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US 2010/0076202 A1Published application
Method for producing pyrrolidine derivative
AssigneeDaiichi Pharmaceutical Co., Ltd.
InventorsYoshihiro TAKAYANAGI, Toshihide Yamada, Yukito Furuya, Yoshiyuki Yoneda
Life of this patent
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Abstract
The present invention provides an advantageous method for producing an intermediate which is useful for production of a compound which exhibits excellent VLA-4 inhibitory effect and safety. An intermediate (14) is produced through the following reaction scheme.
Claims20
An oxalic acid salt of the compound represented by formula (g).
A method for producing a compound represented by formula (l):
- (wherein R2 represents a lower alkyl group, and R4 represents an alkyl group which may be substituted or an aralkyl group which may be substituted), comprising:
- reducing a compound represented by formula (h):
- (wherein R5 represents a hydrogen atom or a protecting group for the amino group) to thereby produce a compound represented by formula (i):
- treating the compound represented by formula (i) with a base in an aprotic polar solvent and then reacting with water to thereby produce a compound represented by formula (j):
- and either
- (A) treating the compound represented by formula (j) with an acid in the presence of an alcohol to thereby produce a compound represented by formula (k):
- and treating the compound represented by formula (k) with camphorsulfonic acid to thereby isolate an isomer as an acid adduct salt, or
- (B) treating the compound represented by formula (j) with camphorsulfonic acid to thereby isolate an isomer as an acid adduct salt, or
- (C) isolating the compound represented by formula (j) as a salt and then treating the salt with an acid in the presence of an alcohol to thereby produce a compound represented by formula (k);
- and treating the compound represented by formula (k) with camphorsulfonic acid to thereby isolate an isomer as an acid adduct salt, or
- (D) isolating the compound represented by formula (j) as a salt and then treating the compound with camphorsulfonic acid to thereby isolate an isomer as an acid adduct salt.
8 more elements
A camphorsulfonic acid salt of the compound represented by formula (m).
Dependencies are inferred from the claim text.