US 5,852,017 AGranted

2,3(1H,4H)-quinoxalinediones

AssigneeBASF SE

InventorsWilfried Lubisch, Berthold Behl, Hans Peter Hofmann

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Abstract

2,3(1H,4H)-quinoxalinediones of the formula I ##STR1## where R.sup.1 is hydrogen, an aliphatic radical which has up to 12 carbons and can be substituted by one of the following: phenyl, cyclopentyl, cyclohexyl or --CO--R.sup.3, --CO--O--R.sup.3 or --CO--NH--R.sup.3, where R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl or 1-phenylethyl, a cycloaliphatic radical with up to 12 carbons or phenyl, where the cyclic groups in R.sup.1 can have up to three of the following substituents: 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--O--R.sup.3 and --CO--NH--R.sup.3 ; R.sup.2 is 1-pyrrolyl which can have up to two of the following substituents: C.sub.1 -C.sub.4 -alkyl, phenyl, phenylsulfonyl, nitro, cyano and --CO--O--R.sup.3, --CO--NH--R.sup.3, --CH.sub.2 --O--R.sup.3, --O--R.sup.3 and --CH.dbd.NO--R.sup.3 R radicals are identical or different and are the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl, trichloromethyl, trifluoromethoxy, trichloromethoxy, fluorine, chlorine, bromine, iodine, nitro, cyano and --CO--O--R.sup.3 and --CO--NH--R.sup.3 as well as a fused-on benzene ring; n is 0-3, and 2,3(1H,4H)-quinoxalinediones I' ##STR2## where R.sup.1 has the stated meanings, are suitable as drugs in the treatment of neurodegenerative disorders and neurotoxic disturbances of the central nervous system.

Claims2

Dependent claims

A method for treating a host in need of spasmolytic or anxiolytic treatment which comprises administering to said host a therapeutically effective amount of a 2,3(1H,4H)-quinoxalinedione of the formula I ##STR15## or its tautomer or enantiomer or its physiologically tolerated salt, where R.sup.1 is hydrogen, a cycloaliphatic radical having up to 8 carbons, phenyl, an alkyl radical having up to 12 carbons and which can carry one or two identical or different substituents selected from the group consisting of phenyl, cyclopentyl, cyclohexyl, --CO--R.sup.3, --CO--OR.sup.3, --CO--NH--R.sup.3, --OR.sup.3, --NR.sup.7 R.sup.8, ##STR16## .dbd.N--OR.sup.3, --CN, where R.sup.3 and R.sup.7 are each, independently of one another, hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, and where the cycloaliphatic radical having up to 8 carbon atoms and aromatic rings present in R.sup.1 can carry up to three substituents selected from the group consisting of 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.9, --CO--NH--R.sup.9, --OH, ##STR17## .dbd.N--OR.sup.9, .dbd.O;

where R.sup.9 and R.sup.10 are each, independently of one another, hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl, 1-phenylethyl and 2-phenylethyl,
R.sup.2 is 1-pyrrolyl which can carry one or two of the following substituents:
C.sub.1 -C.sub.4 -alkyl, phenyl, phenylsulfonyl, nitro, cyano or --CO--R.sup.3, --CO--NH--R.sup.3, --NH.sub.2 --O--R.sup.3, --OR.sup.3, --CH.dbd.NO--R.sup.3, --C(O)--R.sup.3, ##STR18## --CH.dbd.CH--R.sup.8, --CH.dbd.N--R.sup.3, where R.sup.8 is --COOR.sup.3, --CONH--R.sup.3, CN or phenyl;
R is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl, trichloromethyl, trifluoromethoxy, trichloromethoxy, fluorine, chlorine, bromine, nitro, cyano or --CO--OR.sup.3, --CO--NHR.sup.3, --SO.sub.2 R.sup.3 or ##STR19## and n is an integer from 0 to 3, where the radicals R are identical or different when n is 2 or 3.

1 more element

A method for treating a host in need of antidepressant treatment which comprises administering to said host a therapeutically effective amount of a 2,3(1H,4H)-quinoxalinedione of the formula I ##STR20## or its tautomer or enantiomer or its physiologically tolerated salt, where R.sup.1 is hydrogen, a cycloaliphatic radical having up to 8 carbons, phenyl, an alkyl radical having up to 12 carbons and which can carry one or two identical or different substituents selected from the group consisting of phenyl, cyclopentyl, cyclohexyl, --CO--R.sup.3, --CO--OR.sup.3, --CO--NH--R.sup.3, --OR.sup.3, --NR.sup.7 R.sup.8, ##STR21## .dbd.N--OR.sup.3, --CN, where R.sup.3 and R.sup.7 are each, independently of one another, hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl, 1-phenylethyl or 2-phenylethyl, and where the cycloaliphatic radical having up to 8 carbon atoms and aromatic rings present in R.sup.1 can carry up to three substituents selected from the group consisting of 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.9, --CO--NH--R.sup.9, --OH, ##STR22## .dbd.N--OR.sup.9, .dbd.O;

where R.sup.9 and R.sup.10 are each, independently of one another, hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl, 1-phenylethyl and 2-phenylethyl,
R.sup.2 is 1-pyrrolyl which can carry one or two of the following substituents:
C.sub.1 -C.sub.4 -alkyl, phenyl, phenylsulfonyl, nitro, cyano or --CO--OR.sup.3, --CO--NH--R.sup.3, --NH.sub.2--O--R.sup.3, --OR.sup.3, --CH.dbd.NO--R.sup.3, --C(O)--R.sup.3, ##STR23## --CH.dbd.CH--R.sup.8, --CH.dbd.N--R.sup.3, where R.sup.8 is --COOR.sup.3, --CONH--R.sup.3, CN or phenyl;
R is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl, trichloromethyl, trifluoromethoxy, trichloromethoxy, fluorine, chlorine, bromine, nitro, cyano or --CO--OR.sup.3, --CO--NHR.sup.3, --SO.sub.2 R.sup.3 or ##STR24## and n is an integer from 0 to 3, where the radicals R are identical or different when n is 2 or 3.

1 more element

Dependencies are inferred from the claim text.

Facts

Application: 08/880,507Filed 23 Jun 1997 · continuation
Priority: DE 42 17 952.130 May 1992
Granted: 22 Dec 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 25/00
Drugs for disorders of the nervous system
A61P 25/08
Drugs for disorders of the nervous system: antiepileptics; Anticonvulsants
A61P 25/20
Drugs for disorders of the nervous system: hypnotics; Sedatives

Family

Serial67,873Parent of this continuation · filed 27 May 1993
Serial261,873Parent of this continuation · filed 17 Jun 1994
Serial512,282Parent of this continuation · filed 8 Aug 1995
US 5,714,489 AParent of this continuation
US 5,852,017 AThis patent

From the US filing history. Foreign family members aren’t listed.