US 5,849,744 AGranted

Pyrrolyl tetrahydrobenzoquinoxaline diones, their preparation and use as glutamate receptor antagonist

AssigneeBASF SE

InventorsWilfried Lubisch, Michael Vierling, Berthold Behl, Hans Peter Hofmann

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Abstract

Pyrrolyltetrahydrobenzoquinoxalinediones of the formula I ##STR1## and their tautomeric and isomeric forms, and their physiologically tolerated salts, in which the variables have the meanings stated in the description, and the preparation thereof are described. The novel compounds are antagonists of the glutamate receptor subtypes and are thus suitable for controlling various diseases.

Claims4

Dependent claims

A pyrrolyltetrahydrobenzoquinoxalinedione of the formula I ##STR75## and its tautomeric forms, and its physiologically tolerated salts, in which the variables have the following meanings:

R.sup.1 hydrogen;
an aliphatic radical which has 1 to 6 carbon atoms and can carry one or two different substituents of the formulae --COOR.sup.4, --CONHR.sup.4, --CO--R.sup.4, --OR.sup.4, --NHR.sup.4, --NH--CO--R.sup.4, --CONHSO.sub.2 R.sup.4 or NHSO.sub.2 R.sup.4 where R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, where the phenyl rings in R.sup.4 can be substituted by 1, 2 or 3 of the following substituents:
C.sub.1 -C.sub.4 -alkyl, CF.sub.3, C.sub.1 -C.sub.4 -alkoxy, F.sub.3 CO--, halogen, nitro, CN, --OH, --CONHR.sup.5 and/or --COOR.sup.5 (R.sup.5 hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl);
--O--R.sup.6 where R.sup.6 can be hydrogen or an aliphatic radical which has up to 4 carbon atoms and can carry one of the following radicals:
--COOR.sup.4, --CONHR.sup.4, --NHCOR.sup.4, --NHSO.sub.2 R.sup.4, --OH or phenyl,
R.sup.2 hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,
R.sup.3 hydrogen or the radical --(CH.sub.2).sub.m --R.sup.7, where m is 0, 1, 2, 3 or 4, and R.sup.7 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, phenylsulfonyl, NO.sub.2, CN, --COO--(CH.sub.2).sub.n --R.sup.8, --CONHSO.sub.2 R.sup.4, --CONH--(CH.sub.2).sub.n --R.sup.8, --CO--R.sup.8, --CH.dbd.CH--CONHR.sup.8, --CH.dbd.CH--COOR.sup.8, --CH.dbd.NOR.sup.8, --CH.sub.2 --NR.sup.8 R.sup.9, CH.sub.2 NH--CY--(CH.sub.2).sub.n R.sup.9, CH.sub.2 NH--CY--X--(CH.sub.2).sub.n --R.sup.9, CH.sub.2 NH--CO--CF.sub.3, CH.sub.2 NH--SO.sub.2 --R.sup.9 ##STR76## where X and Y are, independently of one another, oxygen or NH, n is 0, 1, 2, 3 or 4, R.sup.8 is hydrogen or linear and branched C.sub.1 -C.sub.4 -alkyl which can be substituted by one or two phenyl or pyridyl radicals, and R.sup.9 is hydrogen, linear or branched C.sub.1 -C.sub.6 -alkyl, phenyl or pyridyl, where all the phenyl or pyridyl radicals contained in R.sup.8 and R.sup.9 can carry one or two of the following radicals:
O--C.sub.1 -C.sub.4 -alkyl, F, Cl, Br, I, C.sub.1 -C.sub.4 -alkyl, NO.sub.2, CF.sub.3, --COOR.sup.5, --CONHR.sup.5, NH.sub.2, CN, --SO.sub.2 Ph, --NHSO.sub.2 R.sup.5, --NHCOR.sup.5, OH, --SO.sub.2 --C.sub.1 -C.sub.4 -alkyl, --NHCOCF.sub.3, --SO.sub.2 R.sup.5 and --OCF.sub.3.

5 more elements

Dependencies are inferred from the claim text.

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Abstract

A pyrrolyltetrahydrobenzoquinoxalinedione of the formula I ##STR75## and its tautomeric forms, and its physiologically tolerated salts, in which the variables have the following meanings:

R.sup.1 hydrogen;
an aliphatic radical which has 1 to 6 carbon atoms and can carry one or two different substituents of the formulae --COOR.sup.4, --CONHR.sup.4, --CO--R.sup.4, --OR.sup.4, --NHR.sup.4, --NH--CO--R.sup.4, --CONHSO.sub.2 R.sup.4 or NHSO.sub.2 R.sup.4 where R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, where the phenyl rings in R.sup.4 can be substituted by 1, 2 or 3 of the following substituents:
C.sub.1 -C.sub.4 -alkyl, CF.sub.3, C.sub.1 -C.sub.4 -alkoxy, F.sub.3 CO--, halogen, nitro, CN, --OH, --CONHR.sup.5 and/or --COOR.sup.5 (R.sup.5 hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl);
--O--R.sup.6 where R.sup.6 can be hydrogen or an aliphatic radical which has up to 4 carbon atoms and can carry one of the following radicals:
--COOR.sup.4, --CONHR.sup.4, --NHCOR.sup.4, --NHSO.sub.2 R.sup.4, --OH or phenyl,
R.sup.2 hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,
R.sup.3 hydrogen or the radical --(CH.sub.2).sub.m --R.sup.7, where m is 0, 1, 2, 3 or 4, and R.sup.7 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, phenylsulfonyl, NO.sub.2, CN, --COO--(CH.sub.2).sub.n --R.sup.8, --CONHSO.sub.2 R.sup.4, --CONH--(CH.sub.2).sub.n --R.sup.8, --CO--R.sup.8, --CH.dbd.CH--CONHR.sup.8, --CH.dbd.CH--COOR.sup.8, --CH.dbd.NOR.sup.8, --CH.sub.2 --NR.sup.8 R.sup.9, CH.sub.2 NH--CY--(CH.sub.2).sub.n R.sup.9, CH.sub.2 NH--CY--X--(CH.sub.2).sub.n --R.sup.9, CH.sub.2 NH--CO--CF.sub.3, CH.sub.2 NH--SO.sub.2 --R.sup.9 ##STR76## where X and Y are, independently of one another, oxygen or NH, n is 0, 1, 2, 3 or 4, R.sup.8 is hydrogen or linear and branched C.sub.1 -C.sub.4 -alkyl which can be substituted by one or two phenyl or pyridyl radicals, and R.sup.9 is hydrogen, linear or branched C.sub.1 -C.sub.6 -alkyl, phenyl or pyridyl, where all the phenyl or pyridyl radicals contained in R.sup.8 and R.sup.9 can carry one or two of the following radicals:
O--C.sub.1 -C.sub.4 -alkyl, F, Cl, Br, I, C.sub.1 -C.sub.4 -alkyl, NO.sub.2, CF.sub.3, --COOR.sup.5, --CONHR.sup.5, NH.sub.2, CN, --SO.sub.2 Ph, --NHSO.sub.2 R.sup.5, --NHCOR.sup.5, OH, --SO.sub.2 --C.sub.1 -C.sub.4 -alkyl, --NHCOCF.sub.3, --SO.sub.2 R.sup.5 and --OCF.sub.3.

5 more elements