Propanolamine derivatives substituted by heterocyclic...

Details Propanolamine derivatives substituted by heterocyclic... Propanolamine derivatives substituted by heterocyclic...

1999-09-29

2001-10-16

Fan, Jane (Department: 1614)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S340000, C514S338000, C514S333000, C514S212010, C514S256000, C514S314000, C514S357000, C514S332000, C546S269700, C546S271100, C546S256000, C546S255000, C546S270100, C546S176000, C544S333000

Reexamination Certificate

active

06303639

ABSTRACT:

Under the provisions of Section 119 of 35 U.S.C., Applicants hereby claim the benefit of the filing date of Federal Republic of Germany Patent Application Number 19845402.3, filed Oct. 2, 1998, which Application is hereby incorporated by reference.
The present invention relates to substituted propanolamine derivatives and pharmaceutically tolerated salts and physiologically functional derivatives thereof.
Several classes of active compounds have already been described for treatment of adiposity and disturbances in lipid metabolism:
polymeric adsorbers, such as cholestyramine;
benzothiazepines (WO 93/16055);
bile acid dimers and conjugates (EP 0 489 423); and
4-amino-2-ureido-pyrimidine-5-carboxylic acid amides (EP 0 557 879).
The present invention is based on the object of providing further compounds displaying a therapeutically valuable hypolipidemic action. The present invention therefore relates to compounds of formula (I) or salts thereof:
wherein:
C is phenyl, pyridyl, thienyl, furyl, pyrimidyl, indolyl, thiazolyl, imidazolyl, coumarinyl, phthalimidyl, quinolyl, piperazinyl, tetrazolyl, triazolyl, oxazolyl, isoxazolyl, isothiazolyl, or thieno-, pyridino-, or benzo-fused derivatives thereof, wherein the aromatic or heteroaromatic radical is unsubstituted, or mono- or disubstituted by fluorine, chlorine, bromine, iodine, —OH, —CF
3
,—NO
2
,—CN, —(C
1
-C
8
)-alkoxy, —(C
1
-C
8
)-alkyl, —NH
2
, —NH—R
9
, —N(R
9
)R
10
, —CHO, —COOH, —COOR
11
, —(C═O)—R
12
, —(C
1
-C
6
)-alkyl-OH, —(C
1
-C
6
)-alkyl(—OH)-phenyl, —(C
1
-C
6
)-alkyl-CF
3
, —(C
1
-C
6
)-alkyl-NO
2
, —(C
1
-C
6
)-alkyl-CN, —(C
1
-C
6
)-alkyl-NH
2
, —(C
1
-C
6
)-alkyl-NH—R
9
, —(C
1
-C
6
)-alkyl-N(R
9
)R
10
, —(C
1
-C
6
)-alkyl-CHO, —(C
1
-C
6
)-alkyl-COOH, —(C
1
-C
6
)-alkyl-COOR
11
, —(C
1
-C
6
)-alkyl-(C═O)—R
12
, —O—(C
1
-C
6
)-alkyl-OH, —O—(C
1
-C
6
)-alkyl-CF
3
, —O—(C
1
-C
6
)-alkyl-NO
2
, —O—(C
1
-C
6
)-alkyl-CN, —O—(C
1
-C
6
)-alkyl-NH
2
, —O—(C
1
-C
6
)-alkyl-NH—R
9
, —O—(C
1
-C
6
)-alkyl-N(R
9
)R
10
, —O—(C
1
-C
6
)-alkyl-CHO, —O—(C
1
-C
6
)-alkyl-COOH, —O—(C
1
-C
6
)-alkyl-COOR
11
, —O—(C
1
-C
6
)-alkyl-(C═O)—R
12
, —N—SO
3
H, —SO
2
—CH
3
, or —O—(C
1
-C
6
)-alkyl-O—(C
1
-C
6
)-alkylphenyl, wherein one or more hydrogen(s) in the alkyl radicals is optionally replaced by fluorine;
D is phenyl, pyridyl, thienyl, furyl, pyrimidyl, indolyl, thiazolyl, imidazolyl, coumarinyl, phthalimidyl, quinolyl, piperazinyl, tetrazolyl, triazolyl, oxazolyl, isoxazolyl, isothiazolyl, or 4,5,6,7-tetrahydrobenzisoxazole, or thieno-, pyridino-, or benzo-fused derivatives thereof, wherein the aromatic or heteroaromatic radical is unsubstituted, or is mono- or disubstituted by fluorine, chlorine, bromine, iodine, —OH, —CF
3
, —NO
2
, —CN, —(C
1
-C
8
)-alkoxy, —(C
1
-C
8
)-alkyl, —NH
2
, —NH—R
9
, —N(R
9
)R
10
, —CHO, —COOH, —COOR
11
, —(C═O)—R
12
, —(C
1
-C
6
)-alkyl-OH, —(C
1
-C
6
)-alkyl(—OH)-phenyl, —(C
1
-C
6
)-alkyl-CF
3
, —(C
1
-C
6
)-alkyl-NO
2
, —(C
1
-C
6
)-alkyl-CN, —(C
1
-C
6
)-alkyl-NH
2
, —(C
1
-C
6
)-alkyl-NH—R
9
, —(C
1
-C
6
)-alkyl-N(R
9
)R
10
, —(C
1
-C
6
)-alkyl-CHO, —(C
1
-C
6
)-alkyl-COOH, —(C
1
-C
6
)-alkyl-COOR
11
, —(C
1
-C
6
)-alkyl-(C═O)—R
12
, —O—(C
1
-C
6
)-alkyl-OH, —O—(C
1
-C
6
)-alkyl-CF
3
, —O—(C
1
-C
6
)-alkyl-NO
2
, —O—(C
1
-C
6
)-alkyl-CN, —O—(C
1
-C
6
)-alkyl-NH
2
, —O—(C
1
-C
6
)-alkyl-NH—R
9
, —O—(C
1
-C
6
)-alkyl-N(R
9
)R
10
, —O—(C
1
-C
6
)-alkyl-CHO, —O—(C
1
-C
6
)-alkyl-COOH, —O—(C
1
-C
6
)-alkyl-COOR
11
, —O—(C
1
-C
6
)-alkyl-(C═O)—R
12
, —N—SO
3
H, —SO
2
—CH
3
, —(C
0
-C
6
)-alkyl-pyridyl, —O—(C
1
-C
6
)-alkyl-O—(C
1
-C
6
)-alkylphenyl, or —(C
0
-C
6
)-alkylphenyl, wherein the phenyl radicals are unsubstituted, or mono- or di-substituted by F, Cl, —CF
3
, —OCF
3
, —(C
1
-C
6
)-alkyl, or —O—(C
1
-C
6
)-alkyl and wherein one or more hydrogen(s) in the alkyl radicals is optionally replaced by fluorine;
with the proviso that C and D do not simultaneously have the following meaning:
C=phenyl and D=phenyl;
C=phenyl and D=pyridyl;
C=pyridyl and D=phenyl;
C=pyridyl and D=pyridyl;
R
1
, R
2
, R
3
, R
4
each independently of one another is hydrogen, fluorine, chlorine, bromine, iodine, —OH, —CF
3
, —NO
2
, —CN, —(C
1
-C
8
)-alkoxy, —(C
1
-C
8
)-alkyl, —NH
2, —NH—R
9
, —N(R
9
)R
10
, —CHO, —COOH, —COOR
11
, —(C═O)—R
12
, —(C
1
-C
6
)-alkyl-OH, —(C
1
-C
6
)-alkyl(—OH)-phenyl, —(C
1
-C
6
)-alkyl-CF
3
, —(C
1
-C
6
)-alkyl-NO
2
, —(C
1
-C
6
)-alkyl-CN, —(C
1
-C
6
)-alkyl-NH
2
, —(C
1
-C
6
)-alkyl-NH—R
9
, —(C
1
-C
6
)-alkyl-N(R
9
)R
10
, —(C
1
-C
6
)-alkyl-CHO, —(C
1
-C
6
)-alkyl-COOH, (C
1
-C
6
)-alkyl-COOR
11
, —(C
1
-C
6
)-alkyl-(C═O)—R
12
, —O—(C
1
-C
6
)-alkyl-OH, —O—(C
1
-C
6
)-alkyl-CF
3
, —O—(C
1
-C
6
)-alkyl-NO
2
, —O—(C
1
-C
6
)-alkyl-CN, —O—(C
1
-C
6
)-alkyl-NH
2
, —O—(C
1
-C
6
)-alkyl-NH—R
9
, —O—(C
1
-C
6
)-alkyl-N(R
9
)R
10
, —O—(C
1
-C
6
)-alkyl-CHO, —O—(C
1
-C
6
)-alkyl-COOH, —O—(C
1
-C
6
)-alkyl-COOR
11
, —O—(C
1
-C
6
)-alkyl-(C═O)—R
12
, —N—SO
3
H, —SO
2
—CH
3
, or —O—(C
1
-C
6
)-alkyl-O—(C
1
-C
6
)-alkylphenyl, wherein one or more hydrogen(s) in the alkyl radicals is optionally replaced by fluorine;
R
9
to R
12
each independently of one another is hydrogen or —(C
1
-C
8
)-alkyl.
Preferred compounds of formula (I) or salts thereof are those in which one or more radical(s) has or have the following meaning:
C is phenyl, pyridyl, thienyl, furyl, pyrimidyl, indolyl, thiazolyl, imidazolyl, coumarinyl, phthalimidyl, quinolyl, piperazinyl, tetrazolyl, triazolyl, oxazolyl, isoxazolyl, isothiazolyl or benzo-fused derivatives thereof, wherein the aromatic or heteroaromatic radical is unsubstituted, or mono- or disubstituted by fluorine, chlorine, bromine, iodine, —OH, —CF
3
, —NO
2
, —CN, —(C
1
-C
8
)-alkoxy, —(C
1
-C
8
)-alkyl, —(C
3
-C
6
)-cycloalkyl, —NH
2
, —CHO, —COOH, or —OCF
3
;
D is phenyl, pyridyl, thienyl, furyl, pyrimidyl, indolyl, thiazolyl, imidazolyl, coumarinyl, phthalimidyl, quinolyl, piperazinyl, tetrazolyl, triazolyl, oxazolyl, isoxazolyl, isothiazolyl or benzo-fused derivatives thereof, wherein the aromatic or heteroaromatic radical is unsubstituted, or mono- or disubstituted by fluorine, chlorine, bromine, iodine, —OH, —CF
3
, —NO
2
, —CN, —(C
1
-C
8
)-alkoxy, —(C
1
-C
8
)-alkyl, —(C
3
-C
6
)-cycloalkyl, —NH
2
, —CHO, —COOH, or —OCF
3
;
with the proviso that C and D do not simultaneously have the following meaning:
C=phenyl and D=phenyl;
C=phenyl and D=pyridyl;
C=pyridyl and D=phenyl;
C=pyridyl and D=pyridyl;
R
1
, R
2
, R
3
, R
4
each independently of one another is hydrogen, fluorine, chlorine, bromine, iodine, —OH, —CF
3
, —OCF
3
, —NO
2
, —CN, —(C
1
-C
8
)-alkoxy, —(C
1
-C
8
)-alkyl, —(C
3
-C
6
)-cycloalkyl, —NH
2
, —NH—R
9
, —N(R
9
)R
10
, —CHO, —COOH, —COOR
11
, or —(C═O)—R
12
, wherein one or more hydrogen(s) in the alkyl radicals is optionally replaced by fluorine;
R
9
to R
12
each independently of one another is hydrogen or —(C
1
-C
8
)-alkyl.
Particularly preferred compounds of formula (I) or salts thereof are those in which one or more radical(s) has or have the following meaning:
C is phenyl, pyridyl, thienyl, pyrimidyl, indolyl, thiazolyl, quinolyl, oxazolyl, or isoxazolyl, wherein the aromatic or heteroaromatic radical is unsubstituted, or is mono- or disubstituted by fluorine, chlorine, bromine, or —(C
1
-C
8
)-alkyl;
D is phenyl, pyridyl, thienyl, pyrimidyl, indolyl, thiazolyl, quinolyl, imidazolyl, triazolyl, oxazolyl or isoxazolyl, wherein the aromatic or heteroaromatic radical is unsubstituted, or is mono- or disubstituted by fluorine, chlorine, bromine, or —(C
1
-C
8
)-alkyl;
with the proviso that C and D do not simultaneously have the following meaning:
C=phenyl and D=phenyl;
C=phenyl and D=pyridyl;
C=pyridyl and D=phenyl;
C=pyridyl and D=pyridyl;
R
1
, R
2
, R
3
, R
4
each independently of one another is hydrogen, fluorine, chlorine, bromine, iodine, —OH, —CF
3
, —OCF
3
, —NO
2
, —CN, —(C
1
-C
8
)-alkoxy, —(C
1
-C
8
)-alkyl, —(C

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