The Upjohn Co.

Michael F Lipton

Martin Gall

Donald J Cram

Thomas A Hylton

Paul A Meulman

Steve Nichols

Burris D Tiffany

Crystalline, non-hygroscopic adinazolam methanesulfonate, per se, preparable from xylene or preferably from a C.sub.1 to C.sub.2 -alkanol/C.sub.4 to C.sub.6 -alkyl acetate liquid mixture, aids processability of adinazolam methanesulfonate in pharmaceutical production plants.

Non-hygroscopic adinazolam methanesulfonate salt and process therefor

An improved process for preparing a 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepine product, e.g., adinazolam, directly from the corresponding 1-hydrogen-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepine starting material, e.g., from estazolam, by conducting the reaction between the estazolam-type compound and the dimethylaminomethylene salt in the selected solvent in the presence of an alkali metal carbonate, and thereafter extracting the 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine from an aqueous organic solvent mixture thereof into a halogenated C.sub.1 to C.sub.3 -alkane solvent while maintaining the pH of the aqueous phase between pH 3.0 and 4.0, and thereafter recovering the product from the halogenated alkane solvent.

Preparing

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Kalamazoo, MI, United States of America

Michael F Lipton