Glucopyranoside derivatives

1. A compound of formula I

in which

X denotes

in which the 6-membered aromatic ring may be mono- or disubstituted by Hal, OR 5 , NR 5 R 6 , CN, COOR 5 , CONR 5 R 6 , —OCOA, NR 5 COR 6 and/or NR 5 SO 2 A,

R denotes Carb, Ar or Het,

R 5 , R 6 each, independently of one another, denote H or A,

Carb denotes cycloalkyl having 3-7 C atoms,

Ar denotes phenyl, naphthyl or biphenyl, which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, benzyl, OR 5 , NR 5 R 6 , NO 2 , CN, CONR 5 R 6 , NR 5 COA, OCOA, NR 5 CONR 5 R 6 , NR 5 SO 2 A, CHO, COA, SO 2 NR 5 R 6 , S(O) p A and/or —(CR 5 R 6 ) m —COOR 5 ,

Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which may be mono-, di- or trisubstituted by Hal, A, benzyl, OR 5 , NR 5 R 6 , NO 2 , CN, CONR 5 R 6 , NR 5 COA, OCOA, NR 5 CONR 5 R 6 , NR 5 SO 2 A, CHO, COA, SO 2 NR 5 R 6 , S(O) p A, —(CR 5 R 6 ) m —COOR 5 , ═S, ═NR 1 and/or ═O (carbonyl oxygen),

A denotes unbranched or branched alkyl having 1-10 C atoms, in which one, two or three CH 2 groups may be replaced, independently of one another, by O, S, SO, SO 2 , NR 5 , —C≡C— and/or by —CH═CH—groups and/or in which 1-7 H atoms may be replaced by F and/or Cl,

or cycloalkyl having 3-7 C atoms,

Hal denotes F, Cl, Br or I,

m denotes 0, 1, 2 or 3, and

p denotes 0, 1 or 2,

or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

2. A compound according to claim 1 , in which

R 5 , R 6 each, independently of one another, denote H or methyl, or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

3. A compound according to claim 1 , in which

R denotes Ar,

or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

4. A compound according to claim 1 , in which

Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, A and/or OR 5 ,

or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

5. A compound according to claim 1 , in which

A denotes unbranched or branched alkyl having 1-6 C atoms, in which 1-7 H atoms may be replaced by F and/or Cl,

or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

6. A compound according to claim 1 , in which

X denotes

R denotes Ar,

R 5 denotes H or A,

Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, A and/or OR 5 ,

A denotes unbranched or branched alkyl having 1-6 C atoms, in which 1-7 H atoms may be replaced by F and/or Cl, and

Hal denotes F, Cl, Br or I,

or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

7. A compound, which is one of the following compounds

No.

Name

“A1”

6-(β-D-Glucopyranos-1-yl)-1-(4-methoxyphenyl)indane

“A2”

6-(β-D-Glucopyranos-1-yl)-1S-(4-methoxyphenyl)indane

“A3”

6-(β-D-Glucopyranos-1-yl)-1R-(4-methoxyphenyl)indane

“A4”

6-(β-D-Glucopyranos-1-yl)-1-(4-ethoxyphenyl)indane

“A5”

7-(β-D-Glucopyranos-1-yl)-1-(4-methoxyphenyl)-1,2,3,4-

tetrahydronaphthalene or

“A6”

7-(1-Methoxy-D-glucopyranos-1-yl)-1-(4-methoxyphenyl)-

3,4-dihydronaphthalene

or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

8. A process for preparing a compound of formula I according to claim 1 or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, comprising cleaving off R 1 from a compound of formula II

in which

X has the meaning indicated for the compound of formula I,

and R 1 denotes a hydroxyl-protecting group,

and/or

converting a base or acid compound of formula I into one of its salts.

9. A pharmaceutical composition comprising at least one compound of formula I according to claim 1 and/or or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, and or more pharmaceutically acceptable excipients and/or adjuvants.

10. A pharmaceutical composition according to claim 9 , further comprising at least one further pharmaceutically active compound.

11. A method for the treatment of type 1 and/or type 2 diabetes, comprising administering to a patient in need thereof an effective amount of a compound according to claim 1 .

12. A method of lowering blood sugar, comprising administering to a patient in need thereof an effective amount of a compound according to claim 1 .

13. A method according to claim 11 , further comprising administering to said patient a further pharmaceutically active ingredient for the treatment of type 1 or type 2 diabetes.

14. A kit comprising separate packs of:

(a) a compound according to claim 1 or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, and

(b) a further pharmaceutically active compound.

15. A method according to claim 12 , further comprising administering to said patient a further pharmaceutically active compound for lowering blood sugar.

16. A method for treating type 1 diabetes, comprising administering to a patient in need thereof an effective amount of a compound according to claim 1 .

17. A method for treating type 2 diabetes, comprising administering to a patient in need thereof an effective amount of a compound according to claim 1 .

18. A method for treating type 1 diabetes, comprising administering to a patient in need thereof an effective amount of a compound according to claim 7 .

19. A method for treating type 2 diabetes, comprising administering to a patient in need thereof an effective amount of a compound according to claim 7 .

20. A method for lowering blood sugar, comprising administering to a patient in need thereof an effective amount of a compound according to claim 7 .