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US 2016/0237107 A1Published application
Synthetic Route to 2'-Deoxy-2',2'-Difluorotetrahydrouridines
AssigneeOtsuka Pharmaceutical Co., Ltd.
InventorsHyeong-wook Choi, Steven Mathieu, Frank Fang, Bryan Matthew Lewis
Life of this patent
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Abstract
The present invention relates to methods and intermediates for synthesizing 2′-deoxy-2′,2′-difluorotetrahydrouridine compounds.
Claims30
A method of producing compound 1:
- or a salt thereof;
- comprising precipitating or crystallizing compound 1 from a solution of compound 2:
- in the presence of a catalyst.
A method of producing compound 1:
- or a salt thereof;
- comprising the steps of:
- (a) hydrogenating a compound of Formula IV:
- wherein R is a hydroxyl protecting group,
- to produce a compound of Formula IIa:
- (b) reducing the compound of Formula IIa to produce a compound of Formula IIIa:
- (c) deprotecting the compound of Formula IIIa to produce compound 2:
- and
- (d) precipitating or crystallizing compound 2 in the presence of a catalyst to produce compound 1:
- or a salt thereof.
7 more elements
A compound of Formula I:
- wherein R is a hydroxyl protecting group;
- R1 is H, a hydroxyl protecting group, or absent;
- is a bond or absent;
- and
- is absent when R1 is H or a hydroxyl protecting group;
- or a salt, or enantiomer, or diastereomer thereof.
3 more elements
Dependencies are inferred from the claim text.