Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1989-05-31
1991-08-13
Dees, Jose G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544100, 546156, 546170, 548537, A61K 3147
Patent
active
050396838
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to azetidinyl quinolone carboxylic acids and esters, antibacterial compositions containing said compounds, methods of using said compounds, and methods of preparing said compounds.
U.S. Pat. No. 4,563,459 refers to 1-cyclopropyl-1,4-dihydro-4-oxo-quinoline carboxylic acids wherein the moiety in the 6-position is hydrogen, fluorine, chlorine, bromine or nitro and the moiety in the 7-position is hydrogen, chlorine, fluorine or NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 represent separate groups or, together with the nitrogen atom on which they are positioned, may form a 5-membered or 6-membered heterocyclic ring.
Japanese Kokai SHO 60-89480 refers to compounds of the formula ##STR2## wherein Z is nitrogen or CH; X is halogen; R.sup.1 and R.sup.2 are hydrogen, acyl or lower alkyl; are disclosed.
SUMMARY OF THE INVENTION
The present invention relates to compounds of the formula ##STR3## wherein R.sup.1 is hydrogen, alkyl of 1 to 6 carbon atoms, or NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently selected from hydrogen and alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation;
R.sup.2 is hydrogen, hydroxy, alkanoylamino of 1 to 6 carbon atoms, morpholino, halogen, hydroxyalkyl of 1 to 6 carbon atoms, COOR.sup.6 wherein R.sup.6 is alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation, alkoxy of 1 to 6 carbon atoms, NR.sup.7 R.sup.8 wherein R.sup.7 and R.sup.8 are independently selected from alkyl of 1 to 6 carbon atoms, alkanoyl of 1 to 6 carbon atoms, hydrogen, alkoxy of 1 to 6 carbon atoms, aminoalkyl of 2 to 6 carbon atoms, alkylaminoalkyl wherein each alkyl group is independently selected from alkyl groups having 2 to 6 carbon atoms, and dialkylaminoalkyl wherein each alkyl group is independently selected from alkyl groups having one to six carbon atoms, with the proviso that only one of R.sup.7 and R.sup.8 may be alkoxy; and
R.sup.3 is hydrogen, alkyl of 1 to 6 carbon atoms, phenyl or substituted phenyl wherein the phenyl group may be substituted with one or two substituents selected from the group consisting of alkyl of 1 to 6 carbon atoms, nitro, amino, halogen (e.g., fluoro, chloro, bromo, or iodo), haloalkyl of 1 or 2 carbon atoms and up to 5 halogen atoms (e.g., fluoro, chloro, bromo or iodo), hydroxyl, or alkoxy of 1 to 6 atoms and pharmaceutically acceptable acid addition salts thereof. The compounds have antibacterial activity.
The present invention also relates to pharmaceutical compositions comprising a pharmaceutically acceptable carrier or diluent and a compound of the formula I or a pharmacutically acceptable salt thereof in an antibacterially effective amount. The present invention also provides a method of treating an animal, including a human being, having a bacterial disease which comprises administering to the animal (e.g., mammal, bird or fish) an antibacterially effective amount of a compound of the formula I or a pharmaceutically acceptable acid addition salt thereof. The present invention also relates to methods of preparing the compounds of formula I.
The compounds of the invention include racemic mixtures and optical isomers. Preferred compounds of the invention are those of formula I wherein R.sup.1 is hydrogen, a pharmaceutically acceptable cation (e.g., sodium or potassium), or amino. Other preferred compounds are those of formula I wherein R.sup.2 is hydrogen, amino, hydroxy, hydroxymethyl, acetylamino or COOR.sup.6, wherein R.sup.6 is hydrogen, a pharmaceutically acceptable cation, or amino. Other preferred compounds are those of formula I wherein R.sup.3 is hydrogen or phenyl. More preferred compounds are those wherein R.sup.1 is hydrogen, a pharmaceutically acceptable cation, or amino; R.sup.2 is hydrogen, amino, or hydroxy and R.sup.3 is hydrogen or phenyl. Specific preferred compounds are as follows: oxylic acid; oline-carboxylic acid; ine-carboxylic acid; and -quinoline-carboxylic acid.
The pharmaceutical compositions of the present invention preferably contain the above pre
REFERENCES:
patent: 4665079 (1987-05-01), Culbertson et al.
patent: 4670444 (1987-06-01), Grohe et al.
Iwata et al., Chemical Abstracts, vol. 10, p. 701, 135095v.
Egawa et al., J. Med. Chem., 27, 1543-8 (1984).
Cair Deborah D.
Dees Jos,e G.
Fedowich Valerie M.
Ginsburg Paul H.
Pfizer Inc.
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