N-(heterocyclyl)benzene or pyridinesulphonamides as...

Details N-(heterocyclyl)benzene or pyridinesulphonamides as... N-(heterocyclyl)benzene or pyridinesulphonamides as...

2002-09-12

2004-01-20

Chang, Ceila (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S212010, C514S231200, C514S255030, C514S256000, C514S326000, C514S336000, C540S484000, C544S106000, C544S242000, C544S333000, C544S358000, C546S194000, C546S212000, C546S214000, C546S255000, C546S280400, C546S283400

Reexamination Certificate

active

06680329

ABSTRACT:

The present invention relates to N-(heterocyclyl)benzene- or -pyridinesulphonamide derivatives, to their preparation and to their therapeutic application.
The compounds of the present invention correspond to formula [I]:
in which:
X represents either a group ═CR
4
— or a nitrogen atom,
W represents a —(CH
2
)
2
—, —(CH
2
)
3
—, —CH
2
—C≡C— (triple bond) or —CH
2
—CH═CH— (double bond in cis or trans configuration) group,
R
2
represents
either a piperidyl group which is optionally substituted:
with one or two groups chosen from hydroxyl, (C
1
-C
4
)alkyl, hydroxy(C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, monofluoromethyl, difluoromethyl, trifluoromethyl and (C
3
-C
6
)cycloalkyl group,
with a group ═CYZ [Y and Z being chosen, independently of each other, from hydrogen atoms, halogen atoms and (C
1
-C
4
)alkyl groups (optionally substituted with 1 to 3 halogen atoms)],
with a group:
 (r=1 to 3) or
with a spiro[(C
3
-C
6
)cycloalkane] group,
or a 1,2,3,6-tetrahydropyridyl group optionally substituted with a (C
1
-C
4
)alkyl group (this (C
1
-C
4
)alkyl group being optionally substituted with 1 to 3 halogen atoms) or a (C
3
-C
6
)cycloalkyl group,
or a hexahydro-1H-azepinyl group optionally substituted in position 4 with a trifluoromethyl or difluoromethylene group,
or a heptahydroazocin-1-yl group,
or an octahydro-1H-azonin-1-yl group,
or a group
 (a-b being a group —CONR′—, m=1 to 2, p=1 to 2 and
R′ is a hydrogen atom or a (C
1
-C
4
)alkyl group),
or a group
 in which
either R
12
is a (C
1
-C
4
)alkyl group, a carboxy(C
1
-C
4
)alkyl group or a (C
1
-C
4
)alkoxycarbonyl(C
1
-C
4
)alkyl group and R
13
is a (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkyl group, or R
12
is a (C
1
-C
4
)alkyl or —CH
2
CF
3
group and R
13
is a
group
 (Q being a carbon or nitrogen atom and r=1 to 3),
or a piperazinyl group optionally substituted with a (C
1
-C
4
)alkyl group or a (C
1
-C
4
)alkylsulphonyl group,
or a morpholinyl group,
R
4
represents
either a halogen atom,
or a hydrogen atom,
R
3
represents
either a (C
1
-C
5
)alkyl group,
or a group —COR
1
, in which R
1
is either a hydrogen atom or a group (C
1
-C
4
)alkyl, —(CH
2
)
n
OCH
3
, —CH
2
O(C
2
H
4
O)
n
CH
3
, —(CH
2
)
n
CF
3
or —(CH
2
)
n
OH (n=1 to 4),
or a group —SO
2
R
5
,
or a group —CONHR
5
,
or a group —SO
2
N(R
5
)
2
, in which R
5
is a (C
1
-C
4
)alkyl group,
A represents
either a phenyl group optionally substituted with 1 to 3 substituents chosen from
a halogen atom and
groups (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, trifluoromethyl, trifluoromethoxy, —CH
2
OR
10
, —CH
2
OCOR
10
, —CH
2
OCONR
10
R
11
, —COOR
10
, —CONR
10
R
11
, nitro, —NR
10
R
11
, —NHCOR
10
and —NH(CH
2
)
q
OR
10
, in which R
10
and R
11
are, independently of each other, a hydrogen atom or a (C
1
-C
4
)alkyl group and q is between 0 and 6,
or a heterocycle chosen from pyridyl, thienyl, furyl, pyrimidinyl and thiazolyl groups, the said groups possibly being substituted like the phenyl group above,
or a (C
5
-C
8
)cycloalkyl group, and B represents
either a pyridyl group optionally substituted with 1 or 2 substituents chosen from a (C
1
-C
4
)alkyl group, a hydroxyl group and a (C
1
-C
4
)alkoxy group,
or an aminopyrazinyl group,
or an aminopyridazinyl group,
or a pyrimidinyl group optionally substituted with an amino group,
or a piperidyl group,
or an aminopyridyl group optionally substituted on the pyridine with a (C
1
-C
4
)alkyl or (C
1
-C
4
)alkoxy group or a halogen atom, the amino group possibly also being substituted with a (C
1
-C
4
)alkyl group,
or an aminophenyl group, the amino group possibly being substituted with a (C
1
-C
4
)alkyl group and the phenyl group possibly being substituted with a (C
1
-C
4
)alkyl group or a halogen atom.
In the context of the invention, the terms below have the following meanings:
a (C
1
-C
4
)alkyl group is a linear or branched, saturated hydrocarbon-based chain containing from 1 to 4 carbon atoms,
a (C
x
-C
y
)cycloalkyl group is a cyclic hydrocarbon-based chain containing from x to y carbon atoms,
a (C
1
-C
4
)alkoxy group is an oxygen radical substituted with a (C
1
-C
4
)alkyl group defined above,
a halogen atom is a chlorine, bromine, iodine or fluorine atom.
In the context of the invention, the halogen atoms are preferably chlorine, fluorine and bromine.
Depending on the nature of the group W, the compounds of formula (I) in accordance with the invention may be represented by formulae (I
1
), (I
2
), (I
3
) and (I
4
) below:
The compounds that are preferred according to the invention are the compounds of formula [I] in which:
X, W, R
4
, A and B are as defined above,
R
2
represents
either a piperidyl group which is optionally substituted:
with one or two groups chosen from hydroxyl, (C
1
-C
4
)alkyl, hydroxy(C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, monofluoromethyl, difluoromethyl, trifluoromethyl and (C
3
-C
6
) cycloalkyl groups,
with a group ═CYZ [Y and Z being chosen, independently of each other, from hydrogen atoms, halogen atoms and (C
1
-C
4
)alkyl groups (optionally substituted with 1 to 3 halogen atoms)],
or a 1,2,3,6-tetrahydropyridyl group optionally substituted with a (C
1
-C
4
)alkyl group (this (C
1
-C
4
)alkyl group being optionally substituted with 1 to 3 halogen atoms) or a (C
3
-C
6
)cycloalkyl group,
or a hexahydro-1H-azepinyl group optionally substituted in position 4 with a trifluoromethyl or difluoromethylene group,
or a group
 in which
R
12
is a (C
1
-C
4
)alkyl group, a carboxy(C
1
-C
4
)alkyl group or a (C
1
-C
4
)alkoxycarbonyl (C
1
-C
4
)alkyl group and R
13
is a (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkyl group,
or a piperazinyl group optionally substituted with a (C
1
-C
4
)alkyl group or a (C
1
-C
4
)alkylsulphonyl group,
or a morpholinyl group,
R
3
represents
either a (C
1
-C
5
)alkyl group,
or a group —COR
1
, in which R
1
is either a hydrogen atom or a group (C
1
-C
4
)alkyl, —(CH
2
)
n
OCH
3
, —CH
2
O(C
2
H
4
O)
n
CH
3
, —(CH
2
)
n
CF
3
or —(CH
2
)
n
OH (n=1 to 4).
Among the preferred compounds defined above, the ones that are particularly preferred are the compounds of formula [I] in which:
X, R
4
and B are as defined above,
W represents a —(CH
2
)
3
— or —CH
2
—CH═CH— (double bond in cis or trans configuration) group,
R
2
represents
either a piperidyl group which is optionally substituted:
with one or two groups chosen from hydroxyl, (C
1
-C
4
)alkyl, hydroxy(C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, monofluoromethyl, difluoromethyl and trifluoromethyl groups,
with a group ═CYZ [Y and Z being chosen, independently of each other, from hydrogen atoms, halogen atoms and (C
1
-C
4
)alkyl groups (optionally substituted with 1 to 3 halogen atoms)],
or a 1,2,3,6-tetrahydropyridyl group optionally substituted with a (C
1
-C
4
)alkyl group (this (C
1
-C
4
)alkyl group being optionally substituted with 1 to 3 halogen atoms),
or a hexahydro-1H-azepinyl group,
or a piperazinyl group optionally substituted with a (C
1
-C
4
)alkylsulphonyl group,
or a morpholinyl group,
R
3
represents a group —COR
1
, in which R
1
is a group (C
1
-C
4
)alkyl, —(CH
2
)
n
OCH
3
or —(CH
2
)
n
CF
3
(n=1 to 4),
A represents
either a phenyl group optionally substituted with 1 to 3 substituents chosen from
a halogen atom and
(C
1
-C
4
)alkyl and (C
1
-C
4
)alkoxy groups,
or a heterocycle chosen from pyridyl and thienyl groups,
or a (C
5
-C
8
)cycloalkyl group.
The preferred configuration of the central amino acid portion of the compounds in accordance with the present invention:
is [S]
The compounds of formula [I] in accordance with the invention may exist in the form of racemates or pure enantiomers or mixtures of enantiomers. They may also exist in the form of acids or free bases or addition salts with pharmaceutically acceptable acids, for

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