Piperidine and piperazine derivatives

1. A compound of formula I

in which

R 1 denotes

which is optionally mono- or disubstituted by A, Hal, NR 2 , (CR 2 ) n CN and/or OR 5 ,

D denotes C or S,

G denotes N,

R 2 is absent,

Q denotes unbranched or branched alkylene having 1, 2, 3 or 4 C atoms, in which 1-5 H atoms may be replaced by A, (CR 2 ) n [X(CR 2 ) n ] p —Y, F and/or Cl,

R 3 denotes H, A, Ar, OR, SR, NR 2 , Hal, NO 2 , CN or (CR 2 ) n [X(CR 2 ) n ] p —Y,

X denotes O, NR or CR 2 ,

Y denotes OR or NR 2 ,

R 5 denotes H or unbranched or branched alkyl having 1, 2, 3, 4, 5 or 6 C atoms, in which 1-7 H atoms may be replaced by F and/or Cl,

E denotes COO(CR 2 ) n , COO(CRR 4 ), CO(CR 2 ) m O, CONH(CR 2 ) n , C(═S)NH(CR 2 ) n , S(O) q NH(CR 2 ) n , S(O) q (CR 2 ) n , COCH 2 CH 2 , CO(CR 2 ) m O(CR 2 ) n , CO(CR 2 ) m NH(CR 2 ) n , CO(CH 2 ) n CO, COCHR 6 CHR 7 , C(═S)O(CR 2 ) n , CO(CRR 4 )(CR 2 ) n , COO(CRR 4 ), (CRR 4 )(CR 2 ) n , S(O) q CR═CR, COCR═CR, CONH(CR 2 ) m CRR 4 or (CR 2 ) m CONR,

R 4 denotes COOR 5 , Ar 1 , NRCOOR 8 , (CR 2 ) n NR 2 or NRCOOA,

R 6 ,R 7 together denote (CH 2 ) 1-4 ,

R 8 denotes phenyl, naphthyl or fluorenyl,

R denotes H or unbranched or branched alkyl having 1, 2, 3, 4, 5 or 6 C atoms,

W denotes Ar or Het,

Ar denotes phenyl, indanyl, naphthyl or biphenyl, each of which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, (CR 2 ) n OR, O(CR 2 ) n , Ar 1 , (CR 2 ) n NR 2 , SR, NO 2 , CN, COOR, CONR 2 , NRCOA, NRSO 2 A, SO 2 NR 2 , S(O) q A, CO-Het, (CR 2 ) n Het, O(CR 2 ) n NR 2 , O(CR 2 ) n Het, NHCOOA, NHCONR 2 , NHCOO(CR 2 ) n NR 2 , NHCOO(CR 2 ) n Het, CR 5 ═CR 5 Ar 1 , SO 2 Het, NHCONH(CR 2 ) n NR 2 , NHCONH(CR 2 ) n Het, OCONH(CR 2 ) n NR 2 , OCONH(CR 2 ) n Het, CONR(CR 2 ) n NR 2 , CONR(CR 2 ) n Het and/or COA,

Het denotes a mono-, bi- or tricyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, O and/or S atoms, which may be unsubstituted or mono-, di- or trisubstituted by Hal, A, (CR 2 ) n Ar 1 , O(CR 2 ) n Ar 1 , (CR 2 ) n OR, (CR 2 ) n NR 2 , SR, NO 2 , CN, COOR, CONR 2 , NRCOA, NRSO 2 A, SO 2 NR 2 , S(O) q A, CO-Het 1 , (CR 2 ) n Het 1 , O(CR 2 ) n NR 2 , O(CR 2 ) n Het 1 , NHCOOA, NHCONR 2 , NHCOO(CR 2 ) n NR 2 , NHCOO(CR 2 ) n -Het 1 , NHCONH(CR 2 ) n NR 2 , NHCONH(CR 2 ) n Het 1 , OCONH(CR 2 ) n NR 2 , OCONH(CR 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),

Ar 1 denotes phenyl which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, CN, A and/or (CR 2 ) n OR,

A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7 H atoms may be replaced by OR, CN, NR 2 , F and/or Cl and/or in which one or two non-adjacent CH 2 groups may be replaced by O, NH, S, SO, SO 2 and/or by CH═CH groups,

or

cyclic alkyl having 3-7 C atoms,

m denotes 1, 2, 3, 4, 5 or 6,

n denotes 0, 1, 2, 3, 4, 5, 6, 7 or 8,

p denotes 1, 2, 3, 4, 5 or 6,

q denotes 0, 1 or 2, and

Hal denotes F, Cl, Br or I,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

2. A compound according to claim 1 in which

R 1 denotes

which is unsubstituted,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

3. A compound according to claim 1 in which R 3 denotes H,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

4. A compound according to claim 1 in which

Q denotes unbranched or branched methylene, ethylene, propyl-ene or butylene,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

5. A compound according to claim 1 in which

R 5 denotes H or unbranched or branched alkyl having 1, 2, 3 or 4 C atoms, in which 1-5 H atoms may be replaced by F,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

6. A compound according to claim 1 in which

R denotes H, methyl or ethyl,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

7. A compound according to claim 1 in which

R denotes H,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

8. A compound according to claim 1 in which

Ar denotes phenyl, indanyl, naphthyl or biphenyl, each of which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, (CR 2 ) n OR, O(CR 2 ) n Ar 1 , (CR 2 ) n NR 2 , SR, NO 2 , CN, COOR, CONR 2 , NRCOA, NRSO 2 A, SO 2 NR 2 , S(O) q A, CO-Het, (CR 2 ) n Het, O(CR 2 ) n NR 2 , CR 5 ═CR 5 Ar 1 and/or SO 2 Het,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

9. A compound according to claim 1 in which

Het denotes a mono- or bicyclic saturated, unsaturated or aromatic heterocycle having 1 to 3 N, O and/or S atoms, which is unsubstituted or mono- or disubstituted by Hal, A, (CR 2 ) n Ar 1 and/or ═O (carbonyl oxygen),

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

10. A compound according to claim 1 in which

Het denotes piperidinyl, piperazinyl, pyrrolidinyl, morpholinyl, furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, indolyl, benzo-1,3-dioxolyl, indazolyl, 2,3-dihydrobenzo-1,4-dioxinyl, chromanyl, thiazolidinyl, isoindolyl, tetrahydrofuranyl, carbazolyl, benzo[b]thiophenyl or benzo-2,1,3-thiadiazolyl, each of which is unsubstituted or mono- or disubstituted by Hal, A, (CR 2 ) n Ar 1 and/or ═O (carbonyl oxygen),

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

11. A compound according to claim 1 in which

A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7 H atoms may be replaced by F and/or Cl,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

12. A compound according to claim 1 in which

m denotes 1, 2, 3 or 4,

n denotes 0, 1, 2, 3 or 4,

P denotes 1, 2, 3 or 4,

q denotes 0, 1 or 2,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

13. A compound according to claim 1 in which

Q denotes unbranched or branched methylene, ethylene, propylene or butylene,

R 3 denotes H,

R 5 denotes H or unbranched or branched alkyl having 1, 2, 3 or 4 C atoms, in which 1-5 H atoms may be replaced by F,

E denotes COO(CR 2 ) n , COO(CRR 4 ), CO(CR 2 ) m O, CONH(CR 2 ) n , S(O) q (CR 2 ) n , COCH 2 CH 2 , CO(CR 2 ) m O(CR 2 ) p , CO(CR 2 ) m NH(CR 2 ) p , C(═S)O(CR 2 ) n , CO(CRR 4 )(CR 2 ) n , COO(CRR 4 ), (CRR 4 )(CR 2 ) n , S(O) q CR═CR, COCR═CR, or (CR 2 ) m CONR,

R 4 denotes COOR 5 , Ar 1 , (CR 2 ) n NR 2 or NRCOOA,

R denotes H or unbranched or branched alkyl having 1, 2, 3, 4, 5 or 6 C atoms,

W denotes Ar or Het,

Ar denotes phenyl, indanyl, naphthyl or biphenyl, each of which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, (CR 2 ) n OR, O(CR 2 ) n Ar 1 , (CR 2 ) n NR 2 , SR, NO 2 , CN, COOR, CONR 2 , NRCOA, NRSO 2 A, SO 2 NR 2 , S(O) q A, CO-Het, (CR 2 ) n Het, O(CR 2 ) n NR 2 , CR 5 ═CR 5 Ar 1 and/or SO 2 Het,

Het denotes a mono- or bicyclic saturated, unsaturated or aro-matic heterocycle having 1 to 3 N, O and/or S atoms, which is unsubstituted or mono- or disubstituted by Hal, A, (CR 2 ) n Ar 1 and/or ═O (carbonyl oxygen),

Ar 1 denotes phenyl which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, CN, A and/or (CR 2 ) n OR,

A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7 H atoms may be replaced by F and/or Cl,

m denotes 1, 2, 3 or 4,

n denotes 0, 1, 2, 3 or 4,

p denotes 1, 2, 3 or 4,

q denotes 0, 1 or 2, and

Hal denotes F, Cl, Br or I,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

14. A compound according to claim 1 in which

R 1 denotes

which is optionally mono- or disubstituted by A, Hal, NR 2 , (CR 2 ) n CN and/or OR 5 ,

Q denotes methylene, ethylene, propylene or butylene,

R 3 denotes H,

R 5 denotes H or unbranched or branched alkyl having 1, 2, 3 or 4 C atoms, in which 1-5 H atoms may be replaced by F,

E denotes COO(CR 2 ) n , COO(CRR 4 ), CO(CR 2 ) m O, CONH(CR 2 ) n , S(O) q (CR 2 ) n , COCH 2 CH 2 , CO(CR 2 ) m O(CR 2 ) p , CO(CR 2 ) m NH(CR 2 ) p , C(═S)O(CR 2 ) n , CO(CRR 4 )(CR 2 ) n , COO(CRR 4 ), (CRR 4 )(CR 2 ) n , S(O) q CR═CR, COCR═CR, or (CR 2 ) m CONR,

R 4 denotes COOR 5 , Ar 1 , (CR 2 ) n NR 2 or NRCOOA,

R denotes H, methyl or ethyl,

W denotes Ar or Het,

Ar denotes phenyl, indanyl, naphthyl or biphenyl, each of which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, (CR 2 ) n OR, O(CR 2 ) n Ar 1 , (CR 2 ) n NR 2 , SR, NO 2 , CN, COOR, CONR 2 , NRCOA, NRSO 2 A, SO 2 NR 2 , S(O) q A, CO-Het, (CR 2 ) n Het, O(CR 2 ) n NR 2 , CR 5 ═CR 5 Ar 1 and/or SO 2 Het,

Het denotes piperidinyl, piperazinyl, pyrrolidinyl, morpholinyl, furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrazinyl, benzimidazolyl, benzotriazolyl, indolyl, benzo-1,3-dioxolyl, indazolyl, 2,3-dihydrobenzo-1,4-dioxinyl, chromanyl, thiazolidinyl, isoindolyl, tetrahydrofuranyl, carbazolyl, benzo[b]thiophenyl or benzo-2,1,3-thiadiazolyl, each of which is unsubstituted or mono- or disubstituted by Hal, A, (CR 2 ) n Ar 1 and/or ═O (carbonyl oxygen),

Ar 1 denotes phenyl which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, CN, A and/or (CR 2 ) n OR,

A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7 H atoms may be replaced by F and/or Cl,

m denotes 1, 2, 3 or 4,

n denotes 0, 1, 2, 3 or 4,

p denotes 1, 2, 3 or 4,

q denotes 0, 1 or 2, and

Hal denotes F, Cl, Br or I,

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

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

Com-

pound

No.

Name and/or structure

“A1”

4-Chlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A2”

6-(3-{4-[2-(4-Chlorophenoxy)acetyl]piperazin-1-yl}propionyl)-

3H-benzoxazol-2-one

“A3”

6-(3-{4-[2-(4-Chlorophenyl)ethylsulfonyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“A4”

N-(4-Trifluoromethoxybenzyl)-4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxamide

“A5”

6-(3-{4-[3-(4-Trifluoromethylphenyl)propionyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“A6”

4-Chlorobenzyl 4-[2-oxo-2-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)ethyl]piperazine-1-carboxylate

“A10”

6-{3-[4-(2,3-Dihydrobenzo-1,4-dioxin-2-carbonyl)piperazin-1-

yl]propionyl}-3H-benzoxazol-2-one

“A11”

6-(3-{4-[2-(4-Fluorophenyl)ethyl]piperazin-1-yl}propionyl)-

3H-benzoxazol-2-one

“A12”

6-{3-[4-(Pyridine-4-carbonyl)piperazin-1-yl]propionyl}-3H-

benzoxazol-2-one

“A13”

6-(3-{4-[2-(2,3-Dimethoxyphenyl)acetyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“A19”

Benzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazine-1-carboxylate

“A20”

3,4-Dimethoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A21”

2-Chlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A22”

2,4-Dichlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A23”

tert-Butylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A24”

4-Methylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A25”

4-Ethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A26”

3,4-Dimethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A27”

4-Chloro-2-methylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A29”

Indan-1-yl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazine-1-carboxylate

“A30”

3-Benzyloxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A31”

Ethoxycarbonylphenylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A32”

Benzohydryl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazine-1-carboxylate

“A33”

3-Methoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A34”

2-Methoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A35”

1-(4-Fluorophenyl)ethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A36”

3-Dimethylaminobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A37”

4-Butoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A38”

4-Methoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A39”

4-Methoxycarbonylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A40”

4-Trifluoromethylsulfanylbenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A41”

4-Isopropylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A43”

4-Chlorobenzyl 4-[3-(5-methyl-2-oxo-2,3-dihydrobenzoxazol-

6-yl)-3-oxopropyl]piperazine-1-carboxylate

“A45”

3,4-Dichlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A46”

2-(4-Fluorophenyl)ethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A47”

Chroman-4-yl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A48”

3-Chlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A49”

3,5-Dichlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A50”

4-Trifluoromethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A51”

2-Fluoro-5-trifluoromethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A52”

6-Bromopyridin-2-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A53”

2-Fluoro-4-trifluoromethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A54”

4-Chloropyridin-2-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A55”

4-Fluorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A56”

4-Methyl-3-nitrobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A57”

Naphthalen-2-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A58”

N-(4-tert-Butylbenzyl)-4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxamide

“A59”

N-(4-Chloro-3-trifluoromethylbenzyl)-4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxamide

“A60”

N-(4-Cyanobenzyl)-4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxamide

“A61”

2-(4-Bromophenyl)ethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A62”

Indan-2-yl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazine-1-carboxylate

“A63”

2-(4-Methoxyphenyl)ethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A64”

Phenethyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazine-1-carboxylate

“A65”

6-(3-{4-[2-(4-Chlorophenyl)acetyl]piperazin-1-yl}propionyl)-

3H-benzoxazol-2-one

“A67”

4-Styrylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A68”

4-Acetylaminobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A69”

N-(4-Chlorobenzyl)-4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxamide

“A70”

4-Methylsulfanylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A71”

Benzo-1,3-dioxol-5-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A72”

4-Trifluoromethoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A75”

Ethyl 2-{4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazin-1-yl}-4-phenylbutyrate

“A77”

4-[2-(4-Chlorophenoxy)acetyl]-1,1-bis[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazin-1-ium

“A78”

2-{4-[3-Oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]-

piperazin-1-yl}-N-pyridin-2-ylacetamide

“A79”

6-{3-[4-(2-Oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A80”

6-(3-{4-[3-(2,4-Dichlorophenyl)propionyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“A81”

6-(3-{4-[5-(3-Trifluoromethylphenyl)-2H-pyrazole-3-

carbonyl]piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“A83”

6-{3-[4-(2-Dimethylamino-3-phenylpropionyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A84”

tert-Butyl ((S)-1-(4-chlorobenzyl)-2-oxo-2-{4-[3-oxo-3-(2-oxo-

2,3-dihydrobenzoxazol-6-yl)propyl]piperazin-1-yl}ethyl)-

carbamate

“A85”

6-(3-{4-[(S)-2-Amino-3-(4-chlorophenyl)propionyl]piperazin-

1-yl}propionyl)-3H-benzoxazol-2-one

“A86”

5-Bromopyridin-3-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A87”

Pyridin-2-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A88”

5-(4-Fluorophenyl)pyridin-3-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A89”

Pyridin-3-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A90”

6-Chloropyridin-3-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A91”

2-Chloropyridin-4-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A92”

N-(3,5-Dichlorobenzyl)-4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxamide

“A93”

2-Trifluoromethoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A94”

3,4,5-Trimethoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A95”

3-Trifluoromethylsulfanylbenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A96”

Furan-2-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A97”

6-{3-[4-(2-Phenylethylsulfonyl)piperazin-1-yl]propionyl}-3H-

benzoxazol-2-one

“A98”

6-{3-[4-((E)-2-Phenylethenesulfonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A99”

6-{3-[4-((E)-2-Methyl-3-phenylacryloyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A100”

6-(3-{4-[(E)-(3-Phenylacryloyl)]piperazin-1-yl}propionyl)-3H-

benzoxazol-2-one

“A101”

N-Methyl-2-{4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazin-1-yl}-N-phenylacetamide

“A102”

3,5-Bistrifluoromethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A103”

3-Chloro-5-trifluoromethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A104”

3,5-Dimethoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A105”

3,5-Dimethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A106”

3,5-Dibromobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A107”

3-Fluoro-5-trifluoromethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A108”

3-Chloro-5-fluorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A109”

3-Trifluoromethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A110”

3,5-Difluorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-

6-yl)propyl]piperazine-1-carboxylate

“A111”

2-Fluorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A112”

3-(Morpholine-4-sulfonyl)benzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A113”

4-Cyanobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A114”

4-Chlorobenzyl 4-[3-oxo-3-(2-oxo-3-prop-2-ynyl-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A115”

6-{3-[4-(5-Chloroindane-2-carbonyl)piperazin-1-yl]propionyl}-

3H-benzoxazol-2-one

“A116”

6-{3-[4-(4-Chlorophenylmethanesulfonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A117”

4-(2-Oxo-5-{4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazin-1-ylmethyl}oxazolidin-3-yl)benzonitrile

“A118”

6-(3-{4-[2-Aminomethyl-3-(4-chlorophenyl)propionyl]-

piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“A119”

4-(2-Dimethylaminoethoxy)benzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A120”

2,4,6-Trimethylbenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“A121”

6-{3-[4-(4-Chlorobenzenesulfonyl)piperazin-1-yl]propionyl}-

3H-benzoxazol-2-one

“A122”

6-(3-{4-[(E)-2-(4-Chlorophenyl)ethenesulfonyl]piperazin-1-

yl}propionyl)-3H-benzoxazol-2-one

“A124”

3-Cyanobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-

yl)propyl]piperazine-1-carboxylate

“A125”

6-(3-{4-[2-(3,5-Difluorophenyl)acetyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“A126”

6-{3-[4-(5-Methyl-1H-indole-2-carbonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A127”

6-{3-[4-(5-Chloro-1H-indole-2-carbonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A128”

6-{3-[4-(6-Chlorochroman-3-carbonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A129”

6-{3-[4-(4′-Methylbiphenyl-2-carbonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“A130”

6-(3-{4-[3-(4-Chlorophenoxy)propionyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

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

Com-

pound

No.

Name and/or structure

“B1”

6-(3-{4-[3-(3,4-Dichlorophenyl)propionyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“B2”

6-(3-{4-[3-(3-Trifluoromethylphenyl)propionyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“B3”

6-{3-[4-((S)-2-Hydroxy-3-phenylpropionyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“B4”

6-{3-[4-(2-Phenylcyclopropanecarbonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“B8”

6-(3-{4-[(E)-3-(3-Trifluoromethylphenyl)acryloyl]piperazin-1-

yl}propionyl)-3H-benzoxazol-2-one

“B9”

6-{3-[4-(4′-Methylbiphenyl-4-carbonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“B10”

6-{3-[4-(5-Trifluoromethyl-1H-benzoimidazole-2-carbonyl)-

piperazin-1-yl]propionyl}-3H-benzoxazol-2-one

“B11”

6-(3-{4-[2-(5-Chloro-3-methylbenzo[b]thiophen-2-yl)acetyl]-

piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“B12”

6-(3-{4-[2-(3,5-Bistrifluoromethylphenyl)acetyl]piperazin-1-

yl}propionyl)-3H-benzoxazol-2-one

“B13”

1-(3,5-Dichlorophenyl)-4-{4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazin-1-yl}butane-1,4-dione

“B14”

5,6-Dichloro-2-(2-oxo-2-{4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazin-1-yl}ethyl)isoindole-1,3-

dione

“B15”

6-(3-{4-[4-Methyl-2-(4-trifluoromethylphenyl)thiazole-5-

carbonyl]piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“B16”

6-(3-{4-[3-(4-Trifluoromethylphenyl)thiophene-2-carbonyl]-

piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“B17”

2-(2-Dimethylaminoethoxy)benzyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“B19”

6-(3-{4-[2-(4-Chlorophenylamino)acetyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“B20”

4-Chlorobenzyl 4-[2-methyl-3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“B21”

3,5-Dichlorobenzyl 4-[2-oxo-2-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)ethyl]piperazine-1-carboxylate

“B22”

6-(2-{4-[3-(4-Chlorophenoxy)propionyl]piperazin-1-yl}acetyl)-

3H-benzoxazol-2-one

“B23”

5-Chloro-2-methoxybenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“B24”

4′-Trifluoromethylbiphenyl-2-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“B25”

6-{3-[4-(4′-Methylbiphenyl-3-carbonyl)piperazin-1-yl]-

propionyl}-3H-benzoxazol-2-one

“B26”

4-(2-Oxo-5-{4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazine-1-carbonyl}oxazolidin-3-yl)benzonitrile

“B27”

6-(3-{4-[2-(3,4-Dichlorophenyl)thiazolidine-4-carbonyl]-

piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“B28”

4-(2-Oxo-4-{4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)-

propyl]piperazine-1-carbonyl}pyrrolidin-1-yl)benzonitrile

“B29”

6-(3-{4-[5-(4-Chlorophenyl)furan-2-carbonyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“B30”

6-(3-{4-[4-(3,4-Dichlorophenyl)-1H-pyrrole-2-carbonyl]-

piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“B31”

6-(3-{4-[4-Methyl-2-(4-trifluoromethylphenyl)thiazole-5-

carbonyl]piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

“B32”

Tetrahydrofuran-2-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“B33”

N-(Tetrahydrofuran-2-ylmethyl)-4-[3-oxo-3-(2-oxo-2,3-

dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxamide

“B34”

6-(3-{4-[3-(3,5-Difluorophenyl)propionyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“B35”

N-(9-Ethyl-9H-carbazol-3-yl)-4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxamide

“B36”

1-Methyl-1H-indol-6-ylmethyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carboxylate

“B37”

6-{3-[4-(3-1H-Indol-3-ylpropionyl)piperazin-1-yl]propionyl}-

3H-benzoxazol-2-one

“B38”

6-{3-[4-(3-Indol-1-ylpropionyl)piperazin-1-yl]propionyl}-3H-

benzoxazol-2-one

“B39”

6-(3-{4-[3-(1-Methyl-1H-pyrazol-4-yl)propionyl]piperazin-1-

yl}propionyl)-3H-benzoxazol-2-one

“B40”

tert-Butyl ((R)-1-(4-chlorobenzyl)-2-oxo-2-{4-[3-oxo-3-(2-oxo-

2,3-dihydrobenzoxazol-6-yl)propyl]piperazin-1-yl}ethyl)-

methylcarbamate

“B41”

O-(4-Chlorobenzyl) 4-[3-oxo-3-(2-oxo-2,3-dihydro-

benzoxazol-6-yl)propyl]piperazine-1-carbothiolate

“B42”

9H-Fluoren-9-ylmethyl ((S)-1-(4-tert-butoxybenzyl)-2-oxo-2-

{4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]-

piperazin-1-yl}ethyl)methylcarbamate

“B43”

6-{3-[4-(5-Chloro-1-methyl-1H-indole-2-carbonyl)piperazin-1-

yl]propionyl}-3H-benzoxazol-2-one

“B44”

6-(3-{4-[3-(4-Dimethylaminophenyl)propionyl]piperazin-1-yl}-

propionyl)-3H-benzoxazol-2-one

“B45”

2-Methyl-5-phenyl-2H-pyrazol-3-ylmethyl 4-[3-oxo-3-(2-oxo-

2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate

“B47”

4-Chlorobenzyl 4-[2-(2-oxo-2,3-dihydrobenzoxazole-6-

sulfinyl)ethyl]piperazine-1-carboxylate

“B48”

“B49”

“B51”

3,5-Dichlorobenzyl 4-[2-(2-oxo-2,3-dihydrobenzoxazole-6-

sulfinyl)ethyl]piperazine-1-carboxylate

“B54”

6-(3-{4-[5-(4-Chlorophenyl)-2H-pyrazole-3-carbonyl]-

piperazin-1-yl}propionyl)-3H-benzoxazol-2-one

or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof.

17. A process for preparing a compound of formula I according to claim 1 , or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof, comprising

a) reacting a compound of formula II

in which R 2 , R 3 , G, E and W have the meanings indicated for the compound of formula I,

with a compound of formula III

in which

R 1 , D and Q have the meanings indicated for the compound of formula I,

and

L denotes Cl, Br, I or a free or reactively functionally modified OH group,

or

b) reacting a compound of formula IV

in which

R 1 , R 2 , R 3 , D and Q have the meanings indicated for the compound of formula I and G=N

with a compound of formula V

L-E-W  V

in which

E and W have the meanings indicated for the compound of formula I,

and

L denotes Cl, Br, I or a free or reactively functionally modified OH group,

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

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

19. A method for treating a tumour that originates from monocytic leukaemia, lung adenocarcinoma, small-cell lung carcinoma, pancreatic cancer, glioblastoma, breast carcinoma, colocarcinoma, acute myeloid leukaemia, chronic myeloid leukaemia, acute lymphatic leukaemia or chronic lymphatic leukaemia, comprising administering an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof, to a subject in need thereof.

20. A method for treating a tumour that originates from monocytic leukaemia, lung adenocarcinoma, small-cell lung carcinoma, pancreatic cancer, glioblastoma, breast carcinoma, colocarcinoma, acute myeloid leukaemia, chronic myeloid leukaemia, acute lymphatic leukaemia or chronic lymphatic leukaemia, comprising administering an effective amount of a compound according to claim 15 , or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof, to a subject in need thereof.

21. A method for treating a tumour that originates from monocytic leukaemia, lung adenocarcinoma, small-cell lung carcinoma, pancreatic cancer, glioblastoma, breast carcinoma, colocarcinoma, acute myeloid leukaemia, chronic myeloid leukaemia, acute lymphatic leukaemia or chronic lymphatic leukaemia, comprising administering an effective amount of a compound according to claim 16 , or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof, to a subject in need thereof.

22. A method according to claim 19 , where the tumour originates from monocytic leukaemia, lung adenocarcinoma, small-cell lung carcinoma, pancreatic cancer, glioblastoma, breast carcinoma or colocarcinoma.

23. A method for treating a tumour that originates from monocytic leukaemia, lung adenocarcinoma, small-cell lung carcinoma, pancreatic cancer, glioblastoma, breast carcinoma, colocarcinoma, acute myeloid leukaemia, chronic myeloid leukaemia, acute lymphatic leukaemia or chronic lymphatic leukaemia, comprising administering an effective amount of a compound according to claim 14 , or a pharmaceutically acceptable tautomer, salt or stereoisomer thereof, to a subject in need thereof.

24. A method according to claim 19 , where the tumour originates from acute myeloid leukaemia, chronic myeloid leukaemia, acute lymphatic leukaemia and/or chronic lymphatic leukaemia.

25. A method according to claim 19 , wherein the compound of formula I or a pharmaceutically acceptable salt thereof is administered in combination with radiotherapy and a compound selected from the group consisting of 1) oestrogen receptor modulator, 2) androgen receptor modulator, 3) retinoid receptor modulator, 4) cytotoxic agent, 5) antiproliferative agent, 6) prenyl-protein transferase inhibitor, 7) HMG-CoA reductase inhibitor, 8) HIV protease inhibitor, 9) reverse transcriptase inhibitor and 10) angiogenesis inhibitors.

26. A compound according to claim 1 in which

E denotes COO(CR 2 ) n , COO(CRR 4 ), CO(CR 2 ) m O, CONH(CR 2 ) n , C(═S)NH(CR 2 ) n , S(O) q NH(CR 2 ) n , S(O) q (CR 2 ) n , CO(CR 2 ) m O(CR 2 ) n , CO(CR 2 ) m NH(CR 2 ) n , CO(CH 2 ) n CO, COCHR 6 CHR 7 , C(═S)O(CR 2 ) n , CO(CRR 4 )(CR 2 ) n , COO(CRR 4 ), (CRR 4 )(CR 2 ) n , S(O) q CR═CR, COCR═CR, CONH(CR 2 ) m CRR 4 or (CR 2 ) m CONR.