Sulfonylcarboxamide derivatives, process for their...

Details Sulfonylcarboxamide derivatives, process for their... Sulfonylcarboxamide derivatives, process for their...

2001-09-27

2003-04-22

Padmanabhan, Sreeni (Department: 1617)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S326000, C514S603000, C514S604000

Reexamination Certificate

active

06552048

ABSTRACT:

The invention relates to sulfonylcarboxamide derivatives and their physiologically acceptable salts and physiologically functional derivatives and to their use for preparing medicines for the prevention and treatment of hyperlipidemia and arteriosclerotic disorders.
Sulfonylcarboxamides have already been described In Chemical Abstracts 96, 142393m (1982).
In DE 2145686, 2-chloro-5-sulfamylbenzoic acid derivatives have already been described as lipid-lowering agents.
The invention is based on the object of providing further compounds which have a therapeutically utilizable hypolipidemic action. In this context, the object was, in particular, also to provide compounds having an increased hypolipidemic action compared to the 2-chloro-5-sulfamylbenzoic acid derivatives from DE 2145686.
Accordingly, the invention relates to compounds of the formula I
in which
X, R1, R2, R3 are, independently of one another, NR6R7, (CH
2
)-pyridyl, (CH
2
)
n
-phenyl, where n can be 0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, CF
3
, NH
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, COO(C
1
-C
6
)-alkyl, COO(C
3
-C
6
)-cycloalkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]
2
;
(C
1
-C
8
)-alkyl, pyrrolidinyl, piperidinyl, piperazinyl, 2-oxopiperazinyl, morpholinyl, tetrahydropyridinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, it being possible for each of the rings to be substituted by phenyl, (C
1
-C
6
)-alkyl-phenyl, —OH, (C
1
-C
8
)-alkyl, (C
1
-C
6
)-alkyl-OH, O-phenyl, S-phenyl, (CO)-(C
1
-C
6
)-alkyl, (CO)-phenyl, where the phenyl substituent is unsubstituted or substituted up to two times by F, Cl, Br, OH, CF
3
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, COOH, COO(C
1
-C
6
)alkyl, COO(C
3
-C
6
)cycloalkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]
2
, CONH(C
3
-C
6
)cycloalkyl, NH
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl;
R6 and R7 are, independently of one another, H, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-OH, (C
1
-C
6
)-alkyl-NH
2
, (C
1
-C
6
)-alkyl-O—(C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, CO—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-NH—C(O)—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-NH—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-N-[(C
1
-C
6
)-alkyl]
2
, (C
1
-C
6
)-alkyl-di-phenyl, (C
1
-C
6
)-alkyl-O-phenyl, CHO, CO-phenyl,
(CH
2
)
n
—Ar, where n can be 0-6, and Ar can be equal to phenyl, biphenylyl, 1- or 2-naphthyl, 1- or 2-tetrahydrofuranyl, 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 2-, 4- or 5-thiazolyl, 2-, 4- or 5-oxazolyl, 1-pyrazolyl, 3-, 4- or 5-isoxazolyl, (C
3
-C
6
)-cycloalkyl, piperidinyl, pyrrolidinyl, oxopyridyl, 2- or 3-pyrrolyl, 2- or 3-pyridazinyl, 2-, 4- or 5-pyrimidinyl, 2-pyrazinyl, 2-(1,3,5-triazinyl), 2-, 3- or 4-morpholinyl, 2- or 5-benzimidazolyl, 2-benzothiazolyl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, tetrazol-5-yl, indol-3-yl, indol-5-yl or N-methylimidazol-2-, -4- or -5-yl and Ar can be substituted up to two times by F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—CH
2
—O, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, COOH, COO(C
1
-C
6
)alkyl, COO(C
3
-C
6
)cycloalkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]
2
, CONH(C
3
-C
6
)cycloalkyl, NH
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl, pyrrolidin-1-yl, morpholin-1-yl, piperidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, (CH
2
)
n
-phenyl, O—(CH
2
)
n
-phenyl, S—(CH
2
)
n
-phenyl, SO
2
—(CH
2
)
n
-phenyl, where n=0-3;
and their physiologically acceptable salts.
Preference is given to compounds of the formula I in which one or more radical(s) is/are as defined below:
R1, R2 are, independently of one another, NR6R7, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyridyl, it being possible for each of the rings to be substituted by phenyl, (C
1
-C
6
)-alkyl-phenyl, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-OH, O-phenyl, S-phenyl, (CO)—(C
1
-C
6
)-alkyl, (CO)-phenyl, where the phenyl substituent is unsubstituted or substituted up to two times by F, Cl, Br, CF
3
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, COOH, COO(C
1
-C
6
)-alkyl, COO(C
3
-C
6
)cycloalkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]
2
, NH
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl;
R6, R7 are, independently of one another, H, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-O—(C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, CO—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-NH—C(O)—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-NH—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-N-[(C
1
-C
6
)-alkyl]
2
, (CH
2
)
n
—Ar, where n can be 0-6 and Ar can be equal to phenyl, biphenylyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2-, 4- or 5-thiazolyl, 2-, 4- or 5-oxazolyl, 3- or 5-isoxazolyl, (C
3
-C
6
)-cycloalkyl, piperidinyl, pyrrolidinyl, 2-, 4- or 5-pyrimidinyl, 2-, 3- or 4-morpholinyl, 2- or 5-benzimidazolyl, 2-benzothiazolyl or indol-3-yl, indol-5-yl and Ar can be substituted up to two times by F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, COOH, COO(C
1
-C
6
)alkyl, COO(C
3
-C
6
)cycloalkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, NH
2
, NH—CO-phenyl, (CH
2
)
n
-phenyl, O—(CH
2
)
n
-phenyl, S—(CH
2
)
n
-phenyl, where n=0-3;
X, R3 are, independently of one another, NR8R9, pyrrolidinyl, piperidinyl, morpholinyl, (C
1
-C
8
)-alkyl, (CH
2
)
n
-phenyl, where n=0-6 and the phenyl radical can be substituted up to two times by F, Cl, Br, CF
3
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, COO(C
1
-C
6
)-alkyl, COO(C
3
-C
6
)cycloalkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CON[(C
1
-C
6
)alkyl]
2
;
R8, R9 are, independently of one another, H, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, CO—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-CO—(C
1
-C
6
)-alkyl, SO
2
-benzyl, SO
2
-benzyl-OCH
3
, (CH
2
)
n
—Ar, where n can be 0-6 and Ar can be equal to phenyl or thienyl and Ar can be substituted up to two times by F, Cl, Br, CF
3
, NO
2
, CN, OCF
3
, O—CH
2
—O, O—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, NH—CO-phenyl, (CH
2
)
n
-phenyl, O—(CH
2
)
n
-phenyl, S—(CH
2
)
n
-phenyl, SO
2
—(CH
2
)
n
-phenyl, where n=0-2;
and their physiologically acceptable salts.
Particular preference is given to compounds of the formula I in which one or more radical(s) is/are as defined below:
R1, R2 are, independently of one another, NR6R7, piperidinyl, piperazinyl, tetrahydropyridyl, it being possible for each of the rings to be substituted by phenyl, (C
1
-C
6
)-alkyl-phenyl, (C
1
-C
6
)-alkyl, (CO)—(C
1
-C
6
)-alkyl;
R6, R7 are, independently of one another, H, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-NH—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-N-[(C
1
-C
6
)-alkyl]
2
, (CH
2
)
n
—Ar, where n can be 0-6 and Ar can be equal to phenyl, 2-, 3- or 4-pyridyl, piperidinyl, pyrrolidinyl, 2-, 4- or 5-pyrimidinyl, 2-, 3- or 4-morpholinyl and Ar can be substituted up to two times by F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl, COOH, NH
2
, (CH
2
)
n
-phenyl, where n can be 0-3;
X is NR8R9, piperazinyl, (C
1
-C
6
)-alkyl, (CH
2
)
n
-phenyl, where n can be 0-6;
R3 is NR10R11, piperazinyl;
R8, R9 are, independently of one another, H, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, CO—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-CO—(C
1
-C
6
)-alkyl, SO
2
-benzyl, SO
2
-benzyl-OCH
3
, (CH
2
)
n
—Ar, where n can be 0-6 and Ar can be equal to phenyl or thienyl;
R10, R11 are, independently of one another, H, (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, CO—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkyl-CO—(C
1
-C
6
)-alkyl, SO
2
-benzyl, SO
2
-benzyl-OCH
3
, (CH
2
)
n
—Ar, where n can be 0-6 and Ar ca

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