) from the reaction mixture;
- and hydrolyzing compound (V) with acid to give MTA;
- or
- In a second alternative, for compounds of formula (V) wherein Z is H, hydrolyzing the reaction mixture with acid;
- and from the reaction mixture, separating out MTA;
- c) converting 2-methyl-3-trifluoromethylaniline (MTA) from either of the above alternatives in step b) to 2-[[2-methyl-3-(trifluoromethyl) phenyl]amino]-3-pyridinecarboxylic acid (flunixin) or pharmaceutically acceptable salts thereof.
5 more elements
A process for preparing 2-methyl-3-trifluoromethylaniline (MTA) comprising hydrolyzing a compound of the formula:
- ##STR21## with hydrogen bromide to give MTA.
Dependencies are inferred from the claim text.