Linear 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;

L is CONR 3′ , NR 3′ CO, SO 2 NR 3′ , NR 3′ SO 2 , CONR 3′ CH 2 , CH 2 CONR 3′ , SO 2 NR 3′ CH 2 , CH 2 SO 2 NR 3′ , NR 3′ , NR 3′ COCH 2 , CH 2 NR 3′ CO, NR 3′ SO 2 CH 2 , CH 2 NR 3′ SO 2 , O, OCH 2 , CH 2 O, S(O)(NR 3′ ),

N(SO)R 3′ ,

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 or NO 2 or by one of the following groups:

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:

Y is N or CR′″;

Y 1 and Y 2 is each independently CH 2 , NR 3 , O, S, SO, SO 2 or S(O)(NR 3′ ), N(SO)R 3′ ,

Z 1 is S, O, NR 3 ;

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

Z 4 is N, CH, CON, COCH;

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

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

Z 7 is C(R 3′ ) 2 , S, O, 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, O and wherein 1 to 5 hydrogen atoms may be replaced by Hal;

R 5 , R 6 , R 7 independently denote H, Hal, CN, 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 by one of the following groups:

or R 5 , R 6 , R 7 denote Ar, Het or Cyc or one of the following groups:

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

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 by one of the following groups:

or R 8 denote 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 or Hal or OH;

m and n denote independently from one another 0, 1, 2 or 3,

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

or a pharmaceutically usable derivative, solvate, salt, prodrug, tautomer, enantiomer, racemate, stereoisomer, compound of formula I wherein one or more H atoms are replaced by D (deuterium), or a mixture thereof.

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

wherein A, R, W, Q, L, 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, L, n and m in equal or unequal amounts.

4. A compound of formula I according to claim 1 , wherein R is methyl.

5. A compound of formula I according to claim 1 , wherein the group L denotes CONH, NHCO, CONHCH 2 , CH 2 CONH, NH, NHCOCH 2 , CH 2 NHCO, O, OCH 2 , CH 2 O, S(O)(NR 3′ ), N(SO)R 3′ ,

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

wherein T, Y, Z 5 , Z 6 , R′″, 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 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, Z 7 , R 3 , R 4 and R 3′ have the meaning given in claim 1 .

8. A compound of formula I according to claim 1 , wherein m and n simultaneously denote 1.

9. A compound according to claim 1 , selected from the following group consisting of:

Example

No

Structure

Chirality

17

Racemic

18

Racemic

19

Racemic

20

Racemic

21

Racemic

22

Racemic

23

Racemic

24

Racemic

25

Racemic

26

Racemic

27

Racemic

28

Chiral SFC, method C, first eluting

29

Racemic

30

Racemic

31

Chiral SFC, method B, first eluting

32

Racemic

33

Racemic

34

Racemic

35

Racemic

36

Racemic

37

Racemic

38

Racemic

39

Chiral SFC, method C, second eluting

40

41

or a pharmaceutically usable derivative, solvate, salt, tautomer, enantiomer, racemate, stereoisomer, or mixture thereof in all ratios.

10. A pharmaceutical composition comprising as active ingredient a compound according to claim 1 together with pharmaceutically tolerable adjuvants and/or excipients, optionally in combination with one or more further active ingredients.