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Title:
1-ISOTHIAZOLIDINONE DERIVATIVE OF AZETIDIN-2-ONE AND ITS PRODUCTION
Document Type and Number:
Japanese Patent JPH11255767
Kind Code:
A
Abstract:

To obtain the subject new compound useful as a stable intermediate for chemically synthesizing physiologically active β-lactam compounds.

A compound of formula I [R1, R3 and R4 are each H or a halogen; R2 is H, a halogen or phthalimide; R5 is H, a lower alkyl, an aryl or the like; (n) is 0-2], for example, (3S,4R)-1-[(4S)-2-benzyl-5,5-dimethyl-3-oxo- isothiazolidin-4-yl]-3-bromo-4-chloro-azetidin-2-one. The compound of formula I is obtained by reacting a penicillanic acid sulfoxideamide with a halogenating agent (for example, thionyl chloride) inn an anhydrous aprotic organic solvent (for example, benzene) at -50 to 150°C to open the thiazoline ring of the penicillanic acid sulfoxideamide, subjecting the reaction product to an intramolecular ring-closing reaction to form an isothiazolidinone ring and simultaneously halogenate the azetidine ring and, if necessary, subsequently oxidizing the reaction product.


Inventors:
HERAK JURE J
Application Number:
JP37088598A
Publication Date:
September 21, 1999
Filing Date:
December 25, 1998
Export Citation:
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Assignee:
PLIVA PHARM & CHEM WORKS
International Classes:
A61K31/395; A61K31/425; A61K31/43; C07D205/08; C07D499/87; C07D275/03; C07D417/04; C07D417/14; C07D499/86; C07D499/897; (IPC1-7): C07D417/04
Attorney, Agent or Firm:
Shigeru Yagita (2 outside)