Warner-lambert Company

Sterling R Putt

David Clarkston Baker

2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone, 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one and acid-addition salts thereof are disclosed. 2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone and its acid-addition salts are prepared by catalytically reducing an acid-addition salt of 2-amino-1-[5-amino-1-(protected)-1H-imidazol-4-yl]ethanone. 6,7-Dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one and its acid-addition salts are prepared by reacting an acid-addition salt of 2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone with a compound able to contribute a formyl group. The later product may subsequently be converted into (R)-3-(2-deoxy-.beta.-D-erythropentofuranosyl)-3,6,7,8-tetrahydroimidazo[4 ,5-d][1,3]diazepin-8-ol. Furanose derivatives of 6,7-dihydroimidazo[4,5-d][1,3]diazepine are also disclosed and their methods of preparation. Lastly, a method for resolving an isomer mixture of 3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4 ,5-d][1,3]diazepin-8-ol compounds is related.

Imidazole compounds, methods for their production and conversion of said

2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone, 6,7-dihydroimidazo[4,5-d][1,3]diazepin-8(3H)-one and acid-addition salts thereof are disclosed. 2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone and its acid-addition salts are prepared by catalytically reducing an acid-addition salt of 2-amino-1-[5-amino-1-(protected)-1H-imidazol-4-yl]ethanone. 6,7-Dihydroimidazo[4,5-d][1,3]-diazepin-8(3H)-one and its acid-addition salts are prepared by reacting an acid-addition salt of 2-amino-1-(5-amino-1H-imidazol-4-yl)ethanone with a compound able to contribute a formyl group. The later product may subsequently be converted into (R)-3-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[ 4,5-d][1,3]diazepin-8-ol. Furanose derivatives of 6,7-dihydroimidazo[4,5-d][1,3]diazepine are also disclosed and their methods of preparation. Lastly, a method for resolving an isomer mixture of 3-(2-deoxy-.beta.-D-erythro-pentafuranosyl)-3,6,7,8-tetrahydroimidazo[4 ,5-d][1,3]diazepin-8-ol compounds is related.

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Ann Arbor, MI, United States of America

Sterling R Putt