Novel synthetic method of tebipenem pivoxil side chain

A technology of tipipenem and a synthesis method, applied in the field of medicinal chemistry, can solve the problems of being unsuitable for industrialized production, having no reaction conditions, and high raw material prices, and achieving the advantages of convenient industrialized production, high operational safety, and cheap and easy-to-obtain raw materials. Effect

Active Publication Date: 2015-01-21
CHANGZHOU RUIBO BIO TECH
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Problems solved by technology

The problem with this route is that the separation of intermediates needs to be separated by column chromatography, and a large amount of butyllithium needs to be used in the reaction process. The price of this raw material is relatively high, and the operation is inconvenient, so it is not suitable for industrial production.
Although these two methods seem to have relatively short routes, the starting materials 2-methylthiothi

Method used

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  • Novel synthetic method of tebipenem pivoxil side chain
  • Novel synthetic method of tebipenem pivoxil side chain
  • Novel synthetic method of tebipenem pivoxil side chain

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Embodiment Construction

[0028] In order to make the technical means, creative features, work flow, and use methods of the present invention achieve the purpose and effect easy to understand, the present invention will be further elaborated below in conjunction with specific reaction formulas.

[0029]

[0030] Synthesis of compound II:

[0031] Add 1200 milliliters of ethanol and 111.3 grams of benzaldehyde (1.05mol) in the reaction flask, under stirring, add 110 milliliters of 25% ammoniacal liquor (1.60mol), after stirring for 15 minutes, add dropwise 92 grams of epichlorohydrin (1.00mol), control The temperature is lower than 40°C, the dropwise addition is completed, react at 35-40°C for 8 hours, and then react at room temperature for 15 hours. After the gas phase detection of epichlorohydrin almost disappears completely, the reaction solution is concentrated to remove about 1 / 3 of the volume of ethanol, and then Add 800 milliliters of toluene, under stirring, control the temperature at 35-40...

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Abstract

The invention discloses a novel synthetic method of a tebipenem pivoxil side chain. The method employs cheap and easily available raw material, has simple experimental operations, high overall yield and is applicable to industrialized production.

Description

Technical field: [0001] The invention relates to the field of medicinal chemistry, in particular to a new method for synthesizing the side chain of Tebipenem pivoxil. Background technique: [0002] Tebipenem pivoxil, the chemical name is (4R,5S,6S)-(pivaloyloxy)methyl-3-((1-(4,5-dihydrothiazoline-2- Base)-azetidin-3-ylmercapto)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo【3.2.0】heptane-2 -ene-2-carboxylate, a new type of broad-spectrum antibiotic for oral administration of penem, was researched and developed by Japan Wyeth Rieter Co., Ltd., and was transferred to Japan Meiji Pharmaceutical Co., Ltd. in March 2002. It was approved and launched in Japan for the first time on August 26, 2009. The product name is Orapenem, and its clinical indications are pneumonia, otitis media and sinusitis in children. At the same time, the product has completed phase II clinical trials for adults and achieved considerable results. Good experimental results, ongoing phase III clinical...

Claims

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Application Information

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IPC IPC(8): C07D417/04
CPCY02P20/55C07D417/04
Inventor 魏峰吴宗铨葛二鹏
Owner CHANGZHOU RUIBO BIO TECH
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