Biphenylsulfonyl cyanamides, method for the production...

Details Biphenylsulfonyl cyanamides, method for the production... Biphenylsulfonyl cyanamides, method for the production...

2000-08-04

2002-04-09

Higel, Floyd D. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S314000, C514S374000, C514S422000, C514S423000, C514S395000, C514S445000, C546S166000, C546S251000, C548S235000, C548S453000, C548S579000, C548S491000, C549S496000, C558S392000, C564S086000

Reexamination Certificate

active

06369069

ABSTRACT:

The invention relates to compounds of the formula (I),
in which the symbols have the following meaning:
R(1) is
1. alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
2. alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, in which one to all hydrogen atoms are replaced by fluorine;
3. alkenyl having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; or
4. —C
n
H
2n−nn
—Y,
nn is zero or 2; and
n is zero, 1, 2, 3 or 4; where n is unequal to zero or 1 if nn is equal to 2;
5. —C
n
H
2n−nn
—Y,
nn is zero or 2; and
n is 1, 2, 3 or 4; where n is unequal to 1 if nn is equal to 2;
where 1, 2 or 3 hydrogen atoms in the divalent radical —C
n
H
2n−nn
— independently of one another are replaced by a radical from the group consisting of
1. aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl;
2. amino;
3. N(R(22)R(23);
4. alkoxycarbonyl;
5. COOR(16);
6. alkyl having 1, 2, 3 or 4 carbon atoms;
7. (C
6
-C
14
)-aryl-(C
1
-C
4
)-alkylcarbonyl, preferably phenylacetyl;
R(2) is
1. hydrogen;
2. alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
3. alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, in which one to all hydrogen atoms are replaced by fluorine;
4. alkenyl having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms;
5. alkynyl having 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
6. —C
n
H
2n−nn
—Z,
nn is zero or 2; and
n is zero, 1, 2, 3 or 4; where n is unequal to zero or 1 if nn is equal to 2;
7. —C
n
H
2n−nn
—Z,
nn is zero or 2; and
n is 1, 2, 3 or 4, where n is unequal to 1 if nn is equal to 2;
where 1, 2 or 3 hydrogen atoms in the divalent radical —C
n
H
2n−nn
— independently of one another are replaced by a radical from the group consisting of
1. aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl;
2. amino;
3. N(R(22)R(23);
4. (C
1
-C
4
)-alkoxycarbonyl;
5. COOR(16);
6. alkyl having 1, 2, 3 or 4 carbon atoms;
R(3) and R(4) independently of one another are hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
R(5), R(6) and R(7) 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
, —CN, —NO
2
, SO
q
—R(8), CO—R(21) or O—R(10);
R(8) is alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, NR(11)R(12) or phenyl which is unsubstituted or is 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(11)R(12);
R(9) and R(21) independently of one another are hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or OR(13);
R(10) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms optionally substituted by (C
1
-C
4
)-alkoxy; or phenyl which is unsubstituted or is 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(11)R(12);
R(11), R(12), R(19) and R(20) independently of one another are hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or (C
1
-C
4
)-alkanoyl, preferably acetyl;
R(13) is hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
X is carbonyl, —CO—NH—, —CO—CO— or sulfonyl;
Y and Z independently of one another are
1. aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl;
2. a radical as defined in 1., which is substituted by 1, 2, 3, 4 or 5 identical or different radicals from the group consisting of alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl, F, Cl, Br, I, CF
3
, SO
q
R(18), OR(16), NR(19)R(20), —CN, NO
2
or CO—R(9); or where two radicals together form a fused heterocyclyl radical, preferably methylenedioxy.
3. heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms;
4. a radical as defined in 3., which is substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxyl or NR(11)R(12);
5. cycloalkyl having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, preferably cyclopropyl, cyclopentyl, cyclohexyl. 1,2,3,4-tetrahydronaphthyl or indanyl;
6. a radical as defined in 5, substituted by aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl;
7. O—R(14);
8. O—R(17);
9. —SO
2
—R(14);
10. arylalkylcarbonyl, preferably phenyl-CH
2
—CO—; or
11. heterocyclyl;
R(14) and R(17) independently of one another are
1. hydrogen;
2. alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
3. alkenyl having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms;
4. —C
n
H
2n−nn
-phenyl,
nn is zero or 2; and
n is zero, 1, 2, 3 or 4; where n is unequal to zero or 1 if nn is equal to 2;
5. a radical as defined in 4., where the phenyl moiety is substituted by 1, 2 or 3 identical or different radicals from the group consisting of alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, F, Cl, Br, I, CF
3
, SO
q
R(15), OR(16), NR(11)R(12), —CN, —NO
2
or CO—R(9); or
R(15) and R(18) independently of one another are alkyl having 1, 2, 3 or 4 carbon atoms, alkyl having 1, 2, 3 or 4 carbon atoms, in which one to all hydrogen atoms are replaced by fluorine, preferably CF
3
, or NR(11)R(12);
R(16) is
1. hydrogen,
2. alkyl having 1, 2, 3 or 4 carbon atoms,
3. alkyl having 1, 2, 3 or 4 carbon atoms, substituted by (C
1
-C
4
)-alkoxy,
4. alkyl having 1, 2, 3 or 4 carbon atoms, in which one to all hydrogen atoms are replaced by fluorine, preferably CF
3
;
5. aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl;
6. a radical as defined in 5., which is substituted by 1, 2 or 3 identical or different radicals from the group consisting of F, Cl, Br, I, CF
3
, NR(19)R(20), —CN, NO
2
;
R(22) and R(23) independently of one another are hydrogen or CO—OR(24);
R(24) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or —C
n
H
2n
-phenyl where n is equal to 1, 2, 3 or 4;
q independently of one another is zero, 1 or 2;
and their physiologically tolerable salts.
Preferred compounds of the formula (I) are those where
R(1) is
1. alkyl having 1, 2, 3, 4 or 5 carbon atoms;
2. alkyl having 1, 2, 3, 4 or 5 carbon atoms, in which one to all hydrogen atoms are replaced by fluorine;
3. alkenyl having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms; or
4. —C
n
H
2n−nn
—Y,
nn is zero or 2; and
n is zero, 1, 2, 3 or 4; where n is unequal to zero or 1 if nn is equal to 2;
5. —C
n
H
2n−nn
—Y,
nn is zero or 2; and
n is 1, 2, 3 or 4; where n is unequal to 1 if nn is equal to 2;
where 1, 2 or 3 hydrogen atoms in the divalent radical —C
n
H
2n−nn
— independently of one another are replaced by a radical from the group consisting of
1. aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl;
2. amino;
3. NR(22)R(23);
4. alkoxycarbonyl;
5. COOR(16);
6. alkyl having 1, 2, 3 or 4 carbon atoms;
7. (C
6
-C
14
)-aryl-(C
1
-C
4
)-alkylcarbonyl, preferably phenyl-acetyl;
R(2)is
1. hydrogen;
2. alkyl having 1, 2, 3, 4, 5 or 5 carbon atoms;
3. alkyl having 1, 2, 3, 4, or 5 carbon atoms, in which one to all hydrogen atoms are replaced by fluorine;
4. alkenyl having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms;
5. alkynyl having 2, 3, 4, or 5 carbon atoms;
6. —C
n
H
2n−nn
—Z,
nn is zero or 2; and
n is zero, 1, 2, 3 or 4; where n is unequal to zero or 1 if nn is equal to 2;
7. —C
n
H
2n−nn
—Z,
nn is zero or 2; and
n is 1, 2, 3 or 4, where n is unequal to 1 if nn is equal to 2;
where 1, 2 or 3 hydrogen atoms in the divalent radical —C
n
H
2n−nn
— independently of one another are replaced by a radical from the group consisting of
1. aryl having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms, preferably phenyl, 1-naphthyl or 2-naphthyl;
2. amino;
3. N(R(22)R(23);
4. (C
1
-C
4
)-alkoxycarbonyl;
5. COOR(16);
6. alkyl having 1, 2, 3 or 4 carbon atoms;
R(3) and R(4) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R(5), R(6) and R(7) i

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