Oxadiazoles, processes for their preparation and their use...

Details Oxadiazoles, processes for their preparation and their use... Oxadiazoles, processes for their preparation and their use...

1999-07-26

2001-08-21

Gerstl, Robert (Department: 1613)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C544S138000, C544S367000, C546S277100, C548S131000

Reexamination Certificate

active

06277872

ABSTRACT:

The invention relates to new oxadiazole derivatives, processes for preparing them and their use as pharmaceutical compositions.
The new oxadiazole derivatives have the structure of general formula (I)
wherein
X and Y denote oxygen or nitrogen, but X and Y do not both simultaneously denote oxygen or nitrogen;
Z denotes a group of formula
 wherein
S
1
and S
2
denote a group of formula
wherein V denotes oxygen, sulphur or NR
7
and B and D, which may be identical or different, may represent a C
1-10-
-alkylene, C
2-10
-alkenylene or C
2-10
-alkynylene bridge, which may in each case be mono- or polysubstituted by ═O, —CN, —CHO, C
6-10
-aryl, COOR
7
, —CONHSO
2
R
7
, —CONR
5
R
6
, —CH═NOR
7
, —COR
8
, —CH(OR
7
)R
8
, —CH(OR
7
)
2
, —CH═CH—R
9
, —NR
5
R
6
, —NHCOR
7
, —NHCONR
5
R
6
, —NHCOOR
7
, —OR
7
, —OCOR
7
, —OCOOR
7
, —OCONR
5
R
6
, —SR
7
, —SOR
7
, —SO
2
R
7
, —SO
3
H, —SO
2
NR
5
R
6
, halogen, 1,3-dioxolane or 1,3-dioxane;
S
1
and S
2
denote a group of formula
wherein V and B may have the meanings given hereinbefore and U represents a C
3-6
-cycloalkyl, C
5-6
-cycloalkyl or C
6-10
-aryl group, which may be mono- or polysubstituted by C
1-4
-alkyl, —CN, —CHO, —COR
8
, —NR
5
R
6
, —OR
7
, —SR
7
, —SO
2
R
7
, —SOR
7
or halogen,
S
1
and S
2
denote a group of formula
wherein B and D are as hereinbefore defined and the two groups D and the two groups R
4
are identical or different,
S
1
and S
2
denote a group of formula
whilst V and D are as hereinbefore defined,
S
1
and S
2
denote a group of formula
wherein V and U are as hereinbefore defined,
S
1
and S
2
denote a group of formula
wherein D is as hereinbefore defined and the two groups D and the two groups R
4
are identical or different,
S
1
and S
2
denote a group of formula
wherein E denotes oxygen, sulphur or NR
7
(with n,m=1,2 or 3 and n+m>2), wherein the group is optionally substituted by halogen, ═O, OR
7
, —OCOR
7
or one or more C
1
-C
6
-alkyl-, C
2-6
alkenyl or C
2-6
-alkynyl groups;
S
1
and S
2
denote a group of formula
wherein V and D are as hereinbefore defined and W may be a group of the formula
 optionally substituted by halogen, ═O, —OR
7
, —OCOR
7
, C
1-4
-alkyl, C
2
-
6
-alkenyl or C
2-6
-alkynyl, wherein E denotes oxygen, sulphur or NR
7
and n, m, I may be 0, 1 or 2, or W is a C-linked 5, 6 or 7-membered heterocyclic group which contains one or more heteroatoms from the group comprising nitrogen, oxygen or sulphur and may optionally be substituted by benzoyl or C
1-4
-alkyl;
S
1
and S
2
denote a group of formula
—V—W
wherein V and W are as hereinbefore defined;
S
1
and S
2
denote a group of formula
wherein B is as hereinbefore defined and the two groups R
7
may be identical or different,
S
1
and S
2
denote a group of formula
wherein the two groups R
7
may be identical or different,
S
3
and S
4
denote a group of formula
wherein B, V and D are as hereinbefore defined,
S
3
and S
4
denote a group of formula
wherein B and D are as hereinbefore defined and the two groups D and the two groups R
4
may be identical or different,
S
3
and S
4
denote a group of formula
whilst V and D are as hereinbefore defined,
S
3
and S
4
denote a group of formula
wherein D is as hereinbefore defined and the two groups D and the two groups R
4
are identical or different,
Q denotes a fused-on, mono- or polyunsaturated 5-, 6- or 7-membered ring which may contain one or more heteroatoms from the group comprising oxygen, nitrogen or sulphur, and may optionally be substituted by OR
7
, NR
5
R
6
, halogen, CN, nitro, CF
3
, COOR
7
, C
1-10
-alkyl, C
2-10
-alkenyl or C
2-10
-alkynyl;
S
5
denotes a group of formula
—D—R
4
wherein D is as hereinbefore defined;
R
1
denotes hydrogen, a C
1-10
-alkyl-, C
2-10
-alkenyl or C
2-10
-alkynyl group, which may optionally be mono- or polysubstituted by —CN, —CHO, —COOR
7
, —CONHSO
2
R
7
, —CONR
5
R
6
, —CH═NOR
7
,—COR
8
, —CH(OR
7
)R
8
, —CH(OR
7
)
2
, —CH═CH—R
9
, —NR
5
R
6
, —NHCOR
7
, —NHCONR
5
R
6
, —NHCOOR
7
, ═O, —OR
7
, —OCOR
7
, —OCOOR
7
, —OCONR
5
R
6
, —SR
7
, —SOR
7
, —SO
2
R
7
, —SO
3
H, —SO
2
NR
5
R
6
, halogen, 1,3-dioxolane or 1,3-dioxane,
R
1
denotes phenyl, which may optionally be mono-, di- or trisubstituted directly or via a C
1-4
-alkylene bridge by one or more of the following groups: halogen, C
1
-C
4
-alkyl, —CF
3
, —CHO, —COOR
7
, —CONR
5
R
6
, —CONHSO
2
R
7
, —CR
7
═NOR
7
(wherein the groups R
7
may be identical or different), —COR
8
, —CH(OH)R
8
, —CH(OR
7
)
2
, —CH═CH—R
9
, —NR
5
R
6
, —NO
2
, —C
1
-C
4
-alkyl-NR
5
R
6
, —NHCOR
7
, —NHCOOR
7
, —NHCONR
5
R
6
, —NH—SO
2
R
7
, —OR
7
, —OCOR
7
, OCONR
5
R
6
, —SR
7
, —SOR
7
, —SO
2
R
7
, —SO
3
H, —SO
2
NR
5
R
6
or by a group of formula
wherein B, V and D are as hereinbefore defined,
R
1
denotes phenyl, which may be substituted by a group of formula
wherein B, V and U are as hereinbefore defined,
R
1
denotes phenyl, which is substituted by a group of formula
wherein B and D are as hereinbefore defined and the two groups D and the two groups R
4
are identical or different,
R
1
denotes phenyl, which is substituted by a group of formula
wherein V and D are as hereinbefore defined,
R
1
denotes phenyl, which is substituted by a group of formula
wherein D is as hereinbefore defined and the two groups D and the two groups R
4
are identical or different,
R
1
denotes phenyl, which is substituted by a group of formula
wherein V and U are as hereinbefore defined,
R
1
denotes phenyl, which is substituted by a group of formula
wherein V, D and W are as hereinbefore defined;
R
1
denotes phenyl, which is substituted by a group of formula
—V—W
wherein V and W are as hereinbefore defined;
R
1
denotes phenyl-C
1
-
6
-alkyl, preferably phenyl- C
1-4
-alkyl, phenyl-C
2
-
6
-alkenyl or phenyl-C
2
-
6
-alkynyl, wherein the phenyl ring may optionally be substituted either directly or via an alkylene bridge having 1 to 4 carbon atoms by one or more, preferably one of the groups: halogen, C
1-4
-alkyl, —CF
3
, —CHO, —COOR
7
,—CONR
5
R
6
, —CONHSO
2
R
7
, —CR
7
═NOR
7
(wherein the groups R
7
may be identical or different), —COR
8
, —CH(OH)R
8
, —CH(OR
7
)
2
, —CH═CH—R
9
, —NR
5
R
6
, —NO
2
, —C
1-4
-alkyl—NR
5
R
6
, —NHCOR
7
, —NHCOOR
7
, —NHCONR
5
R
6
, —NH—SO
2
—R
7
, —OR
7
, —OCOR
7
, —OCONR
5
R
6
, —SR
7
, —SOR
7
, —SO
2
R
7
, —SO
3
H or —SO
2
NR
5
R
6
,
R
1
denotes C
3
-
7
-cycloalkyl-C
1
-
6
-alkyl, C
3
-
7
-cycloalkyl-C
2
-
6
-alkenyl, C
3
-
7
-cycloalkyl-C
2
-
6
-alkynyl, wherein the cycloalkyl group is optionally substituted, either directly or via an alkylene bridge having 1 to 4 carbon atoms, by one or more—preferably one—of the groups —CN, —CHO, —COOR
7
, —CONHSO
2
R
7
, —CONR
5
R
6
, —CH═NOR
7
, —COR
8
, —CH(OR
7
)R
8
, —CH(OR
7
)
2
, —CH═CH—R
9
, —NR
5
R
6
, —NHCOR
7
, —NHCONR
5
R
6
, —NHCOOR
7
, ═O, —OR
7
, —OCOR
7
, —OCOOR
7
, —OCONR
5
R
6
, —SR
7
, —SOR
7
, —SO
2
R
7
, —SO
3
H, —SO
2
NR
5
R
6
, halogen,1,3-dioxolane or 1,3-dioxane,
R
1
denotes a group of formula M, M-C
1
-
6
-alkyl, M-CONH—C
1
-
6
-alkyl, M-CONH—C
2
-
6
-alkenyl, M-CONH—C
2
-
6
-alkynyl, M-NH—CO—C
1
-
6
-alkyl, M-NH—CO—C
1
-
6
-alkenyl, M-NH—CO—C
1
-
6
-alkynyl, M-C
2
-
6
-alkenylene or M-C
2
-
6
-alkynylene, wherein M is a C- or N-linked 5, 6 or 7-membered heterocycle which contains one or more heteroatoms from the group comprising nitrogen, oxygen or sulphur and may optionally be mono- or polysubstituted, preferably monosubstituted by phenyl, substituted phenyl, benzyl, substituted benzyl, C
1-4
-alkyl, halogen, —OR
7
, —CN, —NO
2
, —NH
2
, —CH
2
NR
5
R
6
, —OH, ═O, a ketal, ethyleneketal, —COOH, SO
3
H, —COOR
7
, —CONR
5
R
6
, —COR
8
, —SO
2
—R
7
or —CONR
5
R
6
,
R
1
denotes C
3
-C
7
-cycloalkyl, which is optionally substituted by —CN, —CHO, —COOR
7
, —CONHSO
2
R
7
, —CONR
5
R
6
, —CH═NOR
7
, —COR
8
, —CH(OR
7
)R
8
, —CH(OR
7
)
2
, —CH═CH—R
9
, —NR
5
R
6
, —NHCOR
7
, —NHCONR
5
R
6
, —NHCOOR
7
, ═O, —OR
7
, —OCOR
7
, —OCOOR
7
, —OCONR
5
R
6
, —SR
7
, —SO
2
R
7
, —SOR
7
, —SO

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