Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-09-01
2002-07-09
Gitomer, Ralph (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S293000, C514S300000, C514S311000, C544S159000
Reexamination Certificate
active
06417181
ABSTRACT:
The present invention relates to new naphthyl- and anilide-substituted sulphonamides, processes for their preparation and their use as antiviral agents, in particular against cytomealoviruses.
&agr;,&bgr;-Naphthyl-linked phenylsulphonamides are mainly disclosed in phototechnical publications [cf. for this purpose JP-06 122 669-A2, EP-684 515-A1; JP-59 174 836-A2, DE-2 902 074, U.S. Pat. No. 3,925,347, U.S. Pat. No. 4,035,401, U.S. Pat. No. 3,622,603, U.S. Pat. No. 3,482,971, EP-284 130].
WO 90/09 787 discloses sulphonamides as radio- or chemosensitizing agents and their use in the treatment of tumours.
The compound N-[4-[[[5-(dimethylamino)-1-naphthalenyl]sulphonyl]amino]phenyl]-acetamide is additionally known (J. Inst. Chem. (India) (1976), 4S. Pt 6, 280-5).
The present invention relates to new naphthyl- and anilide-substituted sulphonamides of the general formula (I)
in which
R
1
and R
2
are identical or different and represent hydrogen, formyl, phenyl or benzyl optionally substituted by one to three halogen atoms, or straight-chain or branched alkyl or acyl each having up to 6 carbon atoms, where alkyl or acyl can optionally be substituted by one to three substituents selected from halogen and hydroxyl,
A, D, E and G are identical or different and represent hydrogen, halogen, nitro, cyano, hydroxyl, carboxyl, trifluoromethyl, trifluoromethoxy or straight-chain or branched alkyl, alkoxy or alkoxycarbonyl each having up to 5 carbon atoms,
R
3
represents straight-chain or branched alkenyl having up to 6 carbon atoms, or represents straight-chain or branched alkyl having up to 8 carbon atoms, which optionally carries an amino group which can optionally be substituted by alkyl having up to 4 carbon atoms or by an amino protective group, or the alkyl is optionally identically or differently substituted one to 3 times by hydroxyl, cyano, halogen, azido, nitro, trifluoromethyl, carboxyl or phenyl which, for its part, can be identically or differently substituted up to 2 times by nitro, halogen, hydroxyl or by straight-chain or branched alkyl or alkoxy having up to 4 carbon atoms, or
R
3
represents radicals of the formula
in which
L represents a straight-chain or branched alkanediyl group having up to 6 carbon atoms,
Q represents alkyl having up to 6 carbon atoms, which is optionally substituted by carboxyl, or
represents radicals of the formula
in which
a denotes the number 1 or 2,
R
5
denotes hydrogen,
R
6
denotes cycloalkyl having 3 to 8 carbon atoms or aryl having 6 to 10 carbon atoms or hydrogen, or denotes straight-chain or branched alkyl having up to 8 carbon atoms,
where the alkyl is optionally substituted by cyano, methylthio, hydroxyl, mercapto, guanidyl or by a group of the formula —NR
9
R
10
or R
11
—OC—,
in which
R
9
and R
10
independently of one another denote hydrogen, straight-chain or branched alkyl having up to 8 carbon atoms or phenyl,
and
R
11
denotes hydroxyl, benzyloxy, alkoxy having up to 6 carbon atoms or the abovementioned group —NR
9
R
10
,
or the alkyl is optionally substituted by cycloalkyl having 3 to 8 carbon atoms or by aryl having 6 to 10 carbon atoms, which, for its part, is substituted by hydroxyl, halogen, nitro, alkoxy having up to 8 carbon atoms or by the group —NR
9
R
10
,
in which
R
9
and R
10
have the meaning indicated above,
or the alkyl is optionally substituted by a 5- to 6-membered nitrogen-containing heterocycle or by indolyl, in which the corresponding —NH functions are optionally substituted by alkyl having up to 6 carbon atoms or protected by an amino protective group,
R
7
and R
8
are identical or different and denote hydrogen or an amino protective group,
R
4
represents hydrogen or a radical of the formula
in which
R
5′
, R
6′
, R
7′
and R
8′
have the meaning of R
6
, R
7
and R
8
indicated above and are identical to or different from this,
X has the meaning of R
4
indicated above and can be identical to or different from this meaning,
and their stereoisomers, stereoisomeric mixtures and salts,
with the exception of N-[4-[[[5-(dimethylamino)-1-naphthalenyl]sulphonyl]amino]phenyl]acetamide.
In a preferred embodiment, the invention relates to sulphonamides of the above general formula (I), in which
R
1
and R
2
are identical or different and represent hydrogen, phenyl or straight-chain or branched alkyl or acyl each having up to 6 carbon atoms
A, D, E and G are identical or different and represent hydrogen, halogen, nitro, cyano, hydroxyl, carboxyl, trifluoromethyl, trifluoromethoxy or straight-chain or branched alkyl, alkoxy or alkoxycarbonyl each having up to 5 carbon atoms,
R
3
represents straight-chain or branched alkenyl having up to 6 carbon atoms, or represents straight-chain or branched alkyl having up to 8 carbon atoms. which optionally carries an amino group which can be substituted by alkyl having up to 4 carbon atoms or by an amino protective group, or the alkyl is optionally identically or differently substituted one to 3 times by hydroxyl, cyano, halogen, azido, nitro, trifluoromethyl, carboxyl or phenyl which, for its part, can be identically or differently substituted up to 2 times by nitro, halogen, hydroxyl or by straight-chain or branched alkyl or alkoxy having up to 4 carbon atoms, or
R
3
represents radicals of the formula
in which
L represents a straight-chain or branched alkanediyl group having up to 6 carbon atoms,
Q represents alkyl having up to 6 carbon atoms, which is optionally substituted by carboxyl, or represents radicals of the formula
in which
a denotes the number 1 or 2,
R
5
denotes hydrogen,
R
6
denotes cycloalkyl having 3 to 8 carbon atoms or aryl having 6 to 10 carbon atoms or hydrogen, or denotes straight-chain or branched alkyl having up to 8 carbon atoms,
where the alkyl is optionally substituted by cyano, methylthio, hydroxyl, mercapto, guanidyl or by a croup of the formula —NR
9
R
10
or R
11
—OC—,
in which
R
9
and R
10
independently of one another denote hydrogen, straight-chain or branched alkyl having up to 8 carbon atoms or phenyl,
and
R
11
denotes hydroxyl, benzyloxy, alkoxy having up to 6 carbon atoms or the abovementioned group —NR
9
R
10
,
or the alkyl is optionally substituted by cycloalkyl having 3 to 8 carbon atoms or by aryl having 6 to 10 carbon atoms which, for its part, is substituted by hydroxyl, halogen, nitro, alkoxy having up to 8 carbon atoms or by the group —NR
9
R
10
,
in which
R
1
and R
10
having the meaning indicated above,
or the alkyl is optionally substituted by a 5- to 6-membered nitrogen-containing heterocycle or by indolyl, in which the corresponding —NH functions are optionally substituted by alkyl having up to 6 carbon atoms or protected by an amino protective group,
R
7
and R
8
are identical or different and denote hydrogen or an amino protective group,
R
4
represents hydrogen or a radical of the formula
in which
R
5′
, R
6′
, R
7′
and R
8′
have the meaning of R
5
, R
6
, R
7
and R
8
indicated above and are identical to or different from these, and
X represents hydrogen,
and their stereoisomers, stereoisomeric mixtures and salts,
with the exception of N-[4-[[[5-(dimethylamino)-1-naphthalenyl]sulphonyl]amino]-phenyl]acetamide.
Further preferred compounds are sulphonamides of the above general formula (I), in which
R
3
represents straight-chain or branched alkenyl having up to 6 carbon atoms, or represents straight-chain or branched alkyl having up to 8 carbon atoms, in which the alkyl carries an amino group which can be substituted by alkyl having up to 4 carbon atoms or by an amino protective group, or the alkyl is identically or differently substituted one to 3 times by hydroxyl, cyano, halogen, azido, nitro, trifluoromethyl, carboxyl or phenyl which. for its part, can be identically or differently substituted up to 2 times by nitro, halogen or hydroxyl or by straight-chain or branched
Bender Wolfgang
Eckenberg Peter
Goldmann Siegfried
Hallenberger Sabine
Härter Michael
Bayer Aktiengesellschaft
Chiu Jerrie L.
Gitomer Ralph
Khare Devesh
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