Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-12-04
2004-02-03
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...
C548S307400
Reexamination Certificate
active
06686384
ABSTRACT:
This application claims the benefit of the filing date of German Patent Application No. 10060292.4, filed on Dec. 5, 2000, which application is hereby incorporated by reference.
The invention relates to substituted benzimidazoles of formula I:
in which:
R1 and R5 are, independently of one another, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine; or
R1 and R5 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine; or
R1 and R5 are, independently of one another, OH or O-alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine; or
R1 and R5 are, independently of one another, OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, or —(O)
n
—SO
m
R15, in which n is 0 or 1 and m is 0, 1, or 2; or
R1 and R5 are O-phenyl, in which phenyl is unsubstituted or substituted by one to three substituents selected, independently of one another, from F, Cl, Br, I, alkyl having 1 to 4 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, NR16R17, CN, or (C
1
-C
4
)-alkylsulfonyl, in which the alkyl groups are unsubstituted or partially or completely substituted by fluorine;
R16 and R17 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
R10 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
R11 and R12 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH
2
group of said alkyl is optionally replaced by O or NR18; or
R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring; or
R11 and R12 are, independently of one another, COR19 or SO
2
R20;
R18, R19, and R20 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
R13 and R14 are alkyl having 1 to 4 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine;
R15 is alkyl or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine; or
R15 is OH or NR21 R22;
R21 and R22 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine, and at least one CH
2
group of said alkyl is optionally replaced by O or NR23;
R23 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine; or
R21 and R22, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
but R1 and R5 cannot simultaneously be Cl or CH
3
;
R2, R3, and R4 are H or one of the radicals R2, R3, or R4 is optionally F;
R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, l, CN, alkyl, or O-alkyl, in which the alkyl groups have 1 to 4 carbon atoms and are unsubstituted or partially or completely substituted by fluorine; or
R6, R7, R8, and R9 are cycloalkyl having 3 to 7 carbon atoms, which is unsubstituted or partially or completely substituted by fluorine; or
R6, R7, R8, and R9 are, independently of one another, OH, OCOR24, or NR25R26;
R24 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine;
R25 and R26 are, independently of one another, H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine; or
R25 and R26 are COR27; or
R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring, and at least one CH
2
group thereof is optionally replaced by O or NR18;
R27 is H or alkyl having 1 to 4 carbon atoms, in which alkyl is unsubstituted or partially or completely substituted by fluorine; or
a pharmaceutically tolerable salt or trifluoroacetate thereof.
Other embodiments of compounds of formula I are those in which:
R1 and R5 are, independently of one another, F, Cl, Br, CN, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, CF
2
CF
3
, cycloalkyl having 3 to 7 carbon atoms, O-alkyl having 1 to 4 carbon atoms, OH, OCF
3
, OCH
2
CF
3
, OCF
2
CF
3
, OCOR10, NR11R12, COR13, COOH, COOR14, CONR11R12, —O
m
—SO
2
R15, or O-phenyl;
m is 0 or 1;
R10 is H, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, or CF
2
CF
3
;
R11 and R12 are, independently of one another, H, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, CF
2
CF
3
, and at least one CH
2
group of said alkyl is optionally replaced by O or NR18; or
R11 and R12, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring; or
R11 and R12 are, independently of one another, COR19 or SO
2
R20;
R18, R19, and R20 are, independently of one another, H, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, or CF
2
CF
3
;
R13 and R14 are, independently of one another, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, or CF
2
CF
3
;
R15 is alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, CF
2
CF
3
, OH, O-alkyl having 1 to 4 carbon atoms, OCF
3
, OCH
2
CF
3
, OCF
2
CF
3
, or NR21R22;
R21 and R22 are, independently of one another, H, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, or CF
2
CF
3
; or
R21 and R22, together with the nitrogen atom to which they are bonded, are —(CH
2
)
4
—, —(CH
2
)
5
—, —(CH
2
)
2
—O—(CH
2
)
2
—, or —(CH
2
)
2
—N—R30—(CH
2
)
2
;
R30 is H, CH
3
, or CF
3
;
but R1 and R5 cannot simultaneously be Cl or CH
3
;
R2, R3, and R4 are H or one of the radicals R2, R3, or R4 is optionally F;
R6, R7, R8, and R9 are, independently of one another, H, F, Cl, Br, I, CN, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, CF
2
CF
3
, cycloalkyl having 3 to 7 carbon atoms, OH, O-alkyl having 1 to 4 carbon atoms, OCF
3
, OCH
2
CF
3
, OCF
2
CF
3
, OCOR24, or NR25R26;
R24 is H, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, or CF
2
CF
3
;
R25 and R26 are, independently of one another, H, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, CF
2
CF
3
, or COR27; or
R25 and R26, together with the nitrogen atom to which they are bonded, form a 5-, 6-, or 7-membered ring;
R27 is H, alkyl having 1 to 4 carbon atoms, CF
3
, CH
2
CF
3
, or CF
2
CF
3
; or
a pharmaceutically tolerable salt or trifluoroacetate thereof.
Another embodiment of compounds of formula I are those in which:
R1 and R5 are, independently of one another, F, Cl, Br, CN, methyl, ethyl, isopropyl, CF
3
, cyclopropyl, OH, O-methyl, O-ethyl, O-isopropyl, OCF
3
, O-acetyl, NH
2
, N(CH
3
)
2
, N(CH
2
CH
3
)
2
, N-pyrrolidino, N-piperidino, N-morpholino, N-(N′-methyl)-piperazino, NHSO
2
Me, acetyl, COOH, COOR14, CONR11R12, SO
2
R15, or O-phenyl;
R11 and R12 are, independently of one another, H, methyl, or ethyl;
R14 is methyl or ethyl;
R15 is CH
3
, CF
3
, OH, OCH
3
, OCF
3
, or NR21R22;
R21 and R22 are, independently of one another, H or methyl;
but R1 and R5 cannot simultaneously be Cl or CH
3
;
R2, R3, and R4 are H;
R6, R7, R8, and R9 are, independently of one another, H, F, Cl, CN, CH
3
, C
2
H
5
isopropyl, CF
3
, cyclopropyl, OH, OCH
3
, OCF
3
, O-acetyl, or NR25R26;
R25 and R26 are, independently of one another, H, methyl, or acetyl; or
a pharmaceutically tolerable salt or trifluoroacetate thereof.
Another embodiment of compounds of formula I are those in which:
R1 and R5 are, independently of one another, F, Cl, Br, CN, methyl, ethyl, isopropyl, CF
3
, cyclopropyl, OH, O-methyl, O-ethyl, O-isopropyl, OCF
3
, O-acetyl, NH
2
, N(CH
3
)
2
, N(CH
2
CH
3
)
2
, N-pyrrolidino, N-piperidino, N-morpholino, N-(N′-methyl)-piperazino, NHSO
2
Me, acetyl, COOH, COOR14, CONR11R12, SO
2
R15, or O-phenyl;
R11 and R12 are, independently of one another, H, methyl, or ethyl;
R14 is methyl or ethyl;
R15 is
Bleich Markus
Gekle Michael
Heinelt Uwe
Hofmeister Armin
Lang Hans-Jochen
Aventis Pharma Deutschland GmbH
McKane Joseph K.
Shameem Golam M. M.
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