Intermediate useful for the synthesis of TGF-beta inhibitors and a method of preparing TGF-beta inhibitors using the same
AssigneeMedpacto Inc.
InventorSeung Ho Lee
Life of this patent
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Abstract
The present invention provides an intermediate for synthesizing a TGF-β inhibitor represented by Chemical Formula 1 and an improved method for preparing the TGF-β inhibitor represented by Chemical Formula 1 using the same. The preparation method according to the present invention can not only allow inexpensive and safe reagents to be used, but also simplify the synthesis steps and purification methods to improve the reaction yield, thereby maximizing the production efficiency of the TGF-β inhibitor represented by Chemical Formula 1 to be used usefully for mass production.
Claims19
A method for preparing a compound of Chemical Formula 1, the method comprising:
- obtaining a compound of Chemical Formula 4 by reacting a compound of Chemical Formula 2 with a compound of Chemical Formula 3, and
- obtaining a compound of Chemical Formula 1 by deprotecting the compound of Chemical Formula 4:
- wherein, in the formulae,
- X and Y are each independently halogen;
- PG is a protecting group selected from the group consisting of butoxycarbonyl (Boc), benzyloxycarbonyl (Cbz), 9-fluorenylmethoxycarbonyl (Fmoc), acetyl, benzoyl and tosyl;
- Ra is independently hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C3-6 cycloalkyl, hydroxyl, —O-C1-6 alkyl, —O-C1-6 haloalkyl, —O-C3-6 cycloalkyl, amino, —NH-C1-6 alkyl, —NH-C1-6 haloalkyl, —NH-C3-6 cycloalkyl, —S-C1-6 alkyl, —S-C1-6 haloalkyl, —S-C3-6 cycloalkyl, cyano, or nitro;
- and
- m is 0, 1, 2, 3 or 4.
A compound represented by Chemical Formula 4:
- in the formula,
- Y is halogen;
- PG is a protecting group selected from the group consisting of butoxycarbonyl (Boc), benzyloxycarbonyl (Cbz), 9-fluorenylmethoxycarbonyl (Fmoc), acetyl, benzoyl and tosyl;
- Ra is independently hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C3-6 cycloalkyl, hydroxyl, —O-C1-6 alkyl, —O-C1-6 haloalkyl, —O-C3-6 cycloalkyl, amino, —NH-C1-6 alkyl, —NH-C1-6 haloalkyl, —NH-C3-6 cycloalkyl, —S-C1-6 alkyl, —S-C1-6 haloalkyl, —S-C3-6 cycloalkyl, cyano, or nitro;
- and
- m is 0, 1, 2, 3 or 4.
Dependencies are inferred from the claim text.