Substituted and unsubstituted benzooxathiazoles and...

Details Substituted and unsubstituted benzooxathiazoles and... Substituted and unsubstituted benzooxathiazoles and...

2001-08-09

2003-05-20

Vollano, Jean F. (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C549S090000

Reexamination Certificate

active

06566390

ABSTRACT:

This application claims priority to German Patent Application 10038709.8-44, filed Aug. 9, 2000, which is hereby incorporated by reference, in its entirety.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to substituted and unsubstituted 3H-benzo-[1,2,3]oxathiazole 2,2-dioxides, 1,3-dihydrobenzo[1,2,5]thiadiazole 2,2-dioxides and 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides, to their preparation and to their use in medicaments.
2. Description of the Related Art
Aminobenzosultam derivatives acting as lipoxygenase inhibitors are known (WO 92/05164). Also known is the use of corresponding bifunctional derivatives as charge transporters in photoreceptors (JP 95/325942). Andersen et al. described the synthesis of toluenesulfonyl-protected derivatives and studies of reactions of these derivatives with nucleophiles (K. Andersen et al., J. Phys. Org. Chem., 10, 175-181 (1997); K. Andersen et al., J Org. Chem., 60, 2003-2007 (1995)).
SUMMARY OF THE INVENTION
It was an object of the present invention to provide novel substituted and unsubstituted benzooxathiazoles and their preparation and use as pharmaceutically active compounds. In particular, it was an object to provide novel substituted and unsubstituted benzooxathiazoles for treating type 1 and type 2 diabetes, insulin resistance and pathological obesity.
The present invention relates to compounds of the formula I
in which
X is CH
2
, O, N;
Y is CH
2
, O, N;
R1, R2, R3 are each independently of one another
H, F, Cl, Br, I, NH
2
, OH, NO
2
, COOH;
COO(C
1
-C
6
)alkyl, CONH
2
, CONH(C
1
-C
16
)alkyl, CONH(C
1
-C
16
)alkenyl, CONH(C
1
-C
6
)alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C
1
-C
10
)alkyl or O-(C
1
-C
10
)alkyl-phenyl, CONH(C
1
-C
6
)alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
O-(C
1
-C
6
)alkyl;
(C
1
-C
6
)alkyl, (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl, (C
1
-C
6
)alkyl-COOH, (C
1
-C
6
)alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
Phenyl, biphenyl, 1-or 2-naphthyl, 2-,3-or 4-pyridyl, 2-or 3-furanyl or 2-or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl, CONH
2
; (C
3
-C
18
)cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C
1
-C
6
)alkyl-phenyl or O-(C
1
-C
6
)alkyl-phenyl,
NCO, NSO
3
-(C
1
-C
10
)alkyl; or in each case two of the radicals R1 and R2 or R2 and R3 or R1 and R3 together form a fused aryl radical, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl, CONH
2
;
or its physiologically acceptable salts or prodrugs.
The invention preferably relates to compounds of the formula I wherein
X is O, N;
Y is O, N;
R1 is H, F, Cl, Br, I, NH
2
, OH, NO
2
, COOH;
COO(C
1
-C
6
)alkyl, CONH
2
, CONH(C
1
-C
6
)alkyl, CONH(C
1
-C
6
)alkenyl, CONH(C
1
-C
6
)alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C
1
-C
10
)alkyl or O-(C
1
-C
10
)alkyl-phenyl, CONH(C
1
-C
6
)alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
O-(C
1
-C
6
)alkyl;
(C
1
-C
6
)alkyl, (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl, (C
1
-C
6
)alkyl-COOH, (C
1
-C
6
)alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
Phenyl, biphenyl, 1-or 2-naphthyl, 2-, 3-or 4-pyridyl, 2-or 3-furanyl or 2-or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl, CONH
2
; (C
3
-C
18
)cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C
1
-C
6
)alkyl-phenyl or O-(C
1
-C
6
)alkyl-phenyl,
NCO, NSO
3
-(C
1
-C
10
)alkyl;
R2 is H, F, Cl, Br, I, NH
2
, OH, NO
2
, COOH;
COO(C
1
-C
6
)alkyl, CONH
2
, CONH(C
1
-C
16
)alkyl, CONH(C
1
-C
16
)alkenyl, CONH(C
1
-C
6
)alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C
1
-C
10
)alkyl or O-(C
1
-C
10
)alkyl-phenyl, CONH(C
1
-C
6
)alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
O-(C
1
-C
6
)alkyl;
(C
1
-C
6
)alkyl, (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl, (C
1
-C
6
)alkyl-COOH, (C
1
-C
6
)alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
Phenyl, biphenyl, 1-or 2-naphthyl, 2-, 3-or 4-pyridyl, 2-or 3-furanyl or 2-or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl, CONH
2
; (C
3
-C
18
)cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C
1
-C
6
)alkyl-phenyl or O-(C
1
-C
6
)alkyl-phenyl,
NCO, NSO
3
-(C
1
-C
10
)alkyl;
R3 is H, F, Cl, Br, I, NH
2
, OH, NO
2
, COOH;
COO(C
1
-C
6
)alkyl, CONH
2
, CONH(C
1
-C
16
)alkyl, CONH(C
1
-C
16
)alkenyl, CONH(C
1
-C
6
)alkyl-phenyl, where phenyl may be mono- to trisubstituted by O-(C
1
-C
10
)alkyl or O-(C
1
-C
10
)alkyl-phenyl, CONH(C
1
-C
6
)alkyl-benzimidazole, where the benzimidazole ring may be mono- to trisubstituted by S-phenyl, wherein the S-phenyl may be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
O-(C
1
-C
6
)alkyl;
(C
1
-C
6
)alkyl, (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl, (C
1
-C
6
)alkyl-COOH, (C
1
-C
6
)alkyl-aryl, where aryl may be phenyl, naphthyl, biphenyl, thienyl or pyridyl and the aryl moiety may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl,
CONH
2
;
Phenyl, biphenyl, 1-or 2-naphthyl, 2-, 3-or 4-pyridyl, 2-or 3-furanyl or 2-or 3-thienyl, where the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings may in each case be mono- to trisubstituted by F, Cl, Br, I, OH, CF
3
, NO
2
, CN, OCF
3
, O-(C
1
-C
10
)alkyl, NH
2
, NH(C
1
-C
6
)alkyl, COOH, COO(C
1
-C
6
)alkyl, CONH
2
; (C
3
-C
18
)cycloalkyl, where in the alkyl radicals one or more hydrogens may be replaced by fluorine or one hydrogen may be replaced by OH, (C
1
-C
6
)alkyl-phenyl or O-(C
1
-C
6
)alkyl-phenyl, NCO, NSO
3
-(C
1
-C
10
)alkyl;
or its physiologically acceptable salts or prodrugs.
The invention furthermore preferably relates to compounds of the formu

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