- PROCESS FOR THE PREPARATION OF HIGHLY PURE PRULIFLOXACIN
-
The present invention provides an industrially advantageous process for the preparation of highly pure prulifloxacin of formula I and its pharmaceutically acceptable salts. The present i innvention a also provides a novel process for the purification of prulifloxacin acid addition salt.
- -
-
Page/Page column 14-15
(2009/09/05)
-
- Studies on pyridonecarboxylic acids. V. A practical synthesis of ethyl 6,7-difluoro-1-methyl-4-oxo-4H-[1,3]thiazeto[3,2-α]quinoline 3-carboxylate, a key intermediate for the new tricyclic quinolone, prulifloxacin (nm441) and versatile new syntheses of the 2-thioquinoline skeleton
-
A practical synthesis of ethyl 6,7-difluoro-1-methyl-4-oxo4H- [1,3]thiazeto[3,2-α]quinoline-3-carboxylate (9), the key intermediate for 6- fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl-1-piperazinyl]- 4-oxo-4H-[1,3]thiazeto[3,2-α]quinoline-3-carboxylic acid (2), NM441, was developed. The crucial points of this synthetic mute are the chlorination of ethyl 4-acetoxy-2-(ethylthio)-6,7-difluoroquinoline-3-carboxylate (12) and the subsequent deacetylation of the resulting 2-(1-chloroethyl)thio compound 13 followed by the intramolecular cyclization reaction. Versatile new syntheses of 2-thioquinoline skeleton were also developed. The first mute includes the intramolecular cyclization of the N,S-acetal 22 which was prepared from 2,4,5-trifluorobenzoic acid in three steps. The second one contains the regioselective attack of lithium enolate of ethyl acetate to the novel 2-(methylthio)-4H-[3,1]benzothiazine-4-one 29 at the 4-position followed by the intramolecular cyclization of the resulting β-ketoester 30.
- Matsuoka,Segawa,Makita,Ohmachi,Kashima,Nakamura K.-,Hattori,Kitano,Kise
-
p. 1773 - 1779
(2007/10/03)
-
- STUDIES ON PYRIDONECARBOXYLIC ACIDS. 1. SYNTHESIS AND ANTIBACTERIAL EVALUATION OF 7-SUBSTITUTED-6-HALO-4-OXO-4H-THIAZETOQUINOLINE-3-CARBOXYLIC ACIDS
-
A series of thiazetoquinoline-3-carboxylic acids and their esters were prepared and evaluated for antibacterial activity.The derivatives with a hydrogen or methyl group at C-1, fluorine at C-6, and piperazinyl or 4-methyl-1-piperazinyl group at C-7 showed superior in vitro antibacterial activity, and the derivatives with 4-methyl-1-piperazinyl group at C-7 had potent in vivo activity.Compound 29a (NM394) showed excellent in vitro antibacterial activity and low toxicity but poor absorption from the gastrointestinal tract.Compound 29ee (NM441), an N- derivative of 29a, was found to possess a favorable pharmacokinetic profile and oral activity superior to that of ciprofloxacin in experimental animals.
- Segawa, Jun,Kitano, Masahiko,Kazuno, Kenji,Matsuoka, Masato,Shirahase, Ichiro,et al.
-
p. 4727 - 4738
(2007/10/02)
-
- 7[4-(5 methyl-2-oxo-1,3-dioxalen-4-yl)methyl 1-piperzinyl]-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acids
-
Quinolinecarboxylic acid derivatives of the formula (I) STR1 and pharmaceutically acceptable salts thereof, wherein R1 is hydrogen, straight or branch chain lower alkyl or phenyl unsubstituted or substituted by one or more halo moieties; R
- -
-
-
- Substituted thiazetoquinoline-3-carboxylic acids and pharmaceutically acceptable salts thereof
-
Anti-bacterial and anti-fungal compounds of formula I and pharmaceutically acceptable salts thereof: STR1 in which R1 is hydrogen, alkyl or substituted or unsubstituted phenyl; R2 is hydrogen, alkyl, alkoxy, hydroxy, halgen, nitro or substituted or unsubstituted amino; R3 is hydrogen or substituted or unsubstituted alkyl; R4 and R5 are the same or different and are alkyl or hydroxyalkyl or R4 and R5 together with the nitrogen atom to which they are attached form an unsubstituted or substituted heterocyclic ring having the depicted nitrogen atom as the sole heteroatom or which may have nitrogen, oxygen or sulphur atoms as additional heteroatoms; and X is halogen.
- -
-
-
