5-(1,2,3-triazol-4-yl)-7H-pyrrolo[2,3-D]pyrimidine derivatives

1. A compound of the formula I

in which

R 1 denotes A, —C(R 3 )(R 4 )—Ar, —C(R 3 )(R 4 )-Het or —C(R 3 )(R 4 )-Cyc,

R 2 , R 2a each, independently of one another, denote H, A, Hal, CN, —[C(R 3 ) 2 ] n —Ar′, —[C(R 3 ) 2 ] n -Het′, —[C(R 3 ) 2 ] n -Cyc, OR 3 or N(R 3 ) 2 ,

R 3 denotes H,

R 4 denotes H, A, —[C(R 3 ) 2 ] m OR 3 , —[C(R 3 ) 2 ] m N(R 3 ) 2 or —[C(R 3 ) 2 ] m Het 1 ,

A denotes unbranched or branched alkyl having 1-6 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by O, N and/or S atoms and/or by —CH═CH— groups and/or, in addition, 1-7 H atoms may be replaced by F,

Cyc denotes cycloalkyl having 3, 4, 5, 6 or 7 C atoms,

Ar denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, A, OR 3 , N(R 3 ) 2 , NO 2 , CN, COOR 3 , CON(R 3 ) 2 , NR 3 COA, NR 3 SO 2 A, COR 3 , SO 2 N(R 3 ) 2 and/or S(O) n A,

Ar′ denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, A, OR 3 , N(R 3 ) 2 , SR 3 , NO 2 , CN, COOR 3 , CON(R 3 ) 2 , NR 3 COA, NR 3 SO 2 A, SO 2 N(R 3 ) 2 , S(O) m A, CO-Het 1 , Het 1 , [C(R 3 ) 2 ] n N(R 3 ) 2 , [C(R 3 ) 2 ] n Het 1 , O[C(R 3 ) 2 ] n N(R 3 ) 2 , O[C(R 3 ) 2 ] n Het 1 , NHCOOA, NHCON(R 3 ) 2 , NHCOO[C(R 3 ) 2 ] n N(R 3 ) 2 , NHCOO[C(R 3 ) 2 ] n Het 1 , NHCONH[C(R 3 ) 2 ] n N(R 3 ) 2 , NHCONH[C(R 3 ) 2 ] 1 Het 1 , OCONH[C(R 3 ) 2 ] n N(R 3 ) 2 , OCONH[C(R 3 ) 2 ] n Het 1 , CO-Het 1 , CHO and/or COA,

Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, and/or O and/or S atoms which is unsubstituted or mono- or disubstituted by Hal, A, OR 3 , N(R 3 ) 2 , NO 2 , CN, COOR 3 , CON(R 3 ) 2 , NR 3 COA, NR 3 SO 2 A, COR 3 , SO 2 NR 3 and/or S(O) n A,

Het′ denotes a mono-, bi- or tricyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which is unsubstituted or may be mono- or disubstituted by Hal, A, OR 3 , N(R 3 ) 2 , SR 3 , NO 2 , CN, COOR 3 , CON(R 3 ) 2 , NR 3 COA, NR 3 SO 2 A, SO 2 N(R 3 ) 2 , S(O) m A, CO-Het 1 , Het 1 , [C(R 3 ) 2 ] n N(R 3 ) 2 , [C(R 3 ) 2 ] n Het 1 , O[C(R 3 ) 2 ] n N(R 3 ) 2 , O[C(R 3 ) 2 ] n Het 1 , NHCOOA, NHCON(R 3 ) 2 , NHCOO[C(R 3 ) 2 ] n N(R 3 ) 2 , NHCOO[C(R 3 ) 2 ] n Het 1 , NHCONH[C(R 3 ) 2 ] 1 N(R 3 ) 2 , NHCONH[C(R 3 ) 2 ] n Het 1 , OCONH[C(R 3 ) 2 ] n N(R 3 ) 2 , OCONH[C(R 3 ) 2 ] n -Het 1 , CO-Het 1 , CHO, COA, ═S, ═NH, =NA and/or ═O (carbonyl oxygen),

Het 1 denotes a monocyclic saturated heterocycle having 1 to 2 N and/or O atoms, which may be mono- or disubstituted by A, OA, OH, Hal and/or ═O (carbonyl oxygen),

Hal denotes F, Cl, Br or I

N denotes 0, 1 or 2

m denotes 1 or 2,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

2. A compound according to claim 1 in which

R 1 denotes —C(R 3 )(R 4 )—Ar,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

3. A compound according to claim 1 in which

R 2 , R 2a each, independently of one another, denotes H or A,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

4. A compound according to claim 1 in which

R 4 denotes H, —[C(R 3 ) 2 ] m N(R 3 ) 2 or —[C(R 3 ) 2 ] m Het 1 ,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

5. A compound according to claim 1 in which

A denotes unbranched or branched alkyl having 1-6 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by an O, N and/or S atom and/or, in addition, 1-7 H atoms may be replaced by F,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

6. A compound according to claim 1 in which

Ar denotes phenyl which is unsubstituted or mono- or disubstituted by Hal and/or A,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

7. A compound according to claim 1 in which

Het 1 denotes a monocyclic saturated heterocycle having 1 to 2 N and/or O atoms, which may be mono- or disubstituted by A,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

8. A compound according to claim 1 in which

Het 1 denotes azetidinyl, pyrrolidinyl, tetrahydroimidazolyl, tetrahydropyrazolyl, piperidinyl, morpholinyl, piperazinyl, oxazolidinyl or isoxazolidinyl, each of which is unsubstituted or mono- or disubstituted by A,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

9. A compound according to claim 1 in which

R 1 denotes —C(R 3 )(R 4 )—Ar,

R 2 , R 2a each, independently of one another, denote H or A,

R 3 denotes H,

R 4 denotes H, —[C(R 3 ) 2 ] m N(R 3 ) 2 or —[C(R 3 ) 2 ] m Het 1 ,

A denotes unbranched or branched alkyl having 1-6 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by an O, N and/or S atom and/or, in addition, 1-7 H atoms may be replaced by F,

Ar denotes phenyl which is unsubstituted or mono- or disubstituted by Hal and/or A,

Het 1 denotes a monocyclic saturated heterocycle having 1 to 2 N and/or O atoms, which may be once or twice by A,

Hal denotes F, Cl, Br or I,

M denotes 1 or 2,

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

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

Compound

No.

Name and/or structure

“A1”

5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-4-(2-

methoxyethoxy)-7H-pyrrolo[2,3-d]pyrimidine

“A2”

5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-4-methoxy-7H-

pyrrolo[2,3-d]pyrimidine

“A3”

5-[1-(3-Fluorobenzyl)-1H-1,2,3-triazol-4-yl]-4-(2-

methoxyethoxy)-7H-pyrrolo[2,3-d]pyrimidine

“A4”

(3-{4-[4-(2-Methoxyethoxy)-7H-pyrrolo[2,3-d]-

pyrimidin-5-yl]-1,2,3-triazol-1-yl}-3-phenylpropyl)-

dimethylamine

“A5”

5-[1-(3-Azetidin-1-yl-1-phenylpropyl)-1H-1,2,3-triazol-

4-yl]-4-(2-methoxyethoxy)-7H-pyrrolo[2-3-d]-

pyrimidine

“A6”

5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-7H-pyrrolo[2,3-d]-

pyrimidine

“A7”

5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-2-methoxy-7H-

pyrrolo[2,3-d]pyrimidine

“A8”

5-(1-Benzyl-1H-1,2,3-triazol-4-yl)-2,4-dimethoxy-7H-

pyrrolo[2,3-d]pyrimidine

“A9”

5-{1-[1-(2,3-Difluorophenyl)-3-piperidin-1-yl-propyl]-

1H-1,2,3-triazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidine

or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios.

11. A process for the preparation of a compound of the formula I according to claim 1 or a pharmaceutically usable salt, tautomer or stereoisomer thereof, comprising:

cleaving off an indole-protecting group from a compound of the formula II

in which R 1 , R 2 , R 2a and R 3 have the meanings indicated in claim 1 and R denotes the indole-protecting group,

and/or converting a base or acid of the formula I into one of its salts.

12. A medicament composition comprising ing at least one compound of the formula I according to claim 1 or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios, and optionally excipients and/or adjuvants.

13. A method for inhibiting PDK-1 in vitro, which comprises contacting a compound according to claim 1 or a pharmaceutically usable salt, tautomer or stereoisomer thereof, including mixtures thereof in all ratios, with PDK-1.