Sulfoximine 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 N;

A denotes one of the following groups:

X is N or CR′″;

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, or a 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)(NR 3′ ), N(SO)R 3′ , 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 R′″, R″″ independently denote one of the following groups:

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, or NR 3 ;

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

Z 4 is N, CH, CON, or COCH;

Z 5 is NR 8 , CHR 5 , S(O)(NR 3′ ), N(SO)R 3′ ,

Z 6 is CH 2 , CO, S(O)(NR 3′ ), N(SO)R 3′ ,

Z 7 is C(R 3′ ) 2 , S, O, or NR 3′ ;

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, and O, and wherein 1 to 5 hydrogen atoms may be replaced by Hal;

R 5 , R 6 , R 7 independently denote H, Hal, NR 3 R 4 , NO 2 , or a 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)(NR 3′ ), N(SO)R 3′ , 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 R 5 , R 6 , R 7 denote Ar, Het, Cyc,

R 8 denotes H or 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 SO, SO 2 , S(O)(NR 3′ ), N(SO)R 3′ , CO, COO, OCO, CONR 3 , NR 3 CO,

and further wherein 1 to 5 hydrogen atoms may be replaced by CN, OR 3 , SR 3 , Hal, NR 3 R 4 , NO 2 ,

or R 8 denotes one of the following groups:

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 , Hal, and OH;

m and n are both 1;

t and q denote independently from one another 0, 1, 2 or 3, with t+q≥1

and wherein at least one of Z 5 and Z 6 is S(O)(NR 3′ ), N(SO)R 3′ ,

or

wherein at least one of R′″, R″″, R 5 , R 6 , R 7 , and R 8 is or contains a sulfoximine group selected from:

or

wherein at least one of R′″, R″″, R 5 , R 6 , R 7 and R 8 is a straight chain or branched alkyl group having 1 to 12 carbon atoms, wherein at least one CH 2 -group is replaced by S(O)(NR 3′ ),

N(SO)R 3′ ,

or a pharmaceutically acceptable salt, tautomer, enantiomer, racemate, or a stereoisomer thereof, including mixtures thereof in all ratios, or a compound of formula I wherein one or more H atoms are replaced by D (deuterium).

2. The compound of claim 1 selected from the group consisting of formula Ia and Ib:

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. The compound of claim 1 , wherein R is methyl.

5. The compound of claim 1 , wherein A is:

6. The compound of claim 1 , wherein Q is:

7. The compound of claim 1 , wherein R 5 , R 6 , and R 7 are independently selected from H, SO 2 CH 3 , SO 2 CH 2 CH 3 , SO 2 CH 2 CH 2 OH, SO 2 CH 2 CH 2 OCH 3 , S(O)(NR 3′ )CH 3 , S(O)(NR 3′ )CH 2 CH 3 , S(O)(NR 3′ )CH 2 CH 2 OH, S(O)(NR 3′ )CH 2 CH 2 OCH 3 , N(SO)R 3′ CH 3 , N(SO)R 3′ CH 2 CH 3 , N(SO)R 3′ CH 2 CH 2 OH, N(SO)R 3′ CH 2 CH 2 OCH 3 ,

Hal, NR 3 R 4 , NO 2 , phenyl, 2-, 3- or 4-hydroxy or methoxyphenyl, alkyl, alkoxy (Oalkyl), hydroxyalkylene, alkoxyalkylene, COOH, COOalkyl, CONHalkyl, CONH 2 , CON(CH 3 ) 2 , NHCOalkyl, NHCH 2 CH 3 , NHCH 2 CH 2 CH 3 , NHCOCH 2 CH 2 OH, 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 , CH 2 NH 2 , NH 2 , CH(OH)CH 3 , CH(OR 3 )CH 3 ,

wherein t+q is 2 or 3.

8. The compound of claim 1 , wherein one of the groups R′″, R″″, R 5 , R 6 , R 7 and R 8 is selected from

9. The compound of claim 1 , wherein at least one of Z 5 and Z 6 is selected from the group

or

wherein at least one of R′″, R″″, R 5 , R 6 , R 7 and R 8 is or contains a sulfoximine group selected from:

or

wherein at least one of R′″, R″″, R 5 , R 6 , R 7 and R 8 is a straight chain or branched alkyl group having 1 to 12 carbon atoms, wherein at least one CH 2 -group is replaced by

or a pharmaceutically acceptable salt, tautomer, enantiomer, racemate, or a stereoisomer thereof, including mixtures thereof in all ratios, or a compound of formula I wherein one or more H atoms are replaced by D (deuterium).

10. A compound of formula C:

wherein

A′ is:

T′ is N or CH;

R 7 is

 or a straight chain or branched alkyl having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups are replaced by a group selected from

and wherein 1 to 5 hydrogen atoms may be replaced by Hal, NR 3 R 4 , NO 2 , OR 3 , Het, Ar, or Cyc;

R′ is H, Hal or straight chain or branched alkyl having 1 to 12 carbon atoms;

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, and O, and wherein 1 to 5 hydrogen atoms may be replaced by Hal;

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

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 , Hal, and OH;

R 5 is H, Hal, NR 3 R 4 , NO 2 , or a 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)(NR 3′ ), N(SO)R 3′ , 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 R 5 is Ar, Het, Cyc,

Z 7 is C(R 3′ ) 2 , S, O, or NR 3′ ;

t and q denote independently from one another 0, 1, 2 or 3, with t+q≥1;

or a pharmaceutically acceptable salt, tautomer, enantiomer, racemate, or a stereoisomer thereof, including mixtures thereof in all ratios, or a-compound of formula I wherein one or more H atoms are replaced by D (deuterium).

11. A compound, wherein the compound is selected from:

or a pharmaceutically acceptable salt, tautomer, enantiomer, racemate, or stereoisomer thereof, including mixtures thereof in all ratios, or a compound from the foregoing list wherein one or more H atoms are replaced by D (deuterium).

12. A pharmaceutical composition comprising as active ingredient a compound according to claim 1 together with pharmaceutically tolerable adjuvants and/or excipients.