Glycosidase inhibitors

1. A compound of formula (I)

wherein

R is straight chain or branched alkyl having 1 to 6 carbon atoms, wherein 1 to 5 hydrogen atoms may be replaced by Hal or OH;

W is CH or N;

A denotes one of the following groups:

X is N or CR′″;

X 1 , X 2 is N or CR′″;

X 3 is N or CR′″″;

X 4 is N or CR 9 ;

R 9 denotes Hal, NR 3 R 4 , CHR 3 R 4 , OR 3 , CN, straight chain or branched alkyl having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups may be replaced by a group selected from O, NR 3 , S, SO, SO 2 , S(O)(NH), CO, COO, OCO, CONR 3 , NR 3 CO and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR 3 R 4 or NO 2 ;

Y is O, S, SO or SO 2 ;

R′, R″ denote each independently H, Hal or straight chain or branched alkyl having 1 to 12 carbon atoms;

R′″, R″″ independently denote H, Hal, NR 3 R 4 , CHR 3 R 4 , OR 3 , CN, straight chain or branched alkyl having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups may be replaced by a group selected from O, NR 3 , S, SO, SO 2 , S(O)(NH), CO, COO, OCO, CONR 3 , NR 3 CO and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR 3 R 4 or NO 2 ;

R′″″ denotes H, Hal, NR 3 R 4 , CHR 3 R 4 , CN, straight chain or branched alkyl having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups may be replaced by a group selected from O, NR 3 , S, SO, SO 2 , S(O)(NH), CO, COO, OCO, CONR 3 , NR 3 CO and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR 3 R 4 or NO 2 ;

R 3 , R 4 denote each independently H or a straight chain or branched alkyl group having 1 to 12 carbon atoms;

Q denotes one of the following groups:

Z 1 is S, O, NR 3 ;

Z 2 , Z 3 independently denote CR 5 , CR 6 or N;

Z 2 ′ is CR 5 ′ or N;

Z 4 is N, CH, CON, COCH;

Z 5 is S, O, NR 8 , SO 2 , CHR 5 ;

Z 5′ is S, O, NR 8 , SO 2 ;

Z 6 is CH 2 , CO;

s denotes 0 or 1;

T is N, CH or CR 7 ;

R 3 ′ denotes H or a straight chain or branched alkyl group having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups may be replaced by a group selected from SO 2 , CO, O and wherein 1 to 5 hydrogen atoms may be replaced by Hal;

R 3 ″ denotes a straight chain or branched alkyl group having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups are replaced by a group selected from SO 2 , CO, O and wherein 1 to 5 hydrogen atoms may be replaced by Hal;

R 5 , R 5 ′, R 6 , R 7 independently denote H, Hal, NR 3 R 4 , NO 2 , straight chain or branched alkyl having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups may be replaced by a group selected from O, NR 3 , S, SO, SO 2 , S(O)(NH), CO, COO, OCO, CONR 3 , NR 3 CO and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR 3 R 4 , NO 2 , OR 3 , Het, Ar, Cyc, or denote Ar, Het or Cyc;

R 8 denotes H, methyl or straight chain or branched alkyl having 2 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups may be replaced by a group selected from O, NR 3 , S, SO, SO 2 , S(O)(NH), CO, COO, OCO, CONR 3 , NR 3 CO and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR 3 R 4 or NO 2 ;

Hal denotes F, Cl, Br or I;

Het denotes a saturated, unsaturated or aromatic ring, being monocyclic or bicyclic or fused-bicyclic and having 3- to 8-members and containing 1 to 4 heteroatoms selected from N, O and S, which may be substituted by 1 to 3 substituents selected from R 5 , Hal and OR 3 ;

Ar denotes a 6-membered carbocyclic aromatic ring or a fused or non-fused bicyclic aromatic ring system, which is optionally substituted by 1 to 3 substituents independently selected from R 5 , OR 3 and Hal;

Cyc denotes a saturated or an unsaturated carbocyclic ring having from 3 to 8 carbon atoms which is optionally substituted by 1 to 3 substituents independently selected from R 5 or Hal or OH;

m and n simultaneously denote 1;

and solvates, salts, tautomers, enantiomers, racemates and stereoisomers thereof, including mixtures thereof in all ratios and compounds of formula I, wherein one or more H atoms are replaced by D (deuterium).

2. A compound chosen from the group consisting of formula Ia and Ib:

wherein A, R, W, Q, n and m have the meaning given in claim 1 .

3. A mixture comprising compounds Ia and Ib according to claim 2 , having identical groups A, R, W, Q, n and m, in equal or unequal amounts.

4. A compound of formula I according to claim 1 , wherein R is methyl and/or W is N.

5. A compound of formula I according to claim 1 , wherein A denotes one of the following groups:

6. A compound of formula I according to claim 1 , wherein Q denotes one of the following groups:

wherein X, R′″, R″″, R 5 , R 5′ , R 6 , R 7 and R 8 have the meaning given in claim 1 .

7. A compound of formula I according to claim 1 , wherein R 5 , R 6 , R 7 are independently H, Hal, NR 3 R 4 , phenyl, 2-, 3- or 4-hydroxy or methoxyphenyl, alkyl, CF 3 , alkoxy (Oalkyl), hydroxyalkylene, alkoxyalkylene, COOH, COOalkyl, CONHalkyl, CONH 2 , CON(CH 3 ) 2 , NHCOalkyl, CO—N-morpholinyl, CON(CH 3 )CH 2 CH 2 N(CH 3 ) 2 , CO-1-piperidinyl, CO-4-hydroxy-1-piperidinyl, CO-1-piperazinyl, CO-4-methyl-1-piperazinyl, CH 2 —N-morpholinyl, CH 2 N(H)COCH 3 , CH 2 N(CH 3 )COCH 3 , substituted Cyc or Het, or unsubstituted Cyc or Het.

8. A compound of formula I according to claim 6 , wherein R 5 , R 6 , R 7 are independently H, Hal, NR 3 R 4 , phenyl, 2-, 3- or 4-hydroxy or methoxyphenyl, alkyl, CF 3 , alkoxy (Oalkyl), hydroxyalkylene, alkoxyalkylene, COOH, COOalkyl, CONHalkyl, CONH 2 , CON(CH 3 ) 2 , NHCOalkyl, CO—N-morpholinyl, CON(CH 3 )CH 2 CH 2 N(CH 3 ) 2 , CO-1-piperidinyl, CO-4-hydroxy-1-piperidinyl, CO-1-piperazinyl, CO-4-methyl-1-piperazinyl, CH 2 —N-morpholinyl, CH 2 N(H)COCH 3 , CH 2 N(CH 3 )COCH 3 , substituted Cyc or Het, or unsubstituted Cyc or Het.

9. The compound of claim 1 , wherein R is methyl, CH 2 OH, CF 3 , CHF 2 , or CH 2 F.

10. A compound according to claim 1 , selected from the following group:

Configuration

No

Structure

specification

 93

racemic

111

racemic

127

128

129

130

131

132

133

134

221

S-enantiomer

222

S-enantiomer

223

S-enantiomer

224

S-enantiomer

225

S-enantiomer

226

S-enantiomer

227

S-enantiomer

228

S-enantiomer

229

S-enantiomer

230

S-enantiomer

and solvates, salts, tautomers, enantiomers, racemates and stereoisomers thereof, including mixtures thereof in all ratios.

11. A pharmaceutical composition comprising as active ingredient a compound according to claim 1 or a solvate, salt, tautomer, enantiomer, racemate, or stereoisomer thereof, together with pharmaceutically tolerable adjuvants and/or excipients, optionally in combination with one or more further active ingredients.

12. A pharmaceutical composition comprising as active ingredient a compound according to claim 10 , or a solvate, salt, tautomer, enantiomer, racemate, or stereoisomer thereof, together with pharmaceutically tolerable adjuvants and/or excipients, optionally in combination with one or more further active ingredients.