Process for preparing benzothiophenecarboxamide derivatives
AssigneeShionogi & Co., Ltd.
InventorsTsunetoshi Honma, Yoshiharu Hiramatsu
Life of this patent
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Abstract
A process for preparing a compound having PGD2 antagonism represented by the formula (I), or a pharmaceutically acceptable salt or hydrate thereof, which process comprises reacting an amino alcohol of the formula (II) or its salt with a compound of the formula (III) or its reactive derivative, oxidizing the product with halo oxoacid in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyls, reacting the product with an ylide under the conditions for Wittig reaction, and optionally deprotecting the product. 1
Claims9
A process for preparing a compound of the formula (I)
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- wherein R is hydrogen or a hydroxy-protecting group;
- X is hydrogen or alkyl;
- and double bond represents either E- or Z-configuration, or a pharmaceutically acceptable salt or hydrate thereof, which comprises reacting an amino alcohol of the formula (II):
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- or a salt thereof with a compound of the formula (III):
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- wherein R is hydrogen or a hydroxy-protecting group or a reactive derivative thereof to yield a compound of the formula (I-2):
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- wherein R is as defined above;
- oxidizing the compound (I-2) with halo oxoacid in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyls to yield a compound of the formula (I-3):
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- wherein R is as defined above;
- reacting the compound (I-3) with an ylide under the conditions for Wittig reaction and, if desired, deprotecting the reaction product.
A process for preparing a compound of the formula (I-3):
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- wherein R is hydrogen or a hydroxy-protecting group, which comprises oxidizing a compound of the formula (I-2):
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- wherein R is as defined above with halo oxoacid in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyls.
A process for preparing an amino alcohol of the formula (II) or a salt thereof, which comprises reducing a compound of the formula (II-2):
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- wherein R2 is alkyl and R3 is hydrogen or alkyl is reduced with a reducing agent-Lewis acid system.
A process for preparing an amino alcohol of the formula (II) or a salt thereof, which comprises converting a compound of the formula (II-2):
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- wherein R2 and R3 are as defined above into an alcohol of the formula (II-3):
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- wherein R3 is as defined above;
- and reducing the alcohol with metal sodium-alcohol or reducing agent-Lewis acid system.
Dependencies are inferred from the claim text.