Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-02-17
2000-08-29
Owens, Amelia
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
560 9, 560 23, 560 44, C07D33714, C07C20500, C07C22900
Patent
active
061111155
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to new processes for preparing "Zaltoprofen", i.e., 2-(10,11-dihydro-10-oxodibenzo-[b,f]thiepin-2-yl)propionic acid. The invention further relates to new compounds which are favorably employable for the processes for the preparation of Zaltoprofen.
BACKGROUND OF THE INVENTION
Zaltoprofen is known as a pharmaceutically active compound which shows excellent anti-inflammatory effect as well as excellent analgesic effect.
Japanese Patent Provisional Publication No. 55-53282 describes a process for preparing Zaltoprofen which comprises hydrolyzing ethyl 5-(.alpha.-cyanoethyl)-2-phenylthiophenylacetate to give 5-(.alpha.-cyanoethyl)-2-phenylthiophenylacetic acid, subjecting the resulting compound to cyclization and amidation of cyano group, and hydrolyzing the amide group of the resulting compound.
Japanese Patent Provisional Publication No. 57-106678 describes an improved process for preparing Zaltoprofen which comprises hydrolyzing ethyl 5-(.alpha.-cyanoethyl)-2-phenylthiophenylacetate to give 2-(3-carboxymethyl-4-phenylthiophenyl)propionic acid and cyclizing the resulting compound in the presence of a condensation agent.
Japanese Patent Provisional Publications No. 62-292780 and No. 63-10756 describe a process for preparing Zaltoprofen which starts from a haloketal compound.
Japanese Patent Provisional Publication No. 63-2970 describes a process for preparing Zaltoprofen in which methyl 5-propionyl-2-phenylthiophenylacetate is reacted with an orthoformic acid ester and metallic zinc or zinc halide to produce methyl 2-(3-methoxycarbonylmethyl-4-phenylthiophenyl)propionate, and this product is employed for the preparation of Zaltoprofen.
As described above, a variety of processes for preparing Zaltoprofen are known. However, more improved processes are desired from the viewpoints of availability of the starting materials and easy handling of the materials participating in the reactions for the preparation, as well as economical viewpoints such as yields.
The present invention has an object to provide new processes for preparing Zaltoprofen.
Specifically, the invention has an object to provide new processes for preparing Zaltoprofen which are advantageously employable in industry from the viewpoints of availability of the starting materials and easy handling of the materials participating in the reactions for the preparation, as well as economical viewpoints such as yields.
SUMMARY OF THE INVENTION
The present invention resides in a process for preparing 2-(10,11-dihydro-10-oxodibenzo[b,f]thiepin-2-yl)propionic acid which comprises subjecting 2-(4-amino-3-carboxymethylphenyl)propionic acid or its salt to diazotization and subsequent reaction with thiophenol to produce 2-(3-carboxymethyl-4-phenylthiophenyl)propionic acid or its salt, and subjecting the product to cyclization reaction--(Preparation-I).
The invention also resides in a process for preparing 2-(10,11-dihydro-10-oxodibenzo[b,f]thiepin-2-yl)propionic acid which comprises subjecting 2-(4-amino-3-carboxymethylphenyl)propionic acid or its salt to diazotization and subsequent reaction with a halogenating agent to produce 2-(3-carboxymethyl-4-halogenophenyl)propionic acid or its salt, causing a reaction of the product with thiophenol to produce 2-(3-carboxymethyl-4-phenylthiophenyl)propionic acid or its salt, and subjecting the product to cyclization reaction--(Preparation-II).
The invention further resides in a process for preparing 2-(10,11-dihydro-10-oxodibenzo[b,f]thiepin-2-yl)propionic acid which comprises subjecting 2-(4-amino-3-carboxymethylphenyl)propionic acid or its salt to diazotization and subsequent reaction with thiosalicylic acid to produce 2-[3-carboxymethyl-4-(2-carboxyphenylthio)phenyl]propionic acid or its salt, esterifying the product to give a 2-[3-(lower)alkoxycarbonylmethyl-4-(2-(lower)alkoxycarbonylphenylthio)phen yl]propionic acid (lower)alkyl ester, cyclizing the resulting ester to produce a 2-(10,11-dihydro-11-(lower)alkoxycarbonyl-10-oxodibenzo[b,f]thiepin-2-yl)p ropionic acid
Harada Katsumasa
Kobayashi Kunio
Nishino Shigeyoshi
Sasaki Hiroshi
Yamamoto Masao
Nippon Chemiphar Co., Ltd.
Owens Amelia
Ube Industries Ltd.
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