2-fluorofucosyl-N-aroylglucosamine derivatives, intermediates, therefor, and processes for producing these
AssigneeDaikin Industries, Ltd.
InventorsYutaka Ohira, Takao Iida
Life of this patent
Estimating the term…
Abstract
2-Fluorofucosyl-N-aroylglucosamine derivatives which are obtained by substitution of a hydroxyl group at the 3- or 4-position of N-aroylglucosamine with 2-fluorofucose, their intermediates and preparation methods thereof. The 2-fluorofucosyl-N-aroylglucosamine derivatives which are useful medicinal components for the treatment, improvement and prevention of inflammation and diseases accompanying inflammation, their intermediates and preparation methods thereof can be provided.
Claims22
2-Fluorofucosyl-N-aroylglucosamine derivatives represented by the following general formula (1):
- ##STR49## wherein X and Y in said general formula (1) are groups represented by following general formulas (A) or (B), if X is general formula (A), Y is general formula (B), and if X is general formula (B), Y is general formula (A) ##STR50## herein, in said general formula (A), R is a hydrogen atom, a protective group of the hydroxyl group, phosphate residue, sulfate residue, or a sialyl group represented by the following general formula (a), ##STR51## wherein R.sup.6 in the above general formula (a) shows a hydrogen atom, sodium atom or C1-10 alkyl group;
- R.sup.7 shows a hydrogen atom, C1-10 alkanoyl group or C7-15 aroyl group;
- R.sup.8 shows an acetyl group, hydroxyacetyl group or C1-10 alkanoyloxyacetyl group), further, in the above general formula (1), R.sup.1 is a hydrogen atom, hydroxyl group, C1-10 alkanoyloxy group having no substituent or having one or more substituents, C7-15 aroyloxy group, arylthio group having no substituent or having one or more substituents, C1-18 alkoxy group, branched long chain alkoxy group, arylmethoxy group having no substituent or having one or more substituents, or 2-trisilylethoxy group having C1-4 alkyl group or phenyl group, or a group represented by following general formulas (b) or (c), ##STR52## wherein R.sup.9 in the above general formulas (b) and (c) shows a hydrogen atom, C1-10 alkanoyl group, C7-15 aroyl group or phenylmethoxy group having no substituent or having substituents;
- R.sup.10 shows a hydrogen atom, hydroxyl group, 2-trisilylethoxy group having C1-4 alkyl group or phenyl group, C1-30 alkoxy group, or a group represented by following general formula (d);
- and R.sup.11 shows a hydrogen atom or --O--C(.dbd.NH)CCl.sub.3, ##STR53## wherein R.sup.12 in the above general formula (d) shows a hydrogen atom or benzoyl group;
- R.sup.13 shows an azide, amine or sphingosine represented by NHCO R.sup.14 (R.sup.14 is a C15-25 alkyl group);
- R.sup.11 shows a hydrogen atom or --O--C(.dbd.NH)CCl.sub.3, and in the above general formula (1), (A) and (B), R.sup.2, R.sup.3 and R.sup.4 are a hydrogen atom, C1-10 alkanoyl group, C7-15 aroyl group, or phenylmethyl group having no substituent or having substituents (wherein at least two of R.sup.2, R.sup.3 and R.sup.4 may be the same or different from each other) and R.sub.5 shows an aroyl group having no substituent or having substituents.
A method for preparing the 2-fluorofucosyl-N-aroylglucosamine derivatives wherein a compound represented by the following general formulas (A') and (B') and an aroylglucosamine derivative represented by the following general formula (C') are used when preparing the 2-fluorofucosyl-N-aroylglucosamine derivatives represented by said general formula (1), (wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 in said general formulas (A'), (B') and (C') are the same as described above;
- R.sup.17, R.sup.18, R.sup.19 and R.sup.20 are reactive groups, respectively;
- and R.sup.17 shows reactivity with R.sup.19 or R.sup.20 ;
- and R.sup.18 shows reactivity with R.sup.19 or R.sup.20).
Intermediates of 2-fluorofucosyl-N-aroylglucosamine derivatives represented by the following general formula (4), (wherein R.sup.15 shows a phenyl group having no substituent or having substituents;
- and R.sup.16 shows an aroyl group having no substituent or having substituents).
The method for preparing the intermediates of 2-fluorofucosyl-N-aroylglucosamine derivatives comprises reaction of the aroylglucosamine derivative represented by the following general formula (i) with the compound represented by general formula (B'), when preparing the intermediates of 2-fluorofucosyl-N-aroylglucosamine derivatives represented by general formula (4), ##STR59## 20.
Dependencies are inferred from the claim text.