Optically active benzoxazines and benzothiazines and a...

Details Optically active benzoxazines and benzothiazines and a... Optically active benzoxazines and benzothiazines and a...

A - Human Necessities

61

K

167/211, 260/243

A61K 31/54 (2006.01) C07C 205/37 (2006.01) C07D 265/36 (2006.01) C07D 279/16 (2006.01) C07D 498/06 (2006.01) C07D 513/06 (2006.01)

Patent

CA 2002395

ABSTRACT Optically active 7,8-difluoro-3,4-dihydro-3- methyl-2H-[1,4]benzoxazines and 7,8-difluoro-3,4-dihydro-2- methyl-2H-[1,4]benzoxazines and the corresponding benzothiazines of formula III, Image III where, one of the substituents R1, R2, R3 and R4 is CH20H or -CH2Z, the remaining being hydrogen, X denotes fluoro, chloro, methyl or hydrogen, Y is oxygen or sulfur and Z is hydrogen, fluoro or protected hydroxyl are obtained as the stereochemically pure products of a stereospecific synthesis using a 3,4-difluoronitrobenzene substituted with a stereochemically pure 2-(1-hydroxyisopropoxy), 2-(2- hydroxypropoxy), 2-(1-hydroxyisopropylthio) or 2-(2- hydroxypropylthio) substituent. The obtained compounds are suited for the production of optically active pyridobenzoxazines and pyridobenzothiazines, among which are useful antibacterial optically active quinolones, particularly (S)-(-)-ofloxacin.

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