Diphenyl-substituted heterocycles with 6-membered ring,...

Details Diphenyl-substituted heterocycles with 6-membered ring,... Diphenyl-substituted heterocycles with 6-membered ring,...

1999-04-12

2001-05-22

Shah, Mukund J. (Department: 1611)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S227800, C514S236200, C514S242000, C544S060000, C544S112000, C544S113000, C544S180000, C544S182000, C544S220000

Reexamination Certificate

active

06235738

ABSTRACT:

The invention relates to novel diphenyl-substituted heterocycles with 6-membered ring, processes for the preparation thereof and the use thereof as medicaments. The novel compounds have the structure of general formula (I):
in which:
A is a 6-membered heterocycle, saturated or unsaturated, which can contain 1, 2 or 3 heteroatoms selected from the group of oxygen, nitrogen or sulfur, and is optionally substituted one or more times with —OR
8
, ═O or C
1
-C
6
-alkyl, wherein the C
1
-C
6
-alkyl residue can in its turn be substituted with halogen, hydroxy or —NR
6
R
7
;
X is oxygen, sulfur or NR
6
;
R
1
is an C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl residue, which can optionally be substituted one or more times with ═O, —CN, —CHO, C
6
-C
10
-aryl, —COOR
8
, —CONHSO
2
R
8
, —CONR
6
R
7
, —CH═NOR
8
, —COR
8
, —NR
6
R
7
, —NHCOR
8
, —NHCONR
6
R
7
, —NHCOOR
8
, —OR
8
, —OCOR
8
, —OCOOR
8
, —OCONR
6
R
7
, —SR
8
, —SOR
8
, —SO
2
R
8
, SO
3
H, —SO
2
NR
6
R
7
, halogen or with a N-oxide of formula —NOR
6
R
7
; R
2
and R
3
, which can be the same or different, are hydrogen, mercapto, —NR
6
R
7
, halogen, nitro, CF
3
, CN, —OR
8
, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl, C
2
-C
10
-alkynyl, C
6
-C
10
-aryl, C
6
-C
10
-aryl-(C
1
-C
6
)alkyl-, or C
6
-C
10
-aryloxy;
R
4
and R
5
which can be the same or different, are hydrogen, mercapto, —NR
6
R
7
, halogen, nitro, CF
3
, CN, —OR
8
, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl, C
2
-C
10
-alkynyl, C
6
-C
10
-aryl, C
6
-C
10
-aryl-(C
1
-C
6
)alkyl-, or C
6
-C
10
-aryloxy;
R
6
is hydrogen, C
3
-C
6
-cycloalkyl, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl, each of them being optionally substituted one or more times with phenyl, benzyl or —OR
8
, or
R
6
is C
6
-C
10
-aryl, preferably phenyl, which can optionally be substituted with halogen, —OR
8
, C
1
-C
4
-alkyl, preferably with —CH
3
, —SO
3
H or —COOR
8
;
R
7
is hydrogen, C
3
-C
6
-cycloalkyl, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl, each of them being optionally substituted one or more times with phenyl, benzyl or —OR
8
, or
R
7
is C
6
-C
10
-aryl, preferably phenyl, which can optionally be substituted with halogen, —OR
8
, C
1
-C
4
-alkyl, preferably with —CH
3
, —SO
3
H or —COOR
8
; or
R
6
and R
7
together with the nitrogen atom form a 5- or 6-membered saturated or unsaturated ring, which can contain other heteroatoms such as nitrogen, oxygen or sulfur, wherein the heterocycle can be substituted with a branched or non-branched alkyl group with 1-4 carbon atoms, phenyl or benzyl;
R
8
is hydrogen, C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, a benzyl or phenyl residue, which is optionally substituted one or more times with OH, chlorine, bromine or OCH
3
, optionally in the form of racemates, enantiomers, diastereomers and mixtures thereof, and optionally in the form of addition salts with pharmacologically acceptable acids.
Preferred are the compounds of general formula (I) in which:
A is a 6-membered heterocycle, saturated or unsaturated, which can contain 1, 2 or 3 nitrogen atoms, and is optionally substituted one or more times with ═O or C
1
-C
4
-alkyl;
X is oxygen, sulfur or NR
6
;
R
1
is an C
1
-C
6
-alkyl residue, which is optionally substituted one or more times with ═O, —CN, —CHO, phenyl, —COOR
8
, —CONHSO
2
R
8
, —CONR
6
R
7
, —CH═NOR
8
, —COR
8
, —NR
6
R
7
, —NHCOR
8
, —NHCONR
6
R
7
, —NHCOOR
8
, —OR
8
, —OCOR
8
, —OCOOR
8
, —OCONR
6
R
7
, —SR
8
, —SOR
8
, —SO
2
R
8
, —SO
3
H, —SO
2
NR
6
R
7
, fluorine, chlorine, bromine or with a N-oxide of formula —NOR
6
R
7
;
R
2
and R
3
which can be the same or different, are hydrogen, SH, —NR
6
R
7
, fluorine, chlorine, bromine, nitro, CF
3
, CN, —OR
8
, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, phenyl, benzyl or phenyloxy;
R
4
and R
5
which can be the same or different, are hydrogen, SH, —NR
6
R
7
, fluorine, chlorine, bromine, nitro, CF
3
, CN, —OR
8
, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, phenyl, benzyl or phenyloxy;
R
6
is hydrogen, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, each of them being optionally substituted one or more times with hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy, or
R
6
is phenyl, which can optionally be substituted with fluorine, chlorine, bromine, —OR
8
, C
1
,-C
4
-alkyl, preferably with —CH
3
, —SO
3
H or —COOR
8
;
R
7
is hydrogen, C
3
-C
6
-cycloalkyl, C
1-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, each of them being optionally substituted one or more times with hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy, or
R
7
is phenyl, which can optionally be substituted with fluorine, chlorine, bromine, —OR
8
, C
1
-C
4
-alkyl, preferably with —CH
3
, —SO
3
H or —COOR
8
; or
R
6
and R
7
together with the nitrogen atom form a 5- or 6-membered saturated or unsaturated ring, which can contain other heteroatoms such as nitrogen or oxygen, wherein the heterocycle can be substituted with C
1
-C
4
-alkyl, phenyl or benzyl;
R
8
is hydrogen, C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, a benzyl or phenyl residue, which is optionally substituted one or more times with OH, chlorine, bromine or OCH
3
, optionally in the form of racemates, enantiomers, diastereomers and mixtures thereof, and optionally in the form of addition salts with pharmacologically acceptable acids.
Particularly preferred are the compounds of general formula (I) in which:
A is a 6-membered heterocycle, saturated or unsaturated, which can contain 1, 2 or 3 nitrogen heteroatoms, and is optionally substituted one or more times with ═O or C
1
-C
4
-alkyl;
X is oxygen;
R
1
is an C
1
-C
4
-alkyl residue, which is substituted with —CONHSO
2
R
8
, —CONR
6
R
7
, —CH═NOR
8
, —NR
6
R
7
, —NHCOR
8
, —NHCONR
6
R
7
, —NHCOOR
8
, —OCONR
6
R
7
, —SO
2
NR
6
R
7
, or with a N-oxide of formula —NOR
6
R
7
;
R
2
and R
3
which can be the same or different, are hydrogen, —NR
6
R
7
, fluorine, chlorine, bromine, nitro, CF
3
, CN, —OR
8
, C
1
-C
4
-alkyl, phenyl, benzyl or phenyloxy;
R
4
and R
5
which can be the same or different, are hydrogen, —NR
6
R
7
, fluorine, chlorine, bromine, nitro, CF
3
, CN, —OR
8
, C
1
-C
4
-alkyl, phenyl, benzyl or phenyloxy;
R
6
is hydrogen, C
3
-C
6
-cycloalkyl or C
1
-C
4
-alkyl, each of them being optionally substituted one or more times with hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy, or
R
6
is phenyl, which can optionally be substituted with fluorine, chlorine, bromine, —OR
8
, C
1
-C
4
-alkyl, preferably with —CH
3
, —SO
3
H or —COOR
8
;
R
7
is hydrogen, C
3
-C
6
-cycloalkyl or C
1
-C
4
-alkyl, each of them being optionally substituted one or more times with hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy, or
R
7
is phenyl, which can optionally be substituted with fluorine, chlorine, bromine, —OR
8
, C
1
-C
4
-alkyl, preferably with —CH
3
, —SO
3
H or —COOR
8
; or
R
6
and R
7
together with the nitrogen atom form a 5- or 6-membered ring, saturated or unsaturated, which can contain other heteroatoms such as nitrogen or oxygen, wherein the heterocycle can be substituted with C
1
-C
4
-alkyl, phenyl or benzyl;
R
8
is hydrogen, C
1
-C
4
-alkyl, a benzyl or phenyl residue, which is optionally substituted one or more times with OH, chlorine, bromine or OCH
3
, optionally in the form of racemates, enantiomers, diastereomers and mixtures thereof, and optionally in the form of the addition salts with pharmacologically acceptable acids.
Most preferred are the compounds of general formula (I), in which:
A is a 6-membered heterocycle, saturated or unsaturated, which can contain 1, 2 or 3 nitrogen heteroatoms, and is optionally substituted one or more times with ═O or C
1
-C
4
-alkyl;
X is oxygen;
R
1
is C
1
-C
4
-alkyl, which is substituted with —NR
6
R
7
or with a N-oxide of formula —NOR
6
R
7
;
R
2
and R
3
are hydrogen;
R
4
and R
5
are hydrogen;
R
6
is hydrogen or C
1
-C
4
-alkyl;
R
7
is hydrogen or C
1
-C
4
-alkyl; or
R
6
and R
7
together with the nitrogen atom form a saturated or unsaturated ring, selected from the group consisting of pyrr

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