Patent GB-1317781-A (GB)
Title: D-glucofuranose compounds and process for preparing them
Inventor: JAQUES R
IPC: C07H15/207
Filed: 1970-06-25
Abstract: 1317781 D-Glucofuranose compounds CIBA GEIGY AG 25 June 1970 [3 July 1969] 30865/70 Heading C2C Novel compounds of Formula I: in which R<SP>1</SP> 1  represents a hydrogen atom or a lower alkyl radical, R<SP>1</SP> 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 R<SP>1</SP> 3  and R<SP>1</SP> 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 R<SP>1</SP> 3  may also represent a hydrogen atom, and R<SP>1</SP> 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 R<SP>1</SP> 2 , R<SP>1</SP> 3 , R<SP>1</SP> 5  and R<SP>1</SP> 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 R<SP>1</SP> 1 , R<SP>1</SP> 3 , R<SP>1</SP> 5  and R<SP>1</SP> 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 <SP>0</SP> represents a lower alkyl radical and R 2 <SP>0</SP> represents a hydrogen atom or the acyl radical of an aliphatic carboxylic acid, or R 1 <SP>0</SP> and R 2 <SP>0</SP> together represent an optionally substituted methylene group -X-, and at least one of R 3 <SP>0</SP>, R 5 <SP>0</SP> and R 6 <SP>0</SP> represents a free or reactive esterified hydroxy group and the others have the meanings of R<SP>1</SP> 3 , R<SP>1</SP> 5 , and R<SP>1</SP> 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 R<SP>1</SP> 1  and R<SP>1</SP> 2  have the same meanings as R 1 <SP>0</SP> and R 2 <SP>0</SP> respectively, and R 1 <SP>0</SP> and R 2 <SP>0</SP> together represent an optionally substituted methylene group -X-, with a compound of the formula R<SP>1</SP> 1 -OH in the presence of an acid, and, if desired, reacting a resulting compound of the Formula I, in which R<SP>1</SP> 1  represents a hydrogen atom, with an alcohol of the formula R<SP>1</SP> 1 -OH in the presence of an acid, or converting in a resulting compound of the Formula I, in which R<SP>1</SP> 1  represents a hydrogen atom and R<SP>1</SP> 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 R<SP>1</SP> 1 -OH, and/or, if desired, reacting a resulting compound of the Formula I in which R<SP>1</SP> 1  represents a lower alkyl radical, with an acid in the presence of water, and, if none of R<SP>1</SP> 1 , R<SP>1</SP> 3 , R<SP>1</SP> 5  and R<SP>1</SP> 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.