Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-06-20
1998-12-15
Bernhardt, Emily
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514250, 544344, 544354, A61K 31495, C07D40114, C07D40304
Patent
active
058497439
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to quinoxaline-2,3(1H),4H)-diones of the general formula I ##STR2## and their tautomeric and enantiomeric forms and their physiologically tolerated salts, where the variables have the following meanings: identical or different substituents phenyl, cyclopentyl, cyclohexyl, --COR.sup.3, --CO--O--R.sup.3, --CO--NH--R.sup.3, OR.sup.3, ##STR3## where R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, and where the cycloaliphatic radical or phenyl ring contained in R.sup.1 or representing R.sup.1 can carry up to three identical or different substituents from the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro, cyano, --CO--OR.sup.5, --CO--NH--R.sup.5, --OH, ##STR4## and where R.sup.5 has, independently of R.sup.3, the same meanings as R.sup.3, ##STR5## where R.sup.6 is one of the following radicals: ##STR6## where R.sup.7 is hydrogen, branched or linear C.sub.1 -C.sub.4 -alkyl which can also carry one or two phenyl rings, and R.sup.8 is one of the radicals ##STR7## where R.sup.10 is hydrogen and a branched or linear C.sub.1 -C.sub.4 -alkyl which can also carry one or two phenyl rings, which can also carry one or two phenyl rings, and ##STR8## m is an integer from 1 to 4, p and q are, independently of one another, a number from 0 to 4, R.sup.10, and the pyridine ring representing R.sup.8 and R.sup.9 where appropriate or present in R.sup.9 where appropriate, can be substituted by halogen, --NO.sub.2, --CF.sub.3, --CN, --OH, --OCH.sub.3, --NH.sub.2, --NHCOCH.sub.3, --OCF.sub.3, --CO.sub.2 --(C.sub.1 -C.sub.4 -alkyl), --CO.sub.2 H, --CONH.sub.2, --CONH--(C.sub.1 -C.sub.4 -alkyl), --CH.sub.2 --NHCOCF.sub.3, --CH.sub.2 NH.sub.2 and C.sub.1 -C.sub.4 -alkyl, -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl, trichloromethyl, trifluoromethoxy, trichloromethoxy, fluorine, chlorine, bromine, iodine, nitro and cyano, and a fused-on benzene ring which in turn can carry up to two of the radicals mentioned above for R (without the fused-on benzene ring), and
The invention also relates to the use of compounds I as drugs for human and veterinary medicine.
Derivatives of quinoxaline-2,3(1H,4H)-dione ##STR9## R', R", R'"=substituents have been proposed in several publications for the treatment of disorders of the central nervous system and as hypnotics and sedatives. For example, EP-A315959, EP-A374534 and EP-A377112 describe compounds in which R'" is halogen, nitro, cyano, hydroxyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy and the groups --SO.sub.2 H, SO.sub.2 R.sup.x, --SONH.sub.2, --SO.sub.2 NHR.sup.x and SO.sub.2 NR.sub.2.sup.x, where R.sup.x is C.sub.1 -C.sub.4 -alkyl, and a fused-on benzene ring which may also be substituted. In U.S. Pat. No. 3,992,378, the substituent R'" is C.sub.1 -C.sub.2 -fluoroalkyl, and in PCT 91/13878, besides halogen and nitro, it is C.sub.1 -C.sub.6 -alkyl, alkoxy, aryloxy and aralkoxy.
Furthermore, EP-A 8864 also mentions piperidinyl, pyrrolidinyl and piperazinyl as substituents R'". Compounds of the latter type are also disclosed in Ind. J. Chem. 28B (1989) 888-890; in an examination, which is also mentioned herein, of their utilizability as helminthicides for controlling hookworms and tapeworms, these compounds proved to be unsuitable.
Imidazolyl- and triazolylquinoxalines have been claimed in WO92/07847, specifically likewise as inhibitors of glutamate receptors.
The known compounds have the disadvantage that they are able to overcome the blood-brain barrier only poorly, if at all, and therefore their effect on the central nervous system is unsatisfactory.
It is an object of the present invention to provide novel and more effective quinoxaline-2,3(1H,4H)-diones.
We have found that this object is achieved by the compounds I defined at the outset.
We have also found various processes, which are described in detail hereinafter, for preparing the quinoxaline-2,3(1H,4H)-diones I and their use as drugs for human and veterinary medicine.
In p
REFERENCES:
patent: 3992378 (1976-11-01), St. Clair et al.
Lees, Pharmacology and Pathophysiology 5, pp. 51-74 (1996).
Lubisch et al., Chemical Abstracts, vol. 123, No. 256765 (Abstract for DE 4340045 (Jun. 1, 1995).
Sastry et al Indian J. of Chem. B, 28, 1989-pp. 888-890.
Chem. Abstr. DE 4217952 (May 30, 1992), Lubisch et al.
Behl Berthold
Hofmann Hans Peter
Lubisch Wilfried
BASF - Aktiengesellschaft
Bernhardt Emily
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