1,4: 3,6 - Dian hydro - d - glucitol mono nitrate esters, process for their preparation and their use

摘要

1356374 1,4; 3,6 - Dianhydro - D - glucibols AMERICAN HOME PRODUCTS CORP 24 April 1972 [29 April 1971] 18821/72 Heading C2C Novel compounds (I) and (II) in which R is C 1-6 alkanoyl, C 1-6 alkyl (including cyclobutyl, cyclopentyl and cyclohexyl), benzoyl, benzyl, sulphanoyl or carbamoyl are prepared (1) by a process in which 1,4:3,6-dianhydro-D-glucitol, 2 or 5-nitrate is (a) acylated to introduce a C 1-6 alkanoyl or benzoyl group, (b) alkylated to introduce a C 1-6 alkyl or benzyl group, (c) reacted with a sulphamoyl halide preferably in pyridine to introduce a sulphamoyl group, or (d) reacted with phosgene and the product formed thereby treated with ammonia to introduce a carbamoyl group, or (2) by nitration of the corresponding 2 or 5 -O-R substituted 1,4:3,6-dianydro-D-glucitol. Acylation is carried out in the presence of a tertiary amine using an acid anhydride or halide. Alkylation is carried out with a halide in an alkanol in the presence of silver oxide. The introduction of a carbamoyl group is carried out in an inert solvent preferably dioxan. Compounds (I) and (II) are 1,4:3,6-dianhydro-D- glucitol - 5 or 2 - acetate - 2 or 5 - nitrate, - 5 or 2 - carbamate - 2 or 5 - nitrate, - 2 - ethyl - 5- nitrate and -5-nitrate-2-sulphamate. Compounds (I) and (II) lower systemic blood pressure and coronary resistance and form with a carrier a pharmaceutical composition which may be administered parenterally.