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DR ANTHONY MELVIN CRASTO, WORLDDRUGTRACKER

Clinafloxacin from kyorin

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Apr 052014
 

File:Clinafloxacin.png

Clinafloxacin

7-(3-Aminopyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid

7-(3-Amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-l,4-dihydro-4-oxo-3-quinolinecarboxylic acid

(±)-7-(3-Amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

105956-99-8  cas no

Clinafloxacin (INN) is a fluoroquinolone antibiotic. Its use is associated with phototoxicity and hypoglycaemia.[1]

Clinafloxacin is a novel quinolone with wide activity against the plethora of microorganisms encountered in intraabdominal infections.

Clinafloxacin is a chlorofluoroquinolone with excellent bioavailability and activity against gram-positive, gram-negative, and anaerobic pathogens . Typical MICs for α-streptococci are 0.06–0.12 µg/mL . MIC90 values for methicillin-resistant Staphylococcus aureus (MRSA) average 1.0 µg/mL. The MIC90 for enterococci is typically 0.5 µg/mL . Both intravenous and oral formulations have been developed . Several studies have demonstrated the efficacy of clinafloxacin monotherapy for serious infections  Clinafloxacin was also active in animal models of endocarditis, including endocarditis due to ciprofloxacin-resistant S. aureus infection .

Clinafloxacin HCl, CI-960 HCl, 105956-99-8, Clinafloxacin hydrochloride (USAN), Clinafloxacin hydrochloride [USAN], AC1L1SJB,
Molecular Formula: C17H18Cl2FN3O3   Molecular Weight: 402.247523
……………………………………..
EP 0195316
http://www.google.com/patents/EP0195316A1?cl=en
preparation process for the compound of the invention.

Figure imgb0002
    Example 28 7-(3-Amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-l,4-dihydro-4-oxo-3-quinolinecarboxylic acid

  • A mixture of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-di- hydro-4-oxo-3-quinolinecarboxylic acid (0.6 g), anhydrous acetonitrile (6 ml), 3-aminopyrrolidine (0.35 g) and DBU (0.31 g) was refluxed for an hour. Then, 3-aminopyrrolidine (0.2 g) was more added and further refluxed for 2 hours. After cooling, the resulting precipitate was collected by filtration, dissolved in water (9 ml) containing sodium hydroxide (0.12 g) and neutralized with acetic acid. The resulting precipitate was collected by filtration and washed with water and acetonitrile successively to give the title compound (0.52 g) as colorless powder, mp 237-238 °C (decompd.).
  • Analysis (%) for C17H17ClFN3O3·H2O, Calcd. (Found): C, 53.20 (52.97); H, 4.99 (4.62); N, 10.95 (10.83).

Example 29 7-(3-Amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-l,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride

  • To a suspension of 7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (100 mg) in ethanol (2 ml) was added 0.2 ml of ethanol solution of hydrogen chloride (7.0 mmol HC1/ml) and then the mixture was concentrated. The resulting residue was recrystallized from methanol to give the title compound (79 mg) as light yellow prisms, mp 263-265 °C (decompd.).
  • Analysis (%) for C17H17ClFN3O3.HCl, Calcd. (Found): C, 50.76 (50.50); H, 4.51 (4.44); N, 10.45 (10.38).

…………………..

J. Med. Chem., 23, 1358 (1980)

Figure imgb0024
  • structural formula D

    Figure imgb0028

    may be readily prepared from the known starting material methyl 5-oxo-l-(phenylmethyl)-3-pyrrolidinecarboxylate, A, [J. Org. Chem., 26, 1519 (1961)] by the following reaction sequence.

    Figure imgb0029
  • The compound wherein R3 is hydrogen, namely 3-pyrrolidinemethanamine, has been reported in J. Org. Chem., 26, 4955 (1961).
Journal of Medicinal Chemistry, 1988 ,  vol. 31, p. 983 – 991

 

References

  1. Rubinstein, E. (2001). “History of quinolones and their side effects.”. Chemotherapy. 47 Suppl 3: 3–8; discussion 44–8.doi:10.1159/000057838PMID 11549783.

 

EP0106489A2 * Sep 6, 1983 Apr 25, 1984 Warner-Lambert Company Antibacterial agents
EP0153163A2 * Feb 15, 1985 Aug 28, 1985 Warner-Lambert Company 7-Substituted-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids; 7-substituted-1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acids; their derivatives; and a process for preparing the compounds
BE899399A1 * Title not available
GB2057440A * Title not available

 

 

Examples of
reported trade
names for products
containing the 6-
6-Fluoroquinolin- fluoroquinolin-
4(1H)-one 4(1H)-one Structure
amifloxacin
Figure US20120046259A1-20120223-C00019
balofloxacin
Figure US20120046259A1-20120223-C00020
ciprofloxacin Cipro®, Ciprobay, & Ciproxin
Figure US20120046259A1-20120223-C00021
clinafloxacin
Figure US20120046259A1-20120223-C00022
danofloxacin Advocin & Advocid
Figure US20120046259A1-20120223-C00023
difloxacin Dicural® & Vetequinon
Figure US20120046259A1-20120223-C00024
enrofloxacin Baytril®
Figure US20120046259A1-20120223-C00025
fleroxacin Megalone
Figure US20120046259A1-20120223-C00026
flumequine Flubactin
Figure US20120046259A1-20120223-C00027
garenoxacin
Figure US20120046259A1-20120223-C00028
gatifloxacin Tequin® & Zymar®
Figure US20120046259A1-20120223-C00029
grepafloxacin Raxar
Figure US20120046259A1-20120223-C00030
ibafloxacin
Figure US20120046259A1-20120223-C00031
levofloxacin Levaquin®, Gatigol, Tavanic, Lebact, Levox, & Cravit
Figure US20120046259A1-20120223-C00032
lomefloxacin Maxaquin®
Figure US20120046259A1-20120223-C00033
marbofloxacin Marbocyl® & Zenequin
Figure US20120046259A1-20120223-C00034
moxifloxacin Avelox® & Vigamox®
Figure US20120046259A1-20120223-C00035
nadifloxacin Acuatin, Nadoxia, & Nadixa
Figure US20120046259A1-20120223-C00036
norfloxacin Noroxin®, Lexinor, Quinabic, & Janacin
Figure US20120046259A1-20120223-C00037
ofloxacin Floxin®, Oxaldin, & Tarivid
Figure US20120046259A1-20120223-C00038
orbifloxacin Orbax® & Victas
Figure US20120046259A1-20120223-C00039
pazufloxacin
Figure US20120046259A1-20120223-C00040
pefloxacin
Figure US20120046259A1-20120223-C00041
pradofloxacin
Figure US20120046259A1-20120223-C00042
prulifloxacin
Figure US20120046259A1-20120223-C00043
rufloxacin Uroflox
Figure US20120046259A1-20120223-C00044
sarafloxacin Floxasol, Saraflox, Sarafin
Figure US20120046259A1-20120223-C00045
sitafloxacin
Figure US20120046259A1-20120223-C00046
sparfloxacin Zagam
Figure US20120046259A1-20120223-C00047
temalioxacin Omniflox
Figure US20120046259A1-20120223-C00048

 

 

enoxacin Penetrex & Enroxil
Figure US20120046259A1-20120223-C00061
gemifloxacin Factive
Figure US20120046259A1-20120223-C00062
tosufloxacin
Figure US20120046259A1-20120223-C00063
trovafloxacin Trovan
Figure US20120046259A1-20120223-C00064
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