Biphenylsulfonyl-substituted imidazole derivatives, their...

Details Biphenylsulfonyl-substituted imidazole derivatives, their... Biphenylsulfonyl-substituted imidazole derivatives, their...

2001-01-17

2002-04-16

Higel, Floyd D. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S322500, C548S334500, C514S400000, C514S821000

Reexamination Certificate

active

06372917

ABSTRACT:

Imidazole derivatives having biphenylsulfonyl substitution, process for their preparation, their use as a medicament or diagnostic, and a medicament comprising them
The invention relates to compounds of the formula I
in which the symbols have the following meaning:
R(1) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or —C
a
H
2a
-phenyl, where the phenyl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(8)R(9);
R(8) and R(9) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
a is zero, 1 or 2; or
R(1) is —C
b
H
2b
-heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, where the heteroaryl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(10 )R(11);
R(10) and R(11) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
b is zero, 1 or 2; or
R(1) is —C
d
H
2d
-cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms;
d is zero, 1 or 2;
R(2) and R(3) independently of one another are hydrogen, F, Cl, Br, I, CF
3
, —CN, —NO
2
, CH
2
OR(17), CO—R(6) or O—R(7);
R(17) is hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
R(6) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, OR(30) or phenyl which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(31)R(32);
R(31) and R(32) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R(30) is hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
R(7) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, or phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(12)R(13);
R(12) and R(13) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms; or
R(7) is heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(14)R(15);
R(14) and R(15) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms; or
R(2) and R(3) 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
2g
-phenyl, where the phenyl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(18)R(19);
R(18) and R(19) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
g is zero, 1 or 2; or
R(2) and R(3) independently of one another are —C
l
H
2l
-heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, where the heteroaryl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(20)R(21);
R(20) and R(21) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
l is zero, 1 or 2; or
R(2) and R(3) independently of one another are SO
n
—R(22);
n is zero, 1 or 2;
R(22) 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
C
2s
-phenyl which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(34)R(35);
R(34) and R(35) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
s is zero, 1 or 2;
R(4) is SO
p
—R(16),
p is zero, 1 or 2;
R(16) is alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or phenyl, which is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxyl or NR(26)R(27);
R(26) and R(27) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
and their physiologically tolerable salts.
Preferred compounds of the formula I are those in which:
R(1) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or —C
a
H
2a
-phenyl, where the phenyl moiety is unsubstituted or substituted by 1 or 2 identical or different radicals from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(8)R(9);
R(8) and R(9) independently of one another are hydrogen or methyl;
a is zero or1; or
R(1) is heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms which is unsubstituted or substituted by a radical from the group consisting of F, Cl, Br, CF
3
, CH
3
, methoxy, hydroxyl or NR(10)R(11);
R(10) and R(11) independently of one another are hydrogen or methyl; or
R(1) is —C
d
H
2
-cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms;
d is zero or 1;
R(2) and R(3) independently of one another are hydrogen, F, Cl, Br, CF
3
, —CN, —NO
2
, CH
2
OR(17), CO—R(6) or O—R(7);
R(17) is hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R(6) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, OR(30) or phenyl, which is unsubstituted or substituted by 1 or 2 identical or different radicals from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(31)R(32);
R(31) and R(32) independently of one another are hydrogen or methyl;
R(30) is hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R(7) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or phenyl, which is unsubstituted or substituted by 1 or 2 identical or different radicals from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(12)R(13);
R(12) and R(13) independently of one another are hydrogen or methyl; or
R(7) is heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, which is unsubstituted or substituted by 1 or 2 identical or different radicals from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(14)R(15);
R(14) and R(15) independently of one another are hydrogen or methyl; or
R(2) and R(3) 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, where the phenyl moiety is unsubstituted or substituted by 1 or 2 identical or different radicals from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(18)R(19);
R(18) and R(19) independently of one another are hydrogen or methyl;
g is zero or 1; or
R(2) and R(3) independently of one another are heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, which is unsubstituted or substituted by a radical from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(20)R(21);
R(20) and R(21) independently of one another are hydrogen or methyl; or
R(2) and R(3) independently of one another are SO
n
—R22,
n is zero, 1 or 2;
R(22) 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, where the phenyl moiety is unsubstituted or substituted by 1 or 2 identical or different radicals from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(34)R(35);
R(34) and R(35) independently of one another are hydrogen or methyl;
s is zero or1;
R(4) is SO
p
—R(16),
p is zero, 1 or 2;
R(16) is alkyl having 1, 2, 3 or 4 carbon atoms or phenyl, which is unsubstituted or substituted by 1 or 2 identical or different radicals from the group consisting of F, Cl, Br, CF
3
, methyl, methoxy, hydroxyl or NR(26)R(27); R(26) and R(27) independently of one another are hydrogen or methyl;
and their physiologically tolerable salts.
Particularly preferred compounds of the formula I are those in which:
R(1) is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or phenyl, which is unsubstituted or substituted by a radical from the group consisting of F, Cl, Br, CF
3
, methyl,

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