IMIDAZOLE-RIBOSYL CYCLOPHOSPHATE COMPOUNDS AND THERAPEUTIC COMPOSITIONS

1316034 Imidazole ribosyl cyclophosphates BOEHRINGER MANNHEIM GmbH 25 May 1971 [27 May 1970] 16951/71 Heading C2P The invention comprises compounds of the Formula I where R is hydrogen or -(CH 2 ) n -A, n is 2 or 3, A is -SO 3 H or -COR1 and R1 is OH, C 1-6 alkoxy, alkylamino or dialkylamino, and the salts thereof. Compounds of Formula I in which R is other than hydrogen may be prepared by reacting inosine-31,51-monophosphate with a compound of the Formula II where X is -CO- or -SO 2 -, heating the product with an aqueous solution of an alkali metal hydroxide and optionally, when an acid is obtained, converting the acid into an ester or amide. Compounds of Formula I in which R is hydrogen may be prepared by (a) reacting 21 - O - acetyl - inosine - 31,51 - monophosphate in a polar organic solvent with a metal hydride and then with chlorodimethylether, and heating the N1 - methoxymethyl - 21 - O - acetyl - inosine - 31,51 - monophosphate obtained with an alkali metal hydroxide solution, or (b) by dissolving the 51-phosphate of 5-amino-1#-D- ribosyl-4-imidazole carboxamide and morpholino - N,N - dicyclohexylcarboxamidinium salt in a pyridine-water mixture, removing the water and heating the solution obtained with dicyclohexylcarbodiimide. The compounds of Formula I may be used as the active ingredients in pharmaceutical compositions, together with a solid or liquid diluent or carrier. 21 - O - Acetyl - inosine - 31,51 - monophosphate triethylammonium salt may be prepared by reacting inosine-31,51-monophosphate with acetic anhydride and triethylamine.