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US 2013/0296274 A1Published application
Pyrrolidinones as metap-2 inhibitors
AssigneeMerck Patent GmbH
InventorsTimo Heinrich, Frank Zenke, Michel Calderini, Djordje Musil
Life of this patent
Estimating the term…
Abstract
Compounds of the formula I in which R1, R2, R3 and R4 have the meanings indicated in Claim 1, are inhibitors of methionine aminopeptidase and can be employed for the treatment of tumours.
Claims14
Compounds of the formula I
- in which
- R1 denotes [C(R4)2]nAr1, (CH2)nHet, (CH2)nCyc,
- or A,
- R2 denotes C(R4)2]nAr2, CH[B(OH)2]CH2Het,
- (CH2)nHet, (CH2)nCyc, CH(C≡CH)phenyl or A,
- R3 denotes OH, Hal, NH2, CN, CF3, CHF2 or N3,
- R4 denotes H or alkyl having 1, 2, 3 or 4 C atoms,
- R2 and R4 together also denote alkylene having 2, 3, 4 or 5 C atoms, where one CH2 group may also be replaced by NH, NA, N—COA, N—(CH2)nAr3, N—(CH2)nHet2, CH-A, CH—O—(CH2)nAr3, N—SO2A or O
- and/or may be substituted by A,
- Ar1 denotes phenyl, naphthyl or biphenyl, each of which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, OH, OA, NH2, NHA, NA2, NO2, CN, COOH, COOA, CONH2, CONHA, CONA2, NHCOA, NHSO2A, COA, CHO, Het1, SO2NH2 and/or SO2A,
- Ar2 denotes phenyl, naphthyl or biphenyl, each of which is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted by Hal, A, OH, OA, NH2, NHA, NA2, NO2, CN, COOH, COOA, CONH2, CONHA, CONA2, NHCOA, NHSO2A, COA, CHO, Het1, SO2NH2 and/or SO2A,
- Ara denotes phenyl which is unsubstituted or mono-, di- or trisubstituted by Hal, OH, OA and/or A,
- 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-, di- or trisubstituted by Hal, A, OH, OA, NH2, NHA, NA2, NO2, CN, COOH, COOA, (CH2)nCONH2, (CH2)nCONHA, (CH2)nCONA2, NHCOA, NHSO2A, COA, CHO, Het1, SO2NH2, SO2A and/or ═O,
- Het1 denotes a monocyclic saturated, unsaturated or aromatic heterocycle having 1 to 4 N, and/or O and/or S atoms which is unsubstituted or mono-, di- or trisubstituted by Hal, A, OH, OA, NH2, NHA, NA2, NO2, CN, COOH and/or COOA,
- Het2 denotes pyridyl, pyrimidinyl, furyl, thienyl, imidazolyl, pyrrolyl, oxazolyl, oxadiazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl or thiadiazole,
- A denotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7H atoms may be replaced by F, Cl, Br, OH, CHO, COA, COOA, CN, CONA2, CONHA and/or CONH2,
- and/or in which one or two non-adjacent CH and/or CH2 groups may be replaced by O, N and/or NR4,
- or Cyc,
- Cyc denotes cyclic alkyl having 3-7 C atoms,
- Hal denotes F, Cl, Br or I,
- n denotes 0, 1, 2, 3 or 4,
- and pharmaceutically usable salts, tautomers and stereoisomers thereof, including mixtures thereof in all ratios.
19 more elements
Dependencies are inferred from the claim text.