US 5,668,136 A · Trisubstituted benzene derivatives, composition and methods of treatment · patentgrep

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Abstract

A benzene, pyridine or pyrimidine derivative having the below shown formula is novel and useful as an anti-arteriosclerotic agent. ##STR1## wherein R.sup.1 stands for a lower alkyl group, an amino group which may be substituted, or the like; R.sup.2 stands for a group represented by the formula: ##STR2## (wherein R.sup.16 stands for an alkyl group having 1 to 6 carbon atoms, or the like) or the like; R.sup.3 stands for a group represented by the formula: --O--(CH.sub.2).sub.m --Y (Y stands for an imidazolyl or piperazinyl group, or the like and m is 1 to 6) or the like; R.sup.5 stands for a hydrogen atom, a lower alkyl group, or the like; A stands for a group represented by the formula: ##STR3## (wherein R.sup.6 stands for a hydrogen atom, a lower alkyl group, or the like), --N.dbd., or the like; and B stands for a group represented by the formula: ##STR4## (wherein R.sup.4 stands for a hydrogen or the like), --N.dbd., or the like.

Claims23

Dependent claims

A benzene compound represented by the general formula (I):

##STR235## wherein R.sup.1 stands for a halogen atom, a lower alkyl, a lower alkoxy, a nitro or a cyano group, a group represented by the formula:
##STR236## wherein R.sup.7 and R.sup.8 may be the same or different and each stands for a hydrogen atom, a lower alkyl or a lower alkylsulfonyl group, and u is 0 or an integer of 1 or 2 or alternatively, R.sup.7 and R.sup.8 may form a ring together with the nitrogen atom to which R.sup.7 and R.sup.8 are bonded, a group represented by the formula:
--CH.sub.2 OR.sup.9 wherein R.sup.9 stands for a hydrogen atom or a lower alkyl group, a group represented by the formula:
--COOR.sup.10 wherein R.sup.10 stands for a hydrogen atom or a lower alkyl group, a group represented by the formula:
##STR237## wherein R.sup.11 and R.sup.12 may be the same or different and each stands for a hydrogen atom or a lower alkyl group or a group represented by the formula:
##STR238## wherein t is 0 or an integer of 1 or 2;
and R.sup.13 stands for a hydrogen atom or a lower alkyl group;
R.sup.2 stands for a group represented by the formula:
##STR239## wherein R.sup.14, R.sup.15 and R.sup.16 may be the same or different and each stands for a hydrogen atom or an alkyl, cycloalkyl, alkenyl or alkyloxyalkyl group;
alternatively, R.sup.15 and R.sup.16 may form a ring together with the nitrogen atom to which R.sup.15 and R.sup.16 are bonded, a group represented by the formula:
--NH--R.sup.18 wherein R.sup.18 stands for an alkyl group or a group represented by the formula:
##STR240## wherein R.sup.19 stands for an alkyl group and n is an integer of 1 to 3;
R.sup.3 stands for a group represented by the formula:
--(CH.sub.2).sub.p --X-- (CH.sub.2).sub.m --Y wherein X stands for a group represented by the formula:
--O--, --S--, ##STR241## --SO.sub.2 --, --NH--, --CH.sub.2 -- or --CH.dbd.CH--;
p is 0 or 1;
m is an integer of 1 to 6;
Y is selected from the group consisting of ##STR242## which may have a substituent (s), said substituent (s) for Y being a (a) C.sub.1 -C.sub.6 lower alkyl group,
(b) a C.sub.1 -C.sub.6 lower alkoxy group, an aryl group or an aryl group substituted with a substituent(s) selected from a C.sub.1 -C.sub.6 lower alkyl group, a C.sub.1 -C.sub.6 lower alkoxy group, C.sub.1 -C.sub. 6 lower alkylsulfonyl group, a halogen atom, a nitro group, a C.sub.1 -C.sub.6 lower alkylsulfonylamino group, or a di (C.sub.1 -C.sub.6 lower alkyl)sulfonylamino group,
(c) a group represented by the formula:
--(E).sub.a --COOR.sup.21 wherein E is a C.sub.1 -C.sub.6 alkylene or C.sub.1 -C.sub.6 alkenylene group, and R.sup.21 is an H atom, a lower alkyl group, or an amino group, and a is 0 or 1,
(d) a group represented by the formula:
--(CH.sub.2).sub.v --OH wherein v is 0 or an integer of 1 to 6,
(e) a halogen atom,
(f) a group represented by the formula:
--(CH.sub.2).sub.b --NH--(CH.sub.2).sub.c --CH.sub.3 wherein b is 0 or an integer of 1 to 4 and c is 0 or an integer of 1 to 5,
(g) a group represented by the formula:
--(CH.sub.2).sub.a --SO.sub.2 R.sup.22 wherein d is 0 or an integer of 1 to 6 and R.sup.22 is a C.sub.1 -C.sub.6 lower alkyl group, or
(h) a group represented by the formula:
##STR243## wherein e is an integer of 1 to 6, and R.sup.23 and R.sup.24 may be the same or different and each stands for a hydrogen or a C.sub.1 -C.sub.6 lower alkyl
or Y is a C.sub.1 -C.sub.6 lower alkoxy group or a group represented by the formula:
##STR244## W wherein V stands for a group represented by the formula:
--O--, --S--, ##STR245## --SO.sub.2 --, --NH-- or --CH.sub.2 --;
q and s are each an integer of 1 to 6;
R.sup..degree. stands for a hydrogen atom or a lower alkyl group;
W has the same definition as Y above;
R.sup.6 stands for a hydrogen atom;
R.sup.4 stands for a hydrogen;
R.sup.5 stands for a hydrogen atom;
or a pharmacologically acceptable salt thereof.

37 more elements

A benzene compound represented by the general formula:

##STR251## wherein R.sup.1 stands for a halogen atom, a lower alkyl, a lower alkoxy, a nitro or a cyano group, a group represented by the formula:
##STR252## wherein R.sup.7 and R.sup.8 may be the same or different and each stands for a hydrogen atom, a lower alkyl or a lower alkylsulfonyl group, and u is 0 or an integer of 1 or 2 or alternatively, R.sup.7 and R.sup.8 may form a ring together with the nitrogen atom to which R.sup.7 and R.sup.8 are bonded, a group represented by the formula:
--CH.sub.2 OR.sup.9 wherein R.sup.9 stands for a hydrogen atom or a lower alkyl group, a group represented by the formula:
--COOR.sup.10 wherein R.sup.10 stands for a hydrogen atom or a lower alkyl group, a group represented by the formula:
##STR253## wherein R.sup.11 and R.sup.12 may be the same or different and each stands for a hydrogen atom or a lower alkyl group or a group represented by the formula:
##STR254## wherein t is 0 or an integer of 1 or 2;
and R.sup.13 stands for a hydrogen atom or a lower alkyl group;
R.sup.2 stands for a group represented by the formula:
##STR255## wherein R.sup.14 stands for a hydrogen atom or an alkyl, cycloalkyl, alkenyl or alkyloxyalkyl group;
R.sup.15 stands for a hydrogen atom or an alkyl, cycloalkyl, alkenyl or alkyloxyalkyl group;
and R.sup.16 stands for alkyl, cycloalkyl, alkenyl or alkyloxyalkyl group;
or R.sup.15 and R.sup.16 may form a ring together with the nitrogen atom to which R.sup.15 and R.sup.16 are bonded, or R.sup.2 stands for a group represented by the formula:
--NH--R.sup.18 wherein R.sup.18 stands for an alkyl group or a group represented by the formula:
##STR256## wherein R.sup.19 stands for an alkyl group and n is an integer of 1 to 3;
R.sup.3 stands for a group represented by the formula:
--(CH.sub.2).sub.p --X-- (CH.sub.2).sub.m --Y wherein X stands for a group represented by the formula:
--O--, --S--, ##STR257## --SO.sub.2 --, --NH--, --CH.sub.2 -- or --CH.dbd.CH--;
p is 0 or 1;
m is an integer of 1 to 6;
Y is selected from the group consisting of ##STR258## which may have a substituent (s), said substituent (s) for Y being a (a) C.sub.1 -C.sub.6 lower alkyl group,
(b) a C.sub.1 -C.sub.6 lower alkoxy group, an aryl group or an aryl group substituted with a substituent(s) selected from a C.sub.1 -C.sub.6 lower alkyl group, a C.sub.1 -C.sub.6 lower alkoxy group, C.sub.1 -C.sub.6 lower alkylsulfonyl group, a halogen atom, a nitro group, a C.sub.1 -C.sub.6 lower alkylsulfonylamino group, or a di (C.sub.1 -C.sub.6 lower alkyl) sulfonylamino group,
(c) a group represented by the formula:
--(E).sub.a --COOR.sup.21 wherein E is a C.sub.1 -C.sub.6 alkylene or C.sub.1 -C.sub.6 alkenylene group, and R.sup.21 is an H atom, a lower alkyl group, or an amino group, and a is 0 or 1,
(d) a group represented by the formula:
--(CH.sub.2).sub.v --OH wherein v is 0 or an integer of 1 to 6,
(e) a halogen atom,
(f) a group represented by the formula:
--(CH2).sub.b --NH--(CH.sub.2).sub.c --CH.sub.3 wherein b is 0 or an integer of 1 to 4 and c is 0 or an integer of 1 to 5,
(g) a group represented by the formula:
--(CH.sub.2).sub.a --SO.sub.2 R.sup.22 wherein d is 0 or an integer of 1 to 6 and R.sup.22 is a C.sub.1 -C.sub.6 lower alkyl group, or
(h) a group represented by the formula:
##STR259## wherein e is an integer of 1 to 6, and R.sup.23 and R.sup.24 may be the same or different and each stands for a hydrogen or a C.sub.1 -C.sub.6 lower alkyl
or Y is a C.sub.1 -C.sub.6 lower alkoxy group or a group represented by the formula:
##STR260## wherein V stands for a group represented by the formula:
--O--, --S--, ##STR261## --SO.sub.2 --, --NH-- or --CH.sub.2 --;
q and s are each an integer of 1 to 6;
R stands for a hydrogen atom or a lower alkyl group;
W has the same definition as Y above;
R.sup.6 stands for a hydrogen atom;
R.sup.4 stands for a hydrogen;
R.sup.5 stands for a hydrogen atom;
and
in addition, two of R.sup.1, R.sup.4, R.sup.5 and R.sup.6 may form a benzene ring, which may be substituted;
or a pharmacologically acceptable salt thereof.

41 more elements

A benzene compound represented by the general formula:

##STR262## wherein R.sup.1 stands for a lower alkyl, or a group represented by the formula:
##STR263## (wherein R.sup.7 and R.sup.8 may be the same or different and each stands for a hydrogen atom, or a lower alkyl and u is 0 or an integer of 1 or 2;
R.sup.16 stands for a hydrogen atom or an alkyl, cycloalkyl, alkenyl or alkyloxyalkyl group;
m is an integer of 1 to 6;
Y is selected from the group consisting of ##STR264## which may have a substituent (s), said substituent (s) for Y being a (a) C.sub.1 -C.sub.6 lower alkyl group,
(b) a C.sub.1 -C.sub.6 lower alkoxy group, an aryl group or an aryl group substituted with a substituent(s) selected from a C.sub.1 -C.sub.6 lower alkyl group, a C.sub.1 -C.sub.6 lower alkoxy group, C.sub.1 -C.sub.6 lower alkylsulfonyl group, a halogen atom, a nitro group, a C.sub.1 -C.sub.6 lower alkylsulfonylamino group, or a di (C.sub.1 -C.sub.6 lower alkyl)sulfonylamino group,
(c) a group represented by the formula:
--(E).sub.a --COOR.sup.21 wherein E is a C.sub.1 -C.sub.6 alkylene or C.sub.1 -C.sub.6 alkenylene group, and R.sup.21 is an H atom, a lower alkyl group, or an amino group, and a is 0 or 1,
(d) a group represented by the formula:
--(CH.sub.2).sub.v --OH wherein v is 0 or an integer of 1 to 6,
(e) a halogen atom,
(f) a group represented by the formula:
--(CH.sub.2).sub.b --NH--(CH.sub.2).sub.c --CH.sub.3 wherein b is 0 or an integer of 1 to 4 and c is 0 or an integer of 1 to 5,
(g) a group represented by the formula:
--(CH.sub.2).sub.a --SO.sub.2 R.sup.22 wherein d is 0 or an integer of 1 to 6 and R.sup.22 is a C.sub.1 -C.sub.6 lower alkyl group, or
(h) a group represented by the formula:
##STR265## wherein e is an integer of 1 to 6, and R.sup.23 and R.sup.24 may be the same or different and each stands for a hydrogen or a C.sub.1 -C.sub.6 lower alkyl or Y is a group represented by the formula:
##STR266## wherein V stands for a group represented by the formula:
--O--, --S--, ##STR267## --SO.sub.2 --, --NH-- or --CH.sub.2 --;
q and s are each an integer of 1 to 6;
R.sup.20 stands for a hydrogen atom or a lower alkyl group;
W has the same definition as Y above;
or a pharmacologically acceptable salt thereof.

20 more elements

A benzene compound represented by the general formula:

##STR268## wherein R.sup.1 stands for a halogen atom, a lower alkyl, a lower alkoxy, a nitro or a cyano group, a group represented by the formula:
##STR269## wherein R.sup.7 and R.sup.8 may be the same or different and each stands for a hydrogen atom, a lower alkyl or a lower alkylsulfonyl group, and u is 0 or an integer of 1 or 2 or alternatively, R.sup.7 and R.sup.8 may form a ring together with the nitrogen atom to which R.sup.7 and R.sup.8 are bonded, a group represented by the formula:
--CH.sub.2 OR.sup.9 wherein R.sup.9 stands for a hydrogen atom or a lower alkyl group, a group represented by the formula:
--COOR.sup.10 wherein R.sup.10 stands for a hydrogen atom or a lower alkyl group, a group represented by the formula:
##STR270## wherein R.sup.11 and R.sup.12 may be the same or different and each stands for a hydrogen atom or a lower alkyl group or a group represented by the formula:
##STR271## wherein t is 0 or an integer of 1 or 2;
and R.sup.13 stands for a hydrogen atom or a lower alkyl group;
R.sup.2 stands for a group represented by the formula:
##STR272## wherein R.sup.14, R.sup.15 and R.sup.16 may be the same or different and each stands for a hydrogen atom or an alkyl, cycloalkyl, alkenyl or alkyloxyalkyl group;
R.sup.3 stands for a group represented by the formula:
--(CH.sub.2).sub.p --X-- (CH.sub.2).sub.m --Y wherein X stands for a group represented by the formula:
--O--, --S--, ##STR273## --SO.sub.2 --, --NH--, --CH.sub.2 -- or --CH.dbd.CH--;
p is 0 or 1;
m is an integer of 1 to 6;
and Y is selected from the group consisting of ##STR274## which may have a substituent (s), said substituent (s) for Y being a (a) C.sub.1 -C.sub.6 lower alkyl group,
(b) a C.sub.1 -C.sub.6 lower alkoxy group, an aryl group or an aryl group substituted with a substituent (s) selected from a C.sub.1 -C.sub.6 lower alkyl group, a C.sub.1 -C.sub.6 lower alkoxy group, C.sub.1 -C.sub.6 lower alkylsulfonyl group, a halogen atom, a nitro group, a C.sub.1 -C.sub.6 lower alkyl sulfonylamino group, or a di (C.sub.1 -C.sub.6 lower alkyl) sulfonylamino group,
(c) a group represented by the formula:
--(E).sub.a --COOR.sup.21 wherein E is a C.sub.1 -C.sub.6 alkylene or C.sub.1 -C.sub.6 alkenylene group, and R.sup.21 is an H atom, a lower alkyl group, or an amino group, and a is 0 or 1,
(d) a group represented by the formula:
--(CH.sub.2).sub.v --OH wherein v is 0 or an integer of 1 to 6,
(e) a halogen atom,
(f) a group represented by the formula:
--(CH.sub.2).sub.b --NH--(CH.sub.2).sub.c --CH.sub.3 wherein b is 0 or an integer of t to 4 and c is 0 or an integer of 1 to 5,
(g) a group represented by the formula:
--(CH.sub.2).sub.a --SO.sub.2 R.sup.22 wherein d is 0 or an integer of 1 to 6 and R.sup.22 is a C.sub.1 -C.sub.6 lower alkyl group, or
(h) a group represented by the formula:
##STR275## wherein e is an integer of 1 to 6, and R.sup.23 and R.sup.24 may be the same or different and each stands for a hydrogen or a C.sub.1 -C.sub.6 lower alkyl
or Y is a C.sub.1 -C.sub.6 lower alkoxy group or a group represented by the formula:
##STR276## wherein V stands for a group represented by the formula:
--O--, --S--, ##STR277## --SO.sub.2 --, --NH-- or --CH.sub.2 --;
q and s are each an integer of 1 to 6;
R.sup.20 stands for a hydrogen atom or a lower alkyl group;
W has the same definition as Y above;
R.sup.6 stands for a hydrogen atom;
R.sup.4 stands for a hydrogen;
R.sup.5 stands for a hydrogen atom;
or a pharmacologically acceptable salt thereof.

34 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/757,908Filed 11 Sep 1991
Priority: JP 2-25189725 Sep 1990
Granted: 16 Sep 1997
Term ends: Not estimatedThe source records don’t support an estimate.

Classification23 codes

C07D 233/64
Having two double bonds between ring members or between ring members and non-ring members: with substituted hydrocarbon radicals attached to ring…
A61P 3/06
Drugs for disorders of the metabolism: antihyperlipidemics
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
C07C 275/40
Having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton: being further substituted by…

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