PROCEDIMIENTO PARA LA PREPARACION DE O-ESTERES DE MONOSACA-RIDOS.

摘要

1317781 D-Glucofuranose compounds CIBA GEIGY AG 25 June 1970 [3 July 1969] 30865/70 Heading C2C Novel compounds of Formula I: in which R1 1 represents a hydrogen atom or a lower alkyl radical, R1 2 represents a hydrogen atom or the acyl radical of an aliphatic carboxylic acid or a salicyloyl or O-lower alkanoylsalicyloyl radical, and each of R1 3 and R1 5 represents a lower alkyl or lower alkenyl group or a benzyl group optionally substituted by lower alkyl, lower alkoxy or trifluoromethyl groups or halogen atoms, or for a salicyloyl or O-lower alkanoyl-salicyloyl radical, or for an O-benzyl-salicyloyl O-lower alkyl-salicyloyl or halogeno-salicyloyl radical, and R1 3 may also represent a hydrogen atom, and R1 6 represents a lower alkyl or lower alkenyl group or a phenyl or benzyl group optionally substituted by lower alkyl, lower alkoxy or trifluoromethyl groups or halogen atoms, or for a salicyloyl or O-lower alkanoyl-salicyloyl radical, or for an O-benzylsalicyloyl, O-lower alkyl-salicyloyl or halogenosalicyloyl radical, with the proviso that at least one of R1 2 , R1 3 , R1 5 and R1 6 represents a salicyloyl or O-lower alkanoyl-salicyloyl radical, or an O-benzyl-salicyloyl O-lower alkyl-salicyloyl or halogeno-salicyloyl radical, and with the further proviso that at least one of R1 1 , R1 3 , R1 5 and R1 6 represents one of the optionally substituted hydrocarbon radicals indicated for these groups, are prepared by reacting a compound of Formula II: in which R 1 0 represents a lower alkyl radical and R 2 0 represents a hydrogen atom or the acyl radical of an aliphatic carboxylic acid, or R 1 0 and R 2 0 together represent an optionally substituted methylene group -X-, and at least one of R 3 0, R 5 0 and R 6 0 represents a free or reactive esterified hydroxy group and the others have the meanings of R1 3 , R1 5 , and R1 6 , respectively, with salicylic acid or O-lower alkanoyl salicylic acid or a reactive derivative thereof, and reacting a resulting compound of the Formula I in which R1 1 and R1 2 have the same meanings as R 1 0 and R 2 0 respectively, and R 1 0 and R 2 0 together represent an optionally substituted methylene group -X-, with a compound of the formula R1 1 -OH in the presence of an acid, and, if desired, reacting a resulting compound of the Formula I, in which R1 1 represents a hydrogen atom, with an alcohol of the formula R1 1 -OH in the presence of an acid, or converting in a resulting compound of the Formula I, in which R1 1 represents a hydrogen atom and R1 2 preferably stands for an acyl radical of an aliphatic carboxylic acid, the free hydroxy group in 1-position into an esterified hydroxy group and treating the resulting ester with an alcohol of the formula R1 1 -OH, and/or, if desired, reacting a resulting compound of the Formula I in which R1 1 represents a lower alkyl radical, with an acid in the presence of water, and, if none of R1 1 , R1 3 , R1 5 and R1 6 is an optionally substituted hydrocarbon group as specified above, introducing such a group. A resulting compound I can be converted into a different compound I by usual methods, e.g. etherification, hydrolysis, esterification, hydrogenolysis &c. The preparation of compounds II is also described. Pharmaceutical compositions comprise a compound of Formula I together with a pharmaceutical carrier. The compositions have antiinflammatory and analgesic activity.