Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-04-13
2001-07-03
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S374000, C514S378000, C514S383000, C514S392000, C514S400000, C514S403000, C514S427000, C548S144000, C548S235000, C548S247000, C548S267200, C548S320500, C548S340100, C548S375100, C548S561000
Reexamination Certificate
active
06255327
ABSTRACT:
The invention relates to new diphenyl-substituted 5-ring heterocycles, processes for preparing them and their use as pharmaceutical compositions.
The new compounds have the structure of general formula (I)
wherein
A denotes a 5-membered saturated or unsaturated heterocycle other than 1,2,4-oxadiazole, which may contain 1, 2 or 3 heteroatoms selected from the group comprising oxygen, nitrogen or sulphur and is optionally mono- or polysubstituted by —OR
8
, ═O or C
1
-C
6
-alkyl, whilst the C
1
-C
6
-alkyl group may in turn be substituted by halogen, hydroxy or —NR
6
R
7
;
X denotes oxygen, sulphur or NR
6
;
R
1
denotes a C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl group which may optionally be mono- or polysubstituted by ═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
, —SR8, —SOR
8
, —SO
2
R8, —SO
3
H, —SO
2
NR
6
R
7
, halogen or by an N-oxide of the formula —NOR
6
R
7
;
R
2
and R
3
, which may be identical or different, denote hydrogen, mercapto, —NR
6
R
7
, halogen, nitro, CF
3
, CN, —OR
8
, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl,
R
2
and R
3
denote C
6
-C
10
-aryl, aryl-C
1
-C
6
-alkyl, C
6
-C
10
-aryloxy;
R
4
and R
5
, which may be identical or different, denote hydrogen, mercapto, —NR6R
7
, halogen, nitro, CF3, CN, —OR
8
, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl,
R
4
and R
5
denote C
6
-C
10
-aryl, aryl-C
1
-C
6
-alkyl, C
6
-C
10
-aryloxy;
R
6
denotes hydrogen, C
3
-C
6
-cycloalkyl, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl, each of which may be mono- or polysubstituted by phenyl, benzyl or —OR
8
,
R6 denotes C
6
-C
10
-aryl, preferably phenyl, which may optionally be substituted by halogen, —OR
8
, C
1
-C
4
-alkyl, preferably —CH
3
, —SO
3
H or —COOR
8
;
R
7
denotes hydrogen, C
3
-C
6
-cycloalkyl, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl or C
2
-C
10
-alkynyl, each of which may be mono- or polysubstituted by phenyl, benzyl or —OR
8
,
R
7
denotes C
6
-C
10
-aryl, preferably phenyl, which may optionally be substituted by halogen, —OR
8
, C
1
-C
4
-alkyl, preferably —CH
3
, —SO
3
H or —COOR
8
; or
R
6
and R
7
together with the nitrogen atom form a saturated or unsaturated 5- or 6-membered ring, which may contain nitrogen, oxygen or sulphur as further heteroatoms, whilst the heterocycle may be substituted by a branched or unbranched alkyl group having 1 to 4 carbon atoms, by phenyl or by benzyl;
R
8
denotes hydrogen, C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, a benzyl or phenyl group which is optionally mono- or polysubstituted by OH, chlorine, bromine or OCH
3
, optionally in the form of their racemates, their enantiomers, in the form of their diastereomers and the mixtures thereof, and optionally the pharmacologically acceptable acid addition salts thereof.
Preferred compounds of general formula (I) are those wherein
A denotes a 5-membered saturated or unsaturated heterocycle other than 1,2,4-oxadiazole, which may contain 1, 2 or 3 heteroatoms selected from the group comprising oxygen, nitrogen or sulphur and is optionally mono- or polysubstituted by C
1
-C
4
-alkoxy, OH, ═O or C
1
-C
4
-alkyl, whilst the C
1
-C
4
-alkyl group may in turn be substituted by fluorine, chlorine, bromine, OH or —NR
6
R
7
;
X denotes oxygen, sulphur or NR
6
;
R
1
denotes a C
1
-C
6
-alkyl group which may optionally be mono- or polysubstituted by ═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
, —OR8, —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 by an N-oxide of the formula —NOR
6
R
7
;
R
2
and R
3
which may be identical or different denote 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 or C
2
-C
6
-alkynyl,
R
2
and R
3
denote phenyl, benzyl, phenyloxy;
R
4
and R
5
which may be identical or different denote to 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 or C
2
-C
6
-alkynyl,
R
4
and R
5
denote phenyl, benzyl, phenyloxy;
R
6
denotes hydrogen, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, each of which may be mono- or polysubstituted by hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy,
R
6
denotes phenyl, which may optionally be substituted by fluorine, chlorine, bromine, —OR
8
, C
1
-C
4
-alkyl, preferably —CH
3
, —SO
3
H, or —COOR
8
;
R
7
denotes hydrogen, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, each of which may be mono- or polysubstituted by hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy,
R
7
denotes phenyl, which may optionally be substituted by fluorine, chlorine, bromine, —OR
8
, C
1
-C
4
-alkyl, preferably —CH
3
, —SO
3
H, or —COOR
8
; or
R
6
and R
7
together with the nitrogen atom form a saturated or unsaturated 5- or 6-membered ring which may contain nitrogen or oxygen as further heteroatoms, whilst the heterocycle may be substituted by C
1
-C
4
-alkyl, phenyl or benzyl;
R
8
denotes hydrogen, C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, a benzyl or phenyl group which may optionally be mono- or polysubstituted by OH, chlorine, bromine or OCH
3
, optionally in the form of their racemates, their enantiomers, in the form of their diastereomers and the mixtures thereof, and optionally the pharmacologically acceptable acid addition salts thereof.
Particularly preferred are compounds of general formula (I) wherein
A denotes a 5-membered saturated or unsaturated heterocycle other than 1,2,4-oxadiazole, which may contain 1, 2 or 3 heteroatoms selected from the group comprising oxygen or nitrogen and is optionally mono- or polysubstituted by C
1
-C
4
-alkoxy, OH, ═O or C
1
-C
4
-alkyl, whilst the C
1
-C
4
-alkyl group may in turn be substituted by fluorine, chlorine, bromine, OH or —NR
6
R
7
;
X denotes oxygen;
R
1
denotes a C
1
-C
4
-alkyl group which is substituted by —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 by an N-oxide of the formula —NOR
6
R
7
;
R
2
and R
3
which may be identical or different denote 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 may be identical or different denote hydrogen, —NR
6
R
7
, fluorine, chlorine, bromine, nitro, CF3, CN, —OR
8
, C
1
-C
4
-alkyl, phenyl, benzyl or phenyloxy;
R
6
denotes hydrogen, C
3
-C
6
-cycloalkyl or C
1
-C
4
-alkyl, each of which may be mono- or polysubstituted by hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy,
R
6
denotes phenyl, which may optionally be substituted by fluorine, chlorine, bromine, —OR
8
, C
1
-C
4
-alkyl, preferably —CH
3
, —SO
3
H, or —COOR
8
;
R
7
denotes hydrogen, C
3
-C
6
-cycloalkyl or C
1
-C
4
-alkyl, each of which may be mono- or polysubstituted by hydroxy, phenyl, benzyl or C
1
-C
4
-alkoxy,
R
7
denotes phenyl, which may optionally be substituted by fluorine, chlorine, bromine, —OR
8
, C
1
-C
4
-alkyl, preferably —CH
3
, —SO
3
H, or —COOR
8
; or
R
6
and R
7
together with the nitrogen atom form a saturated or unsaturated 5- or 6-membered ring which may contain nitrogen or oxygen as further heteroatoms, whilst the heterocycle may be substituted by C
1
-C
4
-alkyl, phenyl or benzyl;
R
8
denotes hydrogen, C
1
-C
4
-alkyl, a benzyl or phenyl group which may optionally be mono- or polysubstituted by OH, chlorine, bromine or OCH
3
, optionally in the form of their racemates, their enantiomers, in the form of their diastereomers and the mixtures thereof, and optionally the pharmacologically acceptable acid addition salts thereof.
Also preferred according to the invention are compounds of general formula (I) wherein
A denotes a furan, tetrahydrofuran, dioxolane, pyrrole, pyrroline, pyrrolidin
Bechtel Wolf-Dietrich
Bignotti Maura
Brenner Michael
Cereda Enzo
Palluk Rainer
Boehringer Ingelheim Pharma KG
Devlin Mary-Ellen M.
Gerstl Robert
Raymond Robert P.
Stempel Alan R.
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