Parke-davis Company

Warner-lambert Company

David Clarkston Baker

Theodore H Haskell

Sterling R Putt

9-(2-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds and their production by enzymatic removal of the 3-O-acyl and 5-O-acyl groups of a 9-(2,3-di-O-acyl-.beta.-D-arabinofuranosyl)adenine compound or a 9-(2,3,5-tri-O-acyl-.beta.-D-arabinofuranosyl)adenine compound. The monoester compounds are useful as antiviral agents. The compounds are water-soluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.

Method for the production of

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.

2-Amino-1-(5-amino-1H-imidazol-4-yl)ethanone and method of preparation

9-(5-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds and their production by reacting 9-(.beta.-D-arabinofuranosyl)adenine with a reactive derivative of an alkanoic acid. The compounds are useful as antiviral agents. The compounds are water-soluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.

9-(5-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds

9-(2-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds and their production by enzymatic removal of the 3-O-acyl and 5-O-acyl groups of a 9-(2,3-di-O-acyl-.beta.-D-arabinofuranosyl)adenine compound or a 9-(2,3,5-tri-O-acyl-.beta.-D-arabinofuranosyl)adenine compound. The monoester compounds are useful as antiviral agents. The compounds are watersoluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.

9-(2-O-Acyl-.beta.-D-arabinofuranosyl)-adenine compounds and method for

9-(3-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds, 9-(2,3-di-O-acyl-.beta.-D-arabinofuranosyl)adenine compounds, and their production by reacting in each case the corresponding 5-silyl ether derivative with a tetraalkylammonium fluoride. The compounds are useful as antiviral agents. The compounds are water-soluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.

9-(3-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds,

9-(3,5-Di-O-acyl-.beta.-D-arabinofuranosyl)adenine compounds and their production by reacting in each case a 9-(5-O-tri-substituted-silyl-2,3-di-O-acyl-.beta.-D-arabinofuranosyl)adeni ne compound with a tetraalkylammonium fluoride. The compounds are useful as antiviral agents. The compounds are stable and being lipophilic are adaptable to long-acting and depot injectable pharmaceutical formulation.

Growing community of inventors

Ann Arbor, MI, United States of America

David Clarkston Baker