Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-02-24
2000-10-24
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514 81, 544337, 544354, A61K 31498, C07D24144
Patent
active
061368059
DESCRIPTION:
BRIEF SUMMARY
The invention relates to quinoxalinedione derivatives, their production and use in pharmaceutical agents.
It is known that quinoxaline derivatives have an affinity to the quisqualate receptors and, because of the affinity, are suitable as pharmaceutical agents for the treatment of diseases of the central nervous system.
The compounds according to the invention have formula I ##STR2## in which
R.sup.1 means--(CH.sub.2).sub.n --CR.sup.2 H--(CH.sub.2).sub.m --Z and
R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are the same or different and mean hydrogen, C.sub.1-6 alkyl, in which optionally one or more hydrogen atoms are replaced by halogen atoms, nitro, halogen, NR.sup.9 R.sup.10, cyano, SO.sub.p R.sup.11, SO.sub.2 NR.sup.12 R.sup.13, SO.sub.3 H, SO.sub.3 C.sub.1-6 alkyl or OR.sup.14 whereby
R.sup.2 means hydrogen or --(CH.sub.2).sub.q --R.sup.3,
R.sup.3 means hydrogen, hydroxy, C.sub.1-6 alkoxy or NR.sup.15 R.sup.16,
n, m or q each mean 0, 1, 2 or 3,
Z means POXY, OPOXY, SO.sub.2 R.sup.17, COR.sup.18, halogen, cyano or tetrazole,
R.sup.11 means H, C.sub.1-6 alkyl, phenyl,
p means 0, 1 or 2,
R.sup.12 and R.sup.13, independently or one another, mean hydrogen or C.sub.1-4 alkyl,
R.sup.14 means A--R.sup.19 or a C.sub.6-12 aryl or hetaryl radical, which can be substituted with halogen, C.sub.1-6 alkoxy, hydroxy, cyano, NR.sup.20 R.sup.21, C.sub.1-6 alkyl optionally substituted with halogen and/or COR.sup.22, and
A means straight-chain or branched, saturated or unsaturated alkylene with C.sub.1-20 carbon atoms, in which one or more carbon atoms can be replaced by O, S and/or NR.sup.26 and which can be substituted in one or more places with halogen, and
R.sup.19 means hydrogen, NR.sup.24 R.sup.25, halogen, C.sub.1-6 alkyl, which optionally is substituted in several places with halogen, C.sub.1-6 alkoxy, COR.sup.23, CN or a C.sub.6-12 aryl or hetaryl radical, which can be substituted with halogen, C.sub.1-6 alkoxy, hydroxy, cyano, NR.sup.20 R.sup.21, C.sub.1-6 alkyl, which can be substituted with halogen, and/or COR.sup.22, and
R.sup.18 means hydrogen, C.sub.1-4 alkyl, hydroxy, C.sub.1-6 alkoxy or NR.sup.27 R.sup.28,
R.sup.17, R.sup.22 and R.sup.23 mean hydroxy, C.sub.1-6 alkoxy or NR.sup.29 R.sup.30,
R.sup.26 means hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkanoyl,
X and Y are the same or different and mean hydroxy, C.sub.1-6 alkoxy, C.sub.1-4 alkyl or NR.sup.27 R.sup.28,
R.sup.9 R.sup.10, R.sup.20 and R.sup.21 and/or R.sup.25 and R.sup.24 are the same or different and mean hydrogen, CO--C.sub.1-6 alkyl, phenyl or C.sub.1-6 alkyl, which can optionally be substituted with C.sub.1-4 alkoxy or an amino group optionally mono- or disubstituted with C.sub.1-4 alkyl, or together with the nitrogen atom form a 5- or 7-membered saturated heterocycle that can contain another N, S or O atom and can be substituted or form an unsaturated 5-membered heterocycle that can contain 1-3 N atoms and can be substituted,
R.sup.15 and R.sup.16, R.sup.27 and R.sup.28, R.sup.29 and R.sup.30 are the same or different and mean hydrogen, C.sub.1-4 alkyl, phenyl or together with the nitrogen atom form a 5- or 7-membered saturated heterocycle that can contain another oxygen, sulfur or nitrogen atom and can be substituted or form an unsaturated 5-membered heterocycle that can contain 1-3 N atoms and can be substituted, R.sup.14 does not mean H or C.sub.1-6 alkyl optionally substituted in 1-3 places with halogens.
The compounds of general formula I also contain the possible tautomeric forms and comprise the E or Z isomers or, if a chiral center is present, the racemates or enantiomers.
The substituents are preferably in 6- and/or 7-position.
Alkyl is defined respectively as a straight-chain or branched alkyl radical, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl.
Halogen is defined respectively as fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine.
As aryl radicals R.sup.14 and R.sup.19, for example, naphthyl, biphenylyl and especially phenyl can be mentioned.
Hetar
REFERENCES:
patent: 5166155 (1992-11-01), Jorgensen et al.
Epperson et al, Bioorganic & Medicinal Chemistry Letters, vol.3,p.2801-2804, 1993.
Francis et al.,Journal of Neurochemistry,vol.60, p. 1589-1604, 1993.
McBurney,Neurobiology of Aging,vol.15,p.271-273, 1994.
Huth Andreas
Kruger Martin
Neuhaus Roland
Ottow Eckhard
Schneider Herbert
Raymond Richard L.
Scnering Aktiengesellschaft
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