Five-membered heterocycles having biphenylsulfonyl...

Details Five-membered heterocycles having biphenylsulfonyl... Five-membered heterocycles having biphenylsulfonyl...

1998-01-21

2002-01-01

Higel, Floyd D. (Department: 1613)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S398000, C514S399000, C514S400000, C548S323100, C548S328500, C548S324100, C548S325500, C548S333500, C548S334500

Reexamination Certificate

active

06335451

ABSTRACT:

The invention relates to compounds of the formula I
in which the symbols have the following meaning:
R1 is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or —C
a
H
2a
—phenyl,
said —C
a
H
2a
-phenyl being unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl and NR(8)R(9);
R(8) and R(9) independently of one another are H or (C
1
-C
4
)alkyl;
a is zero, 1or 2; or
R1 is —C
b
H
2b
—(C
1
-C
9
)heteroaryl,
which is unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxy and NR(10)R(11);
R(10) and R(11) independently of one another are H or (C
1
-C
4
)alkyl;
b is zero, 1 or 2; or
R1 is —C
d
H
2d
—(C
3
-C
7
)cycloalkyl;
d is zero, 1 or 2;
R2 and R3 independently of one another are hydrogen, F, Cl, Br, I, CF
3
, —C≡N, —NO
2
, CH
2
OR17, CO—R6 or O—R7;
R17 is hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms
R6 is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, OR30 or phenyl,
said phenyl being unsubstituted or substituted by 1-3 substituents selected from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl and NR(31)R(32);
R(31) and R(32) independently of one another are H or (C
1
-C
4
)-alkyl;
R30 is hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
R7 is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, or phenyl,
said phenyl being unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl and NR(12)R(13);
R(12) and R(13) independently of one another are H or (C
1
-C
4
)-alkyl; or
R7 is (C
1
-C
9
)heteroaryl, which is unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxyl and NR(14)R(15);
R(14) and R(15) independently of one another are H or (C
1
-C
4
)-alkyl; or
R2 and R3 independently of one another are alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms or —C
g
H
2
g-phenyl,
said —C
g
H
2
g-phenyl being unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl and NR(18)R(19);
R(18) and R(19) independently of one another are H or (C
1
-C
4
)alkyl;
g is zero, 1 or 2; or
R2 and R3 independently of one another are —C
I
H
21
-(C
1
-C
9
)heteroaryl,
which is unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxyl and NR(20)R(21);
R(20) and R(21) independently of one another are H or (C
1
-C
4
)alkyl;
I is zero, 1 or 2; or
R2 and R3 independently of one another are SO
n
—R22;
n is zero, 1 or 2;
R22 is alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms or —C
s
H
2s
-phenyl,
said —C
s
H
2s
-phenyl being unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl and NR(34)R(35);
R(34) and R(35) independently of one another are H or (C
1
-C
4
)-alkyl;
s is zero, 1 or 2;
R4 and R5 independently of one another are hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, F, Cl, Br, I, CF
3
, —C≡N, —NO
2
, SO
p
—R16, CO—R23 or O—R24;
p is zero, 1or 2;
R16 is alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or phenyl,
said phenyl being unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl and NR(26)R(27);
R(26) and R(27) independently of one another are H or (C
1
-C
4
)-alkyl;
R23 is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or OR25;
R25 is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
R24 is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or phenyl,
said phenyl being unsubstituted or substituted by 1-3 substituents selected from F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl and NR(28)R(29);
R(28) and R(29) independently of one another are H or (C
1
-C
4
)-alkyl;
and their physiologically tolerable salts.
Preferred compounds of the formula I are those in which:
R1 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or —C
a
H
2a
-phenyl,
said —C
a
H
2a
-phenyl being unsubstituted or substituted by 1-2 substituents selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(8)R(9);
R(8) and R(9) independently of one another are H or methyl;
a is zero or 1; or
R1 is (C
1
-C
9
)heteroaryl,
which is unsubstituted or substituted by one substituent selected from F, Cl, Br, CF
3
, CH
3
, methoxy, hydroxyl and NR(10)R(11);
R(10) and R(11) independently of one another are H or methyl; or
R1 is —C
d
H
2d
-(C
3
-C
7
)cycloalkyl;
d is zero or 1;
R2 and R3 independently of one another are hydrogen, F, Cl, Br, CF
3
, —C≡N, —NO
2
, CH
2
OR17, CO—R6 or O—R7;
R17 is hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R6 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, OR30 or phenyl,
said phenyl being unsubstituted or substituted by 1-2 substituents selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(31)R(32);
R(31) and R(32) independently of one another are H or methyl;
R30 is hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R7 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or phenyl,
said phenyl being unsubstituted or substituted by 1-2 substituents selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(12)R(13);
R(12) and R(13) independently of one another are H or methyl; or
R7 is (C
1
-C
9
)heteroaryl,
which is unsubstituted or substituted by one substituent selected from F, Cl, Br, CF
3
, CH
3
, methoxy, hydroxyl and NR(14)R(15);
R(14) and R(15) independently of one another are H or methyl; or
R2 and R3 independently of one another are alkyl having 1, 2, 3 or 4 carbon atoms, cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms or —C
g
H
2g
-phenyl,
said —C
g
H
2g
-phenyl being unsubstituted or substituted by 1-2 substituents selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(18)R(19);
R(18) and R(19) independently of one another are H or methyl;
g is zero or 1; or
R2 and R3 independently of one another are (C
1
-C
9
)heteroaryl,
which is unsubstituted or substituted by one substituent selected from F, Cl, Br, CF
3
, CH
3
, methoxy, hydroxyl and NR(20)R(21);
R(20) and R(21) independently of one another are H or methyl; or
R2 and R3 independently of one another are SO
n
—R22,
n is zero, 1 or 2;
R22 is alkyl having 1, 2, 3 or 4 carbon atoms, cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms or —C
s
H
2s
-phenyl,
said —C
s
H
2s
-phenyl being unsubstituted or substituted by 1-2 substituents selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(34)R(35);
R(34) and R(35) selected from H and methyl;
s is zero or 1;
R4 and R5 independently of one another are hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, F, Cl, Br, CF
3
, —C≡N, —NO
2
, SO
p
—R16, CO—R23 or O—R24;
p is zero, 1 or 2;
R16 is alkyl having 1, 2, 3 or 4 carbon atoms or phenyl, said phenyl being unsubstituted or substituted by 1-2 substituents selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(26)R(27);
R(26) and R(27) independently of one another are H or methyl;
R23 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or OR25;
R25 is hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R24 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or phenyl,
said phenyl being unsubstituted or substituted by 12-2 substituents selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(28)R(29);
R(28) and R(29) independently of one another are H or methyl;
and their physiologically tolerable salts.
Particularly preferred compounds of the formula I are those in which:
R1 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or phenyl,
said phenyl being unsubstituted or substituted by one substituent selected from F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl and NR(8)R(9);
R(8) and R(9) independently of one another are H or methyl; or
R1 is (C
1
-C
9
)heteroaryl,
which is unsubstituted or substituted by one substituent selected from F, Cl, Br, CF
3
, CH
3
, methoxy, hydroxyl and NR(10)R(11);
R(10) and R(11) independen

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