Acylphenylurea derivatives, a process for their preparation...

Details Acylphenylurea derivatives, a process for their preparation... Acylphenylurea derivatives, a process for their preparation...

2001-06-08

2003-01-14

Aulakh, Charanjit S. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C546S237000, C546S247000, C549S496000, C560S019000, C562S512000, C562S579000, C564S044000, C514S461000, C514S532000, C514S571000, C514S594000

Reexamination Certificate

active

06506778

ABSTRACT:

This application claims priority benefit of Federal Republic of Germany Application 10028175.3-42, filed Jun. 9, 2000, and Federal Republic of Germany Application 10116768.7 filed Apr. 4, 2001, both of which are incorporated by reference.
The invention is directed to acylphenylurea derivatives, their physiologically tolerated salts, and their physiologically functional derivatives.
Acylphenylurea derivatives have already been described as insecticides (EP 0 136 745, EP 0 167 197, DE 29 26 480, J. Agric. Food Chem. 1999, 47, 3116-3424, which are incorporated by reference).
In one embodiment, the invention provides compounds that display a blood glucose-lowering effect, which can be exploited therapeutically.
These include compounds of the formula (I)
in which
A is phenyl, naphthyl, it being possible for the phenyl or naphthyl radical to be substituted up to three times by: F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkenyl, O—(C
1
-C
6
)-alkynyl, S—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkenyl, S—(C
1
-C
6
)-alkynyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—NH
2
, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkenyl, (C
1
-C
6
)-alkynyl, (C
3
-C
7
)-cycloalkyl, (C
3
-C
7
)-cycloalkyl-(C
1
-C
4
)-alkylene, (C
0
-C
6
)-alkylene-COOH, (C
0
-C
6
)-alkylene-COO(C
1
-C
7
)-alkyl, CONH
2
, CONH(C
1
-C
6
)-alkyl, CON[(C
1
-C
6
)-alkyl)]
2
, CONH(C
3
-C
6
)-cycloalkyl, (C
0
-C
6
)-alkylene-NH
2
, (C
0
-C
6
)-alkylene-NH(C
2
-C
6
)-alkyl, (C
0
-C
6
)-alkylene-N[(C
1
-C
6
)-alkyl]
2
, NH—CO—(C
1
-C
6
)-Alkyl, NH—CO-phenyl, or NH—SO
2
-phenyl, it being possible for the phenyl ring to be substituted up to twice by F, Cl, CN, OH, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, CF
3
, OCF
3
, COOH, COO(C
1
-C
6
)-alkyl or CONH
2
;
R1, R2 are, independently of one another, H, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, CO—(C
1
-C
6
)-alkyl, COO—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkylene-COOH, or (C
1
-C
6
)-alkylene-COO—(C
1
-C
6
)-alkyl;
R3, R4, R5, R6 are, independently of one another, H, F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkenyl, O—(C
1
-C
6
)-alkynyl, S—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkenyl, S—(C
1
-C
6
)-alkynyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—NH
2
, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkenyl, (C
1
-C
6
)-alkynyl, (C
3
-C
7
)-cycloalkyl, (C
3
-C
7
)-cycloalkyl-(C
1
-C
4
)-alkylene, COOH, COO(C
1
-C
6
)-alkyl, CONH
2
, CONH(C
1
-C
6
)-alkyl, CON[(C
1
-C
6
)-alkyl]
2
, CONH(C
3
-C
7
)-cycloalkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N[(C
1
-C
6
)-alkyl]
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl, or NH—SO
2
-phenyl, it being possible for the phenyl ring to be substituted up to twice by F, Cl, CN, OH, (C
1
-C
6
)-Alkyl, O—(C
1
-C
6
)-alkyl, CF
3
, OCF
3
, COOH, COO(C
1
-C
6
)-alkyl or CONH
2
;
X is O or S;
R7 is (C
1
-C
10
)-alkylene-COOH, (C
6
-C
10
)-alkylene-COO—(C
1
-C
6
)-alkyl, (C
1
-C
10
)-alkylene-CONH
2
, (C
1
-C
10
)-alkylene-CONH—(C
1
-C
6
)-alkyl, (C
1
-C
10
)-alkylene-CON—[(C
1
-C
6
)-alkyl]
2
, (C
1
-C
10
)-alkylene-NH
2
, (C
1
-C
10
)-alkylene-NH(C
1
-C
6
)-alkyl, (C
1
-C
10
)-alkylene-N[(C
1
-C
6
)-alkyl]
2
, or (C
1
-C
10
)-alkylene-B;
B is (C
3
-C
7
)-cycloalkyl, phenyl, pyrrolyl, Imidazolyl, thiazolyl, azetidinyl, thienyl, piperidinyl, pyrrolidinyl, morpholinyl, pyridyl-methyl or furyl, in which cycloalkyl, phenyl, pyrrolyl, imidazolyl, thiazolyl, azetidinyl, thienylmethyl, piperidinyl, pyrrolidinyl, morpholinyl, pyridyl or furyl may in each case be substituted up to twice by Cl, F, CN, CF
3
, OCF
3
, COOH, COO—(C
1
-C
6
)-alkyl, CONH
2
, CONH—(C
1
-C
6
)-alkyl, CON—[(C
1
-C
6
)-alkyl]
2
, (C
1
-C
6
)-alkyl, OH, or O—(C
1
-C
6
)-alkyl;
and their physiologically tolerated salts thereof,
except the compounds of the formula:
and compounds of the formula (I) in which the radicals are, at the same time:
A
phenyl;
X
O;
R1
H;
R7
-(C
1
-C
4
)-alkyl-B;
B
(C
3
-C
7
)-cycloalkyl, or a heteroaryl.
Compounds of the formula (I) can include those in which
A is phenyl, naphthyl, it being possible for the phenyl or naphthyl radical to be substituted up to three times by F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkenyl, O—(C
1
-C
6
)-alkynyl, S—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkenyl, S—(C
1
-C
6
)-alkynyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—NH
2
, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkenyl, (C
1
-C
6
)-alkynyl, (C
3
-C
7
)-cycloalkyl, (C
3
-C
7
)-cycloalkyl-(C
1
-C
4
)-alkylene, (C
0
-C
6
)-alkylene-COOH, (C
0
-C
6
)-alkylene-COO(C
1
-C
6
)-alkyl, CONH
2
, CONH(C
1
-C
6
)-alkyl, CON[(C
1
-C
6
)-alkyl]
2
, CONH(C
3
-C
7
)-cycloalkyl, (C
0
-C
6
)-alkylene-NH
2
, (C
0
-C
6
)-alkylene-NH(C
2
-C
6
)-alkyl, (C
0
-C
6
)-alkylene-N[(C
1
-C
6
)-alkyl]
2
, NH—CO—(C
1
-C
6
)-alkyl, NH—CO-phenyl, or NH—SO
2
-phenyl, it being possible for the phenyl ring to be substituted up to twice by F, Cl, CN, OH, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, CF
3
, OCF
3
, COOH, COO(C
1
-C
6
)-alkyl or CONH
2
;
R1, R2 are, independently of one another, H, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, CO—(C
1
-C
6
)-alkyl, COO—(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkylene-COOH, or C
1
-C
6
)-alkylene-COO—(C
1
-C
6
)-alkyl;
R3, R4, R5, R6 are, independently of one another, H, F, Cl, Br, OH, CF
3
, NO
2
, CN, OCF
3
, O—(C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkenyl, O—(C
1
-C
6
)-alkynyl, S—(C
1
-C
6
)-alkyl, S—(C
1
-C
6
)-alkenyl, S—(C
1
-C
6
)-alkynyl, SO—(C
1
-C
6
)-alkyl, SO
2
—(C
1
-C
6
)-alkyl, SO
2
—NH
2
, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkenyl, (C
1
-C
6
)-alkynyl, (C
3
-C
7
)-cycloalkyl, (C
3
-C
7
)-cycloalkyl-(C
1
-C
4
)-alkylene, COOH, COO(C
1
-C
6
)-alkyl, CONH
2
, CONH(C
1
-C
6
)-alkyl, CON[(C
1
-C
6
)-alkyl]
2
, CONH(C
3
-C
7
)-cycloalkyl, NH
2
, NH(C
1
-C
6
)-alkyl, N[(C
1
-C
6
)-alkyl]
2
, NH—CO—(C
1
-C
6
)-alkyl, or NH—CO-phenyl, NH—SO
2
-phenyl, it being possible for the phenyl ring to be substituted up to twice by F, Cl, CN, OH, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, CF
3
, OCF
3
, COOH, COO(C
1
-C
6
)-alkyl or CONH
2
;
X is O or S;
R7 is (C
1
-C
10
)-alkylene-COOH, (C
6
-C
10
)-alkylene-COO—(C
1
-C
6
)-alkyl, (C
1
-C
10
)-alkylene-CONH
2
, (C
1
-C
10
)-alkylene-CONH—(C
1
-C
6
)-alkyl, (C
1
-C
10
)-alkylene-CON—[(C
1
-C
6
)-alkyl]
2
, (C
1
-C
10
)-alkylene-NH
2
, (C
1
-C
10
)-alkylene-NH(C
1
-C
6
)-alkyl, (C
1
-C
10
)-alkylene-N[(C
1
-C
6
)-alkyl]
2
, or (C
1
-C
10
)-alkylene-B;
B is (C
3
-C
7
)-cycloalkyl, phenyl, pyrrolyl, imidazolyl, thiazolyl, azetidinyl, thienylmethyl, piperidinyl, pyrrolidinyl, morpholinyl, pyridyl-methyl or furyl, in which cycloalkyl, phenyl, pyrrolyl, imidazolyl, thiazolyl, azetidinyl, thienyl, piperidinyl, pyrrolidinyl, morpholinyl, pyridyl or furyl may in each case be substituted up to twice by Cl, F, CN, CF
3
, OCF
3
, COOH, COO—(C
1
-C
6
)-alkyl, CONH
2
, CONH—(C
1
-C
6
)-alkyl, CON—[(C
1
-C
6
)-alkyl]
2
, (C
1
-C
6
)-alkyl, OH, or O—(C
1
-C
6
)-alkyl
and their physiologically tolerated salts thereof,
except the compounds of the formula
and compounds of the formula (I) in which the radicals are, at the same time:
A
phenyl;
X
O;
R1
H;
R7
-(C
1
-C
4
)-alkyl-B;
B
(C
3
-C
7
)-cycloalkyl, or heteroaryl.
Further examples of compounds of the formula (I) are those in which
A is phenyl, it being possible for the phenyl radical to be substituted up to twice by F, Cl, Br, or O—(C
1
-C
6
)-alkyl;
R1, R2 are, independently of one another, H, (C
1
-C
6
)-alkyl, or CO—(C
1
-C
6
)-alkyl;
R3, R4, R5, R6 are, independently of one another, H, Cl, F, (C
1
-C
6
)-alkyl, O—(C
1
-C
6
)-alkyl, or —COO—(C
1
-C
6
)-alkyl;
X is O;
R7 is (C
1
-C
10
)-alkylene-COOH, (C
6
-C
10
)-alkylene-COO—(C
1
-C
6
)-alkyl, or (C
1
-C
10
)-alkylene-CONH
2
;
and their physiologically tolerated salts thereof,
except the compounds of the formula:
In another embodiment, the invention relates to the use of compounds of the formula (I)
in which
A is phenyl, naphthyl, it being possible for the phenyl or naphthyl radical to be substituted up to three times by F, Cl, Br, OH, CF
3
, NO
2
,

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