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US 2026/0258162 A1Published application
Novel oligosaccharide, production intermediate for novel oligosaccharide, production method for novel oligosaccharide, and production method for production intermediate for novel oligosaccharide
AssigneeDaiichi Sankyo Company, Limited
InventorsTsuyoshi UEDA, Ryusei ITOH, Tatsuya NAKAMURA
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Abstract
The present invention addresses the problem of providing a novel oligosaccharide, which is a biantennary glycan having an α2,6-sialic acid structure at a non-reducing end, and a method for producing the oligosaccharide, and an intermediate thereof, and a method for producing the intermediate. Provided are a novel oligosaccharide represented by the following formula A-22, a method for producing the oligosaccharide shown in FIG. 1, and an intermediate thereof and a method for producing the intermediate.
Claims25
A method for producing an oligosaccharide represented by the following formula A-22:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups,
- the method comprising the steps of:
- (step I-1)
- producing a compound represented by the following formula A-8:
- the step comprising the step of:
- subjecting a compound represented by formula A-3:
- and a compound represented by the following formula A-5:
- to α-1,3-glycosidic linkage and α-1,6-glycosidic linkage to give a compound represented by the following formula A-6:
- (step I-2) producing a compound represented by the following formula A-11:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups,
- the step comprising the step of:
- subjecting the compound represented by formula A-8 and a compound represented by the following formula A-9:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups,
- to β-1,4-glycosidic linkage to give a compound represented by the following formula A-10:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups;
- (step I-3) subjecting the compound represented by formula A-11 and a compound represented by the following formula A-12:
- to β-1,2-glycosidic linkage to give a compound represented by the following formula A-13:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups,
- then eliminating each phthaloyl group as a protecting group of an amino group and each acetyl group on a hydroxyl group on the compound represented by formula A-13 to give a compound represented by the following formula A-14:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups,
- and then protecting the amino group in the compound represented by formula A-14 by a protecting group selected from an aryloxycarbonyl (COOAr) group, an acetyl (Ac) group, a 2,2,2-trichloroethoxycarbonyl (Troc) group, or a phthaloyl (Phth) group to give a compound represented by the following formula A-15:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, R5 is an aryloxycarbonyl (COOAr) group, an acetyl (Ac) group, or a 2,2,2-trichloroethoxycarbonyl (Troc) group and R6 is a hydrogen atom, or R5 and R6 together with a nitrogen atom attached thereto form a phthalimide group,
- or eliminating each acetyl (Ac) group on the compound represented by formula A-13 to give the compound represented by formula A-15 wherein R5 and R6 together with a nitrogen atom attached thereto form a phthalimide group;
- (step I-4) producing a compound represented by the following formula A-20:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, and M+ is a sodium ion, lithium ion, potassium ion, or protonated triethylamine cation,
- the step comprising:
- subjecting the compound represented by A-15 and a compound represented by the following formula A-16:
- to β-1,4-glycosidic linkage to give a compound represented by the following formula A-17:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, R5 is an aryloxycarbonyl (COOAr) group, an acetyl (Ac) group, or a 2,2,2-trichloroethoxycarbonyl (Troc) group and R6 is a hydrogen atom, or R5 and R6 together with a nitrogen atom attached thereto form a phthalimide group,
- and then eliminating each protecting group of an amino group and each acyl-based protecting group of a hydroxyl group in the compound represented by formula A-17 to give a compound represented by formula A-18:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, and M+ is a sodium ion, lithium ion, potassium ion, or protonated triethylamine cation;
- and
- (step I-5) producing the oligosaccharide represented by formula A-22 by reacting the compound represented by formula A-20 with a compound represented by the following formula A-21:
30 more elements
4-5. (canceled)
(canceled)
15-23. (canceled)
A method for producing a compound represented by the following formula A-17:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, R5 is an aryloxycarbonyl (COOAr) group, an acetyl (Ac) group, or a 2,2,2-trichloroethoxycarbonyl (Troc) group and R6 is a hydrogen atom, or R5 and R6 together with a nitrogen atom attached thereto form a phthalimide group,
- the method comprising the step of:
- producing a compound represented by the following formula A-15:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, R5 is an aryloxycarbonyl (COOAr) group, an acetyl (Ac) group, or a 2,2,2-trichloroethoxycarbonyl (Troc) group and R6 is a hydrogen atom, or R5 and R6 together with a nitrogen atom attached thereto form a phthalimide group,
- and then subjecting the compound and a compound represented by the following formula A-16:
- to β-1,4-glycosidic linkage to give the compound represented by formula A-17.
3 more elements
A method for producing a compound represented by the following formula A-18:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, and M+ is a sodium ion, lithium ion, potassium ion, or protonated triethylamine cation,
- the method comprising:
- eliminating each protecting group of an amino group and each acyl-based protecting group of a hydroxyl group in a compound represented by the following formula A-17:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, R5 is an aryloxycarbonyl (COOAr) group, an acetyl (Ac) group, or a 2,2,2-trichloroethoxycarbonyl (Troc) group and R6 is a hydrogen atom, or R5 and R6 together with a nitrogen atom attached thereto form a phthalimide group.
1 more element
An oligosaccharide represented by the following formula A-22 or A′-22:
- wherein R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups:
28-31. (canceled)
A compound selected from the group consisting of the compounds represented by the following formulas A-13, A-14, A-14-FMA, A-15, A-17, A-18-FF or a its salt, A-19-FF or a its salt, A-20-FF or a its salt and A′-20-FF or a its salt:
- wherein, in the compounds represented by Formulas A-13, A-14, A-14-FMA, A-18-FF, A-19-FF and A-20-FF, R1 is a C1 to C6 alkyl group or a phenyl group, and the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, and
- wherein, in the compounds represented by Formulas A-15 and A-17, R1 is a C1 to C6 alkyl group or a phenyl group, the phenyl group is optionally substituted with one to three C1 to C6 alkoxy groups, R5 is an aryloxycarbonyl (COOAr) group, an acetyl (Ac) group, or a 2,2,2-trichloroethoxycarbonyl (Troc) group and R6 is a hydrogen atom, or R5 and R6 together with a nitrogen atom attached thereto form a phthalimide group.
33-40. (canceled)
Dependencies are inferred from the claim text.