Substituted sulphonyl cyanamides, method for producing same...

Details Substituted sulphonyl cyanamides, method for producing same... Substituted sulphonyl cyanamides, method for producing same...

2000-11-03

2003-06-03

McKane, Joseph K. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S399000, C548S322500, C548S325100, C548S327100, C548S333100

Reexamination Certificate

active

06573288

ABSTRACT:

The present invention relates to compounds of the formula (I)
in which the symbols have the following meanings:
X is equal to
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 F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxy or NR(19)R(20);
R(19) and R(20) independently of one another are H 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 series consisting of F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxy or NR(21)R(22);
R(21) and R(22) independently of one another are H or alkyl having 1, 2, 3 or 4 carbon atoms;
b is zero, 1 or 2; or
R(1) is —C
c
H
2c
-cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms;
c 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(23), CO—R(24) or O—R(25);
R(23) is hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
R(24) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, OR(26) or phenyl;
where phenyl is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the series consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxy or NR(27)R(28);
R(27) and R(28) independently of one another are H or alkyl having 1, 2, 3 or 4 carbon atoms;
R(26) is hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
R(25) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, or phenyl;
where phenyl is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the series consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxy or NR(29)R(30);
R(29) and R(30) independently of one another are H or alkyl having 1, 2, 3 or 4 carbon atoms; or
R(25) 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 series consisting of F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxy or NR(31)R(32);
R(31) and R(32) independently of one another are H 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
d
H
2d
-phenyl, where the phenyl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the series consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxy or NR(33)R(34);
R(33) and R(34) independently of one another are H or alkyl having 1, 2, 3 or 4 carbon atoms;
d is zero, 1 or 2; or
R(2) and R(3) independently of one another are
 —C
e
H
2e
-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 series consisting of F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxy or NR(35)R(36);
R(35) and R(36) independently of one another are H or alkyl having 1, 2, 3 or 4 carbon atoms;
e is zero, 1 or 2; or
R(2) and R(3) independently of one another are
 —SO
f
—R(37);
R(37) 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
g
H
2g
-phenyl, where the phenyl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the series consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxy or NR(38)R(39);
R(38) and R(39) independently of one another are
H or alkyl having 1, 2, 3 or 4 carbon atoms;
f is zero, 1 or 2;
g is zero, 1 or 2;
R(4) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, 1-naphthyl, 2-naphthyl, —C
i
H
2i
-cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms or —C
i
H
2i
-phenyl, where the phenyl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the series consisting of alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, F, Cl, Br, I, CF
3
, SO
j
R(48), OR(49), NR(50)R(51), —CN, —NO
2
or CO—R(52);
i is zero, 1 or 2;
R(48) is alkyl having 1, 2, 3 or 4 carbon atoms or NR(53)R(54);
R(53) and R(54) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
j is zero, 1 or 2;
R(49) is hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R(50) and R(51) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
R(52) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms or OR(55);
R(55) is hydrogen, alkyl having 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms; or
R(4) and R(6) together with the carbon atom carrying them are cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms or fluorenyl;
R(5), R(6), R(7) and R(8) independently of one another are hydrogen, F, CF
3
, O—R(56), alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms, —C
k
H
2k
-phenyl, where the phenyl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the series consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxy or NR(57)R(58);
R(57) and R(58) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms;
k is zero, 1 or 2;
R(56) 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 series consisting of F, Cl, Br, I, CF
3
, methyl, methoxy, hydroxy or NR(59)R(60);
R(59) and R(60) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms, or
R(56) 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 series consisting of F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxy or NR(61)R(62);
R(61) and R(62) independently of one another are hydrogen or alkyl having 1, 2, 3 or 4 carbon atoms; or
R(5) and R(7) together are a second bond between the carbon atoms carrying the radicals R(6) and R(8), where R(4), R(6) and R(8) are as defined above;
R(9) is alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, alkenyl having 2, 3, 4, 5, 6, 7 or 8 carbon atoms, or —C
I
H
2I-II
—A;
II is zero or 2; and
I is zero, 1, 2, 3 or 4;
where I is unequal to zero or 1, when II is equal to 2;
R(10) is hydrogen;
alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms; or
alkenyl having 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
—C
m
H
2m-mm
—B,
mm is zero or 2; and
m is zero, 1, 2, 3 or 4;
where m is unequal to zero or 1, when mm is equal to 2;
R(11) and R(12) independently of one another are hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
Z is carbonyl or sulfonyl;
A and B 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, substituted by 1, 2 or 3 identical or different radicals from the series consisting of alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, F, Cl, Br, I, CF
3
, SO
n
R(63), OR(64), NR(65)R(66), —CN, —NO
2
or CO—R(67);
3. heteroaryl having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms;
4. a radical as defined in 3, substituted by 1, 2 or 3 identical or different radicals from the series consisting of F, Cl, Br, I, CF
3
, CH
3
, methoxy, hydroxy or NR(68)R(69);
5. cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms;
6. O—R(70); or
7. O—R(71);
n is zero, 1 or 2;
R(70) and R(71) independently of one another are
1. hydrogen;
2. alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms;
3. —C
o
H
2o-oo
-phenyl,
oo is zero or 2; and
o is zero, 1, 2, 3 or 4;
where o is unequal to zero or 1, when oo is equal to 2;
4. a radical as defined in 3, where the phenyl moiety is substituted by 1, 2 or 3 identical or different radicals from the series consisting of alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, F, Cl, Br, I, CF
3
, SO
p
R(72), OR(73), NR(74)R(75), —CN, —NO
2
or CO—R(76); or
5. alkenyl having 2, 3

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