Substituted cinnamic, acid guanidides, process for their...

Details Substituted cinnamic, acid guanidides, process for their... Substituted cinnamic, acid guanidides, process for their...

2001-09-18

2002-06-04

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C514S255030, C514S426000, C514S428000, C514S592000, C514S593000, C514S603000, C544S383000, C548S557000, C548S567000, C548S568000, C548S569000, C564S040000, C564S041000, C564S042000

Reexamination Certificate

active

06399824

ABSTRACT:

This application claims the benefit of foreign priority under 35 U.S.C. §119 of German patent application no. 10046993.0, filed on Sep. 22, 2000, the contents of which are incorporated by reference herein.
The invention relates to substituted cinnamic acid guanidides of the formula I
in which:
at least one of R(1), R(2), R(3), R(4) and R(5) is —X
a
—Y
b
—L
n
—U;
X is CR(16)R(17), O, S or NR(18);
where R(16), R(17) and R(18) independently of one another are H or an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls;
a is zero or;
Y is alkylene having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, alkylene-T having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms in the alkylene group, T, or T-alkylene having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms in the alkylene group;
where T is NR(20), phenylene, O or S, where the phenylene is not substituted or is substituted by 1-3 substituents chosen from F, Cl, CF
3
, methyl, methoxy and NR(21)R(22);
where R(20), R(21) and R(22) independently of one another are H or an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls;
b is zero or 1;
L is O, S, NR(23) or C
k
H
2k
;
where k is 1, 2, 3, 4, 5, 6, 7 or 8;
where R(23) is H or an alkyl group having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls;
n is zero or 1;
U is
 or a nitrogen-containing heterocycle having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, which is substituted by an —SO
2
NR(30)R(31)-group;
where R(30) and R(31) independently of one another are H or an alkyl group having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms,
where in the alkyl group, independently of one another, one or more CH
2
groups can be replaced by O, NR(35), C═O, S or C═S;
where R(35) is H or alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls; or
R(30) and R(31) independently of one another are H, an alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, where the alkyl is chosen from partially fluorinated alkyls and completely fluorinated alkyls, (C
3
-C
8
)-cycloalkyl, phenyl-(C
1
-C
4
)-alkyl or (C
3
-C
8
)-cycloalkyl-(C
1
-C
4
)-alkyl,
where in the alkyl or in the cycloalkyl ring, independently of one another, one or more CH
2
groups can be replaced by 0, NR(35), C═O, S or C═S; or
R(30) and R(31) together are 4 or 5 methylene groups,
where, independently of one another, one or more CH
2
groups can be replaced by O, NR(35), C═O, S or C═S; or
R(31) and R(35) together are 4 or 5 methylene groups;
R(32), R(33) and R(34) independently of one another are H, F, Cl, Br, I, (C
1
-C
4
)-alkyl, partially fluorinated (C
1
-C
4
)-alkyl, completely fluorinated (C
1
-C
4
)-alkyl, O—(C
1
-C
4
)-alkyl, partially fluorinated O—(C
1
-C
4
)-alkyl, completely fluorinated O—(C
1
-C
4
)-alkyl, NO
2
, or NR(28)R(29);
where R(28) and R(29) independently of one another are H or an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls;
where the N-containing heterocycles are N- or C-bridged and are unsubstituted or are substituted by 1-3 substituents selected from the group consisting of F, Cl, CF
3
, methyl, methoxy and NR(36)R(37);
R(36) and R(37) independently of one another are H, an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated, and completely fluorinated alkyls, or benzyl;
and the remaining substituents of R(1), R(2), R(3), R(4) and R(5) independently of one another are H, F, Cl, Br, I, SO
2
NH
2
, SO
2
CH
3
, NO
2
, NR(24)R(25), CN, unsubstituted (C
1
-C
8
)-alkyl, partially fluorinated (C
1
-C
8
)-alkyl, completely fluorinated (C
1
-C
8
)-alkyl, unsubstituted O—(C
1
-C
8
)-alkyl, partially fluorinated O—(C
1
-C
8
)-alkyl, completely fluorinated O—(C
1
-C
8
)-alkyl, (C
3
-C
8
)-cycloalkyl, (C
3
-C
8
)-cycloalkyl-(C
1
-C
4
)-alkyl or phenyl-(C
1
-C
4
)-alkyl,
where the phenyl is not substituted or is substituted by 1-3 substituents selected from the group consisting of F, Cl, CF
3
, methyl, methoxy and NR(11)R(12);
R(11), R(12), R(24) and R(25) independently of one another are H or an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls;
R(6) and R(7) independently of one another are H, F, Cl, Br, I, CN, an alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls, and completely fluorinated alkyls, cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms or phenyl,
where the phenyl is not substituted or is substituted by 1-3 substituents selected from the group consisting of F, Cl, CF
3
, methyl, methoxy and NR(14)R(15);
R(14) and R(15) independently of one another are H or an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls;
and their pharmaceutically tolerable salts.
In one embodiment, the compounds of the formula I are those in which:
at least one of the substituents R(1), R(2), R(3), R(4) and R(5) is —X—U;
X is CR(16)R(17), O, S or NR(18);
R(16), R(17) and R(18) independently of one another are H or an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls;
U is
 or a nitrogen-containing heterocycle having 1, 2, 3, 4, 5, 6, 7, 8 or 9 carbon atoms, which is substituted by an —SO
2
NR(30)R(31)-group;
R(30) and R(31) independently of one another are hydrogen or alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms,
where in the alkyl chain, independently of one another, one or more CH
2
groups can be replaced by O, NR(35), C═O, S or C═S;
R(35) is H or an alkyl having 1, 2, 3, 4 or 5 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated alkyls and completely fluorinated alkyls; or
R(30) and R(31) independently of one another are H, an alkyl having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, where the alkyl is chosen from partially fluorinated alkyl and completely fluorinated alkyl, (C
3
-C
8
)-cycloalkyl, phenyl-(C
1
-C
4
)-alkyl or (C
3
-C
8
)-cycloalkyl-(C
1
-C
4
)-alkyl,
where in the alkyl or in the cycloalkyl ring, independently of one another, one or more CH
2
groups can be replaced by O, NR(35), C═O, S or C═S; or
R(30) and R(31) together are 4 or 5 methylene groups,
where, independently of one another, one or more CH2 groups can be replaced by O, NR(35), C═O, S or C═S; or
R(31) and R(35) together are 4 or 5 methylene groups;
R(32), R(33) and R(34) independently of one another are H, F, Cl, Br, I, (C
1
-C
4
)-alkyl, O—(C
1
-C
4
)-alkyl, CF
3
or NR(28)R(29);
R(28) and R(29) independently of one another are H or alkyl having 1, 2, 3 or 4 carbon atoms;
where the N-containing heterocycles are N- or C-bridged and are not substituted or are substituted by 1-3 substituents selected from the group consisting of F, Cl, CF
3
, methyl, methoxy and NR(36)R(37);
R(36) and R(37) independently of one another are H, an alkyl having 1, 2, 3 or 4 carbon atoms, where the alkyl is chosen from unsubstituted alkyls, partially fluorinated, and completely fluorinated alkyls, or benzyl;
and the remaining substituents of R(1), R(2), R(3), R(4) and R(5) independently of one another are H, F, Cl, Br, I, SO
2
NH
2
, SO
2
CH
3
, NO
2
, NR(24)R(25), CN, unsubstituted (C
1
-C
4
)-alkyl, partially fluorinated (C
1
-C
4
)-alkyl, completely fluorinated (C
1
-C
4
)-alkyl, unsubstituted O—(C
1
-C
4
)-alkyl, partially fluorinated O—(C
1
-C
4
)-alkyl, completely fluorinated O—(C
1
-C
4
)-alkyl, (C
3
-C
6
)-cycloalkyl, (C
3
-C
6
)-cycloalkyl-(C
1

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