Title:
(S)-BENZOQUINOLIZINE CARBOXYLIC ACIDS AND THEIR USE AS ANTIBACTERIAL AGENTS
Document Type and Number:
WIPO Patent Application WO2000068229
Kind Code:
A3
Abstract:
The present invention relates to S-(-)-optically pure benzoquinolizine carboxylic acid of formula I, and their pharmaceutically acceptable salts, derivatives, pseudopolymorphs, and hydrates, substantially free of their R-(+)-isomers, to processes for their preparation and to pharmaceutical compositions comprising an active compound of the invention. The compounds have excellent antibacterial activity. The compounds and compositions can be used for the treatment of local and systemic bacterial infections, diseases and disorders caused by antibiotic-sensitive and antibiotic-resistant microbial strains, without the concomitant liability of adverse effects associated with the racemic mixture of the active compound of the invention.
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Inventors:
PATEL M V (IN)
GUPTE S V (IN)
CHUGH Y (IN)
SAOJI D G (IN)
AGARWAL S K (IN)
DE SOUZA N J (IN)
KHORAKIWALA H F (IN)
GUPTE S V (IN)
CHUGH Y (IN)
SAOJI D G (IN)
AGARWAL S K (IN)
DE SOUZA N J (IN)
KHORAKIWALA H F (IN)
Application Number:
PCT/IN2000/000054
Publication Date:
March 22, 2001
Filing Date:
May 08, 2000
Export Citation:
Assignee:
PATEL M V (IN)
GUPTE S V (IN)
CHUGH Y (IN)
SAOJI D G (IN)
AGARWAL S K (IN)
SOUZA N J DE (IN)
KHORAKIWALA H F (IN)
GUPTE S V (IN)
CHUGH Y (IN)
SAOJI D G (IN)
AGARWAL S K (IN)
SOUZA N J DE (IN)
KHORAKIWALA H F (IN)
International Classes:
A61K31/4745; C07C279/14; C07D455/04; (IPC1-7): A61K31/4745; A61P31/04; A61P31/06; C07D455/04
Other References:
DATABASE WPI Week 198838, Derwent World Patents Index; AN 1988-266538, XP002131774
DATABASE WPI Week 199404, Derwent World Patents Index; AN 1994-031789, XP002131775
HASHIMOTO, K. ET AL: "A practical synthesis of (S)-(-)-nadifloxacin: Novel acid-catalyzed racemization of tetrahydroquinaldine derivative", CHEM. PHARM. BULL., vol. 44, no. 4, 1996, pages 642 - 645, XP000877125
TAKAHASHI, N. ET AL: "Reduction of in vitro clastogenicity induced by the mixture of optical isomers of nadifloxacin during storage", ARZNEIMITTEL-FORSCHUNG, vol. 45, no. 2, 1995, pages 195 - 197, XP000877120
MORITA, S. ET AL: "An efficient synthesis of a key intermediate towards (S)-(-)-nadifloxacin", TETRAHEDRON ASYMMETRY, vol. 6, no. 1, 1995, pages 245 - 254, XP004048518
KIDO, M. ET AL: "Crystal structures of nadifloxacin anhydride and its hemihydrate", CHEM. PHARM. BULL., vol. 42, no. 4, 1994, pages 872 - 876, XP000960588
MORITA, S. ET AL: "Synthesis and antibacterial activity of the metabolites of 9-fluoro-6,7-dihydro-8(4-hydroxy-1-piperidyl)-5-methyl-1-oxo-1H,5H-benzo(i,j)quinolizine-2-carboxylic acid (OPC-7251)", CHEM. PHARM. BULL., vol. 38, no. 7, 1990, pages 2027 - 2029, XP000877122
ISHIKAWA, H. ET AL: "Studies on antibacterial agents. I. Synthesis of substituted 6,7-dihydro-1-oxo-1H,5H-benzo(i,j)-quinolizine-2-carboxylic acids", CHEM. PHARM. BULL., vol. 37, no. 8, 1989, pages 2103 - 2108, XP000877246
NISHIJIMA, S. ET AL: "Activiy of eight fluoroquinolones against both methicillin-susceptible and -resistant Staphylococcus aureus isolated from skin infections", THE JOURNAL OF DERMATOLOGY, vol. 22, no. 2, 1995, pages 153 - 155, XP000884341
NISHIJIMA, S. ET AL: "Sensitivity of Staphylococcus aureus, isolated from skin infections in 1994, to 19 antimicrobial agents", THE JOURNAL OF INTERNATIOAL MEDICAL RESEARCH, vol. 23, no. 5, 1995, pages 328 - 334, XP000884323
NISHIJIMA, S. ET AL: "Activity of nadifloxacin against methicilllin resistant Staphylococcus aureus isolated from skin infections: Comparative study with seven other fluoroquinolones", THE JOURNAL OF INTERNATIONAL MEDICAL RESEARCH, vol. 24, no. 1, 1996, pages 12 - 16, XP000884325
DATABASE WPI Week 198327, Derwent World Patents Index; AN 1983-702951, XP002131776
DATABASE WPI Week 199404, Derwent World Patents Index; AN 1994-031789, XP002131775
HASHIMOTO, K. ET AL: "A practical synthesis of (S)-(-)-nadifloxacin: Novel acid-catalyzed racemization of tetrahydroquinaldine derivative", CHEM. PHARM. BULL., vol. 44, no. 4, 1996, pages 642 - 645, XP000877125
TAKAHASHI, N. ET AL: "Reduction of in vitro clastogenicity induced by the mixture of optical isomers of nadifloxacin during storage", ARZNEIMITTEL-FORSCHUNG, vol. 45, no. 2, 1995, pages 195 - 197, XP000877120
MORITA, S. ET AL: "An efficient synthesis of a key intermediate towards (S)-(-)-nadifloxacin", TETRAHEDRON ASYMMETRY, vol. 6, no. 1, 1995, pages 245 - 254, XP004048518
KIDO, M. ET AL: "Crystal structures of nadifloxacin anhydride and its hemihydrate", CHEM. PHARM. BULL., vol. 42, no. 4, 1994, pages 872 - 876, XP000960588
MORITA, S. ET AL: "Synthesis and antibacterial activity of the metabolites of 9-fluoro-6,7-dihydro-8(4-hydroxy-1-piperidyl)-5-methyl-1-oxo-1H,5H-benzo(i,j)quinolizine-2-carboxylic acid (OPC-7251)", CHEM. PHARM. BULL., vol. 38, no. 7, 1990, pages 2027 - 2029, XP000877122
ISHIKAWA, H. ET AL: "Studies on antibacterial agents. I. Synthesis of substituted 6,7-dihydro-1-oxo-1H,5H-benzo(i,j)-quinolizine-2-carboxylic acids", CHEM. PHARM. BULL., vol. 37, no. 8, 1989, pages 2103 - 2108, XP000877246
NISHIJIMA, S. ET AL: "Activiy of eight fluoroquinolones against both methicillin-susceptible and -resistant Staphylococcus aureus isolated from skin infections", THE JOURNAL OF DERMATOLOGY, vol. 22, no. 2, 1995, pages 153 - 155, XP000884341
NISHIJIMA, S. ET AL: "Sensitivity of Staphylococcus aureus, isolated from skin infections in 1994, to 19 antimicrobial agents", THE JOURNAL OF INTERNATIOAL MEDICAL RESEARCH, vol. 23, no. 5, 1995, pages 328 - 334, XP000884323
NISHIJIMA, S. ET AL: "Activity of nadifloxacin against methicilllin resistant Staphylococcus aureus isolated from skin infections: Comparative study with seven other fluoroquinolones", THE JOURNAL OF INTERNATIONAL MEDICAL RESEARCH, vol. 24, no. 1, 1996, pages 12 - 16, XP000884325
DATABASE WPI Week 198327, Derwent World Patents Index; AN 1983-702951, XP002131776
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