Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-10-30
2002-11-26
Stockton, Laura L. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S398000, C514S399000, C514S400000
Reexamination Certificate
active
06486189
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, 1, 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, hydroxyl 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 consistng 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
2g
-phenyl,
said —C
g
H
2g
-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 —ClH
2l
—(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, 1 or 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
Faber Sabine
Jansen Hans-Willi
Kleemann Heinz-Werner
Lang Hans Jochen
Schwark Jan-Robert
Finnegan Henderson Farabow Garrett & Dunner LLP
Hoechst Aktiengesellschaft
Stockton Laura L.
LandOfFree
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